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Mitochondria targeting Photocytotoxic Oxidovanadium(IV) Complexes of Curcumin and (Acridinyl)dipyridophenazine in Visible Light
Author(s) -
Banerjee Samya,
Prasad Puja,
Khan Imran,
Hussain Akhtar,
Kondaiah Paturu,
Chakravarty Akhil R.
Publication year - 2014
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201300569
Subject(s) - chemistry , aqueous solution , phenazine , singlet oxygen , hela , nuclear chemistry , photochemistry , visible spectrum , stereochemistry , curcumin , medicinal chemistry , oxygen , in vitro , biochemistry , organic chemistry , materials science , optoelectronics
Oxidovanadium(IV) complexes, [VO(acac)(L)Cl] ( 1 ), [VO(cur)(L)Cl] ( 2 ), and [VO(scur)(L)Cl] ( 3 ) {acac = acetylacetonate, cur = curcumin monoanion, scur = diglucosylcurcumin monoanion, L = 11‐(9‐acridinyl)dipyrido[3, 2‐a:2',3'‐c]phenazine (acdppz)}, were prepared and characterized. The complexes are non‐electrolytic in DMF and 1:1 electrolytic in aqueous DMF. The one‐electron paramagnetic complexes showed a d‐d band near 725 nm in aqueous DMF and green emission near 520 nm in aqueous DMSO. The complexes exhibited an irreversible V IV /V III redox response near –0.85 V versus SCE in aqueous DMF. The complexes showed good binding strengths to calf thymus DNA ( K b : 3.1 × 10 5 –9.6 × 10 5 M –1 ) and efficient pUC19 DNA photocleavage activity in red light of 705 and 785 nm by singlet oxygen ( 1 O 2 ) pathway. Complexes 1 and 2 exhibited significant photocytotoxicity (IC 50 : 0.1–1.0 μM) in visible light (400–700 nm) with low dark toxicity (IC 50 : >20 μM) in HeLa and HaCaT cells. Complex 3 was cytotoxic in both light and dark. DNA ladder formation experiments indicated cell death via apoptotic pathway. Confocal microscopy done with 1 and 2 revealed primarily cytosolic localization of the complexes with significant presence of the complex in the mitochondria as evidenced from the imaging data using mitotracker red.