Iron(III) Catecholates for Cellular Imaging and Photocytotoxicity in Red Light. Issue 9 (14th July 2014)

• Record Type: Journal Article
• Authors: Basu, Uttara; Pant, Ila; Khan, Imran; Hussain, Akhtar; Kondaiah, Paturu; Chakravarty, Akhil R.
• Is Part Of: Chemistry, an Asian journal. Volume 9:Issue 9(2014:Sep.)
• Page Start: 2494
• Page End: 2504
• Publication Date: 2014-07-14
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201402207
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Iron(III) complexes [Fe(<bold>L</bold>)(<bold>L′</bold>)(NO<sub>3</sub>)]—in which <bold>L</bold> is phenyl‐<italic>N</italic>, <italic>N</italic>‐bis[(pyridin‐2‐yl)methyl]methanamine (<bold>1</bold>), (anthracen‐9‐yl)‐<italic>N</italic>, <italic>N</italic>‐bis[(pyridin‐2‐yl)methyl]methanamine (<bold>2</bold>), (pyreny‐1‐yl)‐<italic>N</italic>, <italic>N</italic>‐bis[(pyridin‐2‐yl)methyl]methanamine (<bold>3</bold>, <bold>4</bold>, <bold>5</bold>), and <bold>L′</bold> is catecholate (<bold>1</bold>, <bold>2</bold>, <bold>3</bold>), 4‐<italic>tert</italic>‐butyl catecholate (<bold>4</bold>), and 4‐(2‐aminoethyl)‐benzene‐1, 2‐diolate (<bold>5</bold>)—were synthesized and their photocytotoxic properties examined. The five electron‐paramagnetic complexes displayed a Fe<sup>III</sup>/Fe<sup>II</sup> redox couple near −0.4 V versus a saturated calomel electrode (SCE) in DMF/0.1 <sc>m</sc> tetrabutylammonium perchlorate (TBAP). They showed unprecedented photocytotoxicity in red light (600–720 nm) to give IC<sub>50</sub>≈15 μ<sc>M</sc> in various cell lines by means of apoptosis to generate <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">reactive oxygen species</named-content>. 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.</p> </abstract>