Synthesis and in vitro biological evaluation of three 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine iridium(III) complexes as new telomerase inhibitors

Synthesis and in vitro biological evaluation of three... There iridium(III) complexes, [Ir(3-MeO-Phtpy)Cl3] (1), [Ir(2-MeO-Phtpy)Cl3] (2) and [Ir(4-MeO-Phtpy)Cl3] (3) with 4′-(3-methoxyphenyl)-2,2′:6′,2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2,2′:6′,2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (4-MeO-Phtpy) as ligands, respectively, were synthesized and evaluated for their antiproliferative activities. In these complexes, the iridium(III) center adopts a six-coordinate distorted octahedral geometry. Among them, complex 1 exhibited the most potent activity, with IC50 values of 3.19–27.77 μM against four cancer cell lines (BEL-7404, Hep-G2, NCI-H460 and MGC80-3 cells). Cellular mechanism studies suggested that complexes 1–3 directly targeted c-myc promoter elements and inhibited the telomerase activity. In addition, complexes 1–3 may trigger cell apoptosis via a mitochondrial dysfunction pathway. We postulated that the difference in the in vitro antitumor activities of complexes 1–3 is mainly dependent on the position of the methoxy group on the phenyl ring of the iridium ligand. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png European Journal of Medicinal Chemistry Elsevier

Synthesis and in vitro biological evaluation of three 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine iridium(III) complexes as new telomerase inhibitors

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Publisher
Elsevier
Copyright
Copyright © 2017 Elsevier Masson SAS
ISSN
0223-5234
eISSN
1768-3254
D.O.I.
10.1016/j.ejmech.2017.10.035
Publisher site
See Article on Publisher Site

Abstract

There iridium(III) complexes, [Ir(3-MeO-Phtpy)Cl3] (1), [Ir(2-MeO-Phtpy)Cl3] (2) and [Ir(4-MeO-Phtpy)Cl3] (3) with 4′-(3-methoxyphenyl)-2,2′:6′,2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2,2′:6′,2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (4-MeO-Phtpy) as ligands, respectively, were synthesized and evaluated for their antiproliferative activities. In these complexes, the iridium(III) center adopts a six-coordinate distorted octahedral geometry. Among them, complex 1 exhibited the most potent activity, with IC50 values of 3.19–27.77 μM against four cancer cell lines (BEL-7404, Hep-G2, NCI-H460 and MGC80-3 cells). Cellular mechanism studies suggested that complexes 1–3 directly targeted c-myc promoter elements and inhibited the telomerase activity. In addition, complexes 1–3 may trigger cell apoptosis via a mitochondrial dysfunction pathway. We postulated that the difference in the in vitro antitumor activities of complexes 1–3 is mainly dependent on the position of the methoxy group on the phenyl ring of the iridium ligand.

Journal

European Journal of Medicinal ChemistryElsevier

Published: Jan 1, 2018

References

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