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Co(II) complexes of curcumin and a ferrocene-based curcuminoid: a study on photo-induced antitumor activity

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Abstract

Co(II) complexes having a ferrocene-based curcuminoid (Fc-curH) ligand viz. [Co(L)2(Fc-cur)]ClO4 (1, 2), where L is phenanthroline base, namely, 1,10-phenanthroline (phen in 1) and dipyrido[3,2-a:2’,3’-c]phenazine (dppz in 2) have been synthesized, characterized and evaluated as photochemotherapeutic agents in vitro. The corresponding Co(II) complexes of the naturally occurring polyphenol curcumin (curH), namely, [Co(L)2(cur)]ClO4 (3, 4), where L is phen (in 3) and dppz (in 4) were synthesized and their photo-induced anticancer activities compared with their ferrocene containing counterparts 1 and 2. The Co(II) acetylacetonato complex viz. [Co(phen)2(acac)]ClO4 (5) was structurally characterized through X-ray crystallography and used as control for cellular experiments. The Co(II) complexes having ferrocene-based curcuminoid are remarkably stable at physiological condition with higher lipophilicity compared to their curcumin analogues. The complexes display significant binding propensity to calf thymus (ct) DNA and human serum albumin (HSA). The complexes 14 display remarkable visible light induced cytotoxicity with the ferrocenyl analogues showing more phototoxic index (PI). The Co(II) curcumin complexes localize in the nucleus and mitochondria of A549 cells. The primary cell death mechanism is believed to be apoptotic in nature induced by light assisted generation of reactive oxygen species (ROS).

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Acknowledgements

We are greatful to Department of Science and Technology (DST) INSPIRE Program, Government of India for financial support (IFA14-CH-164). The authors thank DST and Department of SAIF, Gauhati University for a CCD difractometer facility. We are thankful to Dr. Ranjit Thakuria for his kind help in X-ray crystallographic procedures. The authors sincerely thank Prof. A. R. Chakravarty, Indian Institute of Science, Bangalore for allowing us to use his cell culture facility.

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The original online version of this article was revised due to correction in figure 6

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Das, D., Noor, A., Raza, M.K. et al. Co(II) complexes of curcumin and a ferrocene-based curcuminoid: a study on photo-induced antitumor activity. J Biol Inorg Chem 26, 881–893 (2021). https://doi.org/10.1007/s00775-021-01899-z

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