Substituent effect on the preferred DNA binding mode and affinity of a homologous series of naphthalene diimides |
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| Authors: | McKnight Ruel E Reisenauer Eric Pintado Manuel V Polasani Shivani R Dixon Dabney W |
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| Institution: | a Department of Chemistry, State University of New York at Geneseo, 1 College Circle, Geneseo, NY 14454, USA
b Department of Chemistry, Georgia State University, PO Box 4098, Atlanta, GA 30302, USA |
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| Abstract: | A combination of isothermal titration calorimetry (ITC), topoisomerase I DNA unwinding assays, and ethidium bromide displacement studies were employed to investigate the binding of a homologous series of naphthalene diimides (NDI) to DNA. Our results suggest that the nature of the substituent plays a significant role in both the preferred binding mode and relative binding affinity of the compounds of this study. Only intercalative-type binding (K = 15 ± 3 × 106 M−1) was observed for the NDI with the smallest substituent (trimethyl-ethylamino), while larger members of the series (diethylmethyl-, dipropylmethyl- and dibutylmethyl-ethylamino substituents) adopted an additional binding mode of higher affinity (K1 = 31 − 78 × 106 M−1). |
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| Keywords: | Isothermal titration calorimetry Topoisomerase I assay Naphthalene diimide DNA binding constant Intercalation |
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