DNA-binding and in vitro cytotoxic activity of platinum(II) complexes of curcumin and caffeine.

Abstract:

:Three Pt(II) complexes containing the natural ligands curcumin and caffeine, namely [Pt(curc)(PPh3)2]Cl (1), [PtCl(curc)(DMSO)] (2) (curc = deprotonated curcumin) and trans-[Pt(caffeine)Cl2(DMSO)] (3), were synthesized and fully characterized. The data obtained suggest that, for both 1 and 2, the anion of curcumin is coordinated to the platinum ion via the oxygen atoms of the β-diketonate moiety. Spectroscopic features reveal that in 2 and 3, a DMSO molecule is S-bonded to the metal centre. For 3, all data indicate a square-planar geometry formed by a 9-N bonded caffeine, two trans chloride anions and a DMSO. The three complexes undergo changes in solution upon incubation for 24 h; 1 and 2 release curcumin while 3 isomerizes from trans to cis configuration. The DNA-binding and cytotoxic properties of 1-3 were evaluated in vitro. Despite their structural similarity, curcuminate-containing 1 and 2 exhibit distinct DNA interactions. While 1 appears to intercalate between nucleobase pairs, inducing the oxidative degradation of the biomolecule, 2 behaves as a groove binder, by means of electrostatic forces. Caffeine-containing 3 exhibits a behaviour that is comparable to that of 2. Complexes 1 and 2 showed moderate to high cytotoxicity and selectivity against several cancer cell lines, while 3 is inactive. Compounds 1 and 2 can be further activated by visible-light irradiation.

journal_name

J Inorg Biochem

authors

Censi V,Caballero AB,Pérez-Hernández M,Soto-Cerrato V,Korrodi-Gregório L,Pérez-Tomás R,Dell'Anna MM,Mastrorilli P,Gamez P

doi

10.1016/j.jinorgbio.2019.110749

subject

Has Abstract

pub_date

2019-09-01 00:00:00

pages

110749

eissn

0162-0134

issn

1873-3344

pii

S0162-0134(19)30086-8

journal_volume

198

pub_type

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