Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Five copper complexes supported by terpyridine ligands were prepared and characterized, viz. [Cu3Cl4(naphtpy)2][CuCl2] (1), [Cu2Cl2(naphtpy)2](ClO4)2 (2), [CuCl2(naphtpy)]2(MeOH)3(H2O) (3), [CuCl2(Cltpy)] (4) and [Cu(Cltpy)2](ClO4)2 (5); (where naphtpy stands for 4’‐((naphthalen‐2‐yl)methoxy)‐2,2′:6...

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Published in:Chembiochem : a European journal of chemical biology 2020-08, Vol.21 (16), p.2348-2355
Main Authors: Grau, Jordi, Caubet, Amparo, Roubeau, Olivier, Montpeyó, David, Lorenzo, Julia, Gamez, Patrick
Format: Article
Language:English
Subjects:
Adenocarcinoma
antineoplastic agents
Apoptosis
Cell death
Cervix
chemical nuclease
Cisplatin
Coordination compounds
Copper
Copper chloride
Copper compounds
Cytotoxicity
Necrosis
Ovarian cancer
Ovarian carcinoma
oxidative cleavage
Time dependence
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Summary:Five copper complexes supported by terpyridine ligands were prepared and characterized, viz. [Cu3Cl4(naphtpy)2][CuCl2] (1), [Cu2Cl2(naphtpy)2](ClO4)2 (2), [CuCl2(naphtpy)]2(MeOH)3(H2O) (3), [CuCl2(Cltpy)] (4) and [Cu(Cltpy)2](ClO4)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 IC50 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. Some things take time: How terpyridine‐based copper complexes inhibit cancer‐cell growth depends on the functional group para to the central pyridine ring. With naphthalen‐2‐yl, the activity after 24 h of incubation with cell lines is higher than that of cisplatin. With chlorine, the complexes are still almost inactive after 24 h, but their cytotoxicity increases dramatically after 72 h.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.202000154