A Fluorinated Ruthenium Porphyrin as a Potential Photodynamic Therapy Agent: Synthesis, Characterization, DNA Binding, and Melanoma Cell Studies

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Abstract

When the new porphyrin 5,10-(4-pyridyl)-15,20-(pentafluorophenyl)porphyrin is reacted with 2 equiv of Ru(bipy)(2)Cl(2) (where bipy = 2,2'-bipyridine) formation of the target ruthenated porphyrin is achieved with 40% yield. Strong electronic transitions are observed in the visible region of the spectrum associated with the porphyrin Soret and four Q-bands. A shoulder at slightly higher energy than the Soret band is attributed to the Ru(dpi) to bipy(pi*) metal to ligand charge transfer (MLCT) band. The bipyridyl pi to pi* transition occurs at 295 nm. Cyclic voltammetry experiments reveal two single-electron redox couples in the cathodic region at E(1/2) = -0.80 and -1.18 V vs Ag/AgCl associated with the porphyrin. Two overlapping redox couples at E(1/2) = 0.83 V vs Ag/AgCl due to the Ru(III/II) centers is also observed. DNA titrations using calf thymus (CT) DNA and the ruthenium porphyrin give a K(b) = 7.6 x 10(5) M(-1) indicating a strong interaction between complex and DNA. When aqueous solutions of supercoiled DNA and ruthenium porphyrin are irradiated with visible light (energy lower than 400 nm), complete nicking of the DNA is observed. Cell studies show that the ruthenated porphyrin is more toxic to melanoma skin cells than to normal fibroblast cells. When irradiated with a 60 W tungsten lamp, the ruthenium porphyrin preferentially leads to apoptosis of the melanoma cells over the normal skin cells.

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