Synthesis of analogues of a flexible thiopyrylium photosensitizer for purging blood-borne pathogens and binding mode and affinity studies of their complexes with DNA |
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Authors: | McKnight Ruel E Ye Mao Ohulchanskyy Tymish Y Sahabi Sadia Wetzel Bryan R Wagner Stephen J Skripchenko Andrey Detty Michael R |
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Institution: | Department of Chemistry, State University of New York at Geneseo, 1 College Circle, Geneseo, NY 14454, USA. mcknight@geneseo.edu |
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Abstract: | A series of thio- and selenopyrylium analogues of 2,4-di(4-dimethylaminophen-yl)-6-methylthiopyrylium iodide were prepared in five steps from 4-dimethylaminophenyl-propargyl aldehyde and the corresponding lithium acetylide. When bound to DNA, all of the dyes absorb at wavelengths >600nm, which avoids the hemoglobin band I maximum at 575nm. The binding of the series of dyes to double-stranded DNA was examined spectrophotometrically and by isothermal titration calorimetry to determine binding constants, by a topoisomerase I DNA unwinding assay, by competition dialysis with poly(dGdC)](2) and poly(dAdT)](2), and by ethidium bromide displacement studies to examine propensities for intercalation, and by circular dichroism studies. The dyes were found to show mixed binding modes. |
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