Search results for "Tereo"

showing 10 items of 6150 documents

NMR Investigation of Structures of G-Protein Coupled Receptor Folding Intermediates

2016

Folding of G-protein coupled receptors (GPCRs) according to the two-stage model (Popot, J. L., and Engelman, D. M. (1990) Biochemistry 29, 4031-4037) is postulated to proceed in 2 steps: partitioning of the polypeptide into the membrane followed by diffusion until native contacts are formed. Herein we investigate conformational preferences of fragments of the yeast Ste2p receptor using NMR. Constructs comprising the first, the first two, and the first three transmembrane (TM) segments, as well as a construct comprising TM1-TM2 covalently linked to TM7 were examined. We observed that the isolated TM1 does not form a stable helix nor does it integrate well into the micelle. TM1 is significant…

0301 basic medicine10120 Department of ChemistryBioquímicaSaccharomyces cerevisiae Proteins1303 BiochemistryProtein ConformationStereochemistrySaccharomyces cerevisiaeBiochemistryMicelleRessonància magnètica nuclear1307 Cell BiologyG03 medical and health sciencesprotein coupled receptorGPCRProtein Domains540 Chemistry1312 Molecular BiologyAmino Acid SequenceNuclear Magnetic Resonance BiomolecularMolecular BiologyMicellesG protein-coupled receptorSequence Homology Amino Acid030102 biochemistry & molecular biologyChemistryProteïnes de membranaFoldingCell BiologyTransloconPeptide FragmentsTransmembrane proteinNMRFolding (chemistry)Crystallography030104 developmental biologyStructural biology10036 Medical ClinicProtein Structure and FoldingReceptors Mating FactorHelixProtein folding
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2,3-Dihydrobenzofuran privileged structures as new bioinspired lead compounds for the design of mPGES-1 inhibitors

2016

International audience; 2,3-Dihydrobenzofurans are proposed as privileged structures and used as chemical platform to design small compound libraries. By combining molecular docking calculations and experimental verification of biochemical interference, we selected some potential inhibitors of microsomal prostaglandin E2 synthase (mPGES)-1. Starting from low affinity natural product 1, by our combined approach we identified the compounds 19 and 20 with biological activity in the low micromolar range. Our data suggest that the 2,3-dihydrobenzofuran derivatives might be suitable bioinspired lead compounds for development of new generation mPGES-1 inhibitors with increased affinity.

0301 basic medicine300323-Dihydrobenzofuran privileged structure; Cancer; Inflammation; Molecular docking; mPGES-1 inhibitors; Biochemistry; Clinical Biochemistry; Molecular Biology; Molecular Medicine; Organic Chemistry; Drug Discovery3003 Pharmaceutical Science; 3003Amino Acid MotifsClinical BiochemistryGene ExpressionPharmaceutical Science01 natural sciencesClinical biochemistryBiochemistry[ CHIM ] Chemical SciencesProtein Structure Secondary[ SDV.CAN ] Life Sciences [q-bio]/Cancerchemistry.chemical_compoundLow affinityDrug DiscoveryEnzyme Inhibitors23-Dihydrobenzofuran privileged structure; Molecular docking; mPGES-1 inhibitors; Cancer; InflammationProstaglandin-E SynthasesCancerAnti-Inflammatory Agents Non-SteroidalBiological activityProto-Oncogene Proteins c-metIntramolecular OxidoreductasesMolecular Docking SimulationMolecular dockingMolecular Medicinelipids (amino acids peptides and proteins)Cell SurvivalStereochemistryMolecular Sequence Data2Antineoplastic Agents[SDV.CAN]Life Sciences [q-bio]/Cancer3-Dihydrobenzofuran privileged structureInhibitory Concentration 50Structure-Activity Relationship03 medical and health sciencesCell Line TumorMicrosomesHumans[CHIM]Chemical SciencesMolecular BiologyBenzofuransInflammationNatural product010405 organic chemistryDrug Discovery3003 Pharmaceutical ScienceOrganic ChemistryEpithelial CellsmPGES-1 inhibitorsCombinatorial chemistryCombined approach0104 chemical sciences030104 developmental biologychemistryDrug DesignDrug Screening Assays Antitumor
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Synthesis and antitumor activities of 1,2,3-triazines and their benzo- and heterofused derivatives

2017

1,2,3-Triazines are a class of biologically active compounds that exhibit a broad spectrum of activities, including antibacterial, antifungal, antiviral, antiproliferative, analgesic and anti-inflammatory properties. This review, which covers the literature from the end of last century to 2016, treats, through a comprehensive, systematic approach, the 1,2,3-triazine and related benzo- and hetero-fused derivatives possessing antitumor activity. Their efficacy, combined with a simple synthesis confers to these molecules a great potential as scaffold for the development of antitumor compounds.

0301 basic medicineAntifungalModels MolecularHetero-fused 1123-Triazines Benzo[123]triazines Hetero-fused 123-triazines Antiproliferative activity Antitumor activity Nitrogen heterocyclesStereochemistrymedicine.drug_class12Antineoplastic AgentsChemistry Techniques SyntheticAntiproliferative activity01 natural sciences03 medical and health sciencesBroad spectrumNeoplasmsDrug DiscoverymedicineBenzene DerivativesAnimalsHumans3]triazinesPharmacologyAntitumor activity3-triazines1; 2; 3-Triazines; Benzo[1; 2; 3]triazines; Hetero-fused 1; 2; 3-triazines; Antiproliferative activity; Antitumor activity; Nitrogen heterocyclesBenzo[1ChemistryTriazinesNitrogen heterocyclesOrganic ChemistryBiological activityGeneral MedicineSettore CHIM/08 - Chimica FarmaceuticaCombinatorial chemistry0104 chemical sciences010404 medicinal & biomolecular chemistry030104 developmental biologyAntitumor activity
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Role of quercetin on Caco-2 cells against cytotoxic effects of alternariol and alternariol monomethyl ether.

2015

Molds of the genus Alternaria have been reported as contaminants of a variety of food and feed. Alternaria toxins such as alternariol (AOH) and its naturally occurring monomethyl ether (AME) produce cytotoxicity and oxidative stress in cell cultures. On the other hand, it has been proved that natural polyphenols have antioxidant effect. Quercetin (Quer) is a polyphenol present in berries and other commodities which exhibits these effects. The aims were to evaluate the cytotoxicity of AOH, AME and the binary combination of them, and the cytoprotective effect of Quer exposed simultaneously with AOH, AME and the mycotoxin mixture in human adenocarcinoma (Caco-2) cells. The cytotoxicity and the…

0301 basic medicineAntioxidantStereochemistrymedicine.medical_treatmentAlternariolToxicology03 medical and health scienceschemistry.chemical_compoundLactones0404 agricultural biotechnologymedicineHumansViability assayFood scienceMycotoxinCytotoxicity04 agricultural and veterinary sciencesGeneral Medicine040401 food science030104 developmental biologychemistryCaco-2PolyphenolQuercetinCaco-2 CellsQuercetinFood ScienceEthersFood and chemical toxicology : an international journal published for the British Industrial Biological Research Association
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Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation

2016

Signal Transducer and Activator of Transcription 5 (STAT5) protein, a component of the STAT family of signaling proteins, is considered to be an attractive therapeutic target because of its involvement in the progression of acute myeloid leukemia. In an effort to discover potent molecules able to inhibit the phosphorylation-activation of STAT5, twenty-two compounds were synthesized and evaluated on the basis of our knowledge of the activity of 2-(3’,4’,5’-trimethoxybenzoyl)-3-iodoacetamido-6-methoxy benzo[b]furan derivative 1 as a potent STAT5 inhibitor. Most of these molecules, structurally related to compound 1, were characterized by the presence of a common 3’,4’,5’-trimethoxybenzoyl moi…

0301 basic medicineApoptosisAntineoplastic Agentchemistry.chemical_compoundBenzophenone0302 clinical medicinehemic and lymphatic diseasesFuranDrug DiscoverySTAT5 Transcription FactorTumor Cells CulturedThiopheneMoietyPhosphorylationSTAT5Molecular StructurebiologyChemistryBiological activityGeneral MedicineApoptosis; BCR/ABL expressing leukemia; In vitro antiproliferative activity; STAT5 inhibitors; Structure-activity relationship; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry; PharmacologyLeukemia Myeloid Acute030220 oncology & carcinogenesisBCR/ABL expressing leukemiaApoptosis; BCR/ABL expressing leukemia; In vitro antiproliferative activity; STAT5 inhibitors; Structure-activity relationship; Antineoplastic Agents; Apoptosis; Benzofurans; Benzophenones; Cell Proliferation; Dose-Response Relationship Drug; Drug Screening Assays Antitumor; Humans; K562 Cells; Leukemia Myeloid Acute; Molecular Structure; Phosphorylation; STAT5 Transcription Factor; Structure-Activity Relationship; Tumor Cells Cultured; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry; PharmacologyHumanStereochemistryAntineoplastic AgentsArticleNOBenzophenones03 medical and health sciencesK562 CellHumansStructure–activity relationshipBenzofuransCell ProliferationPharmacologyIndole testDose-Response Relationship DrugIn vitro antiproliferative activitySTAT5 inhibitorsDrug Discovery3003 Pharmaceutical ScienceOrganic ChemistryApoptosiSTAT5 inhibitorStructure-activity relationshipIn vitro030104 developmental biologybiology.proteinBenzofuranDrug Screening Assays AntitumorK562 Cells
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Development of Novel Peptide-Based Michael Acceptors Targeting Rhodesain and Falcipain-2 for the Treatment of Neglected Tropical Diseases (NTDs)

2017

This paper describes the development of a class of peptide-based inhibitors as novel antitrypanosomal and antimalarial agents. The inhibitors are based on a characteristic peptide sequence for the inhibition of the cysteine proteases rhodesain of Trypanosoma brucei rhodesiense and falcipain-2 of Plasmodium falciparum. We exploited the reactivity of novel unsaturated electrophilic functions such as vinyl-sulfones, -ketones, -esters, and -nitriles. The Michael acceptors inhibited both rhodesain and falcipain-2, at nanomolar and micromolar levels, respectively. In particular, the vinyl ketone 3b has emerged as a potent rhodesain inhibitor (k2nd = 67 × 106 M-1 min-1), endowed with a picomolar b…

0301 basic medicineCathepsin LAntimalarialPeptideHeLa Cell01 natural sciencesCysteine Proteinase InhibitorDipeptideDrug DiscoveryPeptide sequencechemistry.chemical_classificationTrypanocidal AgentbiologyNeglected DiseasesStereoisomerismDipeptidesTrypanocidal AgentsMAJOR CYSTEINE PROTEASE PLASMODIUM-FALCIPARUM TRYPANOSOMA-BRUCEI CONFORMATIONAL-ANALYSIS BIOLOGICAL EVALUATION HIGHLY POTENT VINYL-ESTER INHIBITORS PEPTIDOMIMETICS SUBSTRATEMolecular Docking SimulationCysteine EndopeptidasesBiochemistryMolecular MedicineHumanProteasesNeglected DiseaseStereochemistryPhenylalaninePlasmodium falciparumTrypanosoma brucei bruceiCysteine Proteinase InhibitorsMolecular Dynamics SimulationTrypanosoma bruceiAntimalarialsStructure-Activity Relationship03 medical and health sciencesparasitic diseasesHumansStructure–activity relationship010405 organic chemistryDrug Discovery3003 Pharmaceutical ScienceHydrogen BondingTrypanosoma brucei rhodesiensePlasmodium falciparumbiology.organism_classificationMalaria0104 chemical sciencesTrypanosomiasis African030104 developmental biologychemistryCarbamateCarbamatesCysteine EndopeptidaseHeLa CellsCysteineJournal of Medicinal Chemistry
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Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

2016

Abstract A natural like O -glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N -(3-methyl-1-(4-nitrophenyl)-1 H -pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43  μ M. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in…

0301 basic medicineCell cycle checkpointCell SurvivalReceptor ErbB-2StereochemistryGlycoconjugateAntineoplastic AgentsAntiproliferative activityChemistry Techniques Synthetic03 medical and health sciences0302 clinical medicineCyclin-dependent kinaseCell Line TumorDrug DiscoveryHumansPolycyclic CompoundsMDA-MB231Cyclin B1Cell ProliferationCyclinPharmacologychemistry.chemical_classificationBiological ProductsCyclin-dependent kinase 1G2/M phase arrestp21WAF1 inhibitorbiologyChemistryKinaseDrug Discovery3003 Pharmaceutical ScienceO-glycoconjugate polycyclic compoundOrganic ChemistryGeneral MedicineMolecular biologyG2 Phase Cell Cycle CheckpointsGene Expression Regulation Neoplastic030104 developmental biologyCell culturePyrazolo[34-b]pyrazolo[3′4′:23]azepino[45-f]azocineDrug Design030220 oncology & carcinogenesisbiology.proteinM Phase Cell Cycle CheckpointsReceptors ProgesteroneGlycoconjugatesEuropean Journal of Medicinal Chemistry
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[1,2]Oxazolo[5,4-e]isoindoles as promising tubulin polymerization inhibitors

2016

Abstract A series of [1,2]Oxazolo [5,4- e ]isoindoles has been synthesized through a versatile and high yielding sequence. All the new structures showed in the 1 HNMR spectra, the typical signal in the 8.34–8.47 ppm attributable to the H-3 of the [1,2]oxazole moiety. Among all derivatives, methoxy benzyl substituents at positions 3 and 4 or/and 5 were very effective in reducing the growth of different tumor cell lines, including diffuse malignant peritoneal mesothelioma (DMPM), an uncommon and rapidly malignancy poorly responsive to available therapeutic options. The most active compound 6j was found to impair tubulin polymerization, cause cell cycle arrest at G2/M phase and induce apoptosi…

0301 basic medicineCell cycle checkpointIsoindoles2]Oxazolo[5StereochemistryDiffuse malignant peritoneal mesotheliomaα-hydroxyalkyl ketonesAntineoplastic AgentsApoptosisIsoindoles01 natural sciencesTubulin Polymerization Inhibitors03 medical and health scienceschemistry.chemical_compoundIsomerismTubulinCell Line TumorDrug DiscoveryHumansMoietyProtein Structure QuaternaryOxazole[12]Oxazolo[54-e]isoindolePharmacology010405 organic chemistryChemistryAntitubulin agentsDrug Discovery3003 Pharmaceutical ScienceOrganic ChemistryGeneral MedicineSettore CHIM/08 - Chimica FarmaceuticaTubulin Modulators0104 chemical sciencesAntitubulin agentG2 Phase Cell Cycle Checkpointsα-hydroxyalkyl ketone030104 developmental biologyApoptosisActive compound4-e]isoindolesProton NMRM Phase Cell Cycle CheckpointsAntitubulin agents; Diffuse malignant peritoneal mesothelioma; [1; 2]Oxazolo[5; 4-e]isoindoles; α-hydroxyalkyl ketones; Pharmacology; Drug Discovery3003 Pharmaceutical Science; Organic Chemistry[1Drug Screening Assays AntitumorProtein Multimerization
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New insights into the mechanism of action of pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one derivatives endowed with anticancer potential

2018

Due to the scarce biological profile, the pyrazolo[1,2-a]benzo[1,2,3,4]tetrazine-3-one scaffold (PBT) has been recently explored as promising core for potential anticancer candidates. Several suitably decorated derivatives (PBTs) exhibited antiproliferative activity in the low-micromolar range associated with apoptosis induction and cell cycle arrest on S phase. Herein, we selected the most active derivatives and submitted them to further biological explorations to deepen the mechanism of action. At first, a DNA targeting is approached by means of flow Linear Dichroism experiments so as to evaluate how small planar molecules might interact with DNA, including the interference with the catal…

0301 basic medicineCell cycle checkpointPyrazolo[1TetrazolesBiochemistrychemistry.chemical_compound0302 clinical medicineSalmonAntiproliferative; DNA-interacting; Intercalation; Linear dichroism; Molecular docking; Pyrazolo[12-a]benzo[1234]tetrazin-3-one; Topoisomerase II; Biochemistry; Molecular MedicineDrug DiscoveryDNA-interactingBase PairingADMEbiologyIntercalating AgentsMolecular Docking Simulation030220 oncology & carcinogenesisMolecular Medicinemedicine.symptomtopoisomerase II3StereochemistryIn silico2Antineoplastic Agentslinear dichroism03 medical and health sciencesantiproliferativeintercalationmedicineAnimalsHumansDNA Cleavage2-a]benzo[1Pharmacology4]tetrazin-3-oneBinding SitesTopoisomeraseOrganic ChemistryDNAmolecular dockingSettore CHIM/08 - Chimica FarmaceuticaChemical spaceProtein Structure TertiaryDNA Topoisomerases Type II030104 developmental biologyMechanism of actionchemistryCatalytic cyclebiology.proteinpyrazolo[12-a]benzo[1234]tetrazin-3-oneDNAChemical Biology & Drug Design
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Design, synthesis, and biological evaluation of a new class of benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitu…

2018

A new series of 3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furans were synthesized and screened as antitumor agents. As a general trend, tested compounds showed concentration-dependent antiproliferative activity against HeLa and MCF-7 cancer cell lines, exhibiting GI50 values in the low micromolar range. In most cases, insertion of a methyl substituent on the imidazole moiety improved the antiproliferative activity. Therefore, methyl-imidazolyl-benzo[b]furans compounds were tested in cell cycle perturbation experiments, producing cell cycle arrest with proapoptotic effects. Their core similarity to known colchicine binding site binders led us to further study the structure featur…

0301 basic medicineCell cycle checkpointinduced fit docking studieantitubulin agents01 natural sciencesBiochemistryHeLa and MCF-7 cell linesHeLachemistry.chemical_compoundTubulinFuranDrug DiscoveryImidazoleMoietybiologyHeLa and MCF-7 cell lineG2/M phaseTubulin ModulatorsMolecular Docking SimulationAntiproliferative AgentsMCF-7 CellsMolecular MedicineVLAK protocolantitubulin agentStereochemistryIn silicoSubstituent3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furansAntineoplastic Agentsinduced fit docking studiesantitumor agents03 medical and health sciencesHumanscolchicine binding siteBenzofuransCell ProliferationPharmacologyBinding Sites010405 organic chemistryOrganic ChemistryCell Cycle Checkpoints3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furanbiology.organism_classification0104 chemical sciencesProtein Structure Tertiary030104 developmental biologychemistryantitumor agentDrug DesignColchicineHeLa Cells
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