- Synthesis and characterisation of schiff base macrocyclic Pb(II), zn(ii), Cd(II) and La(III) complexes by template reaction of (±)-trans-1,2- diaminocyclohexane with metal nitrates and salicylaldehyde derivatives
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Eight macrocyclic complexes have been synthesised by template reaction of (±)-trans-1,2-diaminocyclohexane with metal nitrates and 1,10-bis(2-formylphenyl)-1,4,7,10-tetraoxadecane or 1,7-bis(2-formylphenyl)-1,4, 7-trioxaheptane, and their structures are proposed on the basis of elemental analysis, FT-IR, UV-Vis, molar conductivity measurements, 1H The complexes NMR and mass spectra. The metal-to-ligand molar ratios are 1:1 in the complexes, which are 1:2 electrolytes for Pb(II), Cd(II) and Zn(II) and 1:3 electrolytes for La(III).
- Ilhan, Salih
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- Synthesis of N-(bisphosphonomethyl)-aza-15-Crown-5 and N- (bisphosphonomethyl)-aza-18-crown-6 ethers as artificial ion channels: An approach to channel-type molecular structures
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We report the synthesis and characterization of 2 new N- (bisphosphonomethyl)-aza-15-crown-5 1a and N-(bisphosphonomethyl)-aza-18-Crown-6 ethers 1b designed to further investigate the supramolecular assemblies based on exocyclic functional groups of crown ethers. Copyright Taylor & Francis LLC.
- Fallouh,Bernier,Virieux,Cristau,Pirat
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- A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+
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A novel multi-response chemosensor L based on coumarin-chalcone-crown ether was designed and synthesized, which exhibited a high selectivity for the colorimetric detecting Al3+ and Cu2+ and fluorescent recognizing Al3+ and Mg2+ in ethanol. L can monitor Al3+ and Cu2+ via distinct color changes from a slight yellow to pink and to orange, respectively. The sensor L can also monitor Al3+ and Mg2+ by fluorescence emission responses at 592 nm and 547 nm with low detection limits of 0.31 μM and 0.23 μM, respectively. The selectivity of L toward Al3+, Cu2+ and Mg2+ was not interfered by a large number of coexisting ions and was found to be reversible. By means of spectrometric titration, Job's plot, mass spectrometry, 1H NMR titration and IR spectroscopy analysis, it was unanimously confirmed that the sensor L had a stoichiometric ratio of 1:1 with Cu2+ and Mg2+, and 1:2 with Al3+. The order of the stability of the complexes formed by L and Al3+, Cu2+, Mg2+ was as follows: L-Al3+ > L-Cu2+ > L-Mg2+. At the same time, some possible bonding modes and sensing mechanisms were further proposed, and the optimized structure of the sensor L and its sensing mechanism for Al3+, Cu2+ and Mg2+ were confirmed by the calculations of DFT/B3LYP and TD-DFT methods in a suite of Gaussian 09 programs.
- Zhang, Qiang,Ma, Ruifang,Li, Zhuying,Liu, Zizhong
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- Fluorescence enhancement of a signaling system in the simultaneous presence of transition and alkali metal ions: A potential AND logic gate
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Attachment of a laterally non-symmetric cryptand and a macrocycle at the 9- and 10-positions of anthracene leads to a fluorescent signaling system L 1 which gives fluorescence enhancement in the simultaneous presence of alkali and transition metal ions.
- Bag, Bamaprasad,Bharadwaj, Parimal K.
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- Metal ion chemosensors based on diaza-18-crown-6 coupling with azobenzene dye
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Novel naked-eye cation-selective chemosensors were developed from derivatives of diaza-18-crown-6 bearing one or two azobenzenes functionalized with o-acetic acid or p-nitro groups. The chromogenic acid and nitro derivatives exhibited solvatochromic effects with a majority of quinone-hydrazone tautomer in DMSO. The study of sensing properties of all molecules towards several metal ions showed that the one and two nitro-bearing N1 and N2 derivatives responded selectively to Cr3+ in MeCN with a color change from pink to colorless. They also showed selectivity for Hg2+ in DMSO with a color change from purple to light yellow. The detection limit of N1 and N2 that render visual difference to the naked eye are 0.21 ppm and 0.31 ppm for Cr3+ in MeCN, and 1.20 ppm and 1.00 ppm for Hg2+ in DMSO, while that obtained from 3σ method are 0.08 ppm and 0.03 ppm for Hg2+ in DMSO. These results demonstrate a potential use of p-nitro azobenzene diaza-18-crown-6 as naked-eye sensors, notably for Cr3+ that brings acute toxic to aquatic life.
- Koonrugsa, Narongsak,Fuangswasdi, Saowarux
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- Photolysis of polymeric self-assembly controlled by donor-acceptor interaction
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A photodegradable supramolecular polymer was constructed using cucurbit[8]uril (CB[8]) and an alkoxyanthracene guest. The monomeric unit was photostable because of the intramolecular donor-acceptor interaction. However, upon complexation with CB[8], the photolysis of alkoxyanthracene was enhanced, which endowed the supramolecular polymer with great photoreactivity.
- Qian, Tingjuan,Chen, Feiyi,Chen, Yulan,Wang, Yi-Xuan,Hu, Wenping
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- Sodium-Selective Fluoroionophore-Based Optodes for Seawater Salinity Measurement
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A new fluorescent sensor for Na+ is presented. The sensor relies on a Na+ selective fluoroionophore based on a bright red-emitting BODIPY chromophore. The fluorescence of the fluoroionophore is enhanced upon binding of Na+-ions to the highly selective aza-crown ether receptor due to reduction of the photoinduced electron transfer (PET) quenching. Solid state sensing materials were prepared by physically embedding the fluoroionophore into water-swellable biocompatible polymer matrices (polyurethane hydrogels), thus enabling continuous measurements of aqueous samples. Despite the simple design, the sensor showed no leaching of the indicator and featured fast and reversible response. Among different polyurethane hydrogels investigated, the hydrogel D1 featuring the highest water uptake was found to be the most suitable due to the highest dynamics between "off" and "on" states. Due to little or no cross sensitivity to other ions (e.g., Mg2+, Ca2+, K+) and its insensitivity to potential changes in pH, this sensor is promising for use in clinical diagnostics and for biological and marine applications. Fiber-optic sensors based on referenced read-out with a compact phase fluorimeter were prepared. To demonstrate their practical applicability, the sensors were used to determine the salinity in the seawater and brackish water of the Baltic Sea.
- Müller, Bernhard J.,Rappitsch, Tanja,Staudinger, Christoph,Rüschitz, Christian,Borisov, Sergey M.,Klimant, Ingo
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- Sandwich phosphate complexes of macrocyclic tris(urea) ligands and their rotation around the anion
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Four heteroditopic macrocyclic ligands incorporating both anion coordination sites (tris-urea units) and a cation binding fragment (polyether) were designed for possible application in molecular devices. Sandwich-type phosphate complexes were formed, which display a reversible rotation around the anion upon protonation/deprotonation of phosphate and binding of the cation (Emim+).
- Ji, Liguo,Yang, Zaiwen,Zhao, Yanxia,Sun, Meng,Cao, Liping,Yang, Xiao-Juan,Wang, Yao-Yu,Wu, Biao
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- Displacement assay detection by a dimeric lanthanide luminescent ternary Tb(iii)-cyclen complex: High selectivity for phosphate and nitrate anions
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The luminescent dimeric ternary lanthanide-cyclen complexes (2-(Ln.1)2; Ln = Tb/Eu) were designed and both their self-assembly formation and their ability to detect anions via displacement assays were investigated using spectrophotometric titrations in MeOH solution. The formation of 2-(Tb.1)2 and 2-(Eu.1)2 was investigated in solution, and determination of the binding constants and stoichiometry showed that the former was formed almost exclusively over the 1 1 complex 2-(Tb.1) after the addition of two equivalents of 2; while for 2-(Eu.1)2 a mixture of both stoichiometries existed even after the addition of four equivalents of 2. Of these two systems, 2-(Tb.1)2 was studied in details as a probe for anions, where significant changes where observed in the photophysical properties of the complex; with the characteristic Tb(iii)-centred emission being fully switched off upon the sensing of phosphates and nitrate, giving rise to the formation of a H2PO4-:Tb.1 complex in a 1 2 stoichiometry upon sensing of H2PO4- by 2-(Tb.1)2, while NO3- gave 1 1 complex formation and two equivalents of NO3-·Tb.1.
- Caffrey, David F.,Gunnlaugsson, Thorfinnur
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- Synthesis, characterization and mass spectral studies on acrocyclic schiff base complexes of Pb(II), Zn(II) and La(III)
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Six new macrocyclic complexes were synthesized by template reaction of (±)-1,4-bis(3-aminopropoxy)butane with metal(II) nitrate and 1,10-bis(2-formylphenyl)-1,4,7,10-tetraoxadecane or 1,7-bis(2-formylphenyl)-1,4, 7-trioxaheptane and their structures were proposed on the basis of elemental analysis, FT-IR, UV-Vis, molar conductivity measurements, 1H NMR and mass spectra. The metals to ligand molar ratios of the complexes were found to be 1: 1. The complexes are 1: 2 electrolytes for Pb(II) and Zn(II) complexes and 1: 3 electrolytes for La(III) as shown by their molar conductivities (Λm) in DMSO at 10-3 mol L-1. Due to the existence of free ions in these complexes, such complexes are electrically conductive. The configurations of La(III) and Zn(II) complexes were proposed to probably octahedral.
- ?lhan, Salih
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- MODULAR CHEMICAL PROBE FOR DETECTION OF AMINO ACID CITRULLINE IN PHYSIOLOGICAL SAMPLES
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An improved chemical probe for the detection of the amino acid citrulline combines: 1) a reactive head formed of 1,3-dicarbonyl moiety that reacts with a citrulline side chain in an improved manner compared to currently used 1,2-dicarbonyl moieties; and 2) a modular action of the probe where citrulline side chains are labeled first using reactive heads described above, and attachment of a read-out subunit or tag, be it a fluorophore, a nanoparticle, or an antigen is performed separately. The modular nature of the chemical probe increases the sensitivity of the probes due to their smaller size. Additionally, the chemical probes of the present disclosure allow the same sample to be analyzed using a variety of read-out methods.
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Page/Page column 16
(2021/01/29)
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- Fluorescence emission enhancement of a T-shaped benzimidazole with a mechanically-interlocked ‘suit’
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A fluorescent T-shaped benzimidazole was successfully designed and interlocked in a bicyclic macrocycle to form a suit[1]ane through supramolecular templated-synthesis. Compared with the bare fluorophore, suit[1]ane requires nearly two times the concentration to initialize the aggregation-caused quenching effect in solution. Furthermore, an 8-fold higher solid-state fluorescence quantum yield (21.7%) is also achieved. By taking advantage of mechanical bonding and molecular packing, such fluorescence emission enhancement through formation of a suitane opens the way to new complex fluorescent materials.
- Xu, Houyang,Lin, Meng-Di,Yuan, Jun,Zhou, Baiyang,Mu, Yingxiao,Huo, Yanping,Zhu, Kelong
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supporting information
p. 3239 - 3242
(2021/04/06)
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- DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
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To provide a dinuclear metal complex that can be synthesized simply and easily and has a proper anticancer action.SOLUTION: The present disclosure provides a dinucleating ligand represented by the following formula (I) and a dinuclear metal complex thereof (where each X may be the same or different to represent H, Cl, OMe, or, Me, Y is H, a phenyl group, a substituted carbamoyl group or the like).SELECTED DRAWING: None
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Paragraph 0094-0095
(2021/03/19)
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- DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
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To provide a metal complex that has high cancer cell toxicity and has DNA target and cyclen.SOLUTION: The present disclosure provides a dinuclear metal complex represented by the following formula (IV).SELECTED DRAWING: None
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Paragraph 0040-0041
(2021/03/19)
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- DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
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To provide a dinuclear metal complex that can be synthesized simply and easily and has a proper anticancer action.SOLUTION: The present disclosure provides a dinucleating ligand represented by the following formula (I) and a dinuclear metal complex thereof (where X is H or a substituted carbamoyl group, R1, R2, R3, and R4 independently represent H or a C1-8 linear or branched alkyl group).SELECTED DRAWING: None
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Paragraph 0073-0074
(2021/03/19)
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- Isosteviol amphiphilic derivative and preparation method thereof
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The invention discloses structures of isosteviol amphiphilic derivatives and a preparation method of the isosteviol amphiphilic derivatives, and belongs to the technical field of supramolecular chemistry. The compound is based on a natural product isosteviol, the nineteenth position of the compound is connected with a polyether chain, and the ends of the compound are different quaternary ammonium salts; the structural formula of the compound is shown in figure 1, wherein R is pyridine quaternary ammonium salt, imidazole quaternary ammonium salt and the like.
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Paragraph 0029-0030
(2021/04/10)
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- COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF
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Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a -S(=0)(=N-)- functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.
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(2020/09/03)
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- Target protein degradation inducing compound, preparation method thereof and pharmaceutical composition for preventing or treating targeted protein related diseases containing the same as an active ingredient
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The present invention relates to a degraducer for inducing the decomposition of target protein, a producing method thereof, and a pharmaceutical composition for preventing or treating target protein-related diseases by containing the degraducer as an active ingredient. A novel compound represented by chemical formula 1, ULB-L-PTM, by the present invention, as a degraducer compound inducing the decomposition of target protein using cereblon E3 ubiquitin ligase, is able to significantly achieve a target protein degradation-inducing activity with an excellent binding activity of a cereblon E3 ubiquitin ligase binder thereby, being able to achieve an excellent protein degradation activity by targeting protein or polypeptide related to various diseases. The bromodomain-containing pharmaceutical composition for preventing or treating protein-related diseases or conditions contains the novel compound represented by chemical formula 1 as an active ingredient and has a useful effect of providing a health functional food composition for prevention or improvement.(AA) Example 22 (nM, 24h)COPYRIGHT KIPO 2020
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Paragraph 1160; 1162-1164
(2020/05/01)
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- Fingolimod derivatives containing crown ether and bis (2 - methoxyethoxy) structure (by machine translation)
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The invention synthesizes a series of fingolimod derivatives containing crown ether or bis (2 - methoxyethoxy) structure by modifying the structure of the immunosuppressant fingolimod for treating multiple sclerosis in the market. The hypoglycemic effect of the target compound was evaluated by in vivo animal experiments. The results show that the compounds including 1c - 1e, Ic-Ie have a certain effect of reducing blood sugar and have application prospects in the preparation of medicines for treating diabetes. (by machine translation)
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Paragraph 0023; 0030-0032
(2020/06/20)
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- Synthesis method of arylimidazophenanthroline fluorescence dye, and recognition of metal ions
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The invention discloses a synthesis method of an arylimidazophenanthroline fluorescence dye, and recognition of metal ions. The synthesis method is a method for synthesizing arylimidazo[4,5-f]phenanthroline oxa-crown ether compounds from cheap and easily available 1,10-phenanthroline through a series of steps. Fluorescence properties of the arylimidazo[4,5-f]phenanthroline compounds are screened,the complexing property of the compounds and metal ions is verified through screening experiments of different metal ions and experiments of ion concentration and the like, and recognition of the metal ions Zn in tumor cells is achieved. The fluorescence probe has the following technical effects: 1, the compounds respectively have high selectivity to Zn Zn on wide metal ions; and 2, a fluorescence quenching molecular switch responding to Zn can be obtained in MCF-7 cells, and lays a great foundation for the application of the system in fields of biological recognition and the like.
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Paragraph 0012
(2020/02/20)
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- Crown ether compound, preparation method of crown ether compound, and application of crown ether compound in ion recognition
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The invention discloses a crown ether compound having a general formula as shown in formula I or an isomer thereof: In the formula I, n is an integer of 2-5. After extensive and in-depth research, thecrown ether compound with a novel structure is designed and synthesized, the crown ether compound can form complexes with potassium, sodium, and ammonium salts and can specifically recognize sodium ions. Therefore, the types of crown ethers are enriched, the application fields of the crown ethers are broadened, and the crown ether compound can be used in technical fields such as ion recognition and drug carriers.
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Paragraph 0045; 0060-0062
(2020/02/19)
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- MONOMER AND MULTIMERIC ANTI-HBV AGENTS
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The present invention is directed to compounds, compositions and methods for preventing, treating or curing hepatitis B (HBV) infection in human subjects or other animal hosts. The compounds are as also pharmaceutically acceptable, salts, prodrugs, and other derivatives thereof as pharmaceutical compositions and methods for treatment, prevention or eradication of HBV infection.
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Page/Page column 143; 194
(2020/05/15)
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- Incorporation of Fluorine into an OBOC Peptide Library by Copper-Free Click Chemistry toward the Discovery of PET Imaging Agents
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A one-bead one-compound (OBOC) library of peptide-based imaging agents was developed where a 19F-containing moiety was added onto the N-Terminus of octamer peptides through copper-free click chemistry prior to screening of the library. This created a library of complete imaging agents that was screened against CXCR4, a receptor of interest for cancer imaging. The screen directly resulted in the discovery of a peptide-based imaging agent with an IC50 of 138 μM. This proof-of-concept study describes a new type of OBOC peptide library design, where hits discovered from screening can be easily translated into their fluorine-18 counterpart for PET imaging without loss of affinity.
- Luyt, Leonard G.,Murrell, Emily
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supporting information
p. 109 - 113
(2020/03/25)
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- Selective Binding and Quantitation of Calcium with a Cobalt-Based Magnetic Resonance Probe
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We report a cobalt-based paramagnetic chemical exchange saturation transfer (PARACEST) magnetic resonance (MR) probe that is able to selectively bind and quantitate the concentration of Ca2+ ions under physiological conditions. The parent LCo complex features CEST-active carboxamide groups and an uncoordinated crown ether moiety in close proximity to a high-spin pseudo-octahedral CoII center. Addition of Na+, Mg2+, K+, and Ca2+ leads to binding of these metal ions within the crown ether. Single-crystal X-ray diffraction and solid-state magnetic measurements reveal the presence of a cation-specific coordination environment and magnetic anisotropy of CoII, with axial zero-field splitting parameters for the Na+- A nd Ca2+-bound complexes differing by over 90%. Owing to these differences, solution-based measurements under physiological conditions indicate reversible binding of Na+ and Ca2+ to give well-separated CEST peaks at 69 and 80 ppm for [LCoNa]+ and [LCoCa]2+, respectively. Dissociation constants for different cation-bound complexes of LCo, as determined by 1H NMR spectroscopy, demonstrate high selectivity toward Ca2+. This finding, in conjunction with the large excess of Na+ in physiological environments, minimizes interference from related cations, such as Mg2+ and K+. Finally, variable-[Ca2+] CEST spectra establish the ratio between the CEST peak intensities for the Ca2+- A nd Na+-bound probes (CEST80 ppm/CEST69 ppm) as a measure of [Ca2+], providing the first example of a ratiometric quantitation of Ca2+ concentration using PARACEST. Taken together, these results demonstrate the ability of transition metal PARACEST probes to afford a concentration-independent measure of [Ca2+] and provide a new approach for designing MR probes for cation sensing.
- Du, Kang,Thorarinsdottir, Agnes E.,Harris, T. David
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supporting information
p. 7163 - 7172
(2019/05/10)
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- Macrocyclic bis-urea receptor: Synthesis, crystal structure and phosphate binding properties
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A macrocyclic bis-urea receptor (L1) and two acyclic bis-urea analogues (L2 and L3) have been synthesized. The crystal structure of L1 was obtained. The experimental results show that the receptor L1 has high selectivity to H2PO4 ?. Meanwhile, compared with the acyclic receptors L2 and L3, L1 has higher binding ability to H2PO4 ?. The results of density functional theory (DFT) calculations deepened our understanding on L1 conformations stability and its anion-binding property.
- Shu, Xi,Wang, Ruyu,Fan, Yu,Li, Shoujian,Huang, Chao
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supporting information
p. 729 - 733
(2019/02/13)
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- Barium complexes with crown-ether-functionalised amidinate and iminoanilide ligands for the hydrophosphination of vinylarenes
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The detailed multistep syntheses of two nitrogen-based sterically congested iminoanilidine and amidine proligands bearing a tethered 15-member aza-ether-crown macrocycle, namely {I^Acrown}H and {Amcrown}H, are reported. These proligands react with [Ba{N(SiMe2H)2}2·(thf)n] to generate the heteroleptic barium complexes [{I^Acrown}BaN(SiMe2H)2] (5) and [{Amcrown}BaN(SiMe2H)2] (6) in high yields. These complexes exhibit high coordination numbers (resp. eight and seven) and are in addition stabilised by mild Ba?H-Si interactions. Unusually for oxophilic elements such as barium, the amidinate ligand in 6 is only η1-coordinated. Complexes 5 and 6 mediate the intermolecular hydrophosphination of styrene with primary (PhPH2) and secondary (HPPh2) phosphines. Their catalytic performance compares favourably with those of other barium precatalysts for these reactions. During the course of the hydrophosphination of styrene with HPPh2 catalysed by 5, the phosphide complex [{I^Acrown}BaPPh2] (7) could be intercepted and crystallographically characterised.
- Le Coz, Erwann,Roueindeji, Hanieh,Roisnel, Thierry,Dorcet, Vincent,Carpentier, Jean-Francois,Sarazin, Yann
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supporting information
p. 9173 - 9180
(2019/07/04)
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- METHOD
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The invention provides mitochondria-targeted chemiluminescent agents and their use in methods of photodynamic therapy (PDT). In particular, the invention provides compounds of general formula (I), and their pharmaceutically acceptable salts: (I) in which A represents a chemiluminescent moiety; each L, which may be the same or different, is either a direct bond or a linker; each B, which may be the same or different, represents a mitotropic moiety; n is an integer from 1 to 3, preferably 1; and x is an integer from 1 to 3, preferably 1. Such compounds find particular use in the treatment of deeply- sited tumours, e.g. glioblastoma multiforme (GBM), when used in combination with a photosensitizer or photosensitizer precursor.
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Page/Page column 41
(2020/01/11)
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- Acetazolamide-based [18F]-PET tracer: In vivo validation of carbonic anhydrase IX as a sole target for imaging of CA-IX expressing hypoxic solid tumors
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Carbonic anhydrase IX is overexpressed in many solid tumors including hypoxic tumors and is a potential target for cancer therapy and diagnosis. Reported imaging agents targeting CA-IX are successful mostly in clear cell renal carcinoma as SKRC-52 and no candidate was approved yet in clinical trials for imaging of CA-IX. To validate CA-IX as a valid target for imaging of hypoxic tumor, we designed and synthesized novel [18F]-PET tracer (1) based on acetazolamide which is one of the well-known CA-IX inhibitors and performed imaging study in CA-IX expressing hypoxic tumor model as 4T1 and HT-29 in vivo models other than SKRC-52. [18F]-acetazolamide (1) was found to be insufficient for the specific accumulation in CA-IX expressing tumor. This study might be useful to understand in vivo behavior of acetazolamide PET tracer and can contribute to the development of successful PET imaging agents targeting CA-IX in future. Additional study is needed to understand the mechanism of poor targeting of CA-IX, as if CA-IX is not reliable as a sole target for imaging of CA-IX expressing hypoxic solid tumors.
- More, Kunal N.,Lee, Jun Young,Kim, Dong-Yeon,Cho, Nam-Chul,Pyo, Ayoung,Yun, Misun,Kim, Hyeon Sik,Kim, Hangun,Ko, Kwangseok,Park, Jeong-Hoon,Chang, Dong-Jo
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supporting information
p. 915 - 921
(2018/02/09)
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- MYELOPEROXIDASE IMAGING AGENTS
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Provided herein are compounds useful as imaging agents. Exemplary compounds provided herein are useful as myeloperoxidase imaging agents using positron emission tomography or fluorescence imaging techniques. Methods for preparing the compounds provided herein and diagnostic methods using radiolabeled and unlabeled compounds are also provided.
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Page/Page column 73
(2018/06/06)
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- Radiosynthesis, biological evaluation and preliminary microPET study of 18F-labeled 5-resorcinolic triazolone derivative based on ganetespib targeting HSP90
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Heat-shock protein 90 (HSP90) is a molecular chaperone that activates oncogenic transformation in several solid tumors, including lung and breast cancers. Ganetespib, a most promising candidate among several HSP90 inhibitors under clinical trials, has entered Phase III clinical trials for cancer therapy. Despite numerous evidences validating HSP90 as a target of anticancer, there are few studies on PET agents targeting oncogenic HSP90. In this study, we synthesized and biologically evaluated a novel 18F-labeled 5-resorcinolic triazolone derivative (1, [18F]PTP-Ganetespib) based on ganetespib. [18F]PTP-Ganetespib was labeled by click chemistry of Ganetespib-PEG-Alkyne (10) and [18F]PEG-N3 (11) with 37.3 ± 5.11% of radiochemical yield and 99.7 ± 0.09% of radiochemical purity. [18F]PTP-Ganetespib showed proper LogP (0.96 ± 0.06) and good stability in human serum over 97% for 2 h. [18F]PTP-Ganetespib showed high uptakes in breast cancer cells containing triple negative breast cancer (TNBC) MDA-MB-231 and Her2-negative MCF-7 cells, which are target breast cancer cell lines of HSP90 inhibitor, ganetespib, as an anticancer. Blocking of HSP90 by the pretreatment of ganetespib exhibited significantly decreased accumulation of [18F]PTP-Ganetespib in MDA-MB-231 and MCF-7 cells, indicating the specific binding of [18F]PTP-Ganetespib to MDA-MB-231 and MCF-7 cells with high HSP90 expression. In the biodistribution and microPET imaging studies, the initial uptake into tumor was weaker than in other thoracic and abdominal organs, but [18F]PTP-Ganetespib was retained relatively longer in the tumor than other organs. The uptake of [18F]PTP-Ganetespib in tumors was not sufficient for further development as a tumor-specific PET imaging agent by itself, but this preliminary PET imaging study of [18F]PTP-Ganetespib can be basis for developing new PET imaging agents based on HSP90 inhibitor, ganetespib.
- Kang, Julie,Young Lee, Jun,Ta?, ?sa,More, Kunal N.,Kim, Hangun,Park, Jeong-Hoon,Chang, Dong-Jo
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supporting information
p. 3658 - 3664
(2018/10/26)
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- Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity
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A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (-)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition and no significant enhancement was obtained in G202R, N370S and L444P fibroblasts. However, all compounds having at least one (+)-2-O-alkyl iminoxylitol are GCase inhibitors in the nano molar range and are significant GCase activity enhancers in G202R fibroblats, as confirmed by a decrease of glucosylceramide levels and by co-localization studies.
- Stauffert, Fabien,Serra-Vinardell, Jenny,Gómez-Grau, Marta,Michelakakis, Helen,Mavridou, Irene,Grinberg, Daniel,Vilageliu, Llu?sa,Casas, Josefina,Bodlenner, Anne,Delgado, Antonio,Compain, Philippe
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supporting information
p. 3681 - 3705
(2017/07/07)
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- Ratio-type fluorescent probe for simultaneously detecting silver ions and trivalent chromic ions as well as preparation method and application of ratio-type fluorescent probe
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The invention discloses a ratio-type fluorescent probe for simultaneously detecting silver ions and trivalent chromic ions as well as a preparation method and application of the ratio-type fluorescent probe. The fluorescent probe is of a symmetric structure of pyrene-diIL-pyrene and triazole connected by triethylene glycol; when no detected ions exist in a system, the system emits a characteristic fluorescence emission band of an excimer of pyrene when emitting light with specific wavelength is excited; when the silver ions and the trivalent chromic ions are separately added in the system, two detected ions and a recognition group form a complex with a specific structure by different interactions, and an excimer structure of a probe molecule is damaged, thereby separately realizing ratio-type fluorescent detection of the silver ions and the trivalent chromic ions and avoiding the interference of outside conditions in the analysis and detection process. According to the ratio-type fluorescent probe disclosed by the invention, different responses of the silver ions and the trivalent chromic ions in a buffer solution can be distinguished with naked eyes under the irradiation of a portable ultraviolet lamp, and is expected to be used for quantitative analysis of the silver ions and the trivalent chromic ions in samples such as chemical samples and environmental samples.
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Paragraph 0036; 0038; 0043; 0049
(2017/08/28)
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- Synthesis and preliminary evaluation of a 18F-labeled ethisterone derivative [18F]EAEF for progesterone receptor targeting
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To develop a novel progesterone receptor-targeting probe for positron emission tomography imaging, an ethisterone derivative [18F]EAEF was designed and prepared in high decay-corrected radiochemical yield (30–35%) with good radiochemical purity (>98%). [18F]EAEF is a lipophilic tracer (logP?=?0.53?±?0.06) with very good stability in saline and serum. In the biodistribution study, high radioactivity accumulation of [18F]EAEF were found in uterus (5.73?±?1.83% ID/g) and ovary (4.05?±?0.73% ID/g) at 2?hr postinjection (p.i.), which have high progesterone receptor expression after treated with estradiol, while the muscle background has very low uptake (0.50?±?0.17% ID/g). For positron emission tomography imaging, [18F]EAEF showed high uptake in progesterone receptor-positive MCF-7 tumor (3.15?±?0.07% ID/g at 2?hr p.i.) with good tumor to muscle ratio (2.90), and obvious lower tumor uptakes were observed in MCF-7 with EAEF blocking (1.84?±?0.05% ID/g at 2?hr p.i.) or in progesterone receptor-negative MDA-MB-231 tumor (1.80?±?0.03% ID/g at 2?hr p.i.). Based on the good stability and specificity of [18F]EAEF, it may be a good candidate for imaging progesterone receptor and worth further investigation.
- Wu, Xiaowei,You, Linyi,Zhang, Deliang,Gao, Mengna,Li, Zijing,Xu, Duo,Zhang, Pu,Huang, Lumei,Zhuang, Rongqiang,Wu, Hua,Zhang, Xianzhong
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p. 559 - 565
(2017/04/06)
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- Polysilsesquioxane-dendron liquid crystals and method for preparing the same
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Due to excellent processability of the POSS-dendron-structured liquid crystal compound according to the present invention, it is possible to coat and print on the compound and, also, to manufacture large size flexible devices. According to the present invention, it is possible to maximize the physical bond strength between liquid crystals and, thus, to form higher-order structures by controlling the physical bond strength. Since the POSS-dendron-structured liquid crystal compound of the present invention introduces non-functional groups to inorganic chemicals in contrast to the conventional liquid crystals, the compound disperses well into general types of solvents. In addition, the chemical and mechanical properties of the compound of the invention, such as increase of maximum allowable temperature, inhibition of oxidation, increase of surface hardness, etc., improves since polysilsesquioxane includes reactive or non-reactive organic compounds. When the POSS-dendron-structured liquid crystal compound of the invention is used as an additive for liquid crystal layers, it can enhance the orientation of liquid crystal molecules. Moreover, the POSS part of the added liquid crystal compound of the invention may move to the lower surface of the liquid crystal layer and, then, improves the orientation.
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Page/Page column 7; 8
(2017/07/04)
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- Novel 18F-Labeled 1-Hydroxyanthraquinone Derivatives for Necrotic Myocardium Imaging
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Rapid detection and precise evaluation of myocardial viability is necessary to aid in clinical decision making whether to recommend revascularization for patients with myocardial infarction (MI). Three novel18F-labeled 1-hydroxyanthraquinone derivatives were synthesized, characterized, and evaluated as potential necrosis avid imaging agents for assessment of myocardial viability. Among these tracers, [18F]FA3OP emerged as the most promising compound with best stability and highest targetability. Clear PET images of [18F]FA3OP were obtained in rat model of myocardial infarction and reperfusion at 1 h after injection. In addition, the possible mechanisms of [18F]FA3OP for necrotic myocardium were discussed. The results showed [19F]FA3OP may bind DNA to achieve targetability to necrotic myocardium by intercalation. In summary, [18F]FA3OP was a more promising “hot spot imaging” tracer for rapid visualization of necrotic myocardium.
- Ji, Ai-Yan,Jin, Qiao-Mei,Zhang, Dong-Jian,Zhu, Hua,Su, Chang,Duan, Xing-Hua,Bian, Li,Sun, Zi-Ping,Ni, Yi-Cheng,Zhang, Jian,Yang, Zhi,Yin, Zhi-Qi
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supporting information
p. 191 - 195
(2017/03/08)
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- Development of a High-Affinity PET Radioligand for Imaging Cannabinoid Subtype 2 Receptor
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Cannabinoid receptors type 2 (CB2) represent a target with increasing importance for neuroimaging due to its upregulation under various pathological conditions. Encouraged by preliminary results obtained with [11C](Z)-N-(3-(2-methoxyethyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2,3,3-tetramethyl-cyclopropanecarboxamide ([11C]A-836339, [11C]1) in a mouse model of acute neuroinflammation (induced by lipopolysaccharide, LPS), we designed a library of fluorinated analogues aiming for an [18F]-labeled radiotracer with improved CB2 binding affinity and selectivity. Compound (Z)-N-(3-(4-fluorobutyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2,3,3-tetramethyl-cyclopropanecarboxamide (29) was selected as the ligand with the highest CB2 affinity (Ki = 0.39 nM) and selectivity over those of CB1 (factor of 1000). [18F]29 was prepared starting from the bromo precursor (53). Specific binding was shown in vitro, whereas fast metabolism was observed in vivo in CD-1 mice. Animal PET revealed a brain uptake comparable to that of [11C]1. In the LPS-treated mice, a 20-30% higher uptake in brain was found in comparison to that in nontreated mice (n = 3, P 0.05).
- Moldovan, Rare?-Petru,Teodoro, Rodrigo,Gao, Yongjun,Deuther-Conrad, Winnie,Kranz, Mathias,Wang, Yuchuan,Kuwabara, Hiroto,Nakano, Masayoshi,Valentine, Heather,Fischer, Steffen,Pomper, Martin G.,Wong, Dean F.,Dannals, Robert F.,Brust, Peter,Horti, Andrew G.
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p. 7840 - 7855
(2016/10/12)
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- Optimized methods for preparation of 6I-(ω-sulfanyl-alkylenesulfanyl)-β-cyclodextrin derivatives
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A general high-yielding method for the preparation of monosubstituted β-cyclodextrin derivatives which have attached a thiol group in position 6 is described. The thiol group is attached through linkers of different lengths and repeating units (ethylene glycol or methylene). The target compounds were characterized by IR, MS and NMR spectra. A simple method for their complete conversion to the corresponding disulfides as well as a method for the reduction of the disulfides back to the thiols is presented. Both, thiols and disulfides are derivatives usable for well-defined covalent attachment of cyclodextrin to gold or polydopamine-coated solid surfaces.
- Bedná?ová, Eva,Hybelbauerová, Simona,Jind?ich, Jind?ich
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supporting information
p. 349 - 352
(2016/04/05)
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- 18F labeled compd.
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PROBLEM TO BE SOLVED: To provide anF-labeling compound that can label a protein or a peptide at a site other than an N-terminal and is simply synthesizable.SOLUTION: A compound represented by formula (I) is provided. In formula (I), Qis anF or a specific benzoyloxy group substituted with anF and n is an integer of 1-8.
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Paragraph 0054; 0055
(2019/04/02)
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- Label-free fluorescent probe and application thereof in detecting diploid G-quadruplex structure
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The present invention discloses a label-free fluorescent probe and an application thereof in detecting a diploid G-quadruplex structure, wherein the probe is an ether chain connected symmetrical berberine dimer derivative. According to the present invention, the berberine derivative can be used under an ultraviolet lamp in label-free fluorescent detection of a diploid G-quadruplex structure, and has the properties of selective recognition, high sensitivity that has no influence on conformation and thermal stability, and the berberine derivative can enter a cell, and perform detection on the G-quadruplex structure in the cell, so that the probe is has a wide application prospect.
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Paragraph 0039-0040
(2017/03/17)
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- Icotinib hydrochloride, synthesis, crystalline forms, pharmaceutical compositions, and uses thereof
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The invention relates to 4-[(3-ethynylphenyl)amino]-6,7-benzo-12-crown-quinazoline hydrochloride, its new crystalline forms, its therapeutic usage for treatment of diseases mediated by EGFR kinase and its combinatory therapeutic usage together with other therapeutic agents. The invention also provides synthetic methods for preparation of 4-[(3-ethynylphenyl)amino]-6,7-benzo-12-crown-quinazoline hydrochloride, its new crystalline forms, and the relevant synthetic intermediates for synthesis of 4-[(3-ethynylphenyl)amino]-6,7-benzo-12-crown-quinazoline hydrochloride.
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Page/Page column 9; 10
(2016/06/28)
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- Color-Tunable Amphiphilic Segmented π-Conjugated Polymer Nano-Assemblies and Their Bioimaging in Cancer Cells
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We report a unique color tunable amphiphilic segmented π-conjugated polymer design and their π-stack driven diverse self-assembled nanostructures and demonstrate their application as a new classes of aqueous luminescent nanoparticle probes for bioimaging in cervical and breast cancer cells. Oligo-phenylenevinylene (OPV) was employed as rigid luminescent π-core and oligo-ethyleneoxy chains were used as flexible spacers to construct new amphiphilic segmented π-conjugated polymers by Witting-Horner polymerization route. The rigidity of the π-core was varied using tricyclodecanemethyleneoxy, 2-ethylhexyloxy or methoxy pendants and appropriate π-core geometry was optimized to achieve maximum aromatic π-stacking interactions. Solvent-induced chain aggregation of the polymers exhibited a morphological transition from one-dimensional helical nanofibrous to three-dimensional spherical nanoassemblies in good/bad solvent combinations. This morphological transformation was accompanied by the fluorescence color change from blue-to-white-to-yellow. CIE color coordinates exhibited x = 0.25 and y = 0.32 for the white light followed by the collective emission from aggregated and isolated OPV chromophores. Electron and atomic microscopes, steady state photophysical studies, time-resolved fluorescent decay analysis, and dynamic light scattering method enabled us to establish the precise mechanism for the self-assembly of segmented OPV polymers. The polymers produced stable and luminescent aqueous nanoparticles of 200 nm diameter in water. Cytotoxicity studies in cervical and breast cancer cells revealed that these new aqueous luminescent polymer nanoparticles are highly biocompatible and nontoxic to cells up to 60 μg/mL. Cellular uptake studies by confocal microscope further exposed that these nanoparticles were internalized in the cancer cells and they were predominantly accumulated in the nucleus. The present investigation opens up new amphiphilic segmented π-conjugated polymer design for producing diverse supramolecular assemblies and also demonstrates their new application as biocompatible fluorescent nanoprobes for imaging in cancer cells.
- Narasimha, Karnati,Jayakannan, Manickam
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p. 4102 - 4114
(2016/07/06)
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- Crown ether cyclic quinazoline compound, preparation method therefor and application thereof in preparing tumor therapy and imaging drug
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The invention relates to a crown ether cyclic quinazoline derivative and medicinal salts thereof using in tumor therapy and imaging. The crown ether cyclic quinazoline compound is characterized in that a 2-, 3-, 4- substituted aniline is disposed at one end; a 6-, 7- substituted crown ether cyclic quinazoline structure is disposed at the other end; the substituent group R1 is located on the fourth-position aniline of a quinazoline mother ring and is 2-, 3-, 4- substituted alkoxy; and the crown ether cycle is located at the 6, 7 position of the mother ring, and is a 9-crown-3, 12-crown-4 and 15-crown-5, and the structural formula is formula I. The experimental result of antitumor activity in vitro of nonradioactive isotope labeling compounds shows that the compounds are good in inhibitory effect for four kind of cancer cells namely HepG2, A549, sy5y and DU145, and have the potential as cancer treatment medicine; and the body distribution experiment of 18F or 125I labeling compounds show that the compounds are higher in ingestion and certain detention in tumors and faster in blood clearance and have potential applied to tumor imaging.
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Paragraph 0057; 0058; 0059
(2016/10/09)
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- Design and synthesis of an activity-based protein profiling probe derived from cinnamic hydroxamic acid
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In our continued effort to discover new anti-hepatitis C virus (HCV) agents, we validated the anti-replicon activity of compound 1, a potent and selective anti-HCV hydroxamic acid recently reported by us. Generally favorable physicochemical and in vitro absorption, distribution, metabolism, and excretion (ADME) properties exhibited by 1 made it an ideal parent compound from which activity-based protein profiling (ABPP) probe 3 was designed and synthesized. Evaluation of probe 3 revealed that it possessed necessary anti-HCV activity and selectivity. Therefore, we have successfully obtained compound 3 as a suitable ABPP probe to identify potential molecular targets of compound 1. Probe 3 and its improved analogs are expected to join a growing list of ABPP probes that have made important contributions to not only the studies of biochemical and cellular functions but also discovery of selective inhibitors of protein targets.
- Ai, Teng,Qiu, Li,Xie, Jiashu,Geraghty, Robert J.,Chen, Liqiang
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p. 686 - 692
(2016/05/24)
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- New dimeric carbazole-benzimidazole mixed ligands for the stabilization of human telomeric G-quadruplex DNA and as telomerase inhibitors. A remarkable influence of the spacer
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The development of G-quadruplex (G4) DNA binding small molecules has become an important strategy for selectively targeting cancer cells. Herein, we report the design and evolution of a new kind of carbazole-based benzimidazole dimers for their efficient telomerase inhibition activity. Spectroscopic titrations reveal the ligands high affinity toward the G4 DNA with significantly higher selectivity over duplex-DNA. The electrophoretic mobility shift assay shows that the ligands efficiently promote the formation of G4 DNA even at a lower concentration of the stabilizing K+ ions. The TRAP-LIG assay demonstrates the ligand's potential telomerase inhibition activity and also establishes that the activity proceeds via G4 DNA stabilization. An efficient nuclear internalization of the ligands in several common cancer cells (HeLa, HT1080, and A549) also enabled differentiation between normal HFF cells in co-cultures of cancer and normal ones. The ligands induce significant apoptotic response and antiproliferative activity toward cancer cells selectively when compared to the normal cells.
- Maji, Basudeb,Kumar, Krishan,Muniyappa,Bhattacharya, Santanu
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supporting information
p. 8335 - 8348
(2015/08/03)
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- HYDROCHLORIC ACID ICOTINIB, COMPOSITE, CRYSTALLOGRAPHIC FORM, COMBINED MEDICINE AND ITS APPLICATION
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PROBLEM TO BE SOLVED: To provide a production method of a medicine which is an epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor, for treating and preventing excessive non-malignancy hyperplasia, pancreatitis, renal disease, cancer, arterialization or an angiogenesis-related disease of a mammal, or a medicine for germ cell transplantation of a mammal. SOLUTION: There is provided a use of 4-[(3-ethynyl phenyl)amino]-6-7-benzo-12-crown-hydrochloric acid quinazoline, illustrated by following formula, and these novel crystals (I, II, III, IV) for treatment of EGFR kinase-intermediating pathogen, and a use for treatment by joint use with another therapeutic agent. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0043
(2017/01/02)
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- Copper(II)-catalyzed enantioselective intramolecular cyclization of N-alkenylureas
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The first Cu(II)-catalyzed highly enantioselective intramolecular cyclization of N-alkenylureas was developed for the concise assembly of chiral vicinal diamino bicyclic heterocycles. Facile removal of carbonyl group of the carbamido moiety allowed for ready access to enantioenriched cyclic vicinal diamines.
- Fu, Shaomin,Yang, Honghao,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei,Li, Guoqiang
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supporting information
p. 1018 - 1021
(2015/03/30)
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- Preparation of 7-methoxy tacrine dimer analogs and their in vitro/in silico evaluation as potential cholinesterase inhibitors
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Novel types of symmetric bis-7-methoxytacrines connected by oligoethyleneoxy chains 3-5 and nonsymmetric monomeric 7-methoxytacrines containing hydroxyl-terminated oligoethyleneoxy chains 6-8 were prepared, and their in vitro/in silico effects on human recombinant AChE (hAChE) and human plasmatic butyrylcholinesterase (hBChE) were compared, with 7-MEOTA (2) as the standard compound. The symmetric bis-7-MEOTA derivatives 3-5 showed hAChE inhibition similar to that of 2. On the other hand, their effects on hBChE revealed an increasing inhibition trend when the oligoethyleneoxy units between the two 7-MEOTA moieties became longer. Accordingly, compounds 4 and 5 showed better selectivity towards hBChE. The most effective in the inhibition hAChE and hBChE was compound 8 with the longest oligoethyleneglycol chain, whereas compounds 6 and 7 resulted in similar IC50 values. A molecular modeling study using substrates 5 and 8 showed a possible binding conformation and protein-ligand interaction between the substrates and AChE/BChE.
- Lee, Sang Kwang,Park, Min Kyun,Jhang, Ho Eun,Yi, Jinju,Nahm, Keepyong,Cho, Dae Won,Ra, Choon Sup,Musilek, Kamil,Horova, Anna,Korabecny, Jan,Dolezal, Rafael,Jun, Daniel,Kuca, Kamil Kuca
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p. 1654 - 1660
(2015/07/15)
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- Synthesis and cavity size effect of pd-containing macrocycle catalyst for efficient intramolecular hydroamination of allylurethane
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Palladium-containing macrocycle catalysts (PdMCs) with different ring sizes ranging from 24 to 30 members were synthesized. The intramolecular hydroamination of an allylurethane (AU) catalyzed by PdMCs proceeded efficiently to afford the corresponding oxazolidinone (OZ) in 95% isolated yield. The dependence of the hydroamination of AU to OZ on the cavity size indicated that the reaction rate was clearly controlled by both substrate uptake and product release steps.
- Ogawa, Masahiro,Nagashima, Masaki,Sogawa, Hiromitsu,Kuwata, Shigeki,Takata, Toshikazu
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supporting information
p. 1664 - 1667
(2015/04/14)
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- A fluorene-based material containing triple azacrown ether groups: Synthesis, characterization and application in chemosensors and electroluminescent devices
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We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe3+ but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe3+, with the Stern-Volmer coefficients (Ksv) being 1.59 × 105 M-1 in a solvent mixture of tetrahydrofuran and water (THF-H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe3+ in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be -5.88 eV and -2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11630 cd m-2 and 1.47 cd A-1, respectively, from 230 cd m-2 and 0.03 cd A -1 of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe3+ and as an effective electron injection layer to enhance the performance of MEH-PPV.
- Wu, Chia-Shing,Lin, Ying-Ju,Chen, Yun
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p. 1419 - 1429
(2014/03/21)
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- A strain induced change of mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] cycloaddition reaction
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While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An η4-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.
- Tran-Van, Anne-Florence,Goetz, Silas,Neuburger, Markus,Wegner, Hermann A.
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supporting information
p. 2410 - 2413
(2014/05/20)
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- Adaptive amphiphilic dendrimer-based nanoassemblies as robust and versatile siRNA delivery systems
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siRNA delivery remains a major challenge in RNAi-based therapy. Here, we report for the first time that an amphiphilic dendrimer is able to self-assemble into adaptive supramolecular assemblies upon interaction with siRNA, and effectively delivers siRNAs to various cell lines, including human primary and stem cells, thereby outperforming the currently available nonviral vectors. In addition, this amphi-philic dendrimer is able to harness the advantageous features of both polymer and lipid vectors and hence promotes effective siRNA delivery. Our study demonstrates for the first time that dendrimer-based adaptive supramolecular assemblies represent novel and versatile means for functional siRNA delivery, heralding a new age of dendrimer-based self-assembled drug delivery in biomedical applications.
- Liu, Xiaoxuan,Zhou, Jiehua,Yu, Tianzhu,Chen, Chao,Cheng, Qiang,Sengupta, Kheya,Huang, Yuanyu,Li, Haitang,Liu, Cheng,Wang, Yang,Posocco, Paola,Wang, Menghua,Cui, Qi,Giorgio, Suzanne,Fermeglia, Maurizio,Qu, Fanqi,Pricl, Sabrina,Shi, Yanhong,Liang, Zicai,Rocchi, Palma,Rossi, John J.,Peng, Ling
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supporting information
p. 11822 - 11827
(2015/04/14)
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- Design and synthesis of protoporphyrin IX/vitamin B12 molecular hybrids via CuAAC reaction
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The design and synthesis of new molecular hybrids composed of protoporphyrin IX (PPIX) and vitamin B12 via copper catalyzed alkyne azide cycloaddition reaction is described. New, clickable aminoazide and aminoalkyne linkers were prepared and subsequently attached to PPIX (via vinyl group) and to vitamin B12 giving desired building blocks. Preliminary results showed that respective water soluble hybrids were formed under CuAAC reaction. Gratifyingly, Cu incorporation into the PPIX core was avoided, which was important for further biological studies. Copyright
- Loska, Rafa?,Janiga, Anita,Gryko, Dorota
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p. 104 - 117
(2013/04/23)
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- Design and synthesis of polymeric chiral bicyclo[3.3.0] diene as reusable ligand for rhodium-catalyzed asymmetric 1,4-addition
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A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Copyright
- Yang, Hongyu,Xu, Minghua
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supporting information
p. 119 - 122
(2013/08/24)
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- Copoly(p-phenylene) containing azacrown ether: Synthesis, optical properties, and application for chemical sensor
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Copoly(p-phenylene) (P1) containing pendent azacrown ether and ethylene glycol ether was prepared by the Suzuki coupling reaction and applied for chemical sensor. Poly(p-phenylene) derivative P0 without the azacrown ether groups were also synthesized for comparative study. The photophysical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy to elucidate the influence of the azacrown ether groups. The P1 exhibited specific selectivity and high sensitivity toward Zn2+, with the Stern-Volmer coefficient (Ksv) being 3.66 × 106 M-1 at low concentration in mixture solvent of tetrahydrofuran and water (THF/H2O = 9/1, v/v). The P1 maintained high selectivity toward Zn2+ in the presence of fifteen interfering metal cations. This results indicate that copoly(p-phenylene) (P1) is a promising functional material for chemical sensors. Copyright
- Wu, Chia-Shing,Chen, Chiao-Pei,Chen, Yun
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p. 3975 - 3984
(2013/09/02)
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