Iron(III) Complexes of Vitamin B-6 Schiff Base with Boron-Dipyrromethene Pendants for Lysosome-Selective Photocytotoxicity

Sahoo, Somarupa and Podder, Santosh and Garai, Aditya and Majumdar, Shamik and Mukherjee, Nandini and Basu, Uttara and Nandi, Dipankar and Chakravarty, Akhil R (2018) Iron(III) Complexes of Vitamin B-6 Schiff Base with Boron-Dipyrromethene Pendants for Lysosome-Selective Photocytotoxicity. In: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (13). pp. 1522-1532.

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Abstract

Iron(III) complexes of a vitamin B-6 Schiff base and NNN-donor ligands with pendant boron-dipyrromethene (BODIPY) moieties; namely, Fe(L1-3)(L-4,L-5)](NO3) (1-4), where L-1 is benzyl-bis(pyridin-2-yl)methyl]methanamine (bzdpa in 1), L-2 is a noniodinated BODIPY-appended dipicolylamine ligand (in 2, 3), L-3 is the diiodinated BODIPY analogue in 4, L-4 is a vitamin B-6 Schiff base, namely 3-hydroxy-5(hydroxymethyl)-4-{(2-hydroxyphenyl)imino]methyl}-2-meth ylpyridine (in 1, 3, and 4), and L-5 is 2-(2-hydroxyphenylimino)-methyl]phenol (in 2) as a nonpyridoxal Schiff base, were prepared, characterized, and their cellular localization and cytotoxic activity in light and in the dark were studied. The diiodo-BODIPY complex 4 displays remarkable photoinduced cytotoxicity in visible light (400-700 nm), with IC50 values within 0.11-0.25 mu m and about 200-fold lower dark toxicity. Complex 3, being fluorescent, was used for cellular imaging by confocal microscopy. Complex 4 shows supercoiled pUC19 DNA cleavage activity through the generation of singlet oxygen (O-1(2)) as the reactive oxygen species (ROS). Selective uptake of the complexes is observed from competitive cellular incorporation assays in cancer and noncancer cells. The complexes also show no apparent toxicity up to 100 mu m in the immortal human lung epithelial cells HPL1D in both light and the dark. Complex 3 shows preferential accumulation in lysosomes, giving a Pearson's correlation coefficient value of about 0.7.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Additional Information:	Copy right for this article belong to WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Department/Centre:	Division of Biological Sciences > Biochemistry Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	04 May 2018 18:48
Last Modified:	04 May 2018 18:48
URI:	http://eprints.iisc.ac.in/id/eprint/59731

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