Synthesis of meso-(4′-cyanophenyl) porphyrins: efficient photocytotoxicity against A549 cancer cells and their DNA interactions

Dalip Kumar; Bhupendra Mishra; K. P. Chandrashekar; Santosh B. Khandagale; Mukund P. Tantak; Anil Kumar; Kanako Akamatsu; Eriko Kusaka; Kazuhito Tanabe; Takeo Ito

doi:10.1039/C5RA03075G

Synthesis of meso-(4′-cyanophenyl) porphyrins: efficient photocytotoxicity against A549 cancer cells and their DNA interactions†

Dalip Kumar,*^a Bhupendra Mishra,^a K. P. Chandrashekar,^a Santosh B. Khandagale,^a Mukund P. Tantak,^a Anil Kumar,^a Kanako Akamatsu,^b Eriko Kusaka,^b Kazuhito Tanabe^b and Takeo Ito*^b

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* Corresponding authors

^a Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, India
E-mail: E-dalipk@pilani.bits-pilani.ac.in

^b Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
E-mail: takeoito.kyoto@gmail.com

Abstract

We report a facile iodine(III)-mediated synthesis of cyanoporphyrins and their DNA photocleavage activity. Cationic-porphyrin 9a showed intercalative binding towards DNA, whereas Zn(II)-cyanoporphyrinate 9b showed outside electrostatic binding as indicated by their absorption and emission spectra. Porphyrin 9a displayed significant photocytotoxicity against A549 cancer cell line with an IC₅₀ value of 54 nM.

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Synthesis of meso-(4′-cyanophenyl) porphyrins: efficient photocytotoxicity against A549 cancer cells and their DNA interactions†

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Synthesis of meso-(4′-cyanophenyl) porphyrins: efficient photocytotoxicity against A549 cancer cells and their DNA interactions

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