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Iron(III) Catecholates for Cellular Imaging and Photocytotoxicity in Red Light
Author(s) -
Basu Uttara,
Pant Ila,
Khan Imran,
Hussain Akhtar,
Kondaiah Paturu,
Chakravarty Akhil R.
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402207
Subject(s) - hacat , chemistry , hela , saturated calomel electrode , medicinal chemistry , photochemistry , radical , perchlorate , benzene , electron paramagnetic resonance , nuclear chemistry , electrode , electrochemistry , organic chemistry , cell , nuclear magnetic resonance , working electrode , ion , biochemistry , in vitro , physics
Iron(III) complexes [Fe( L )( L′ )(NO 3 )]—in which L is phenyl‐ N , N ‐bis[(pyridin‐2‐yl)methyl]methanamine ( 1 ), (anthracen‐9‐yl)‐ N , N ‐bis[(pyridin‐2‐yl)methyl]methanamine ( 2 ), (pyreny‐1‐yl)‐ N , N ‐bis[(pyridin‐2‐yl)methyl]methanamine ( 3 – 5 ), and L′ is catecholate ( 1 – 3 ), 4‐ tert ‐butyl catecholate ( 4 ), and 4‐(2‐aminoethyl)‐benzene‐1,2‐diolate ( 5 )—were synthesized and their photocytotoxic properties examined. The five electron‐paramagnetic complexes displayed a Fe III /Fe II redox couple near −0.4 V versus a saturated calomel electrode (SCE) in DMF/0.1 m tetrabutylammonium perchlorate (TBAP). They showed unprecedented photocytotoxicity in red light (600–720 nm) to give IC 50 ≈15 μ M in various cell lines by means of apoptosis to generate reactive oxygen species. They were ingested in the nucleus of HeLa and HaCaT cells in 4 h, thereby interacting favorably with calf thymus (ct)‐DNA and photocleaving pUC19 DNA in red light of 785 nm to form hydroxyl radicals.