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Design, Synthesis, and In Vitro Antimalarial Evaluation of New 1,3,5-Tris[(4-(Substituted-Aminomethyl)Phenoxy)Methyl]Benzenes

dc.rights.licenseopenen_US
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorALBENQUE-RUBIO, Sandra
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorGUILLON, Jean
IDREF: 120176289
hal.structure.identifierAgents infectieux, résistance et chimiothérapie - UR UPJV 4294 [AGIR ]
dc.contributor.authorAGNAMEY, Patrice
hal.structure.identifierAgents infectieux, résistance et chimiothérapie - UR UPJV 4294 [AGIR ]
dc.contributor.authorDAMIANI, Céline
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorSAVRIMOUTOU, Solène
hal.structure.identifierAgents infectieux, résistance et chimiothérapie - UR UPJV 4294 [AGIR ]
dc.contributor.authorMUSTIÈRE, Romain
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPINAUD, Noël
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorMOREAU, Stéphane
hal.structure.identifierLaboratoire d'Optique et Biosciences [LOB]
dc.contributor.authorMERGNY, Jean-Louis
hal.structure.identifierInstitut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
dc.contributor.authorRONGA, Luisa
hal.structure.identifierInstitut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
dc.contributor.authorKANAVOS, Ioannis
hal.structure.identifierInstitut de Chimie de la Matière Condensée de Bordeaux [ICMCB]
dc.contributor.authorMARCHIVIE, Mathieu
hal.structure.identifierCentre de recherche Cardio-Thoracique de Bordeaux [Bordeaux] [CRCTB]
hal.structure.identifierPlateforme Technologique d'Innovation Biomédicale [PTIB]
hal.structure.identifierHôpital Xavier Arnozan - CHU de Bordeaux
dc.contributor.authorMOUKHA, Serge
hal.structure.identifierCentre de recherche Cardio-Thoracique de Bordeaux [Bordeaux] [CRCTB]
hal.structure.identifierPlateforme Technologique d'Innovation Biomédicale [PTIB]
hal.structure.identifierHôpital Xavier Arnozan - CHU de Bordeaux
dc.contributor.authorDOZOLME, Pascale
hal.structure.identifierAgents infectieux, résistance et chimiothérapie - UR UPJV 4294 [AGIR ]
dc.contributor.authorSONNET, Pascal
hal.structure.identifierMembranes et cibles thérapeutiques [MCT]
dc.contributor.authorCOHEN, Anita
dc.date.accessioned2025-06-18T10:49:42Z
dc.date.available2025-06-18T10:49:42Z
dc.date.issued2024-09-13
dc.identifier.issn2813-2998en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/206952
dc.description.abstractEnBy taking into account our previously described series of 1,3,5-tris[(4-(substituted-aminomethyl)phenyl)methyl]benzene compounds, we have now designed, prepared, and evaluated in vitro against Plasmodium falciparum a novel series of structural analogues of these molecules, i.e., the 1,3,5-tris[(4-(substituted-aminomethyl)phenoxy)methyl]benzene derivatives. The pharmacological data showed antimalarial activity with IC50 values in the sub and μM range. The in vitro cytotoxicity of these new nitrogen polyphenoxymethylbenzene compounds was also evaluated on human HepG2 cells. The 1,3,5-tris[(4-(substituted-aminomethyl)phenoxy)methyl]benzene derivative 1m was found as one of the most potent and promising antimalarial candidates with favorable cytotoxic to antiprotozoal properties in the P. falciparum strains W2 and 3D7. In conclusion, this 1,3,5-tris[(4-(pyridin-3-ylmethylaminomethyl)phenoxyl)methyl]benzene 1m (IC50 = 0.07 μM on W2, 0.06 μM on 3D7, and 62.11 μM on HepG2) was identified as the most promising antimalarial derivative with selectivity indexes (SI) of 887.29 on the W2 P. falciparum chloroquine-resistant strain, and of 1035.17 on the chloroquine-sensitive and mefloquine decreased sensitivity strain 3D7. It has been previously described that the telomeres of P. falciparum could represent potential targets for these types of polyaromatic compounds; therefore, the capacity of our novel derivatives to stabilize the parasitic telomeric G-quadruplexes was assessed using a FRET melting assay. However, with regard to the stabilization of the protozoal G-quadruplex, we observed that the best substituted derivatives 1, which exhibited some interesting stabilization profiles, were not the most active antimalarial compounds against the two Plasmodium strains. Thus, there were no correlations between their antimalarial activities and selectivities of their respective binding to G-quadruplexes.
dc.language.isoENen_US
dc.subject.enantimalarial activity
dc.subject.en1
dc.subject.en3
dc.subject.en5-tris[(4-(substituted-aminomethyl)phenoxy)methyl]benzene
dc.subject.enG-quadruplexes
dc.subject.ensynthesis
dc.title.enDesign, Synthesis, and In Vitro Antimalarial Evaluation of New 1,3,5-Tris[(4-(Substituted-Aminomethyl)Phenoxy)Methyl]Benzenes
dc.typeArticle de revueen_US
dc.identifier.doi10.3390/ddc3030035en_US
dc.subject.halSciences du Vivant [q-bio]en_US
dc.subject.halChimieen_US
bordeaux.journalDrugs and Drug Candidatesen_US
bordeaux.page615-637en_US
bordeaux.volume3en_US
bordeaux.hal.laboratoriesCentre de Recherche Cardio-Thoracique de Bordeaux (CRCTB) - U1045en_US
bordeaux.issue3en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionINSERMen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
bordeaux.import.sourcehal
hal.identifierhal-04701065
hal.version1
hal.popularnonen_US
hal.audienceInternationaleen_US
hal.exportfalse
workflow.import.sourcehal
dc.rights.ccPas de Licence CCen_US
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Drugs%20and%20Drug%20Candidates&rft.date=2024-09-13&rft.volume=3&rft.issue=3&rft.spage=615-637&rft.epage=615-637&rft.eissn=2813-2998&rft.issn=2813-2998&rft.au=ALBENQUE-RUBIO,%20Sandra&GUILLON,%20Jean&AGNAMEY,%20Patrice&DAMIANI,%20C%C3%A9line&SAVRIMOUTOU,%20Sol%C3%A8ne&rft.genre=article


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