J. Iran. Chem. Soc., Vol. 6, No. 4 December 2009, pp.686~697.

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Aggregation and Solution Behavior of 5-(1-(4-Carboxybutyl) Pyridinum-4-yl) 10,15,20-tris (1-methylpyridinium-4-yl) Porphyrin: A Resonance Light Scattering, Fluorescence and Absorption Spectroscopic Study

H. Dezhampanaha,b, A.-K. Bordbara,* and S. Tangestaninejada

aLaboratory of Biophysical Chemistry, Department of Chemistry, University of  Isfahan, Hezar Jereeb Street, Isfahan, 81746-73441, Iran
bDepartment of Chemistry, Faculty of Science, Guilan University, P.O. Box 1914, Rasht 0098, Iran

Aggregation behavior of  water soluble porphyrins, 5-(1-(4-carboxybutyl) pyridinum-4-yl) 10,15,20-tris (1-methylpyridinium-4-yl) porphyrin (5-CBPyP) in the presence of various concentrations of calf thymus DNA (ct-DNA) and sodium chloride were studied in comparison with meso-tetrakis (4-N-methyl pyridinum) porphyrin (TMPyP), by optical absorption, fluorescence and resonance light scattering (RLS) spectroscopies. Both porphyrins obey Beer’s law in extended range of concentration. Optical absorption and RLS measurements demonstrated nonaggregation for both porphyrins under increasing concentration of ct-DNA and NaCl. However, in comparison, 5-CBPyP had less tendency for aggregation that may be taken as an advantage for its probable application in photodynamic therapy of cancer. The trend of changes in absorption spectra of both porphyrins in the presence of ct-DNA indicates the homogeneous intercalation binding mode. The values of (2.81 ± 0.28) × 106 M-1 and (0.95 ± 0.09) × 106 M-1 were obtained for apparent binding constant of TMPyP and 5-CBPyP from analysis of optical absorption data, respectively. This indicates the less affinity of 5-CBPyP to ct-DNA in comparison with TMPyP. The binding of both porphyrins to ct-DNA quenches fluorescence emission of Ethidium bromide (EB) that is bound to ct-DNA. The quenching process obeys linear Stern-Volmer relationship indicating the displacement of EB from its binding sites by these porphyrins. The results of this technique also represent the intercalation mode of binding for both porphyrins and higher binding affinity of TMPyP compared with 5-CBPyP. 

Keywords: Porphyrin, DNA, Aggregation, Optical absorption, Resonance light scattering, Fluorescence

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