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Rim-differentiation vs. mixture of constitutional isomers: A binding study between pillar[5]arene-based glycoclusters and lectins from pathogenic bacteria

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中国化学快报：英文版 2023年第2期34卷 214-218页

作者： Zhiping Liu Fanny demontrond Anne Imberty Andrew C.-H.Sue Sébastien Vidal Hongxia Zhao Tianjin Key Lab for Modern Drug delivery and High-Efficiency School of Pharmaceutical Science and TechnologyTianjin UniversityTianjin 300072China Institut de chimie et Biochimie Moléculaires et Supramoléculaires Laboratoire de Chimie Organique 2-GlycochimieUMR 5246CNRSUniversitéClaude Bernard Lyon 1Universitéde LyonVilleurbanne 69622France CNRS Univ.Grenoble AlpesCERMAVGrenoble 38000France College of Chemistry and Chemical Engineering Xiamen UniversityXiamen 361005China CNRS Institut de Chimie des Substances NaturellesUniversitéParis-SaclayUPR 2301Gif-sur-Yvette 91198France

Macrocycle-based glycoclusters, on account of their promising anti-adhesive properties against bacteria,are potential therapeutic alternatives to classic antibiotics through the much less explored anti-adhesive strategy. In this study, a series of constitutionally-pure pentavalent glycoclusters was prepared by conjugating assorted azido-carbohydrates onto a penta-propargyl rim-differentiated pillar[5]arene(RD-P[5])scaffold through Cu(I)-catalyzed azide–alkyne cycloaddition “click” reactions. Their binding towards therapeutically relevant bacterial lectins, such as Lec A and Lec B from Pseudomonas aeruginosa and concanavalin A(Con A), were evaluated subsequently by isothermal titration calorimetric studies. Most of these isomerfree RD-P[5] pentavalent glycoclusters, except the fucosylated ones, display good affinities to ***, the dissociation constants observed are similar to those displayed by an analogous pentavalent glycocluster consisting of four P[5] constitutional isomers, in which the RD-P[5] component merely accounts for 7% in the mixture. Our results revealed that high constitutional purity is not essential for achieving effective multivalent interactions between P[5]-based glycoclusters and lectins, presumably as a result of the conformationally labile nature of the P[5] scaffold. This information provides valuable design principles for low-cost and facile syntheses of glycosylated P[5]s for biomedical applications.

关键词： Glycocluster Lectin Pillararene Multivalency Constitutional purity

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Synthesis of sintenin and cytotoxic evaluation of its synthetic analogues

Synthesis of sintenin and cytotoxic evaluation of its synthe...

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The 3～(rd) International Conference on Natural Products :Natural Products -a Must for Human Survival ABSTRACTS

作者： Franoise Guéritte institute de chimie des substances Naturelles CNRS 91198 Gif-sur-Yvette

Cytotoxic compounds are essential during finding new leads of anti-tumor drugs. Recently, a cytotoxic natural ester, Sintenin (1), possessing selective cytotoxicity with an ED50 value of 0.21 μg/ml to P-388 cells was isolated from the leaves and stems of Piper sintenense scattered in *** on our interests of searching for cytotoxic natural products and their derivatives, we have designed a convenient synthetic route with a total yield of 49% (4 steps) to prepare this natural ester and six of its analogues were also prepared. Furthermore, to check the preliminary structure-activity relationship (SAR) of this type of esters, we have also prepared its another seven analogues owing unsaturated double bonds conjugated to the aromatic rings, while possesing some different substituents on the aromatic *** of the synthetic compounds were passed through the cytotoxicity screening on human tumor cell lines such as PC-3, Hela, A549, BEL7404, CNE and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The results provided a preliminary knowledgement for further SAR investigation on this type of natural-based esters.

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Synthesis and Cytotoxicity Evaluation of Some Isoquinoline derivatives Related to 1-Arylnaphthalene Lignans

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Chinese Chemical Letters 2005年第10期16卷 1279-1282页

作者： Hong Xia DING Wei LU Chang Xin ZHOU Hai Bo LI Lei Xiang YANG Qi Jun ZHANG Xiu Mei WU Olivier BAUDOIN Jun Chao CAI Francoise GUERITTE Yu ZHAO department of Traditional Chinese Medicine and Natural Drug Research College of Pharmaceutical Sciences Zhejiang University Hangzhou 31003 Shanghai institute of Material Medica Chinese Academy of Sciences Shanghai 201203 Zhejiang Hisun Naturelite Pharmaceutical R＆D Co. Hangzhou 310006 institute chimie des substances Naturelles CNRS AvenuedelaTerrasse 91198 Gif-sur-Yvette France

Two series of novel compounds designed as hybrids of 1-arylnaphthalene lignans with dihydroisoquinolines or isoquinolines were synthesized and evaluated for their cytotoxicities on human tumor cell lines, such as A549, Hela, PC-3 and KB. Some of the synthetic compounds exhibited their IC 50 values on selected cell lines at μmol/L scale.

关键词： Isoquinoline derivatives 1-arylnaphthalene lignans synthesis cytotoxicity.

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Ubiquitin is double-phosphorylated by PINK1 for enhanced pH-sensitivity of conformational switch

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Protein & Cell 2019年第12期10卷 908-913页

作者： Shang-XiangYe Zhou Gong Ju Yang Yu-Xin An Zhu Liu Qun Zhao Ewen Lescop Xu Dong Chun Tang Wuhan National Laboratory for Optoelectronics Huazhong University of Science and TechnologyWuhan 430074China CAS Key Laboratory of Magnetic Resonance in Biological Systems State Key Laboratory of Magnetic Resonance and Atomic Molecular PhysicsNational Center for Magnetic Resonance at WuhanWuhan Institute of Physics and Mathematics of the Chinese Academy of SciencesWuhan 430071China Institut de chimie des substances Naturelles CNRS UPR 2301Univ Paris-SudUniversite Paris-Saclay91198 Gif-sur-Yvette cedexFrance CAS Key Laboratory of Separation Sciences for Analytical Chemistry Dalian Institute of Chemical Physics of the Chinese Academy of SciencesDalian 116023China

dear Editor,Multisite phosphorylation is observed in many signaling proteins,which confers the proteins new functions.A multisite phosphorylated protein can exhibit switch-like response to cellular stimuli,with the often-clustered phosphorylation sites either unphosphorylated or fully phosphorylated by the same kinase(Kapuy et al..2009).Multisite phosphorylation has also been reported to promote the folding of an intrinsically disordered protein,and consequently modulate the binding affinity to other proteins(Bah et al.,2015).Here we show that multisite phosphorylation makes a protein a better pH sensor,promptly switching between alternative conformational states in response to pH change under physiological conditions.

关键词： prompt folding

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Sodium-Modified Fluorapatite: A Mild and Efficient Reusable Catalyst for the Synthesis of <i>α,α</i>’-Bis(Substituted Benzylidene) Cycloalkanones under Conventional Heating and Microwave Irradiation

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Green and Sustainable Chemistry 2018年第2期8卷 156-166页

作者： Bahija Mounir Fathallaah Bazi Abddelfetah Mounir Mohamed Zahouily Hamid Toufik Laboratoire Materiaux Substances Naturelles Environnement & Modelisation (LMSNEM) Faculte Polydisciplinaire de TazaUniversite Sidi Mohamed Ben Abdellah Fes Maroc Laboratoire de chimie Analytique et physicochimie des Maté riaux Facult&eacute des Sciences Ben M’Sik de Casablanca Universit&eacute Hassan II Casablanca Maroc Higher institute of Nursing Professions and Health Techniques Marrakech Morroco Laboratoire de Maté riaux Catalyse et Valorisation des Ressources Naturelles Facult&eacute des Sciences et Techniques de Mohammedia Universit&eacute Hassan II Casablanca Maroc

A versatile and environmentally friendly method for α,α’-bis(substituted ben-zylidene) cycloalkanones has been developed using a heterogeneous catalysis technology. We have synthesized a series of the α,α’-bis(substituted benzylidene) cycloalkanones, a biologically important class of compounds, via the cross aldol condensation between arylaldehydes and cycloketones using sodium-modified fluorapatite (Na/FAP) as a highly efficient solid catalyst under conventional heating in aqueous media and solventless conditions under microwave. Catalyst reuse, ease of separation of the pure product, and high yields are some of the unique features of this process. Shorter reaction times (4 - 7 min) and higher yields (80% - 94%) were achieved under microwave irradiation conditions.

关键词： Green Chemistry α α’-Bis(Substituted Benzylidene) Cycloalkanones Microwaves Irradiation Conventional Heating Aqueous Media Fluorapatite Activated by Sodium Nitrate (Na/FAP)

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A Phelipanche ramosa KAI2 protein perceives strigolactones and isothiocyanates enzymatically

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Plant Communications 2021年第5期2卷 132-147页

作者： Alexandre de Saint Germain Anse Jacobs Guillaume Brun Jean-Bernard Pouvreau Lukas Braem David Cornu Guillaume Clavé Emmanuelle Baudu Vincent Steinmetz Vincent Servajean Susann Wicke Kris Gevaert Philippe Simier Sofie Goormachtig Philippe delavault François-Didier Boyer Institut Jean-Pierre Bourgin INRAEAgroParisTechUniversitéParis-Saclay78000 VersaillesFrance department of Plant Biotechnology and Bioinformatics Ghent University9052 GentBelgium Center for Plant Systems Biology VIB9052 GentBelgium department of Biomolecular Medicine Ghent University9000 GhentBelgium Center for Medical Biotechnology VIB9000 GhentBelgium Laboratoire de Biologie et Pathologie Végétales(LBPV) Equipe d’Accueil 1157Universitéde Nantes44000 NantesFrance institute for Biology Humboldt-Universit€at zu Berlin10115 BerlinGermany UniversitéParis-Saclay CEACNRSInstitute for Integrative Biology of the Cell(I2BC)91198Gif-sur-YvetteFrance UniversitéParis-Saclay CNRSInstitut de Chimie des Substances NaturellesUPR 230191198Gif-sur-YvetteFrance

Phelipanche ramosa is an obligate root-parasitic weed that threatens major crops in central *** order to germinate,it must perceive various structurally divergent host-exuded signals,including isothiocyanates(ITCs)and strigolactones(SLs).However,the receptors involved are still ***,we identify five putative SL receptors in *** and show that PrKAI2d3 is involved in the stimulation of seed *** demonstrate the high plasticity of PrKAI2d3,which allows it to interact with different chemicals,including *** SL perception mechanism of PrKAI2d3 is similar to that of endogenous SLs in non-parasitic *** provide evidence that PrKAI2d3 enzymatic activity confers hypersensitivity to ***,we demonstrate that methylbutenolide-OH binds PrKAI2d3 and stimulates *** germination with bioactivity comparable to that of *** study demonstrates that *** has extended its signal perception system during evolution,a fact that should be considered for the development of specific and efficient biocontrol methods.

关键词： a/b-hydrolase receptor seed germination stimulant strigolactones isothiocyanates Phelipanche ramosa

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Evidence for the presence of GPRC6A in the rat mesenteric artery

Evidence for the presence of GPRC6A in the rat mesenteric ar...

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第十五届国际药理学大会

作者： Hamo Erika Weston Arthur Longden Thomas Absi Mais Ruat Martial Dodd Robert Edwards Gillian Faculty of Life Sciences The University of Manchester Manchester M13 9PT UK. Faculty of Life Sciences The University of Manchester Manchester M13 9PT UK. Faculty of Life Sciences The University of Manchester Manchester M13 9PT UK. Faculty of Life Sciences The University of Manchester Manchester M13 9PT UK. Signal Transduction and developmental Neuropharmacology CNRS UPR 9040 91198 Gif-sur-Yvette France institute de chimie des substances naturalles UPR 2301 CNRS 91198 Gif-sur-Yvette France Faculty of Life Sciences The University of Manchester Manchester M13 9PT UK.

＜正＞ GPRC6A is an "orphan". G protein-coupled receptor （related to the calcium sensing receptor） which is activated by basic amino acids. Al（3 + ） and the cal cimimetic NPS-568 （see Pi et al., 2005, J Biol Chem 280:40201-9）. The aim of this study was to investigate the possible presence of GPRC6A in rat mesenteric artery （RMA）. In sharp micro-electrode recordings. L-omithine （0.3 mM） produced an endothelium-dependent hyperpolarisation and potentiated the hyperpolarisation to the calcimimetic calindol （100. 300 nM）. The effects of both L-or-nithine and calindol were abolished by the IKCa channel inhibitor TRAM-34 （0.01 mM）. Similar effects （TRAM-34 sensitive hyperpolarisation and potentia-tion of calindol effect） were produced by Al（3+ ）（0.1 mM）. RT-PCR using mRNA extracted from RMA produced an amplicon of the predicted size, which was sequenced and confirmed as GPRC6A. Furthermore, the protein was also i dentified by Western blot using a selective polyclonal antibody. We conclude that GPRC6A is present in RMA endothelial cells and may play a role in the regulation of vascular tone. Funded by the British Heart Foundation

关键词： GPRC6A IKCa channel Calindol Mesenteric Artery

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High-density single antibody electrochemical nanoarrays

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Nano Research 2023年第4期16卷 5412-5418页

作者： Khalil Chennit Yannick Coffinier Shuo Li Nicolas Clément Agnès Anne Arnaud Chovin Christophe demaille UniversitéParis Cité CNRSLaboratoire d’Electrochimie MoléculaireParis F-75013France institute of Electronics Microelectronics and NanotechnologyCNRSUniversity of LilleAvenue PoincaréBP60069Villeneuve d’Ascq 59652France IIS LIMMS/CNRS-IIS UMI2820The University of Tokyo4-6-1 KomabaMeguro-kuTokyo 153-8505Japan

The fabrication and electrochemical interrogation of very high density single-antibody nanoarrays is *** nanodots,15 nm in diameter,arranged in large(cm2)square arrays with a pitch of 200 nm,are used as carriers for primary antibodies(immunoglobulin G(IgG)),further recognized by secondary redox-labeled detection *** scale interrogation of the antibody array by cyclic voltammetry,and nanoscale interrogation of individual nanodots by mediator tethered atomic forcescanning electrochemical microscopy(Mt/AFM-SECM),enable the occupancy of nanodots by single antibody molecules to be *** involving the competitive adsorption of antibodies of different species onto the nanodots evidence the possibility of using single-antibody nanoarrays for digital electrochemical immunoassays.

关键词： single entity electrochemistry electrochemical digital immunoassays atomic force-scanning electrochemical microscopy(AFM-SECM)

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