- Synthesis and chemical properties of conjugated polyacetylenes having pendant fullerene and/or porphyrin units
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Conjugated polyacetylenes having pendant fullerene and/or porphyrin groups were prepared by copolymerization in the presence of [Rh(nbd)Cl] 2-NEt3 in CHCl3. The photochemical and electrochemical properties of the polymers
- Lu, Fushen,Xiao, Shengqiang,Li, Yuliang,Liu, Huibiao,Li, Hongmei,Zhuang, Junpeng,Liu, Yang,Wang, Ning,He, Xiaorong,Li, Xiaofang,Gan, Liangbing,Zhu, Daoben
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- Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities
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A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its met
- Hoogendoorn, Sascha,Blom, Annet E. M.,Willems, Lianne I.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.
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- Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium-Mediated Cross-Coupling
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Dehydroalanine (Dha) is a remarkably versatile non-canonical amino acid often found in antimicrobial peptides. Herein, we present the catalytic modification of Dha by a palladium-mediated cross-coupling reaction. By using Pd(EDTA)(OAc)2 as water-soluble catalyst, a variety of arylboronic acids was coupled to the dehydrated residues in proteins and peptides, such as Nisin. The cross-coupling reaction gave both the Heck product, in which the sp2-hybridisation of the α-carbon is retained, as well as the conjugated addition product. The reaction can be performed under mild aqueous conditions, which makes this method an attractive addition to the palette of bio-orthogonal catalytic methods.
- de Bruijn, A. Dowine,Roelfes, Gerard
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- Synthesis and biological evaluation of nandrolone-bodipy conjugates
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Here, we report synthesis and biological evaluation of fluorescent nandrolone-3-carboxymethyloxime derivatives conjugated with green-emitting bodipy dye via PEG linkers. All the newly-synthesized compounds were evaluated for their effect on cell prolifera
- Jurá?ek, Michal,Rimpelová, Silvie,Pavlí?ková, Vladimíra,Ruml, Tomá?,Lap?ík, Old?ich,Dra?ar, Pavel B.
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- An Efficient Approach for the Synthesis of 1,2,3-Triazole Moiety to Generate Uracil Molecular Architectures Through Cu-Catalyzed Azide–Alkyne Cycloaddition
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A simple and efficient pathway to tether conjugates of monosaccharides or aromatic moieties to uracil establishing a 1,2,3-triazole linker via click chemistry was reported. The reaction of arylimines of 5-amino uracil with propargyl bromide in a basic med
- Mohamed, Asmaa H.
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- The synthesis and dyes complexation properties of novel cyclodextrin derivatives with large conjugate acylhydrazone group
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By reacting β-cyclodextrin with 4-(prop-2-ynyloxy)benzaldehyde, the cyclodextrins (CDs) aromatic aldehyde derivative 6 was prepared in yield of 80 % via click chemistry of the Huisgen [2 + 3] cycloaddition reaction. Further Schiff-base condensation of com
- Wang, Zusheng,Guo, Hongyu,Yang, Fafu,Zhang, Yingmei
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- Tailor-made fluorescent trilobolide to study its biological relevance
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Trilobolide (Tb) is a potent natural counterpart of thapsigargin, which has shown promising results in cancer clinical trials. Here, we report a rational approach to study intracellular localization and biological activity of this sesquiterpene lactone. We conjugated Tb with a green-emitting Bodipy dye attached by alternative linkers of different lengths. The live-cell imaging of the prepared bioconjugates brought clear evidence that Tb-Bodipy localized in the endoplasmic reticulum (ER) of various cancer cell lines. The localization signal was compared with ER-specific dyes. Cytotoxicity of Tb conjugates and impact on the mitochondrial physiology and nitric oxide release were also studied. The nitric oxide production and cytokine secretion in rat peritoneal cells indicate immunobiological potential of these lactone bioconjugates. In summary, our Tb-Bodipy conjugates could help us to reveal the molecular mechanism of trilobolide for its further potential use in biomedical applications.
- Jurá?k, Michal,Rimpelová, Silvie,Kmoní?ková, Eva,Dra?ar, Pavel,Ruml, Tomá?
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- Synthesis and Cytotoxicity Evaluation of Novel Andrographolide-1,2,3-Triazole Derivatives
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A series of new andrographolide-1,2,3-triazole derivatives, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, were synthesized from a natural bioactive labdane type diterpenoid, andrographolide. All the derivatives were screened against human cancer cell lines
- Chinthala, Yakaiah,Manjulatha,Sharma, Pooja,Kvn, Satya Srinivas,Jonnala, Kotesh,Arigari, Niranjana Kumar,Khan, Feroz,Oh, Setty
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- Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity
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A series of novel chalcone-triazole derivatives were synthesized and screened for in vitro anticancer activity on the human cancer cell lines IMR32 (neuroblastoma), HepG2 (hepatoma) and MCF-7 (breast adenocarcinoma), DU-145 (prostate carcinoma), and A549
- Chinthala, Yakaiah,Thakur, Sneha,Tirunagari, Shalini,Chinde, Srinivas,Domatti, Anand Kumar,Arigari, Niranjana Kumar,Srinivas,Alam, Sarfaraz,Jonnala, Kotesh Kumar,Khan, Feroz,Tiwari, Ashok,Grover, Paramjit
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- Copper-supported β-cyclodextrin-functionalized magnetic nanoparticles: Efficient multifunctional catalyst for one-pot ‘green’ synthesis of 1,2,3-triazolylquinazolinone derivatives
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The green synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)oxy)phenyl)quinazolin-4(3H)-one derivatives is reported. The catalyst for this synthesis is copper-supported β-cyclodextrin-functionalized magnetic silica–iron oxide nanoparticles ([Cu@BCD@SiOs
- Bahadorikhalili, Saeed,Ashtari, Arsalan,Ma’mani, Leila,Ranjbar, Parviz Rashidi,Mahdavi, Mohammad
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- Click conjugation of boron dipyrromethene (Bodipy) fluorophores to egfr-targeting linear and cyclic peptides
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Through a simple 1,3-cycloaddition reaction, three BODIPY-peptide conjugates that target the extracellular domain of the epidermal growth factor receptor (EGFR) were prepared and their ability for binding to EGFR was investigated. The peptide ligands K(N3)LARLLT and its cyclic analog cyclo(K(N3)larllt, previously shown to have high affinity for binding to the extracellular domain of EGFR, were conjugated to alkynyl-functionalized BODIPY dyes 1 and 2 via a copper-catalyzed click reaction. This reaction produced conjugates 3, 4, and 5 in high yields (70–82%). In vitro studies using human carcinoma HEp2 cells that overexpress EGFR demonstrated high cellular uptake, particularly for the cyclic peptide conjugate 5, and low cytotoxicity in light (~1 J·cm?2) and darkness. Surface plasmon resonance (SPR) results show binding affinity of the three BODIPY-peptide conjugates for EGFR, particularly for 5 bearing the cyclic peptide. Competitive binding studies using three cell lines with different expressions of EGFR show that 5 binds specifically to EGFR-overexpressing colon cancer cells. Among the three conjugates, 5 bearing the cyclic peptide exhibited the highest affinity for binding to the EGFR protein.
- Jois, Seetharama D.,Kaufman, Nichole E. M.,Singh, Sitanshu S.,Vicente, Maria da Gra?a H.,Williams, Tyrslai M.,Zhou, Zehua
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supporting information
(2021/06/15)
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- Alkyne-tagged apigenin, a chemical tool to navigate potential targets of flavonoid anti-dengue leads
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A flavonoid is a versatile core structure with various cellular, immunological, and phar-macological effects. Recently, flavones have shown anti-dengue activities by interfering with viral translation and replication. However, the molecular target is still elusive. Here we chemically mod-ified apigenin by adding an alkyne moiety into the B-ring hydroxyl group. The alkyne serves as a chemical tag for the alkyne-azide cycloaddition reaction for subcellular visualization. The compound located at the perinuclear region at 1 and 6 h after infection. Interestingly, the compound signal started shifting to vesicle-like structures at 6 h and accumulated at 24 and 48 h after infection. Moreover, the compound treatment in dengue-infected cells showed that the compound restricted the viral protein inside the vesicles, especially at 48 h. As a result, the dengue envelope proteins spread throughout the cells. The alkyne-tagged apigenin showed a more potent efficacy at the EC50 of 2.36 ± 0.22, and 10.55 ± 3.37 μM, respectively, while the cytotoxicities were similar to the original apigenin at the CC50 of 70.34 ± 11.79, and 82.82 ± 11.68 μM, respectively. Molecular docking con-firmed the apigenin binding to the previously reported target, ribosomal protein S9, at two binding sites. The network analysis, homopharma, and molecular docking revealed that the estrogen receptor 1 and viral NS1 were potential targets at the late infection stage. The interactions could attenuate dengue productivity by interfering with viral translation and suppressing the viral proteins from trafficking to the cell surface.
- Badavath, Vishnu Nayak,Boonyasuppayakorn, Siwaporn,Chokmahasarn, Thamonwan,Hengphasatporn, Kowit,Jansongsaeng, Somruedee,Kaewmalai, Benyapa,Khotavivattana, Tanatorn,Rungrotmongkol, Thanyada,Saelee, Thanaphon,Shigeta, Yasuteru
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- Design and synthesis of tetrahydropyrimidinone(thione)-triazole hybrid scaffolds and evaluation of their biological activities
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In this study, we designed and synthesized some new tetrahydropyrimidinone(thione)-triazole hybrid derivatives by click and one-pot Biginelli reactions. FT IR, 1H NMR, and 13C NMR spectra and mass spectrometry, and elemental analysis
- Mirzayi, Sahar,Kakanj, Maryam,Sepehri, Saghi,Alavinejad, Bahar,Bakherad, Zohreh,Ghazi-Khansari, Mahmoud
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p. 1109 - 1116
(2021/10/12)
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- Forthrightly monitoring ferroptosis induced by endoplasmic reticulum stresses through fluorescence lifetime imaging of microviscosity increases with a specific rotor
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To test the hypothesis that the microviscosity changes of Endoplasmic Reticulum (ER) can be a useful indicator of ferroptosis promoted by ER Stresses (ERS), a new ER targeting viscosity rotor, L-Vis-1 was developed and applied in the quantitation of visco
- Liu, Chuanhao,Man, Huizi,Xiao, Yi,Xie, Lijuan,Zheng, Ying,Zhou, Lin
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supporting information
(2022/01/08)
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- 1,2,3-triazole-thiazole hybrids: Synthesis, in vitro antimicrobial activity and antibiofilm studies
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A new series of triazole-thiazole hybrids were designed, synthesized by the Multi-component reaction approach and evaluated in vitro antimicrobial activity. Most of the tested series of compounds exhibited promising inhibitory activity against the bacteri
- Gondru, Ramesh,Kanugala, Sirisha,Raj, Sneha,Ganesh Kumar,Pasupuleti, Mukesh,Banothu, Janardhan,Bavantula, Rajitha
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supporting information
(2020/12/28)
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- Preparation method and application of propyne aryl ether compound
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The invention particularly relates to a method for preparing propyne aryl ether compounds from aryl phenol, halogenated propyne and derivatives of the halogenated propyne, and belongs to the technical field of preparation of the propyne aryl ether compoun
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Paragraph 0075-0076
(2021/08/28)
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- Synthesis and antimicrobial activity of chalcone containing polystyrene
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Three different 4-propargyloxychalcones have been prepared starting from 4-propargyloxy benzaldehyde and chalcones with proper chemical transformation. Polystyrenes containing biologically active chalcone moiety in their structures have been successfully synthesised by the Click reaction from the 4-propargyloxychalones (terminal alkyne) and azido end-functional polystyrene (PS-N3). All the desired products have been obtained with good yield and purity. The structure of the 4-propargyloxychalcones and the chalcone containing polystyrenes have been characterized by FT-IR,1H NMR and UV-Vis spectroscopy. The antibacterial activity of the synthesized 4-propargyloxychalcones their polystyrene derivatives have been evaluated against two bacterial strains, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The results reveal that the tested chalcones and their polystyrene derivatives have moderate antimicrobial activity.
- Ali, Roushown,Chowdhury, Samiul Islam,Hasan, Tariqul,Rain, Farhana Sumi
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p. 456 - 464
(2021/09/28)
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- Anti-melanogenesis and anti-tyrosinase properties of aryl-substituted acetamides of phenoxy methyl triazole conjugated with thiosemicarbazide: Design, synthesis and biological evaluations
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A series of aryl phenoxy methyl triazole conjugated with thiosemicarbazides were designed, synthesized, and evaluated for their tyrosinase inhibitory activities in the presence of L-dopa and L-tyrosine as substrates. All the compounds showed tyrosinase inhibition in the sub-micromolar concentration. Among the derivatives, compound 9j bearing benzyl displayed exceptionally high potency against tyrosinase with IC50 value of 0.11 μM and 0.17 μM in the presence of L-tyrosine and L-dopa as substrates which is significantly lower than that of kojic acid as the positive control with an IC50 value of 9.28 μM for L-tyrosine and 9.30 μM for L-dopa. According to Lineweaver–Burk plot, 9j demonstrated an uncompetitive type of inhibition in the kinetic assay. Also, in vitro antioxidant activities determined by DPPH assay recorded an IC50 value of 68.43 μM for 9i. The melanin content of 9j was determined on B16F10 melanoma human cells which demonstrated a significant reduction of the melanin content. Moreover, the binding energies corresponding to the same ligand as well as computer-aided drug-likeness and pharmacokinetic studies were also carried out. Compound 9j also possessed metal chelation potential correlated to its high anti-TYR activity.
- Hosseinpoor, Hona,Moghadam Farid, Sara,Iraji, Aida,Askari, Sadegh,Edraki, Najmeh,Hosseini, Samanesadat,Jamshidzadeh, Akram,Larijani, Bagher,Attarroshan, Mahshid,Pirhadi, Somayeh,Mahdavi, Mohammad,Khoshneviszadeh, Mehdi
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- Strategic Design of Catalytic Lysine-Targeting Reversible Covalent BCR-ABL Inhibitors**
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Targeted covalent inhibitors have re-emerged as validated drugs to overcome acquired resistance in cancer treatment. Herein, by using a carbonyl boronic acid (CBA) warhead, we report the structure-based design of BCR-ABL inhibitors via reversible covalent targeting of the catalytic lysine with improved potency against both wild-type and mutant ABL kinases, especially ABLT315I bearing the gatekeeper residue mutation. We show the evolutionarily conserved lysine can be targeted selectively, and the selectivity depends largely on molecular recognition of the non-covalent pharmacophore in this class of inhibitors, probably due to the moderate reactivity of the warhead. We report the first co-crystal structures of covalent inhibitor-ABL kinase domain complexes, providing insights into the interaction of this warhead with the catalytic lysine. We also employed label-free mass spectrometry to evaluate off-targets of our compounds at proteome-wide level in different mammalian cells.
- Anantharajan, Jothi,Baburajendran, Nithya,Foo, Klement,Joy, Joma K.,Keller, Thomas H.,Kwek, Perlyn Z.,Li, Rong,Liu, Boping,Poulsen, Anders,Quach, David,Retna, Priya,Tang, Guanghui,Tee, Doris H. Y.,Wee, John L. K.,Yang, Wan-Qi,Yao, Shao Q.,Zhang, Chong-Jing
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supporting information
p. 17131 - 17137
(2021/06/28)
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- Reaction-based fluorescent silk probes with high sensitivity and selectivity to Hg2+and Ag+ions
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The detection and removal of heavy metals in the environment is urgent and meaningful. In this work, two types of fluorescent functionalized silksOSPandASPhave been prepared using worm silk as the substrate. These fluorescent silk probes exhibit an obvious fluorescence quenching effect in the presence of Hg2+or Ag+, enabling silk to specifically detect Hg2+or Ag+. An obvious color response occurs under visible light, from yellow to brown or gray, thereby realizing dual-channel identification of fluorescence and colorimetry. In addition, its sensing mechanism has been studied, and it is found that the probe reacts with metal ions as a reactive response. Compared with the fluorescent probes bearing one C-C/C-C bond, the probes with two terminal C-C/C-C bonds are more sensitive. And the excellent recognition ability can make the limit of detection as low as 0.25 μM. This indicates that silk fluorescent probes can be used to detect Hg2+and/or Ag+
- Cheng, Xinjian,Duan, Lian,Liu, Kaiqi,Xiao, Li
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p. 4877 - 4887
(2021/04/21)
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- Application of artificially synthesized palladium nano-enzyme to catalysis of compound containing phenolic hydroxyl group connection
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The invention provides application of an artificially synthesized palladium nano-enzyme to catalysis of a compound containing phenolic hydroxyl connection. The palladium nano-enzyme is used for catalyzing breakage of a carbon-oxygen bond of propargyloxy connected with an aromatic functional group containing at least one benzene ring; the aromatic functional group containing at least one benzene ring comprises but is not limited to fluorescein, the benzene ring, a pyridine ring, biphenyl, naphthalene, anthracene, coumarin or camptothecin, and the aromatic functional group containing at least one benzene ring can be connected with oxygen or oxygen-carbonyl oxygen or oxygen-carbonyl oxygen-oxygen. By constructing different artificially synthesized palladium nano-enzymes, the carbon-oxygen bond breakage of various molecules can be realized, and the palladium nano-enzymes can be applied to cell imaging and cancer treatment.
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Paragraph 0038-0039; 0042-0043
(2021/09/04)
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- An Ethacrynic Acid-Brominated BODIPY Photosensitizer (EA-BPS) Construct Enhances the Lethality of Reactive Oxygen Species in Hypoxic Tumor-Targeted Photodynamic Therapy
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Despite being a clinically approved intervention for cancer, photodynamic therapy (PDT) still suffers from limitations. Prime among these is a therapeutic response that is mostly oxygen dependent. This limits the utility of PDT in treating hypoxic tumors
- Won, Miae,Koo, Seyoung,Li, Hao,Sessler, Jonathan L.,Lee, Jin Yong,Sharma, Amit,Kim, Jong Seung
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supporting information
p. 3196 - 3204
(2020/12/18)
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- Just Add the Gold: Aggregation-Induced-Emission Properties of Alkynylphosphinegold(I) Complexes Functionalized with Phenylene-Terpyridine Subunits
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A series of organometallic complexes containing an alkynylphosphinegold(I) fragment and a phenylene-terpyridine moiety connected together by flexible linker have been prepared using the specially designed terpyridine ligands. The compounds were studied cr
- Abramova, Evgenia O.,Paderina, Aleksandra V.,Slavova, Sofia O.,Kostenko, Ekaterina A.,Eliseenkov, Eugene V.,Petrovskii, Stanislav K.,Gitlina, Anastasia Yu.,Boyarskiy, Vadim P.,Grachova, Elena V.
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supporting information
p. 18715 - 18725
(2021/12/09)
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- BODIPY based realtime, reversible and targeted fluorescent probes for biothiol imaging in living cells
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Real-time live cell imaging and quantification of biothiol dynamics are important for understanding pathophysiological processes. However, the design and synthesis of rational probes that have reversible and real-time capabilities is still challenging. In
- He, Rongkun,Zhang, Yichuan,Madhu, Suresh,Gao, Quan,Lian, Qianjin,Raghavan, Sriram Srinivasa,Geng, Jin
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supporting information
p. 14717 - 14720
(2020/12/02)
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- Efficient real-time bio-thiol fluorescence detection probe based on BODIPY
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The invention discloses a ratio type fluorescence probe for rapid detection of bio-thiol in real time, and also discloses a preparation method and application of the probe. Spectrum test results showthat the probe has the advantages of ratio type response
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Paragraph 0048; 0088; 0096-0098
(2020/03/05)
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- Design, synthesis and antibacterial activity evaluation of novel 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives
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In this paper, a novel series of 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives are synthesized in two steps. The first step involved Ugi multicomponent reaction of β-alanine, o-(propargyl)benzaldehyde and i
- Zarei, Samaneh,Komeili, Golzar,Bahadorikhalili, Saeed,Yahya-Meymandi, Azadeh,Karami-Zarandi, Morteza,Larijani, Bagher,Biglar, Mahmood,Sadat Ebrahimi, Seyed Esmaeil,Mahdavi, Mohammad
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p. 4254 - 4261
(2020/09/21)
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- A glutathione-responsive photosensitizer with fluorescence resonance energy transfer characteristics for imaging-guided targeting photodynamic therapy
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Here, we have synthesized and characterized a novel activatable photosensitizer (PS) 8a in which two well-designed boron dipyrromethene (BODIPY) derivatives are utilized as the photosensitizing fluorophore and quencher respectively, which are connected by a disulfide linker via two successive Cu (?) catalyzed click reactions. The fluorescence emission and singlet oxygen production of 8a are suppressed via intramolecular fluorescence resonance energy transfer (FRET) from the excited BODIPY-based PS part to quencher unit, but both of them can be simultaneously switched on by cancer-related biothiol glutathione (GSH) in phosphate buffered saline (PBS) solution with 0.05% Tween 80 as a result of cleavage of disulfide. Also, 8a exhibits a bright fluorescence image and a substantial ROS production in A549 human lung adenocarcinoma, HeLa human cervical carcinoma and H22 mouse hepatoma cells having a relatively high concentration of GSH, thereby leading to a significant photocytotoxicity, with IC50 values as low as 0.44 μM, 0.67 μM and 0.48 μM, respectively. In addition, the photosensitizer can be effectively activated and imaged in H22 transplanted hepatoma tumors of mice and shows a strong inhibition on tumor growth. All these results suggest that such a GSH-responsive photosensitizer based on FRET mechanism may provide a new strategy for tumor-targeted and fluorescence imaging-guided cancer therapy.
- Cao, Jing-Jing,Li, Xiao-Qiang,Liu, Jian-Yong,Xu, Gan,Yang, De-Chao,Zhang, Ming-Shan
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supporting information
(2020/03/18)
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- Self-assembled star-shaped aza-BODIPY mesogen affords white-light emission
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A novel multifunctional star-shaped aza-BODIPY mesogen was synthesized by a click reaction. This star-shaped aza-BODIPY mesogen undergoes self-assembly into a hexagonal columnar phase in its bulk state and spherical gels in organic solvents. Based on the
- Liu, Chao,Ding, Wei,Liu, Yuantao,Zhao, Hongmei,Cheng, Xiaohong
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supporting information
p. 102 - 109
(2019/12/25)
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- SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes
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Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes fromdiverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage modification of certain biologically active agents using the developed seleno-SLAPreagents.
- Zhou, Guan,Deng, Xingwang,Pan, Chenyu,Goh, Eunice Tze Leng,Lakshminarayanan, Rajamani,Srinivasan, Rajavel
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supporting information
p. 12546 - 12549
(2020/11/02)
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- Cyclophane-Sustained Ultrastable Porphyrins
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We report the encapsulation of free-base and zinc porphyrins by a tricyclic cyclophane receptor with subnanomolar binding affinities in water. The high affinities are sustained by the hydrophobic effect and multiple [CH···π] interactions covering large [π···π] stacking surfaces between the substrate porphyrins and the receptor. We discovered two co-conformational isomers of the 1:1 complex, where the porphyrin is orientated differently inside the binding cavity of the receptor on account of its tricyclic nature. The photophysical properties and chemical reactivities of the encapsulated porphyrins are modulated to a considerable extent by the receptor. Improved fluorescence quantum yields, red-shifted absorptions and emissions, and nearly quantitative energy transfer processes highlight the emergent photophysical enhancements. The encapsulated porphyrins enjoy unprecedented chemical stabilities, where their D/H exchange, protonation, and solvolysis under extremely acidic conditions are completely blocked. We anticipate that the ultrahigh stabilities and improved optical properties of these encapsulated porphyrins will find applications in single-molecule materials, artificial photodevices, and biomedical appliances.
- Liu, Wenqi,Lin, Chenjian,Weber, Jacob A.,Stern, Charlotte L.,Young, Ryan M.,Wasielewski, Michael R.,Stoddart, J. Fraser
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supporting information
p. 8938 - 8945
(2020/12/25)
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- Curcumin-1,2,3-Triazole conjugation for targeting the cancer apoptosis machinery
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The burden of neoplastic diseasesis widely recognized as a severe cause ofmortality. The clinical inadequacy of most anticancer therapeutics urgently prompted intense drug discovery efforts toward the identification of new chemical entities endowed with a
- Seghetti, Francesca,Di Martino, Rita Maria Concetta,Catanzaro, Elena,Bisi, Alessandra,Gobbi, Silvia,Rampa, Angela,Canonico, Barbara,Montanari, Mariele,Krysko, Dmitri V.,Krysk, Dmitri V.,Papa, Stefano,Fimognari, Carmela,Belluti, Federica
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- Design, synthesis and biological evaluation of new antioxidant and neuroprotective multitarget directed ligands able to block calcium channels
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We report herein the design, synthesis and biological evaluation of new antioxidant and neuroprotective multitarget directed ligands (MTDLs) able to block Ca2+ channels. New dialkyl 2,6-dimethyl-4-(4-(prop-2-yn-1-yloxy)phenyl)-1,4-dihydropyridi
- Angona, Irene Pachòn,Bonet, Alexandre,Borges, Fernanda,Daniel, Solene,Ismaili, Lhassane,Jó?wiak, Krzysztof,Maj, Maciej,Marco-Contelles, José,Martin, Helene,Refouvelet, Bernard,Silva, Tiago Barros,Wnorowski, Artur
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- 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers
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In this study, benzyl-1,2,3-triazole-linked 5-benzylidene (thio)barbiturate derivatives 7a–d and 8a–h were designed as potential tyrosinase inhibitors and free-radical scavengers. The twelve derivatives were synthesized via the [3+2] cycloaddition reactio
- Ranjbar, Sara,Shahvaran, Parisa-sadat,Edraki, Najmeh,Khoshneviszadeh, Mahsima,Darroudi, Mahdieh,Sarrafi, Yaghoub,Hamzehloueian, Mahshid,Khoshneviszadeh, Mehdi
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- Glaucocalyxin A (GLA)-biotin small-molecular probe, and preparation method and application thereof
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The invention relates to a GLA small-molecular probe, and a preparation method and application thereof, belonging to the field of medicinal chemistry. The GLA small-molecular probe structurally comprises three parts, namely GLA, a linker and a reporter (b
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Paragraph 0044-0045
(2020/06/09)
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- Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
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Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
- Lasányi, Dániel,Tolnai, Gergely L.
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supporting information
p. 10057 - 10062
(2019/12/24)
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- Rhodamine-modified boron-dipyrromethene compound and application thereof
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The invention provides a rhodamine-modified boron-dipyrromethene compound and application thereof. The rhodamine-modified boron-dipyrromethene compound has a structure of general formula I and can naturally target and be enriched at a tumor part, quickly
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Paragraph 0042; 0052; 0053; 0054; 0055
(2019/06/30)
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- Integrated phenotypic screening and activity-based protein profiling to reveal potential therapy targets of pancreatic cancer
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Pancreatic cancer has been defined as one of the most complex and challenging cancers to treat, but very few valid therapeutic targets have been identified to date. To address this issue, a 61-compound library was readily created by Ugi reaction followed by phenotypic screening, leading to the discovery of two most potent inhibitors, P21 and P26, which significantly impair BxPC-3 pancreatic cancer cell survival. A series of interacting protein hits, such as GSTO1, FAM213A, RAB6A/6B/39A and USMG5, were subsequently identified by quantitative chemoproteomics studies. The main cellular target, GSTO1, was further validated as a novel pancreatic cancer therapeutic target.
- Liu, Wenyan,Zhang, Zhang,Zhang, Zhi-Min,Hao, Piliang,Ding, Ke,Li, Zhengqiu
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p. 1596 - 1599
(2019/02/07)
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- Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies
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Carbonic anhydrases isoforms CA IX, and XII are known to be highly expressed in various human tissues and malignancies. CA IX is a prominent target for especially colorectal cancers, because it is overexpressed in colorectal cancer and this overexpression
- Zengin Kurt, Belma,Sonmez, Fatih,Ozturk, Dilek,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
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- Design, synthesis,: In silico docking studies and biological evaluation of novel quinoxaline-hydrazide hydrazone-1,2,3-triazole hybrids as α-glucosidase inhibitors and antioxidants
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A new series of quinoxaline-hydrazidehydrazone-1,2,3-triazole hybrids, 14a-j, 15a-j and 16a-e, was designed, synthesized and screened for in vitro α-glucosidase and antioxidant activities. For the synthesis of the target compounds, quinoxaline hydrazides were condensed with benzaldehyde triazoles in the presence of AcOH (cat) in ethanol. The key step in the preparation of compounds 8a-j was the Cu(i)-catalyzed [3+2] cycloaddition reaction (CuAAC) with appropriate alkynes (6, 7) and azides, and 13a-j were prepared from simple aldehydes utilizing the same click reaction as the final step. Quinoxaline hydrazides (3, 3a) were synthesized from o-phenylenediamine and pyruvic acid via three-step reactions comprising cyclization, alkylation and hydrazidation. Among these hybrids, 14a (IC50 = 21.92 μg mL-1), 14b (IC50 = 22.32 μg mL-1), 14c (IC50 = 23.58 μg mL-1) and 15a (IC50 = 24.50 μg mL-1) showed good α-glucosidase inhibition compared with the standard acarbose (IC50 = 22.32 μg mL-1). Further, the scavenging abilities of the synthesized compounds as antioxidants were studied using the DPPH, H2O2, and NO methods; as per the obtained results, compounds 14a, 14b, 14c and 15a displayed good antioxidant activity. Docking studies of the active compounds and acarbose as a standard with α-glucosidase (PDB ID: 2ZEO) were performed to determine the molecular interactions between the inhibitors and the active site of the enzyme. Better binding energies of the active compounds than of the standard acarbose were observed. Therefore, our new hybrid molecules may be useful for further optimization in developing new lead molecules with both α-glucosidase inhibition and antioxidant activities.
- Settypalli, Triloknadh,Chunduri, Venkata Rao,Maddineni, Aruna Kumari,Begari, Nagaraju,Allagadda, Rajasekhar,Kotha, Peddanna,Chippada, Appa Rao
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p. 15435 - 15452
(2019/10/08)
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- Multi-target inhibitors against Alzheimer disease derived from 3-hydrazinyl 1,2,4-triazine scaffold containing pendant phenoxy methyl-1,2,3-triazole: Design, synthesis and biological evaluation
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Alzheimer's disease (AD) is a complex neurological disorder with diverse underlying pathological processes. Several lines of evidence suggest that BACE1 is a key enzyme in the pathogenesis of AD and its inhibition is of particular importance in AD treatme
- Yazdani, Mahnaz,Edraki, Najmeh,Badri, Rashid,Khoshneviszadeh, Mehdi,Iraji, Aida,Firuzi, Omidreza
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p. 363 - 371
(2018/12/11)
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- A molybdenum based metallomicellar catalyst for controlled and chemoselective oxidation of activated alcohols in aqueous medium
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A surfactant based oxodiperoxo molybdenum complex, which could activate molecular oxygen, has been employed as a catalyst for controlled oxidation of benzylic alcohols to corresponding carbonyls. The oxidation reactions were carried out under aqueous environment, however, in the absence of any extraneous base or co-catalyst. Sensitive/oxidizable functional groups like cyano, sulfide, hydroxyl, aryl-hydroxyl, alkene (internal/terminal), alkyne (internal/terminal), and acetal were tolerated during the transformations. Such selectivity is attributed to the mild nature of the catalyst. The methodology could also be scaled-up for multi-gram synthesis and the protocol is likely to find practical use since it requires an inexpensive recyclable-catalyst and easily available oxidant (under green conditions). A plausible mechanism is proposed with the help of preliminary computational study.
- Thiruvengetam, Prabaharan,Chakravarthy, Rajan Deepan,Chand, Dillip Kumar
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p. 123 - 133
(2019/07/19)
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- Naphthalimide-based double-signal turn-on formaldehyde fluorescent nano probe intermediate compound, and preparation method and application thereof
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The invention discloses a preparation method and application of a mitochondrion-targeted double-signal turn-on formaldehyde fluorescent nano probe intermediate compound (V). The method comprises the following steps: activating p-hydroxybenzaldehyde used a
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Paragraph 0031; 0059-0060
(2018/03/26)
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- Synthesis of novel perillyl-dihydropyrimidinone hybrids designed for antiproliferative activity
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A series of fifteen novel dihydropyrimidinone hybrid compounds were synthesized in good yields via a multicomponent reaction combined with the Huisgen reaction. The antiproliferative activity was investigated against nine tumor cell lines, and four hybrid
- Vendrusculo, Vinicius,De Souza, Vanessa P.,M. Fontoura, Luiz Ant?nio,M. D'Oca, Marcelo G.,Banzato, Thais P.,Monteiro, Paula A.,Pilli, Ronaldo A.,De Carvalho, Jo?o Ernesto,Russowsky, Dennis
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p. 1553 - 1564
(2018/10/02)
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- Synthesis of novel C-2- or C-15-labeled BODIPY—estrone conjugates
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Novel BODIPY–estrone conjugates were synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC). Estrone-alkynes or an estrone-azide as starting compounds were synthesized via Michael addition or Sonogashira reaction as key steps. Fluorescent dyes based on BODIPY-core were provided by azide or alkyne functional groups. Fluorescent labeling of estrone was efficiently achieved at the C-2 or C-15 position. The newly-elaborated coupling procedures might have a broad applicability in the synthesis of fluorescent-labeled estrone conjugates suitable for biological assays.
- Bacsa, Ildikó,Konc, Csilla,Orosz, Anna Boglárka,Kecskeméti, Gábor,Rigó, Réka,zvegy-Laczka, Csilla,Mernyák, Erzsébet
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- Harnessing the Maltodextrin Transport Mechanism for Targeted Bacterial Imaging: Structural Requirements for Improved in vivo Stability in Tracer Design
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Diagnosis and localization of bacterial infections remains a significant clinical challenge. Harnessing bacteria-specific metabolic pathways, such as the maltodextrin transport mechanism, may allow specific localization and imaging of small or hidden colo
- Axer, Alexander,Hermann, Sven,Kehr, Gerald,Clases, David,Karst, Uwe,Fischer-Riepe, Lena,Roth, Johannes,Fobker, Manfred,Sch?fers, Michael,Gilmour, Ryan,Faust, Andreas
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supporting information
p. 241 - 250
(2018/01/22)
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- Synthesis and Evaluation of O 2-Derived Diazeniumdiolates Activatable via Bioorthogonal Chemistry Reactions in Living Cells
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A class of O2-alkyl derived diazeniumdiolates 3a-f and 4a-c were designed and synthesized as new bioorthogonal NO precursors, which can be effectively uncaged in the presence of a palladium catalyst via bioorthogonal bond cleavage reactions to generate NO in living cancer cells, eliciting potent antiproliferative activity.
- Lv, Tian,Wu, Jianbing,Kang, Fenghua,Wang, Tingting,Wan, Boheng,Lu, Jin-Jian,Zhang, Yihua,Huang, Zhangjian
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supporting information
p. 2164 - 2167
(2018/04/30)
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- Syntheses and Properties of meso-Substituted Porphyrin Mesogens with Triazole Linkages and Peripheral Alkyl Chains
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Discotic mesogens P/n-M (n=12, 16, 18, M=2 H, Zn and Cu) bearing a porphyrin core, triazole linkages and peripheral 3,4,5-trialkoxybenzyl units have been synthesized by a click-chemistry approach. The thermal behavior, photophysical properties and morphol
- Zhang, Ruilin,Gao, Hongfei,Ren, Yanming,Xiao, Yulong,Hu, Jinliang,Cheng, Xiaohong
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supporting information
p. 536 - 544
(2018/02/12)
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- Synergic effect on oxygen reduction reaction of strapped iron porphyrins polymerized around carbon nanotubes
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In the context of the development of new bio-inspired catalysts, MN4 complexes exhibit a great potential for small molecule activation. In particular, metallated porphyrins and phthalocyanines combined with carbon nanotubes have been tested for the oxygen reduction reaction in electrocatalytic systems, and these nanotube/MN4 hybrids have demonstrated promising properties. Here, a series of hybrid materials made of multi-walled carbon nanotubes (MWNTs) coated with strapped porphyrins have been fabricated. Iron porphyrin derivatives were polymerized around the nanotubes via Hay coupling and the resulting materials were fully characterized. Two porphyrins were probed; both were strapped with the same skeleton and they differed only in the presence or absence of overhung carboxylic acids. In the porphyrin, the carboxylic acid group could possibly act as a proton relay between the medium and the catalyst. Although the presence of the carboxylic acid groups (acting as intramolecular proton relays) did not exhibit a significant influence on the catalytic properties, the combination of both components-the MWNTs and porphyrin-led to a better catalytic activity than those of the nanotubes or the porphyrins taken separately. The synergic affect is due to the MWNTs which ensure the availability of electrons to the porphyrin catalysts and allow the ORR to occur via the 4-electron pathway, avoiding the production of hydrogen peroxide.
- Hanana, Manel,Arcostanzo, Hélène,Das, Pradip K.,Bouget, Morgane,Le Gac, Stéphane,Okuno, Hanako,Cornut, Renaud,Jousselme, Bruno,Dorcet, Vincent,Boitrel, Bernard,Campidelli, Stéphane
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supporting information
p. 19749 - 19754
(2018/12/13)
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- Synthesis, characterization, and antimycobacterial activity of novel thymol-triazole hybrids
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Thymol is a naturally occurring phenolic compound showing various biological activities. A library of novel thymol-triazole hybrids was synthesized and evaluated for their inhibitory activity against Mycobacterium tuberculosis (M.tb), the causative agent of TB. Most of the compounds were found to be active against M.tb H37Rv at 50 μg/mL concentration. These identified compounds have promise to be further optimized into more potent inhibitors against M.tb.
- Negi, Beena,Rawat, Diwan S
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p. 113 - 124
(2018/09/14)
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- Energy Harvesting in a Bodipy-Functionalized Rotaxane
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A rotaxane composed of two separate Bodipy-functionalized units can be synthesized with a high yield. The resulting structure shows a very efficient through-space energy transfer (FRET), acting as an energy funnel. Thus, maximum solar output in the visibl
- Yesilgul, Nisa,Seven, Ozlem,Guliyev, Ruslan,Akkaya, Engin U.
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p. 13228 - 13232
(2018/10/24)
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- P2X3 AND/OR P2X2/3 COMPOUNDS AND METHODS
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The present disclosure provides novel compounds and methods for preparing and using these compounds. In one embodiment, the compounds are of the structure of formula (I), wherein R1-R7 are defined herein. In a further embodiment, these compounds are useful in method for regulating one or both of the P2X3 or P2X2/3 receptors. In another embodiment, these compounds are useful for treating pain in patients by administering one or more of the compounds to a patient. In another embodiment, these compounds are useful for treating respiratory dysfunction in patients by administering one or more of the compounds to a patient.
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Paragraph 0189-0192
(2018/04/17)
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- Novel Cyanoarylporphyrazines with Triazole Groups at the Macrocycle Periphery as Potential Sensibilizers of Photodynamic Therapy and Optical Probes of Intracellular Viscosity
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Novel fluorescent dyes of the cyanoarylporphyrazine series containing peripheral triazole groups have been synthesized. Their photophysical properties and the local viscosity effect on the fluorescence have been studied. The experiments with cell cultures have revealed rapid accumulation of the dyes in the cells cytoplasm. Photo- and dark cytotoxicity of the compounds have been evaluated by means of the MTT test.
- Lermontova,Grigoryev,Peskova,Balalaeva,Boyarskii,Klapshina
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p. 2339 - 2346
(2019/01/04)
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- Curcuminoid-BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
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Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluo
- Weiss, Henning,Reichel, Jeannine,G?rls, Helmar,Schneider, Kilian Rolf Anton,Micheel, Mathias,Pr?hl, Michael,Gottschaldt, Michael,Dietzek, Benjamin,Weigand, Wolfgang
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supporting information
p. 2264 - 2272
(2017/11/16)
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- blue calyx a su-glucose derivative and its preparation method and application
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The invention relates to glucose derivatives of glaucocalyxin A. The glucose derivatives have a structure represented by a formula I or a formula II, wherein R1 represents hydrogen or methoxyl, R2 represents hydrogen or acetyl, and n represents 0 or 1. Th
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Paragraph 0083; 0084
(2017/08/25)
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- Thermodynamic Insights on a Bistable Acid–Base Switchable Molecular Shuttle with Strongly Shifted Co-conformational Equilibria
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Bistable [2]rotaxanes in which the affinities of the two stations can be reversed form the basis of molecular shuttles. Gaining quantitative information on such rotaxanes in which the ring distribution between the two stations is largely nonsymmetric has proven to be very challenging. Herein, we report on two independent experimental methodologies, based on luminescence lifetime measurements and acid–base titrations, to determine the relative populations of the two co-conformations of a [2]rotaxane. The assays yield convergent results and are sensitive enough to measure an equilibrium constant (K≈4000) out of reach for NMR spectroscopy. We also estimate the ring distribution constant in the switched (deprotonated) state (K′?4), and report the highest positional efficiency for stimuli-induced shuttling to date (>99.92 %). Finally, our results show that the pKaof the pH-responsive station depends on the ring affinity of the pH-insensitive station, an observation that paves the way for the design of new artificial allosteric systems.
- Ragazzon, Giulio,Credi, Alberto,Colasson, Benoit
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supporting information
p. 2149 - 2156
(2017/02/18)
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- Mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe, and preparation and application of same
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The invention discloses a preparation method and an application of a mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe. The formaldehyde fluorescent nano-probe is based on both fluorescent resonance energy transfer and self-a
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Paragraph 0054; 0055
(2018/01/11)
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- A double-signal output of the turn - on formaldehyde fluorescent nano probe intermediate and its preparation and use (by machine translation)
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The invention discloses a mitochondrial targeting signal turn - on formaldehyde fluorescent nano probe intermediate (III) of the preparation method and application, method is to benzaldehyde as the starting material, in the presence of acid, for temperatu
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Paragraph 0053; 0054
(2018/01/11)
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