Mitochondria-targeted photoinduced anticancer activity of oxidovanadium(IV) complexes of curcumin in visible light

Puja Prasad, Ila Pant, Imran Khan, Paturu Kondaiah, Akhil R. Chakravarty

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Oxidovanadium(IV) complexes [VO(py-aebmz)(B)]Cl (1, 2) and [VO(napth-py-aebmz)(cur)]Cl [3; py-aebmz = 2-(1H-benzimidazol-2-yl)-N-(pyridin- 2-ylmethylene)ethanamine, HB = acetylacetone (Hacac, 1) and curcumin (Hcur, 2), napth-py-aebmz = naphthalimide conjugated to py-aebmz ] have been prepared, characterized and their photoinduced DNA cleavage activities and photocytotoxicities studied. Complexes 1-3 each exhibited an irreversible cyclic voltammetric response of the VIV/VIII redox couple at around -0.85 V versus SCE in dmf/0.1 M tbap. The complexes showed DNA photocleavage activity in visible light of 454, 530 and 647 nm through hydroxyl radical and singlet oxygen pathways. Fluorescence microscopy data suggest mitochondrial localization of complex 3 bearing a naphthalimide with a two-fold increase in photocytotoxicity in HaCaT cells with an IC50 value of 6.3 μM and a three-fold increase in MCF-7 cells with an IC50 of 5.4 μM compared with complex 2. Both 2 and 3 were non-toxic in the dark. A Schiff-base oxidovanadium(IV) complex of curcumin bearing a pendant naphthalimide specifically targets cellular mitochondria and exhibits remarkable photocytotoxicity in visible light with low dark toxicity in keratinocyte HaCaT and breast cancer MCF-7 cells. The apoptotic cell death involves 1O2 and ·OH species.

Original languageEnglish
Pages (from-to)2420-2431
Number of pages12
JournalEuropean Journal of Inorganic Chemistry
Issue number14
DOIs
StatePublished - May 2014
Externally publishedYes

Keywords

  • Anticancer agents
  • Bioinorganic chemistry
  • Ligand effects
  • Medicinal chemistry
  • Vanadium

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