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Click synthesis, anticancer activity, and molecular docking investigation of some functional 1,2,3-triazole derivatives

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Click synthesis, anticancer activity, and molecular docking investigation of some functional 1,2,3-triazole derivatives

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dc.contributor.author	Hrimla, Meryem
dc.contributor.author	Oubella, Ali
dc.contributor.author	Laamari, My Rachid
dc.contributor.author	Bahsis, Lahoucine
dc.contributor.author	Ghaleb, Adib
dc.contributor.author	Auhmani, Aziz
dc.contributor.author	Morjani, Hamid
dc.contributor.author	Julve Olcina, Miguel
dc.contributor.author	Stiriba, Salah Eddine
dc.contributor.author	Itto, My Youssef Ai
dc.date.accessioned	2023-04-26T16:54:35Z
dc.date.available	2023-04-26T16:54:35Z
dc.date.issued	2022
dc.identifier.citation	Hrimla, Meryem Oubella, Ali Laamari, My Rachid Bahsis, Lahoucine Ghaleb, Adib Auhmani, Aziz Morjani, Hamid Julve Olcina, Miguel Stiriba, Salah Eddine Itto, My Youssef Ai 2022 Click synthesis, anticancer activity, and molecular docking investigation of some functional 1,2,3-triazole derivatives Biointerface Research in Applied Chemistry 12 6 7633 7667
dc.identifier.uri	https://hdl.handle.net/10550/86206
dc.description.abstract	1,2,3-triazole skeleton is a privileged building block for the discovery of new promising anticancer agents. In this report, new 1,4-disubstituted 1,2,3-triazoles with the bioisoster triazole moiety were straightforwardly prepared under copper-catalyzed azide-alkyne [3+2] cycloaddition reactions (CuAAC) regime using a variety of both functional organic azides and terminal alkynes. The resulting functional 1,4-disubstituted 1,2,3-triazole compounds were fully characterized and subsequently tested for their antiproliferative activity against four different cancer cell lines. The cytotoxicity tests carried out with these 1,2,3-triazole derivatives show average IC50 values ranging from 15 to 50 μM by comparison with the standard reference drug, namely doxorubicin. The phosphonate 1,2,3-triazole derivative was found to exhibit the best antiproliferative activity among the studied compounds against the HT-1080 cell lines. It was chosen to evaluate its mode of action in these cancer cell lines. The cell cycle study showed that the phosphonate derivative, compound 8, is the most active inhibitor of the cell cycle at the G0/G1 phase, inducing apoptosis independently of Caspase-3 and causing an increase in the mitochondrial membrane potential (ΔΨm) in the HT-1080 cell lines. Molecular docking studies of this phosphonate derivative into the MMP-2 and MMP-9 metalloproteinases receptors demonstrated the relevance of triazole scaffolds and the pendant phosphonate group in establishing -anion, -alkyl and hydrogen bonding type interactions with residual components in the active MMP pocket.
dc.language.iso	eng
dc.relation.ispartof	Biointerface Research in Applied Chemistry, 2022, vol. 12, num. 6, p. 7633-7667
dc.subject	Química
dc.title	Click synthesis, anticancer activity, and molecular docking investigation of some functional 1,2,3-triazole derivatives
dc.type	journal article
dc.date.updated	2023-04-26T16:54:35Z
dc.identifier.doi	10.33263/BRIAC126.76337667
dc.identifier.idgrec	156548
dc.rights.accessRights	open access