Novel cationic fullerene derivatized s-triazine scaffolds

Novel cationic fullerene derivatized s-triazine scaffolds as photoinduced DNA cleavage agents: design, synthesis, biological evaluation and computational investigation

Manishkumar B. Patel,^a   Uma Harikrishnan,^a   Nikunj N. Valand,^a  Deval S. Mehta,^c   Kuldeep V. Joshi,^a  Sivakumar Prasanth Kumar,^b   Kishor H. Chikhalia,^a  Linz Buoy George,^c   Yogesh T. Jasrai^b and   Shobhana K. Menon*^a 

a. Department of Chemistry, University School of Sciences, Gujarat University, Navrangpura, India 
b. Department of Bioinformatics, Applied Botany Centre (ABC), University School of Sciences, Gujarat University, Navrangpura, India

c. Department of Zoology and Biomedical Technology, University School of Sciences, Gujarat University, Navrangpura, India

A series of novel cationic fullerene (C₆₀) derivatives, bearing substituted s-triazine moiety as a side arm, synthesized by using the 1,3 dipolar cycloaddition reaction of C₆₀ with azomethine ylides generated from the corresponding Schiff bases of substituted s-triazine is reported. All the synthesized compounds were characterized by elemental analysis, FT-IR, ¹H NMR, ¹³C NMR and ESI-MS. The compounds 7a, 7d, 7e and 7f cleaved the supercoiled pBR322 DNA into nicked form efficiently upon visible light irradiation in the presence of NADH. The photoinduced superoxide radical and hydroxyl radical generated may act as molecular species causing the DNA scission. Further, the interaction of synthesized molecules with pBR322 plasmid DNA was investigated using computational approaches.

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http://pubs.rsc.org/en/content/articlelanding/2013/ra/c3ra40950c