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Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Jordi Mas Grau, Amparo Caubet, Olivier Roubeau, David Montpeyó, Júlia Lorenzo, Patrick Gámez

2020ChemBioChem21 citationsDOIOpen Access PDF

Abstract

Abstract Five copper complexes supported by terpyridine ligands were prepared and characterized, viz . [Cu 3 Cl 4 (naphtpy) 2 ][CuCl 2 ] ( 1 ), [Cu 2 Cl 2 (naphtpy) 2 ](ClO 4 ) 2 ( 2 ), [CuCl 2 (naphtpy)] 2 (MeOH) 3 (H 2 O) ( 3 ), [CuCl 2 (Cltpy)] ( 4 ) and [Cu(Cltpy) 2 ](ClO 4 ) 2 ( 5 ); (where naphtpy stands for 4’‐((naphthalen‐2‐yl)methoxy)‐2,2′:6′,2′′‐terpyridine and Cltpy for 4′‐chloro‐2,2′:6′,2′′‐terpyridine). Their ability to interact with DNA was investigated, and their cytotoxic behaviour was examined with three cells lines, namely human ovarian carcinoma cells (A2780), their derived cisplatin‐resistant line (A2780cis), and human cervix adenocarcinoma cells (HeLa). All compounds show good cytotoxic properties (especially after 72 h of incubation). Remarkably, two compounds, 4 and 5 , are still almost inactive after 24 h (particularly 4 ), but are highly active after 72 h, with IC 50 values in the low‐micromolar to sub‐micromolar range. Compounds 1 and 2 induce necrosis, whereas late apoptosis is observed with 3 – 5 , 4 exhibiting a behaviour close to that of cisplatin.

Topics & Concepts

TerpyridineHeLaCisplatinChemistryCytotoxic T cellCopperStereochemistryMedicinal chemistryIn vitroMetalBiochemistryOrganic chemistryBiologyChemotherapyGeneticsMetal complexes synthesis and propertiesMetal-Organic Frameworks: Synthesis and ApplicationsSynthesis and Characterization of Heterocyclic Compounds