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New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline derivatives: synthesis and biological evaluation as novel anticancer agents by targeting G-quadruplex

hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorGUILLON, Jean
hal.structure.identifierCentre de Recherche en Cancérologie de Lyon [UNICANCER/CRCL]
dc.contributor.authorLE BORGNE, Marc
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorMILANO, Vittoria
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorGUÉDIN-BEAUREPAIRE, Aurore
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorMOREAU, Stéphane
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPINAUD, Noël
hal.structure.identifierInstitut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
dc.contributor.authorRONGA, Luisa
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorSAVRIMOUTOU, Solène
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorALBENQUE-RUBIO, Sandra
hal.structure.identifierInstitut de Chimie de la Matière Condensée de Bordeaux [ICMCB]
dc.contributor.authorMARCHIVIE, Mathieu
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorKALOUT, Haouraa
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorWALKER, Charley
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorCHEVALLIER, Louise
hal.structure.identifierSoutien à la Recherche de l'Institut Européen de Chimie Biologique
dc.contributor.authorBURÉ, Corinne
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorLARGY, Eric
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorGABELICA, Valérie
hal.structure.identifierLaboratoire d'Optique et Biosciences [LOB]
dc.contributor.authorMERGNY, Jean-Louis
hal.structure.identifierCentre de Recherche en Cancérologie de Marseille [CRCM]
dc.contributor.authorBAYLOT, Virginie
hal.structure.identifierBoRdeaux Institute in onCology [Inserm U1312 - BRIC]
dc.contributor.authorFERRER, Jacky
hal.structure.identifierBoRdeaux Institute in onCology [Inserm U1312 - BRIC]
dc.contributor.authorIDRISSI, Yamina
hal.structure.identifierBoRdeaux Institute in onCology [Inserm U1312 - BRIC]
dc.contributor.authorCHEVRET, Edith
hal.structure.identifierBoRdeaux Institute in onCology [Inserm U1312 - BRIC]
dc.contributor.authorDESPLAT, Vanessa
hal.structure.identifierUniversity of Szeged [Szeged]
dc.contributor.authorSCHELZ, Zsuzsanna
hal.structure.identifierUniversity of Szeged [Szeged]
dc.contributor.authorZUPKÓ, István
dc.date.issued2024
dc.identifier.issn1424-8247
dc.description.abstractEnThe syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines 12 and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines 13 are reported here in six steps starting from various halogeno-quinazoline-2,4-(1H,3H)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines 12b, 12f, and 12i displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline 13a proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line.
dc.description.sponsorshipInstitut François Rabelais pour la recherche multidisciplinaire sur le cancer - ANR-17-CONV-0002
dc.language.isoen
dc.publisherMDPI
dc.subject.enAntiproliferative activities
dc.subject.en2.4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline
dc.subject.en2.4-bis[(substituted-aminomethyl)phenyl]phenylquinoline
dc.subject.enG-quadruplex
dc.subject.enG4 ligands
dc.subject.enFRET-melting
dc.subject.enNative electrospray mass spectrometry
dc.subject.enTelomerase activity
dc.title.enNew 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline derivatives: synthesis and biological evaluation as novel anticancer agents by targeting G-quadruplex
dc.typeArticle de revue
dc.identifier.doi10.3390/ph17010030
dc.subject.halChimie/Chimie thérapeutique
dc.subject.halSciences du Vivant [q-bio]/Cancer
bordeaux.journalPharmaceuticals
bordeaux.page30
bordeaux.volume17
bordeaux.issue1
bordeaux.peerReviewedoui
hal.identifierhal-04390485
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-04390485v1
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