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Photocytotoxic Activity of Copper(II) and Zinc(II) Complexes of Curcumin and (Acridinyl)dipyridophenazine

Mukherjee, Nandini and Raghavan, Abinaya and Podder, Santosh and Majumdar, Shamik and Kumar, Arun and Nandi, Dipankar and Chakravarty, Akhil R (2019) Photocytotoxic Activity of Copper(II) and Zinc(II) Complexes of Curcumin and (Acridinyl)dipyridophenazine. In: CHEMISTRYSELECT, 4 (33). pp. 9647-9658.

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Official URL: https://dx.doi.org/10.1002/slct.201902281

Abstract

Copper(II) and zinc(II) beta-diketonates of N,N-donor ligands, viz. Cu(dppz)(cur)](NO3) (1), Cu(acdppz)(cur)](NO3) (2), Cu(acdppz) (acac)](NO3) (3), Zn(dppz)(cur)](NO3) (4) and Zn(acdppz)(cur)] (NO3) (5), where dppz is dipyrido3,2-a:2',3'-c]phenazine, acdppz is 11-(9-acridinyl)dipyrido3,2-a:2',3'-c]phenazine, cur and acac are mono-deprotonated curcumin (Hcur) and acetyl acetone (Hacac), were synthesized, characterized and their photocytotoxicity studied. An analogue of complex 3, viz. Cu(acdppz) (acac)(H2O)]Cl 1/2 (NO3) 1= 2 (3a), structurally characterized by X-ray crystallography, has a cationic complex in square-pyramidal geometry with CuN2O3 core with an axial aqua ligand. Complexes 1, 2, 4 and 5 displayed emission at similar to 520 nm (lambda(exc): 430 nm) in dimethyl sulfoxide (DMSO) giving a fluorescence quantum yield value within 0.01-0.06. The complexes, in contrast to free curcumin, were fairly stable in cellular media up to 36 h, with no apparent degradation of the bound curcumin. The complexes were photocytotoxic (IC50: 0.3 4.5 mu M) in human cervical cancer (HeLa), breast cancer (MCF-7) and liver cancer (HepG2) cells. The apoptotic cell death is due to reactive oxygen species formation. Complexes 2 and 5 showed significant uptake in HeLa cells, localizing predominantly in the cytoplasm. Mechanistic data from the pUC19 DNA photocleavage study suggest involvement of acridine and curcumin in photo-generation of singlet oxygen and hydroxyl radicals as the ROS in light of 400-700 nm.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to WILEY-V C H VERLAG GMBH
Keywords: Acridine photosensitizer; Antitumor agents; Copper; Curcumin; Zinc
Department/Centre: Division of Biological Sciences > Biochemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 07 Jan 2020 11:49
Last Modified: 07 Jan 2020 11:49
URI: http://eprints.iisc.ac.in/id/eprint/63856

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