- Adsorption, micellization and antimicrobial activity of formyl-containing cationic surfactant in diluted aqueous solutions
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Surfactants based on dynamic covalent bonds have attracted significant interest over the past few decades due to the coexistence of covalent and non-covalent bonds. However, studies on the fundamental properties of their precursors are rare. Herein, we synthesized a series of formyl-containing cationic surfactants (N-alkyl-N,N-dimethyl-N-(2-(4-formyl-phenoxy)ethyl) ammonium bromides) bearing different hydrophobic chains, which can form dynamic imine bonds. The adsorption, micellization and antimicrobial activity were systematically investigated using surface tension, fluorescence, electrical conductivity, and ITC techniques. The results showed that the insertion of the 2-(4-formyl-phenoxy)ethyl group (equivalent to ~7 methylene groups) endows the surfactant with an asymmetrical double-chain structure, enhancing the hydrophobic interaction. As a result, the critical micelle concentration (cmc) and contribution per methylene group to the standard Gibbs free energy of micellization (?Gmo) were significantly decreased, compared to conventional single surfactant. Upon increasing the hydrophobic chain length, the cmc, the negative logarithm of the surfactant concentration in the bulk phase required to produce a 20 mN·m?1 reduction in the surface tension of the solvent (pC20) and maximum surface excess amount of the adsorbed surfactant (Γmax) all decreased accompanied by an increase in the minimum molecular occupation area (Amin), while the ?Gmo and standard Gibbs free energy of adsorption (?Gadso) become more negative and thus more favorable for the formation of micelles and the adsorption film. Moreover, micellization changed from being entropy-driven to enthalpy-driven and is more sensitive toward NaCl than urea. In addition, the current formyl-containing cationic surfactants exhibit excellent antimicrobial activity against both Gram-positive and Gram-negative bacteria and fungi, especially the surfactant with a hydrophobic chain containing ~20 atoms. Such a study will be favorable for the design of new dynamic covalent surfactants and an understanding of the change in their aggregation.
- He, Shuai,Lu, Pingping,Zhang, Yongmin,Zhou, Yue
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- Design, synthesis, and evaluation of some novel biphenyl imidazole derivatives for the treatment of Alzheimer's disease
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The multi-targeted organized strategy provides effectual and significant results to cure progressive neurodegenerative diseases like AD. Treatment for this awful disease is in infancy till now. A series of novel 4, 5-diphenyl-1H-imidazole linked piperazin
- Ramrao, Salunke Prashant,Shrivastava, Sushant Kumar,Tripathi, Prabhash Nath,Verma, Akash,Waiker, Digambar Kumar
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- 'Naked-eye' quinoline-based 'reactive' sensor for recognition of Hg2+ ion in aqueous solution
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A new 'naked-eye' quinoline-based 'reactive' ratiometric fluorescent probe was prepared. The reactive stoichiometry of the probe with Hg2+ ion was 2:1. The probe exhibited high selectivity towards Hg2+ ion to other metal ions with a
- Zhang, Yanhua,Yan, Yuanyuan,Chen, Suying,Gao, Zhinan,Xu, Hui
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- Fluorophoric [2]rotaxanes: Post-synthetic functionalization, conformational fluxionality and metal ion chelation
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Herein, we report the synthesis of an amino-ether fluorophoric macrocyclic wheel (MC)-based multi-functional [2]rotaxane. This rotaxane was further functionalised into three different analogues, which were denoted as ROTa-c, upon appending three different
- Santra, Saikat,Santra, Saikat,Ghosh, Pradyut
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- Construction of pH-Responsive Supramolecular Assemblies Based on Dynamic Covalent Bonds for Tunable Drug Release
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In the present work, we propose a novel strategy for preparing supramolecular self-assemblies for pH-responsive drug delivery. In alkaline solutions, a novel supra-amphiphile can be fabricated by a cationic surfactant dodecyl[2-(4-formylphenoxy)ethyl] dim
- Sun, Panpan,Lu, Fei,Wu, Aoli,Yin, Yue,Shi, Lijuan,Zheng, Liqiang
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- Visualization of mercury(ii) accumulation: In vivo using bioluminescence imaging with a highly selective probe
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Mercury is a highly toxic environmental pollutant that negatively affects human health. Thus, an in vivo method for noninvasive imaging of mercury(ii) and visualization of its accumulation within living systems would be advantageous. Herein, we describe a reaction-based bioluminescent probe for detection of mercury(ii) in vitro and accumulation in vivo. The application of this probe would help to shed light on the intricate contributions of mercury(ii) to various physiological and pathological processes.
- Ke, Bowen,Chen, Hui,Ma, Lin,Zingales, Sarah,Gong, Deying,Hu, Die,Du, Lupei,Li, Minyong
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- Study of the structure-bioactivity of fleximers: synthesis, crystal structure, Hirshfeld surface analysis, and anti-inflammatory assays
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Synthesized and natural pyridones/pyridines derivatives exhibiting diverse biological activities. 2-pyridone has lactam-lactim tautomerization like thymine and uracil bases. In this study, COX-2 target based series of pyridone/pyridine linked fleximers were designed, synthesized and studied. All analogues binding affinity with COX-2 active site were studied through molecular docking, and anti-inflammatory activity studied by in vivo analysis. Weak interactions were studied to find binding sites among analogues through crystal packing, Hirshfeld surface analysis and in silico analysis. All the analogues exhibited anti-inflammatory activity, while compound (3) is the most active analogue among the series. In contrast, since compound (3) is a pyridine-phthalimide ring-containing analogue, the presence of a phthalimide group probably favors anti-inflammatory activity over other types of rings. The results suggested further investigations on compounds as anti-inflammatory prodrugs.
- Singh, Ved Prakash,Dowarah, Jayanta,Marak, Brilliant N.,Sran, Balkaran Singh,Tewari, Ashish Kumar
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- Synthesis of Novel Porphyrin Derivatives and Their Cytotoxic Activities against A431 Cells
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Three novel porphyrins, including two Schiff-bases porphyrins, 5,10,15-triphenyl-20-[4-(2-(4-formyl)phenoxy)ethoxy]phenyl porphyrin (H2Pp(1)), 5,10,15-triphenyl-20-[4-(2-(4-hydroxyimino)phenoxy)ethoxy]phenyl porphyrin (H2Pp(2)) and 5
- Yao, Ya-Hong,Luo, Yun,Li, Jun,Zhang, Feng-Xing
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- Photophysical properties and photodynamic anti-tumor activity of corrole-coumarin dyads
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A new non-conjugated corrole-coumarin dyad and its gallium complex has been synthesized. Photophysical properties of the dyads were tested in two solvents, exhibiting strong solvent effect on the absorption and fluorescence spectra. Absorption spectra of
- Cheng, Fan,Wang, Hua-Hua,Ali, Atif,Kandhadi, Jaipal,Wang, Hui,Wang, Xiang-Li,Liu, Hai-Yang
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- Oxidation-Induced Breakage of the Imine Bond and Aggregate Transition in a Se-Containing Dynamic Covalent Surfactant
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Controlling the dynamic imine bonds upon a novel trigger except for pH and temperature is still a significant challenge. Here, a Se-containing imine-based dynamic covalent surfactant (HOBAB-BSeEA) was developed for the first time by mixing two precursors
- Lu, Pingping,He, Shuai,Zhou, Yue,Zhang, Yongmin
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- Efficient combination of calix[4]arenes and meso-diphenylporphyrins
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The selective mono-alkylation of a calix[4]arene with a functionalized benzaldehyde followed by the condensation with dipyrrylmethane afforded in good yield a porphyrin substituted by two calix[4]arenes. The same multisite ligand was alternatively obtaine
- Milbradt,Weiss
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- Ugi Reaction-Derived α-Acyl Aminocarboxamides Bind to Phosphatidylinositol 3-Kinase-Related Kinases, Inhibit HSF1-Dependent Heat Shock Response, and Induce Apoptosis in Multiple Myeloma Cells
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Heat shock transcription factor 1 (HSF1) has been identified as a therapeutic target for pharmacological treatment of multiple myeloma (MM). However, direct therapeutic targeting of HSF1 function seems to be difficult due to the shortage of clinically suitable pharmacological inhibitors. We utilized the Ugi multicomponent reaction to create a small but smart library of α-acyl aminocarboxamides and evaluated their ability to suppress heat shock response (HSR) in MM cells. Using the INA-6 cell line as the MM model and the strictly HSF1-dependent HSP72 induction as a HSR model, we identified potential HSF1 inhibitors. Mass spectrometry-based affinity capture experiments with biotin-linked derivatives revealed a number of target proteins and complexes, which exhibit an armadillo domain. Also, four members of the tumor-promoting and HSF1-associated phosphatidylinositol 3-kinase-related kinase (PIKK) family were identified. The antitumor activity was evaluated, showing that treatment with the anti-HSF1 compounds strongly induced apoptotic cell death in MM cells.
- Bach, Matthias,Lehmann, Anna,Brünnert, Daniela,Vanselow, Jens T.,Hartung, Andreas,Bargou, Ralf C.,Holzgrabe, Ulrike,Schlosser, Andreas,Chatterjee, Manik
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- New nitric oxide-releasing indomethacin derivatives with 1,3-thiazolidine-4-one scaffold: Design, synthesis, in silico and in vitro studies
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In this study we present design and synthesis of nineteen new nitric oxide-releasing indomethacin derivatives with 1,3-thiazolidine-4-one scaffold (NO-IND-TZDs) (6a–s), as a new safer and efficient multi-targets strategy for inflammatory diseases. The che
- Sava, Alexandru,Buron, Frederic,Routier, Sylvain,Panainte, Alina,Bibire, Nela,Profire, Lenu?a
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- Biodegradable Polymersomes with Structure Inherent Fluorescence and Targeting Capacity for Enhanced Photo-Dynamic Therapy
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Biodegradable nanostructures displaying aggregation-induced emission (AIE) are desirable from a biomedical point of view, due to the advantageous features of loading capacity, emission brightness, and fluorescence stability. Herein, biodegradable polymers comprising poly (ethylene glycol)-block-poly(caprolactone-gradient-trimethylene carbonate) (PEG-P(CLgTMC)), with tetraphenylethylene pyridinium-TMC (PAIE) side chains have been developed, which self-assembled into well-defined polymersomes. The resultant AIEgenic polymersomes are intrinsically fluorescent delivery vehicles. The presence of the pyridinium moiety endows the polymersomes with mitochondrial targeting ability, which improves the efficiency of co-encapsulated photosensitizers and improves therapeutic index against cancer cells both in vitro and in vivo. This contribution showcases the ability to engineer AIEgenic polymersomes with structure inherent fluorescence and targeting capacity for enhanced photodynamic therapy.
- Abdelmohsen, Loai K. E. A.,Cao, Shoupeng,Dong, Yangyang,Guo, Beibei,Meng, Fenghua,Pijpers, Imke A. B.,Shao, Jingxin,Williams, David S.,Xia, Yifeng,Zhong, Zhiyuan,van Hest, Jan C. M.
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supporting information
p. 17629 - 17637
(2021/07/06)
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- One-Photon Excitation Followed by a Three-Step Sequential Energy–Energy–Electron Transfer Leading to a Charge-Separated State in a Supramolecular Tetrad Featuring Benzothiazole–Boron-Dipyrromethene–Zinc Porphyrin–C60
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A panchromatic triad, consisting of benzothiazole (BTZ) and BF2-chelated boron-dipyrromethene (BODIPY) moieties covalently linked to a zinc porphyrin (ZnP) core, has been synthesized and systematically characterized by using 1H NMR s
- Badgurjar, Deepak,Seetharaman, Sairaman,D'Souza, Francis,Chitta, Raghu
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supporting information
p. 2184 - 2195
(2020/12/25)
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- Synthesis, antimicrobial evaluation, and in silico studies of quinoline—1H-1,2,3-triazole molecular hybrids
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Abstract: Antimicrobial resistance has become a significant threat to global public health, thus precipitating an exigent need for new drugs with improved therapeutic efficacy. In this regard, molecular hybridization is deemed as a viable strategy to afford multi-target-based drug candidates. Herein, we report a library of quinoline—1H-1,2,3-triazole molecular hybrids synthesized via copper(I)-catalyzed azide-alkyne [3 + 2] dipolar cycloaddition reaction (CuAAC). Antimicrobial evaluation identified compound 16 as the most active hybrid in the library with a broad-spectrum antibacterial activity at an MIC80 value of 75.39?μM against methicillin-resistant S. aureus, E. coli, A. baumannii, and multidrug-resistant K. pneumoniae. The compound also showed interesting antifungal profile against C. albicans and C. neoformans at an MIC80 value of 37.69 and 2.36?μM, respectively, superior to fluconazole. In vitro toxicity profiling revealed non-hemolytic activity against human red blood cells (hRBC) but partial cytotoxicity to human embryonic kidney cells (HEK293). Additionally, in silico studies predicted excellent drug-like properties and the importance of triazole ring in stabilizing the complexation with target proteins. Overall, these results present compound 16 as a promising scaffold on which other molecules can be modeled to deliver new antimicrobial agents with improved potency. Graphic abstract: [Figure not available: see fulltext.].
- Awolade, Paul,Cele, Nosipho,Kerru, Nagaraju,Singh, Parvesh
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p. 2201 - 2218
(2020/06/17)
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- Furo[2, 3-b]quinoline-3, 4(2H, 9H)-diketone derivative and preparation method and application thereof
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The invention discloses a furo[2, 3-b]quinoline-3, 4(2H, 9H)-diketone derivative and a preparation method and application thereof, and belongs to the field of medicines and chemical engineering. The structural formulas of the compounds are shown as formul
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Paragraph 0025
(2021/04/07)
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- Quantification and Prediction of Imine Formation Kinetics in Aqueous Solution by Microfluidic NMR Spectroscopy
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Quantitatively predicting the reactivity of dynamic covalent reaction is essential to understand and rationally design complex structures and reaction networks. Herein, the reactivity of aldehydes and amines in various rapid imine formation in aqueous sol
- Cao, Xiaoyu,Chen, Hang,Chen, Si,Ouyang, Jie,Tian, Zhongqun,Utz, Marcel,Wang, Xinchang,Wang, Xiuxiu,Yang, Liulin,You, Lei,Zhuo, Youzhen
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supporting information
p. 9508 - 9513
(2021/06/01)
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- HYPOXANTHINE COMPOUND
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PROBLEM TO BE SOLVED: To provide a novel compound having an inhibitory action of prolyl hydroxylase (PHDs) and useful as a therapeutic agent of an inflammatory bowel disease such as ulcerative colitis. SOLUTION: The present invention relates to a hypoxanthine compound represented by the following formula (I) or a pharmacologically acceptable salt thereof. The compound of the present invention or its pharmaceutically acceptable salt has an inhibitory effect of prolyl hydroxylase and is useful as a therapeutic agent for inflammatory bowel disease such as ulcerative colitis. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0201
(2021/07/17)
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- Design, synthesis, in silico and in vitro studies for new nitric oxide‐releasing indomethacin derivatives with 1,3,4‐oxadiazole‐2‐thiol scaffold
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Starting from indomethacin (IND), one of the most prescribed non‐steroidal anti‐inflammatory drugs (NSAIDs), new nitric oxide‐releasing indomethacin derivatives with 1,3,4‐oxadiazole‐ 2‐thiol scaffold (NO‐IND‐OXDs, 8a‐p) have been developed as a safer and
- Sava, Alexandru,Buron, Frederic,Routier, Sylvain,Panainte, Alina,Bibire, Nela,Constantin, Sandra M?d?lina,Lupa?cu, Florentina Geanina,Foc?a, Alin Viorel,Profire, Lenu?a
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- Bioorthogonal Turn-On BODIPY-Peptide Photosensitizers for Tailored Photodynamic Therapy
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Photodynamic therapy (PDT) leads to cancer remission via the production of cytotoxic species under photosensitizer (PS) irradiation. However, concomitant damage and dark toxicity can both hinder its use. With this in mind, we have implemented a versatile
- Linden, Greta,Vázquez, Olalla
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supporting information
(2020/07/27)
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- Preparation method and application of naphthylamine compounds and salts thereof
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The invention discloses a preparation method and application of naphthylamine compounds and salts thereof, concretely provides a method for synthesizing the naphthylamine compounds by taking 4-formylphenol as a substrate, and also provides a preparation m
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Paragraph 0015
(2020/08/30)
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- Novel stilbene polyether monomer and synthesis and application thereof
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The invention provides a novel stilbene polyether monomer, synthesis thereof and application thereof in controllable preparation of a copolymer with a main chain containing a macrocyclic structure, and belongs to the field of preparation and application o
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Paragraph 0044; 0047; 0050; 0053; 0056; 0059
(2020/11/26)
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- Design, synthesis and biological evaluation of 2,3-dihydro-5,6-dimethoxy-1H-inden-1-one and piperazinium salt hybrid derivatives as hAChE and hBuChE enzyme inhibitors
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2,3-Dihydro-5,6-dimethoxy-2-[4-(4-alkyl-4-methylpiperazinium-1-yl)benzylidine]-1H-inden-1-one halide salt derivatives as a novel donepezil hybrid analogs with the property of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzyme inhibition were designed and synthesized via N-alkylation reaction of 2,3-dihydro-5,6-dimethoxy-2-[4-(4-methylpiperazin-1-yl)benzylidene]-1H-inden-1-one with some alkyl halides. Biological tests demonstrated that most of the synthesized compounds have moderate to good inhibitory activities effect on cholinesterase enzymes. Among them, 10e showed the best profile as a selected compound for inhibition of hAChE (IC50 = 0.32) and hBuChE (IC50 = 0.43 μM) enzymes. Kinetic analysis and molecular docking led to a better understanding of this compound. Kinetic studies disclosed that 10e inhibited acetylcholinesterase in mixed-type and butyrylcholinesterase in non-competitive type. The toxicity results showed that 10e is less toxic than donepezil and has better inhibitory activity against hBuChE when compared to donepezil or Galantamine. Other performed experiments revealed that 10e has an anti-β amyloid effect which is capable of reducing ROS, LDH and MDA also possing positive effect on TAC. On the other hand, it has shown a good anti-inflammation effect.
- Mozaffarnia, Sakineh,Rashidi, Mohammad-Reza,Teimuri-Mofrad, Reza
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- COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF
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It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.
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Paragraph 0287-0288
(2020/07/07)
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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; 0106-0108
(2020/03/05)
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- Preparation of aggregation-induced emission material with light stability
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The invention discloses a hindered amine light stabilizer with an aggregation-induced emission (AIE) performance and a synthesis method thereof. The hindered amine light stabilizer is formed through steps including a step of ensuring that AIE pyrone deriv
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Paragraph 0036; 0037
(2019/02/27)
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- Vinylboronic acid-caged prodrug activation using click-to-release tetrazine ligation
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Bioorthogonal reactions can be performed selectively in the presence of any biological functional group and are widely used to achieve site-selective chemical modifications of biomolecules. The click-to-release reaction is a bioorthogonal bond-cleavage variant that has gained much interest over the last few years. The bioorthogonal reaction between tetrazines and trans-cyclooctenes or vinyl ethers, for example, initiates the release of a small molecule immediately after the cycloaddition with tetrazines. Recently, our group reported that vinylboronic acids (VBAs) give exceptionally high reaction rates in the bioorthogonal inverse electron-demand Diels-Alder reaction with tetrazines that are substituted with boron-coordinating ligands. In the present study, we show that VBAs can be used in a click-to-release variant and demonstrate its bioorthogonality with a VBA-protected doxorubicin prodrug. We show that the cytotoxicity of doxorubicin is silenced by the attachment of the VBA, and activity can be largely restored upon the reaction with a tetrazine, inducing cell death.
- Lelieveldt, Lianne P.W.M.,Eising, Selma,Wijen, Abel,Bonger, Kimberly M.
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supporting information
p. 8816 - 8821
(2019/10/22)
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- A tumor-targeted Photodynamic therapeutic compound
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The present invention relates to a tumor targeting photodynamic therapeutic agent containing a compound represented by chemical formula 1. The compound according to the present invention can significantly improve cancer treatment efficiency.COPYRIGHT KIPO 2019
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Paragraph 0016
(2019/10/19)
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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; 0044; 0045-0047
(2019/06/30)
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- Development of chalcone-O-alkylamine derivatives as multifunctional agents against Alzheimer's disease
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A series of novel chalcone-O-alkylamine derivatives were designed, synthesized and evaluated as multifunctional anti-Alzheimer's disease agents. Based on the experimental results, compound 23c exhibited good inhibitory potency on both acetylcholinesterase
- Bai, Ping,Wang, Keren,Zhang, Pengfei,Shi, Jian,Cheng, Xinfeng,Zhang, Qi,Zheng, Cheng,Cheng, Yao,Yang, Jian,Lu, Xiaoxia,Sang, Zhipei
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- A multifunctional catenated host for the efficient binding of Eu3+ and Gd3+
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A new multifunctional [2]catenane is synthesized by using a phenanthroline-based heteroditopic wheel and Axle, which acts as a receptor for the efficient binding of lanthanide ions such as Eu3+ and Gd3+.
- Nandi, Mandira,Bej, Somnath,Ghosh, Tamal Kanti,Ghosh, Pradyut
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supporting information
p. 3085 - 3088
(2019/04/05)
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- Fe3O4@SiO2@Im-bisethylFc [HC2O4] as a novel recyclable heterogeneous nanocatalyst for synthesis of bis-coumarin derivatives
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Nanomagnetic bisethylferrocene-containing ionic liquid supported on silica-coated iron oxide (Fe3O4@SiO2@Im-bisethylFc [HC2O4]) as a novel catalyst was designed and synthesized. The described catalyst
- Teimuri-Mofrad, Reza,Tahmasebi, Shabnam,Payami, Elmira
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- Interplay between n→π? Interactions and Dynamic Covalent Bonds: Quantification and Modulation by Solvent Effects
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Orbital donor-acceptor interactions play critical roles throughout chemistry, and hence, their regulation and functionalization are of great significance. Herein we demonstrate for the first time the investigation of n→π? interactions through the strategy of dynamic covalent chemistry (DCC), and we further showcase its use in the stabilization of imine. The n→π? interaction between donor X and acceptor aldehyde/imine within 2-X-2′-formylbiphenyl derivatives was found to significantly influence the thermodynamics of imine exchange. The orbital interaction was then quantified through imine exchange, the equilibrium of which was successfully correlated with the difference in natural bond orbital stabilization energy of n→π? interactions of aldehyde and its imine. Moreover, the examination of solvent effects provided insights into the distinct feature of the modulation of n→π? interaction with aprotic and protic solvents. The n→π? interaction involving imine was enhanced in protic solvents due to hydrogen bonding with the solvent. This finding further enabled the stabilization of imine in purely aqueous solution. The strategies and results reported should find application in many fields, including molecular recognition, biological labeling, and asymmetric catalysis.
- Zheng, Hao,Ye, Hebo,Yu, Xiaoxia,You, Lei
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supporting information
p. 8825 - 8833
(2019/06/13)
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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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- Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design
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Targeting KRAS-PDEδ protein-protein interactions with small molecules represents a promising opportunity for developing novel antitumor agents. However, current KRAS-PDEδ inhibitors are limited by poor cellular antitumor potency and the druggability of the target remains to be validated by new inhibitors. To tackle these challenges, herein, novel, highly potent KRAS-PDEδ inhibitors were identified by fragment-based drug design, providing promising lead compounds or chemical probes for investigating the biological functions and druggability of KRAS-PDEδ interaction.
- Chen, Long,Zhuang, Chunlin,Lu, Junjie,Jiang, Yan,Sheng, Chunquan
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supporting information
p. 2604 - 2610
(2018/03/26)
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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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- Smart low molecular weight hydrogels with dynamic covalent skeletons
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We report a new strategy for fabricating a smart low molecular weight hydrogel based on dynamic covalent chemistry from a bola-type supra-gelator, which was facilely fabricated in situ from two non-assembling building blocks, (3-(2-(4-formylphenoxy) ethyl)-1-methyl imidazolium bromide, MA) and (3,3′-dithiobis (propionohydrazide), DSPDZ), through dynamic acylhydrazone bonding. The obtained low molecular weight hydrogels exhibited redox-responsive and controllable self-healing properties. The role of dynamic covalent bonding in the formation of smart hydrogels is revealed in this study, which provides a simple and bottom-up method for constructing smart low molecular weight hydrogels.
- Sun, Panpan,Ren, Shujing,Liu, Fenglin,Wu, Aoli,Sun, Na,Shi, Lijuan,Zheng, Liqiang
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p. 6678 - 6683
(2018/08/28)
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- Organic triplet photosensitive agent with host-guest recognition group and preparation method of organic triplet photosensitive agent
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The invention discloses an organic triplet photosensitive agent with a host-guest recognition group and a preparation method of the organic triplet photosensitive agent, which belong to the technicalfield of the synthesis of photosensitive agents. Hexanediamine is introduced on a meso-position benzene ring position of Bodipy in a C60-Bodipy binary compound organic triplet photosensitive agent tobe used as a supermolecule combination site, the triplet photosensitive agent with a hyperon combination site and a supermolecule main body with a triplet receptor are self-assembled in a solution, and a space distance between the triplet photosensitive agent and the triplet receptor is shortened to a molecular dimensional range, so that the triplet photosensitive agent can transfer the energy without being dispersed in an effective service life range, the non-radiation deactivation probability of a triplet exciton can be reduced, the energy transfer efficiency between the photosensitive agentand the receptor can be increased, and the upconversion efficiency can be increased.
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Paragraph 0069; 0071-0075; 0102; 0105; 0106; 0125; 0128
(2018/08/03)
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- De Novo Design of Phototheranostic Sensitizers Based on Structure-Inherent Targeting for Enhanced Cancer Ablation
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Structure-inherent targeting (SIT) agents are of particular importance for clinical precision medicine; however, there still exists a great lack of SIT phototheranostics for simultaneous cancer diagnosis and targeted photodynamic therapy (PDT). Herein, fo
- Li, Mingle,Long, Saran,Kang, Yao,Guo, Lianying,Wang, Jingyun,Fan, Jiangli,Du, Jianjun,Peng, Xiaojun
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supporting information
p. 15820 - 15826
(2018/11/23)
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- USE OF DISUBSTITUTED BENZENES TO CONTROL INSECTICIDE-RESISTANT PESTS
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The invention is in the technical field of insect control and relates to the use of a disubstituted benzenes for controlling insecticide-resistant pests such as mosquitoes and cockroaches.
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Page/Page column 39
(2018/11/26)
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- Synthesis, biological evaluation, and molecular docking investigation of benzhydrol- and indole-based dual PPAR-γ/FFAR1 agonists
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Type-2 diabetes mellitus is a progressive cluster of metabolic disorders, representing a global public health burden affecting more than 366 million people worldwide. We recently reported the discovery of three series of novel agents showing balanced activity on two metabolic receptors, peroxisome proliferator activated receptor-γ (PPAR-γ) and free fatty acid receptor 1 (FFAR1), also known as GPCR40. Our designing strategy relied on linking the thiazolidinedione head with known GPCR privilege structures. To further investigate this concept, two new scaffolds, the benzhydrol- and indole-based chemotypes, were introduced here in. Our optimization campaign resulted in three compounds; 15a, 15c, and 15d, with affinities in the low micromolar range on both targets. In vivo study of selected test compounds, revealed that 15c possesses a significant anti-hyperglycemic and anti-hyperlipidemic activities superior to rosiglitazone in fat-fed animal models. Molecular docking analysis was conducted to explain the binding modes of both series. These compounds could lead to the development of the unique antidiabetic agent acting as insulin sensitizer as well as insulin secretagogue.
- Darwish, Khaled M.,Salama, Ismail,Mostafa, Samia,Gomaa, Mohamed S.,Khafagy, El-Sayed,Helal, Mohamed A.
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supporting information
p. 1595 - 1602
(2018/04/05)
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- Synthesis and evaluation of a [18F]BODIPY-labeled caspase-inhibitor
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BODIPYs (boron dipyrromethenes) are fluorescent dyes which show high stability and quantum yields. They feature the possibility of selective 18F-fluorination at the boron-core. Attached to a bioactive molecule and labeled with [18F]fluorine, the resulting compounds are promising tracers for multimodal imaging in vivo and can be used for PET and fluorescence imaging. A BODIPY containing a phenyl and a hydroxy substituent on boron was synthesized and characterized. Fluorinated and hydroxy substituted dyes were coupled to an isatin-based caspase inhibitor via cycloaddition and the resulting compounds were evaluated in vitro in caspase inhibition assays. The metabolic stability and the formed metabolites were investigated by incubation with mouse liver microsomes and LC-MS analysis. Subsequently the fluorophores were labeled with [18F]fluorine and an in vivo biodistribution study using dynamic PET was performed.
- Ortmeyer, Christian Paul,Haufe, Günter,Schwegmann, Katrin,Hermann, Sven,Sch?fers, Michael,B?rgel, Frederik,Wünsch, Bernhard,Wagner, Stefan,Hugenberg, Verena
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supporting information
p. 2167 - 2176
(2017/03/23)
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- Overcoming the Limits of Hypoxia in Photodynamic Therapy: A Carbonic Anhydrase IX-Targeted Approach
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A major challenge in photodynamic cancer therapy (PDT) is avoiding PDT-induced hypoxia, which can lead to cancer recurrence and progression through activation of various angiogenic factors and significantly reduce treatment outcomes. Reported here is an acetazolamide (AZ)-conjugated BODIPY photosensitizer (AZ-BPS) designed to mitigate the effects of PDT-based hypoxia by combining the benefits of anti-angiogenesis therapy with PDT. AZ-BPS showed specific affinity to aggressive cancer cells (MDA-MB-231 cells) that overexpress carbonic anhydrase IX (CAIX). It displayed enhanced photocytotoxicity compared to a reference compound, BPS, which is an analogous PDT agent that lacks an acetazolamide unit. AZ-BPS also displayed an enhanced in vivo efficacy in a xenograft mouse tumor regrowth model relative to BPS, an effect attributed to inhibition of tumor angiogenesis by both PDT-induced ROS generation and CAIX knockdown. AZ-BPS was evaluated successfully in clinical samples collected from breast cancer patients. We thus believe that the combined approach described here represents an attractive therapeutic approach to targeting CAIX-overexpressing tumors.
- Jung, Hyo Sung,Han, Jiyou,Shi, Hu,Koo, Seyoung,Singh, Hardev,Kim, Hyo-Jin,Sessler, Jonathan L.,Lee, Jin Yong,Kim, Jong-Hoon,Kim, Jong Seung
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p. 7595 - 7602
(2017/06/14)
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- Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression
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A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an
- Pirat, Celine,Dacquet, Catherine,Leclerc, Veronique,Hennuyer, Nathalie,Beucher-Gaudin, Monique,Zanirato, Ghislaine,Géant, Anne,Staels, Bart,Ktorza, Alain,Farce, Amaury,Caignard, Daniel-Henri,Berthelot, Pascal,Lebegue, Nicolas
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p. 310 - 326
(2017/06/14)
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- Bodipy-squaraine triads: Preparation and study of the intramolecular energy transfer, charge separation and intersystem crossing
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Two triads (BDP-SQ and Styryl-BDP-SQ) were prepared with Bodipy, styrylBodipy and Squaraine (SQ) units. SQ shows unexpected efficient intersystem crossing (ISC. ΦT = 50%), which is attributed to S1→T1 transition. In the two triads, the F?rster Resonance Energy Transfer (FRET) direction, as well as the spatial localization of the T1 state, was judiciously tuned. The cascade photophysical properties of the triads were studied with steady-state and time-resolved optical spectroscopies, as well as with electrochemical characterization and theoretical computations. We show that triplet state was produced in triad BDP-SQ upon photoexcitation, but in Styryl-BDP-SQ the fast FRET and the charge separation (CS) processes compete with the ISC of the SQ unit, and no triplet state was formed upon photoexcitation. The singlet energy transfer kinetics were found to be 1.6 and 0.6 ps, respectively and are solvent polarity dependent. Charge transfer was confirmed with ultrafast transient absorption spectroscopy.
- Dong, Yu,Iagatti, Alessandro,Foggi, Paolo,Zhao, Jianzhang,Mazzone, Gloria,Xu, Kejing,Ji, Wei,Di Donato, Mariangela,Russo, Nino
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p. 560 - 572
(2017/09/08)
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- PHENYL BENZYL ETHER DERIVATIVE AND PREPARATION METHOD AND APPLICATION THEREOF
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Parts of compounds, after being labeled by radionuclide, of the phenyl benzyl ether derivative, are used as Aβ plaque imaging agent. The structural formula of the phenyl benzyl ether derivative is shown by formula (I). The present invention develops a kin
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Paragraph 0157
(2017/06/12)
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- Method of rapidly preparing rhodamine dye with a plurality of active functional groups under mild condition
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The invention relates to a method of rapidly preparing a rhodamine dye with a plurality of active functional groups under the mild condition and belongs to the technical field of fine chemicals. The method is used for synthesizing rhodamine with specific
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Paragraph 0060; 0061; 0062
(2017/09/01)
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- Self-assembly of supra-amphiphile of azobenzene-galactopyranoside based on dynamic covalent bond and its dual responses
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In this paper, dynamic covalent bond has been employed to construct supra-amphiphile of carbohydrate for the first time. In neutral environment, the molecule was fabricated by reacting a hydrophobic building block bearing benzoic aldehyde with a hydrophilic building block bearing hydrazine to form a sugar-containing supra-amphiphile based on acylhydrazone bond. The obtained azobenzene-galactopyranoside (Azo-Gal) supra-amphiphile self-assembled to fibrillar structure in water, which showed dual responses to UV light and pH.
- Wang, Tian-Nan,Yang, Guang,Wu, Li-Bin,Chen, Guo-Song
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supporting information
p. 1740 - 1744
(2016/12/14)
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- Control-synthesized multilayer hyperbranched-hyperbranched polyethers with a tunable molecular weight and an invariant degree of branching
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A strategy to synthesize multilayer hyperbranched-hyperbranched macromolecules with an invariant degree of branching (DB) and a controllable molecular weight (MW) is realized by taking advantages of competing reactions. The invariant DB and tunable MW lead to hyperbranched molecules with controlled sub-nano to nano pores, which have potential applications in supramolecular capsulation, gas storage, separation, and catalysis. Hyperbranched molecules with a low MW are obtained in a one-pot reaction due to the competing reactions between AB2 monomers. For our systems, hyperbranched molecules with much higher yet controlled MW can be achieved by adding additional batches of the same AB2 monomers. When different AB2 monomers with different spacer lengths are fed alternatively, multilayer core-shell hyperbranched macromolecules with a controlled layer thickness or MW are obtained. More importantly, the multilayer hyperbranched-hyperbranched macromolecules show not only tunable MW but also invariant DB. In addition, it is found that the Tg of core-shell hyperbranched molecules is mainly determined by the outermost layer.
- Liu, Tuan,Miao, Xuepei,Geng, Xinxin,Xing, An,Zhang, Liangdong,Meng, Yan,Li, Xiaoyu
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p. 3432 - 3439
(2016/05/09)
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- A sub-milligram-synthesis protocol for in vitro screening of HDAC11 inhibitors
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This work demonstrated the high efficiency of a sub-milligram-synthesis based medicinal chemistry method. Totally 72 compounds, consisting a tri-substituted pyrrolidine core, were prepared. Around 0.1 mg of each compound was solid-phase synthesized. Based on the additive property of UV absorptions of unconjugated chromophores of a molecule, these compounds were quantified by UV measurement. A hit, whose IC50 value was 1.2 μM in HDAC11 inhibition assays, highlights the applicability of the approach reported here in future optimization works.
- Tian, Yinping,Jin, Jin,Wang, Congying,Lv, Wenhui,Li, Xuewei,Che, Xiaona,Gong, Yanchao,Li, Yanjun,Li, Quanli,Hou, Jingli,Wang, Peng G.,Shen, Jie
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supporting information
p. 2434 - 2437
(2016/07/07)
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- Generation of catalytic amphiphiles in a self-reproducing giant vesicle
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Giant vesicles capable of generating a catalytic amphiphile that promoted vesicular membrane production were prepared. The catalyst was derived from decylaniline on the vesicles and a catalytic aldehyde present outside the vesicles. Once the catalyst was
- Sheng, Li,Kurihara, Kensuke
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supporting information
p. 598 - 600
(2016/07/06)
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- Preparation of Bodipy-ferrocene dyads and modulation of the singlet/triplet excited state of bodipy: Via electron transfer and triplet energy transfer
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Modulation of the singlet/triplet excited state of a fluorophore is becoming more important for molecular switches, molecular memory devices, chemical or biological sensors and controllable photodynamic therapy (PDT) etc. Boron-dipyrromethene (Bodipy)-ferrocene (Fc) dyads were prepared for reversible electrochemical switching of the singlet excited state (fluorescence), as well as the triplet excited states of Bodipy. The photophysical properties of the dyads were studied using steady-state UV-vis absorption spectroscopy, fluorescence, electrochemical characterization, time-resolved fluorescence and nanosecond transient absorption spectroscopies. The fluorescence of the Bodipy moieties in the dyads was quenched significantly, due to the photo-induced electron transfer (PET). This conclusion was supported by electrochemical characterization and calculation of the Gibbs free energy changes of PET. We demonstrated that the fluorescence of the Bodipy moiety can be reversibly switched ON and OFF by electrochemical oxidation of the Fc moiety (Fc/Fc+). Furthermore, we proved that the Fc moiety is efficient for quenching of the triplet excited states of Bodipy. Two quenching mechanisms, PET and triplet-triplet-energy transfer (TTET), are responsible for the intramolecular and intermolecular quenching of the triplet excited states of the diiodoBodipy unit.
- Wu, Xueyan,Wu, Wenting,Cui, Xiaoneng,Zhao, Jianzhang,Wu, Mingbo
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supporting information
p. 2843 - 2853
(2016/04/26)
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