Mitochondria‐Targeting Iron(III) Catecholates for Photoactivated Anticancer Activity under Red Light. Issue 7 (2nd February 2016)

• Record Type: Journal Article
• Authors: Basu, Uttara; Pant, Ila; Kondaiah, Paturu; Chakravarty, Akhil R.
• Is Part Of: European journal of inorganic chemistry. Issue 7(2016)
• Page Start: 1002
• Page End: 1012
• Publication Date: 2016-02-02
• Subjects: Bioinorganic chemistry -- Medicinal chemistry -- Anticancer agents -- Iron -- Mitochondrial localization; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejic.201501105
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract: 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. Complexes3 and4 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/0.1M tetrabutylammonium perchlorate. They showed photocytotoxicity in red/visible light in HeLa, HaCaT, MCF‐7, and A549 cells. Complexes1 and2 displayed mitochondrial localization, reactive oxygen species (ROS) generation under red light, and apoptotic cell death. Control complexes3 and4 exhibited uniform distribution throughout the cell. The complexes showed DNA photocleavage under red light (785 nm), forming hydroxyl radicals as the ROS. Abstract : Iron(III) catecholates bearing anthracenyl or pyrenyl groups and a dipicolylamine base with a cationic triphenylphosphonium (TPP) moiety show remarkable photocytotoxicity under red light, mitochondrial localization, reactive oxygen species (ROS) generation, and apoptotic cell death. They showed significant DNA photocleavage activity under red light (785 nm), forming hydroxyl radicals as the ROS.