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Book of Abstracts - Ruhr-Universität Bochum

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P-34<br />

ISBOMC `10 5.7 – 9.7. 2010 <strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong><br />

Photocytotoxicity and DNA Cleavage Activity <strong>of</strong> 2-Ferrocenyl Adducts having<br />

Imidazophenanthroline and Imidazophenanthrene Moieties<br />

Basudev Maity, a Mithun Roy, a Sounik Saha, a Ritankar Majumdar, b Rajan R. Dighe, b and Akhil R.<br />

Chakravarty* a<br />

a Indian Institute <strong>of</strong> Science, Department <strong>of</strong> Inorganic and Physical Chemistry, b Department <strong>of</strong><br />

Molecular Reproduction, Development and Genetics, Sir C V Raman avenue, 560012, Bangalore,<br />

India. E-mail: basudev@ipc.iisc.ernet.in<br />

Ferrocene is an important constituent in the field <strong>of</strong> bioorganometallic chemistry related to nucleic<br />

acids in spite <strong>of</strong> having any effective anticancer activity. 1 It is the ferrocenium cation, the oxidized<br />

form <strong>of</strong> ferrocene, which is responsible for the anticancer activity. 2 The designing <strong>of</strong> new ferrocenebased<br />

molecules showing photo-induced DNA cleavage and/or photocytotoxic activities are <strong>of</strong><br />

interests for their potential applications in the field <strong>of</strong> molecular biology, biotechnology and<br />

particularly in medicine. This presentation includes the synthesis, characterization, interactions with<br />

DNA, photo-induced DNA cleavage activity and photocytotoxicity <strong>of</strong> 2-ferrocenylimidazophenanthroline<br />

(1) 3 and 2-ferrocenyl-imidazophenanthrene (2). To understand the role <strong>of</strong> the<br />

ferrocenyl moiety, 2-phenyl-imidazophenanthroline (3) 4 has been studied as a control species.<br />

Compound 2 has been characterized by X-ray crystallography. The interaction <strong>of</strong> the compounds with<br />

DNA has been studied by UV-visible absorption titration and thermal denaturation methods. All the<br />

compounds show good binding affinity to calf thymus DNA with intrinsic binding constant values <strong>of</strong><br />

~10 5 M -1 . The thermal denaturation data suggest DNA groove binding nature <strong>of</strong> the compounds. They<br />

show poor chemical nuclease activity in the presence <strong>of</strong> H2O2 as an oxidizing agent and are inactive in<br />

the presence <strong>of</strong> cellular reducing agent glutathione. Compound 1 shows significant photo-induced<br />

DNA cleavage activity in UV-A light <strong>of</strong> 365 nm and visible light <strong>of</strong> 488 (blue light) and 530 nm<br />

(green light). The mechanistic investigations <strong>of</strong> the DNA cleavage activity reveal the involvement <strong>of</strong><br />

reactive oxygen species. The photocytotoxicity <strong>of</strong> the compounds in human cervical HeLa cancer cell<br />

line has been studied in UV-A light <strong>of</strong> 365 nm.<br />

References<br />

1. D. R. van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985.<br />

2. G. Tabbì, C. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I.Viano, D. Osella, J. Med. Chem.<br />

2002, 45, 5786-5796.<br />

3. F. Zapata, A. Caballero, A. Espinosa, A. Tárraga, P. Molina, J. Org. Chem. 2008, 73, 4034–4044.<br />

4. N. M. Shavaleev, H. Adams, J. A. Weinstein, Inorg. Chim. Acta 2007, 360, 700–704.<br />

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