GUILLON, Jean; LE BORGNE, Marc; MILANO, Vittoria; GUÉDIN-BEAUREPAIRE, Aurore; MOREAU, Stéphane; PINAUD, Noël; RONGA, Luisa; SAVRIMOUTOU, Solène; ALBENQUE-RUBIO, Sandra; MARCHIVIE, Mathieu; KALOUT, Haouraa; WALKER, Charley; CHEVALLIER, Louise; BURÉ, Corinne; LARGY, Eric; GABELICA, Valérie; MERGNY, Jean-Louis; BAYLOT, Virginie; FERRER, Jacky; IDRISSI, Yamina; CHEVRET, Edith; DESPLAT, Vanessa; SCHELZ, Zsuzsanna; ZUPKÓ, István

doi:10.3390/ph17010030

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GUILLON, Jean
Acides Nucléiques : Régulations Naturelle et Artificielle [ARNA]

LE BORGNE, Marc
Centre de Recherche en Cancérologie de Lyon [UNICANCER/CRCL]

MILANO, Vittoria
Acides Nucléiques : Régulations Naturelle et Artificielle [ARNA]

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Article de revue

Ce document a été publié dans

Pharmaceuticals. 2024, vol. 17, n° 1, p. 30

MDPI

Résumé en anglais

The 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.< Réduire

Mots clés en anglais

Antiproliferative activities

2.4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline

2.4-bis[(substituted-aminomethyl)phenyl]phenylquinoline

G-quadruplex

G4 ligands

FRET-melting

Native electrospray mass spectrometry

Telomerase activity

DOI

http://dx.doi.org/10.3390/ph17010030

Project ANR

Institut François Rabelais pour la recherche multidisciplinaire sur le cancer - ANR-17-CONV-0002

Origine

Importé de hal

Unités de recherche

Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB) - UMR 5026