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Mitochondria‐Targeting Iron(III) Catecholates for Photoactivated Anticancer Activity under Red Light
Author(s) -
Basu Uttara,
Pant Ila,
Kondaiah Paturu,
Chakravarty Akhil R.
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201501105
Subject(s) - chemistry , moiety , perchlorate , catechol , saturated calomel electrode , photochemistry , semiquinone , medicinal chemistry , hela , hacat , radical , reactive oxygen species , stereochemistry , quinone , electrochemistry , organic chemistry , cell , ion , biochemistry , electrode , reference electrode , in vitro
Iron(III) catecholates [Fe(R′‐bpa)(R‐dopa)Cl] ( 1 , 2 ) with a triphenylphosphonium (TPP) moiety, where R′‐bpa is 2‐(TPP‐ N , N ‐bis((pyridin‐2‐yl)methyl)ethanamine) chloride (TPPbpa) and R‐dopa is 4‐{2‐[(anthracen‐9‐yl)methylamino]ethyl}benzene‐1,2‐diol (andopa, 1 ) or 4‐{2‐[(pyren‐1‐yl)‐methylamino]ethyl}benzene‐1,2‐diol (pydopa, 2 ), were synthesized and their photocytotoxicity studied. Complexes 3 and 4 with [phenyl‐ N , N ‐bis(pyridin‐2‐yl)methyl]methanamine (phbpa) were used as controls. The catecholate complexes showed an absorption band near 720 nm. The 5e – paramagnetic complexes showed a Fe III /Fe II irreversible response near –0.45 V and a quasi‐reversible catechol/semiquinone couple near 0.5 V versus saturated calomel electrode (SCE) in DMF/0.1 M tetrabutylammonium perchlorate. They showed photocytotoxicity in red/visible light in HeLa, HaCaT, MCF‐7, and A549 cells. Complexes 1 and 2 displayed mitochondrial localization, reactive oxygen species (ROS) generation under red light, and apoptotic cell death. Control complexes 3 and 4 exhibited uniform distribution throughout the cell. The complexes showed DNA photocleavage under red light (785 nm), forming hydroxyl radicals as the ROS.