- Mechanically induced gelation of a kinetically trapped supramolecular polymer
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The stimuli-induced gelation of a urethane-functionalized ditopic ureidopyrimidinone (UPy) compound is presented, and the mechanism by which the gelation proceeds is proposed. In a 40-120 mM solution in chloroform, the compound can exist in two different aggregated states, namely a low viscous mixture of (cyclic) oligomers or a fibrous gel. As evidenced by IR, NMR, and WAXS, the liquid state is stabilized by hydrogen bonds between the UPy and the back-folded chain, while the fibrous gel is stabilized by lateral hydrogen bonds within stacked UPy dimers. Controlled preparation techniques allow for pathway selection to arrive at one of both states. The remarkable long-term stability of the low viscous state (over 2 months for a 80 mM solution) is in contrast to the fast transformation into a gel by stirring in a few hours. Other mechanical stimuli like shaking, sonicating, and stirring for a shorter period, as well as freezing and thawing the solution, yield weaker gels than those obtained by long stirring. Heating the gels and slow cooling reversibly yield the nonviscous solution. This shows that the formation of UPy-urethane hydrogen bonds kinetically traps the UPy polymers, thereby preventing their lateral aggregation. The application of mechanical stress or freezing disrupts this interaction, allowing for the formation of a stacked nucleus on which further material can grow, eventually leading to gelation of the solution.
- Teunissen, Abraham J. P.,Nieuwenhuizen, Marko M. L.,Rodrguez-Llansola, Fransico,Palmans, Anja R. A.,Meijer
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Read Online
- Self-aggregation inhibits the photonuclease activity of porphyrins.
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A series of tentacle porphyrins having four aminoalkyl groups at the periphery was synthesized, and the DNA binding properties were investigated by absorption and circular dichroism (CD) spectroscopic methods. The aminopropyl chain was found to facilitate binding, and bisignate induced CD spectra revealed that the porphyrins are self-stacked on the DNA surface. The photonuclease activity of the tentacle porphyrins was also studied, and the aminopropylporphyrin showed the highest activity. The activity increased in proportion to the porphyrin load, but higher loads resulted in the decrease of activity. This inhibitory step corresponded to aggregation of the porphyrin. Thus, the aggregation was suggested to shield the inner porphyrin from the solvent, the production of active oxygen species being suppressed.
- Aoki, Katsumasa,Ishikawa, Yoshinobu,Oyama, Miyuki,Tomisugi, Yoshikazu,Uno, Tadayuki
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Read Online
- A practical synthesis of ω-aminoalkanoic acid derivatives from cycloalkanones
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A practical synthetic route to N-Boc protected or Boc-amino acid coupled ω-aminoalkanoic acids is reported and exemplified by the preparation of 8-(t-butoxycarbonylamino)caprylic acid 2 and (N-t-butoxycarbonylphenylalanyl)-8-aminocaprylic acid 3. The sequence does not involve column chromatography, hydrogenation, azide or bromide related rearrangements, and therefore is amenable to scale-up. Homologues of the ω-aminoalkanoic acid derivatives may also be prepared by using different cycloalkanones.
- Ho, Koc-Kan,O'Toole, Doris C.,Achan, Douglas M.,Lim, Kitae T.,Press, Jeffery B.,Leone-Bay, Andrea
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Read Online
- Molecular Umbrellas Modulate the Selective Toxicity of Polyene Macrolide Antifungals
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Antifungal polyene macrolide antibiotics Amphotericin B (AmB) and Nystatin (NYS) were conjugated through the ω-amino acid linkers with diwalled "molecular umbrellas" composed of spermidine-linked deoxycholic or cholic acids. The presence of "umbrella" substituents modulated biological properties of the antibiotics, especially their selective toxicity. Some of the AmB-umbrella conjugates demonstrated antifungal in vitro activity comparable to that of the mother antibiotic but diminished mammalian toxicity, especially the hemolytic activity. In contrast, antifungal in vitro activity of NYS-umbrella conjugates was strongly reduced and all these conjugates demonstrated poorer than NYS selective toxicity. No correlation between the aggregation state and hemolytic activity of the novel conjugates was found.
- Skwarecki, Andrzej S.,Skarbek, Kornelia,Martynow, Dorota,Serocki, Marcin,Bylińska, Irena,Milewska, Maria J.,Milewski, S?awomir
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Read Online
- Design, synthesis and activity study of a novel PI3K degradation by hijacking VHL E3 ubiquitin ligase
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PI3K kinase plays an important role in regulating key processes in cells, such as cell growth, metabolism, proliferation, and apoptosis. The overexpression of PI3K kinase exists in many cancers. The proteolytic target chimera (PROTAC) technology is a new technology that uses the ubiquitin–proteasome system to degrade a given target protein. It has been described that CRBN-based PROTAC targets the degradation of PI3K kinase. However, PROTAC based on VHL has not been reported yet. Here, we connected the previously obtained highly active PI3K inhibitor to the VHL ligand through different small molecules, and obtained a series of PROTAC molecules targeting PI3K kinase. Obtain the most active compound through screening. It provides evidence for the feasibility of PROTAC technology to recruit VHL E3 ligase in PI3K kinase.
- Li, Chuchu,Liu, Xiaoqing,Ma, Mingliang,Wang, Haili
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- TARGET PROTEIN EED DEGRADATION-INDUCING DEGRADUCER, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DISEASES RELATED TO EED, EZH2, OR PRC2, COMPRISING SAME AS ACTIVE INGREDIENT
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The present invention relates to a target protein degradation-inducing Degraducer, a preparation method thereof, and a pharmaceutical composition for preventing or treating diseases related to EED, EZH2, or PRC2 comprising same as an active ingredient. A novel compound represented by formula 1, according to the present invention is a Degraducer compound that induces degradation of a target protein, i.e., embryonic ectoderm development (EED) or polycomb repressive complex 2 (PRC2), utilizing cereblon E3 ubiquitin ligase, von Hippel-Lindau tumor suppressor (VHL) E3 ubiquitin ligase, mouse double minute 2 homolog (MDM2) E3 ubiquitin ligase, and cellular inhibitor of apoptosis protein 1 (cIAP) E3 ubiquitin ligase, wherein the compound has an aspect of remarkably achieving target protein degradation-inducing activity through a ubiquitin proteasome system (UPS), and therefore there is a useful effect in that it is possible to provide a pharmaceutical composition for preventing or treating diseases or conditions related to a target protein, and a functional health food composition for preventing or improving same, comprising said compound as an active ingredient.
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- MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS
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The present invention relates to macrocyclic compounds of formula (I) and their use as chitinase inhibitors as well as to pharmaceutical compositions and methods of preparation thereof. The compounds can in particular be used in the treatment, prevention and/or amelioration of asthma.
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Paragraph 0131; 0134-0135
(2021/07/29)
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- ERK5 DEGRADERS AS THERAPEUTICS IN CANCER AND INFLAMMATORY DISEASES
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Disclosed are bispecific compounds (degraders) that target ERK5 for degradation. Also disclosed are pharmaceutical compositions containing the degraders and methods of using the compounds to treat cancer and inflammatory diseases.
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Paragraph 00169; 00170
(2021/04/02)
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- GLYCOPEPTIDE COMPOUNDS, METHODS FOR PRODUCING THE SAME, AND USES THEREOF
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Disclosed herein are novel compounds and uses thereof. The present compounds are useful in suppressing the growth of various bacteria, including gram-positive and gram-negative bacteria. Accordingly, these compounds may be used to manufacture a medicament or pharmaceutic composition for treating disease and/or disorders associated with bacterial infection, especially antibiotic-resistant bacterial infection. Al so disclosed herein are methods for treating infectious diseases by use of the present compounds, medicament or pharmaceutical composition.
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Paragraph 0158; 0160
(2020/12/14)
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- Discovery, synthesis of novel fusidic acid derivatives possessed amino-terminal groups at the 3-hydroxyl position with anticancer activity
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A series of novel fusidic acid (FA) derivatives were synthesized and screened for their in vitro cytotoxicity against the Hela, U87, KBV and MKN45 cancer cell lines. Selected FA derivatives with anti-tumor activity were firstly identified including compound 4, which exhibited good anti-proliferative activity with IC50 values in the range of 1.26–3.57 μM. Further research revealed that compound 4 induced Hela cells to undergo apoptosis by increasing the ratio of the cells in the Sub-G0/G1 phase via decreasing the neo-synthesized proteins in a dose-dependent manner from 1 to 10 μM. Compound 4 also showed good in vivo anti-tumor activity against the xenograft tumor of Hela cells and had no apparent toxicity. This study highlights the advantage of introducing the medium-length amino-terminal groups at the 3-OH position of FA to enhance its anti-tumor activity and suggests that compound 4 provides a starting point for designing more potent derivatives in the future.
- Ni, Jingxuan,Guo, Mengqi,Cao, Yucheng,Lei, Lei,Liu, Kangli,Wang, Binghua,Lu, Fangfang,Zhai, Rong,Gao, Xiangwei,Yan, Chunhong,Wang, Hongbo,Bi, Yi
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p. 122 - 131
(2018/11/23)
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- Diosgenin-3-derivative as well as preparation method and application thereof
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The invention relates to a diosgenin-3-derivative as well as a preparation method and application thereof. The diosgenin-3-derivative shown as a formula I provided by the invention has a structural formula shown in the description, wherein R1 is amino straight-chain fatty acid residue or amino acid residue; R2 is H or a structural formula shown in the description; R3 is H, C1-C18 alkyl or phenyl.The derivative disclosed by the invention is rich in raw material source, simple and convenient in synthetic route, high in yield and suitable for large-scale production; the derivative has excellentantitumor activity and is superior to diosgenin.
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Paragraph 0038-0041
(2018/03/26)
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- Synthesis, characterization, and biological studies of diosgenyl analogs
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A series of diosgenyl analogs were prepared from diosgenin to evaluate their anticancer activity and antithrombotic property. Analog 4, which had a spiroketal structure with a 6-aminohexanoic acid residue, exhibited the highest potency against all five tumor cell lines. It significantly blocked tumor growth, induced cell apoptosis and autophagy, and regulated cellular calcium concentration, mitochondrial membrane potential, adenosine triphosphate, and cell cycle. In addition, fluorescence-tagged compounds indicated that the analogs could rapidly accumulate in the cytoplasm, but no specific localization in the nucleus of cancer cells was observed. Furthermore, preliminary structure–activity relationship studies demonstrated that spiroketal analogs exhibit better antithrombotic activity than furostanic analogs, which exhibit the opposite effect by promoting thrombosis. Our study indicates that compound 4 may be a promising anticancer drug candidate for cancer patients with thromboembolism.
- Huang, Bao-Zhan,Xin, Guang,Ma, Li-Mei,Wei, Ze-Liang,Shen, Yan,Zhang, Rui,Zheng, Hua-Jie,Zhang, Xiang-Hua,Niu, Hai,Huang, Wen
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p. 272 - 298
(2017/03/17)
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- Synthesis and antibacterial evaluation of novel 3-substituted ocotillol-type derivatives as leads
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Due to the rapidly growing bacterial antibiotic-resistance and the scarcity of novel agents in development, bacterial infection is still a global problem. Therefore, new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, are urgently needed. In this paper, a series of antibacterial ocotillol-type C-24 epimers modified from natural 20(S)-protopanaxadiol were synthesized and evaluated for their antibacterial activity. According to the screening results of Gram-positive bacteria (B. subtilis 168 and MRSA USA300) and Gram-negative bacteria (P. aer PAO1 and A. baum ATCC19606) in vitro, the derivatives exhibited good antibacterial activity, particularly against Gram-positive bacteria with an minimum inhibitory concentrations (MIC) value of 2-16 μg/mL. The subsequent synergistic antibacterial assay showed that derivatives 5c and 6c enhanced the susceptibility of B. subtilis 168 and MRSA USA300 to chloramphenicol (CHL) and kanamycin (KAN) (FICI 0.5). Our data showed that ocotillol-type derivatives with long-chain amino acid substituents at C-3 were good leads against antibiotic-resistant pathogens MRSA USA300, which could improve the ability of KAN and CHL to exhibit antibacterial activity at much lower concentrations with reduced toxicity.
- Bi, Yi,Liu, Xian-Xuan,Zhang, Heng-Yuan,Yang, Xiao,Liu, Ze-Yun,Lu, Jing,Lewis, Peter John,Wang, Chong-Zhi,Xu, Jin-Yi,Meng, Qing-Guo,Ma, Cong,Yuan, Chun-Su
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- DIAMINE CROSSLINKING AGENTS, CROSSLINKED ACIDIC POLYSACCHARIDES AND MEDICAL MATERIALS
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The invention provides a diamine crosslinking agent for acidic polysaccharides consisting of a diamine compound having a primary amino group at both terminals and an ester or thioester bond in the molecule, wherein the number of atom in the linear chain between at least one of the amino groups and the carbonyl carbon in the ester or thioester is 1 to 5; in particular, a diamine crosslinking agent for acidic polysaccharides which is represented by the general formula (I) below: [the symbols in the formula are as described in the specification]; a crosslinked acidic polysaccharide obtained by forming crosslinks by amide bonding between the amino groups in the diamine crosslinking agent and carboxyl groups in an acidic polysaccharide; and a medical material including the crosslinked product.
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Paragraph 0410; 0412; 0413
(2017/01/26)
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- Regulating competing supramolecular interactions using ligand concentration
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The complexity of biomolecular systems inevitably leads to a degree of competition between the noncovalent interactions involved. However, the outcome of biological processes is generally very well-defined often due to the competition of these interaction
- Teunissen, Abraham J. P.,Paffen, Tim F. E.,Ercolani, Gianfranco,De Greef, Tom F. A.,Meijer
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supporting information
p. 6852 - 6860
(2016/06/14)
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- ANTIBACTERIAL AGENTS
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The invention provides an antibacterial compound of formula (I) or a salt thereof, as well as an antibacterial compound of formula (II) or a salt thereof, wherein R1, R2, X, Y and n have any of the values defined in the specification.
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Page/Page column 29; 30; 36
(2016/05/09)
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- Synthesis and pharmacological evaluation of dual acting ligands targeting the adenosine A2A and dopamine D2 receptors for the potential treatment of parkinsons disease
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A relatively new strategy in drug discovery is the development of dual acting ligands. These molecules are potentially able to interact at two orthosteric binding sites of a heterodimer simultaneously, possibly resulting in enhanced subtype selectivity, higher affinity, enhanced or modified physiological response, and reduced reliance on multiple drug administration regimens. In this study, we have successfully synthesized a series of classical heterobivalent ligands as well as a series of more integrated and drug-like dual acting molecules, incorporating ropinirole as a dopamine D2 receptor agonist and ZM 241385 as an adenosine A2A receptor antagonist. The best compounds of our series maintained the potency of the original pharmacophores at both receptors (adenosine A2A and dopamine D2). In addition, the integrated dual acting ligands also showed promising results in preliminary blood-brain barrier permeability tests, whereas the classical heterobivalent ligands are potentially more suited as pharmacological tools.
- J?rg, Manuela,May, Lauren T.,Mak, Frankie S.,Lee, Kiew Ching K.,Miller, Neil D.,Scammells, Peter J.,Capuano, Ben
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p. 718 - 738
(2015/01/30)
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- Design, synthesis, and pharmacological evaluation of fluorescent and biotinylated antagonists of ρ1 GABAC receptors
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The ρ1 GABAC receptor is a ligand-gated chloride ion channel that shows promise as a therapeutic target for myopia, sleep disorders, memory and learning facilitation, and anxiety-related disorders. As such, there is a need for molecular probes to understand the role GABA C receptors play in physiological and pathological processes. To date, no labeled (either radioactive or fluorescent) GABAC selective ligand has been developed that can act as a marker for GABAC receptor visualization and localization studies. Herein, we report a series of fluorescent ligands containing different-sized linkers and fluorophores based around (S)-4-ACPBPA [(4-aminocyclopenten-1-yl)-butylphosphinic acid], a selective GABAC antagonist. One of these conjugates, (S)-4-ACPBPA-C5-BODIPY (13), displayed moderate potency (IC50 = 58.61 μM) and selectivity (>100 times) for ρ1 over α1β2γ2L GABAA receptors. These conjugates are novel lead agents for the development of more potent and selective fluorescent probes for studying the localization and function of GABAC receptors in living cells.
- Gavande, Navnath,Kim, Hye-Lim,Doddareddy, Munikumar R.,Johnston, Graham A. R.,Chebib, Mary,Hanrahan, Jane R.
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supporting information
p. 402 - 407
(2013/06/05)
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- Reagent for introduction of protein or gene
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The present invention provides a reagent for introducing a protein or gene into a cell. The reagent of the present invention is, for example, a reagent for introducing a protein or gene into a cell, which comprises a composition comprising a cationic amino acid type lipid represented by the following formula (I)-1: (wherein in formula (I)-1: L is a single bond, —CONH—, or —S—S—; M1 is —(CH2)k— or —(CH2CH2O)k— (wherein k is an integer between 0 and 14); and m1 and m2 are each independently an integer between 11 and 21 (in this regard, when providing a reagent for introducing a gene into a cell, the case where both m1 and m2 are 15 is excluded)).
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(2013/02/28)
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- Synthesis and cytotoxic activity of methyl glycyrrhetinate esterified with amino acids
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Methyl glycyrrhetinate was esterified at position C3 of ring A using different amino acids. A short, unbranched chain of four carbon atoms with two amino groups in positions 2 and 4 was shown to be the most active compound of this series (IC50 = 0:8 M on liposarcoma Lipo cells). These compounds trigger apoptosis as shown by an acridine orange/ethidium bromide assay, trypan blue tests and DNAladdering experiments.
- Csuk, Rene,Schwarz, Stefan,Siewert, Bianka,Kluge, Ralph,Stroehl, Dieter
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p. 731 - 746
(2012/11/13)
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- Collection of traceable compounds and uses thereof
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The use of a collection of compounds of general formula (I), wherein: n is 0 or 1; p represents an integer between 1 and 6; r represents an integer between 1 and 12; R1 and R′1 represent in particular a hydrogen atom; R2 represents an amino acid side chain or an amino acid derivative; R3 represents a group derived from a carboxylic acid, bearing a basic entity; R4 represents in particular an alkyl group containing 1 to 10 carbon atoms; and A represents a hydrogen atom, a protecting group or a tracing group, in particular a fluorophor, a coloring agent or a quencher, for determining, through binding studies, ligands of receptors whose ligand is unknown or whose ligand useful for carrying out specific affinity binding assays is unknown.
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- Highly stable cyclic dimers based on non-covalent interactions
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Highly stable cyclic dimers have been assembled through a combination of non-covalent interactions, including multiple hydrogen bonding, parallel stacking and hydrophobic shielding. The Royal Society of Chemistry 2006.
- Lafitte, Valerie G. H.,Aliev, Abil E.,Horton, Peter N.,Hursthouse, Michael B.,Hailes, Helen C.
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p. 2173 - 2175
(2008/03/14)
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- INOSITOL-BASED MOLECULAR TRANSPORTERS AND PROCESSES FOR THE PREPARATION THEREOF
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Inositol derivatives in accordance with the present invention are effective in significantly enhancing the transportation of various therapeutic molecules across a biological membrane, which may include the plasma membrane, nuclear membrane or blood-brain barrier.
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(2008/06/13)
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- Anti-HIV agents with dual sites of action
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The present invention provides compounds of the general structure: which are substituted at the 3 and 28 positions, along with pharmaceutical formulations containing the same and methods of treating viral infections employing the same.
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(2008/06/13)
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- Design, synthesis, and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells
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A series of thapsigargin (TG) analogues, containing an amino acid applicable for conjugation to a peptide specifically cleaved by prostate-specific antigen (PSA), has been prepared to develop the drug-moiety of prodrugs for treatment of prostatic cancer. The analogues were synthesized by converting TG into O-8-debutanoylthapsigargin (DBTG) and esterifying O-8 of DBTG with various amino acid linkers. The compounds were evaluated for their ability to elevate the cytosolic Ca2+ concentration ([Ca2+]i) in TSU-Pr1 cells, their ability to inhibit the rabbit skeletal muscle SERCA pump, and their ability to induce apoptosis in TSU-Pr1 human prostatic cancer cells. The activity of analogues, in which DBTG were esterified with ω-amino acids [HOOC(CH2)nNH2, n = 5-7, 10, 11], increased with the linker length. Analogues with 3-[4-(L-leucinoylamino)phenyl]propanoyl, 6-(L-leucinoylamino)hexanoyl, and 12-(L -serinoylamino)dodecanoyl were considerably less active than TG, and analogues with 12-(L-alaninoylamino)dodecanoyl and 12-(L-phenylalaninoylamino)dodecanoyl were almost as active as TG. The 12-(L-leucinoylamino)dodecanoyl gave an analogue equipotent with TG, making this compound promising as the drug-moiety of a PSA sensitive prodrug of TG.
- Jakobsen,Denmeade,Isaacs,Gady,Olsen,Christensen
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p. 4696 - 4703
(2007/10/03)
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- Method for preparing omega -aminoalkanoic acid derivatives from cycloalkanones
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PCT No. PCT/US96/14805 Sec. 371 Date Dec. 16, 1997 Sec. 102(e) Date Dec. 16, 1997 PCT Filed Sep. 10, 1996 PCT Pub. No. WO97/10197 PCT Pub. Date Mar. 20, 1997A convenient synthetic route to omega -aminoalkanoic acids, N-Boc protected omega -aminoalkanoic acids and Boc-amino acid coupled omega -aminoalkanoic acids is disclosed. The method provides high purity compounds that generally do not require further purification.
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- Development of potent and selective plasmin and plasma kallikrein inhibitors and studies on the structure-activity relationship
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Based on structure-activity relationship studies, we designed and synthesized plasmin (PL) and plasma kallikrein (PK) inhibitors. Trans-(4-aminomethylcyclohexanecarbonyl)-Tyr(O-PIC)-octylamide inhibited PL, PK, urokinase (UK) and thrombin (TH) with IC50 values of 0.53, 30, 5.3 and >400 μM, respectively. Trans-(4-aminomethylcyclohexanecarbonyl)-Tyr(O-2-Pyrim)-4-carboxyanilide inhibited PL, PK, UK and TH with IC50 values of 36, 0.56, 440 and >1000 μM, respectively.
- Okada, Yoshio,Tsuda, Yuko,Tada, Mayako,Wanaka, Keiko,Okamoto, Utako,Hijikata-Okunomiya, Akiko,Okamoto, Shosuke
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p. 1964 - 1972
(2007/10/03)
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- Indole derivatives useful to treat estrogen-related neoplasms and disorders
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The present invention relates to novel indole derivatives useful in down-regulating estrogen receptor expression. Also included are methods for the treatment of neoplasms or of controlling the growth of a neoplasm in a patient afflicted with a neoplastic disease, especially estrogen-dependent neoplasms such as those associated with breast, ovarian and cervical tissue. Another embodiment of the present invention is a method of prophylactically treating a patient at risk of developing a neoplastic disease state. Also provided is a method for treating autoimmune diseases. Also included are pharmaceutical compositions of the novel indole derivatives.
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- Urea compounds which are useful as platelet aggregation inhibitors
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Novel urea derivatives are provided which inhibit platelet aggregation. This invention also pertains to pharmaceutical compositions and methods of using such derivatives.
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- Synthesis of medium ring lactams via cyclization reactions using polymer bound HOBT as catalyst
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The synthesis of medium ring lactams (7-, 9-, 11- and 13-membered rings) via cyclization reactions mediated by polymer bound 1-hydroxybenzotriazole (HOBT) is reported.
- Huang,Wei, Huang,Kalivretenos,Kalivretenos, Aristotle G.
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p. 9113 - 9116
(2007/10/02)
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- Chemical combination of 6-deoxy-6-mycoloylamino-α,α-trehalose and N-acetyl-6-O-(aminoacyl)muramoyl dipeptide
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6-Deoxy-6-mycoloylamino-α,α-trehalose, a biologically active derivative of 6,6′-di-O-mycoloyl-α,α-trehalose (TDM), and N-acetyl-6-O-(aminoacyl)-muramoyl dipeptide (MDP) were joined chemically by a succinic acid unit. The compounds synthesized showed activ
- Ishida, Hideharu,Ogawa, Yuji,Imai, Yasuyuki,Kiso, Makoto,Hasegawa, Akira,Sakurai, Takuma,Azuma, Ichiro
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p. 199 - 208
(2007/10/02)
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