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Synthesis of novel DNA binding agents: indole-containing analogs of bis-netropsin

Khalaf, Abedawn I. and Pitt, Andrew R. and Scobie, Martin and Suckling, Colin J. and Urwin, John and Waigh, Roger D. and Fishleigh, Robert V. and Young, Stephen C. (2000) Synthesis of novel DNA binding agents: indole-containing analogs of bis-netropsin. International Journal of Chemical Research (6). pp. 264-265. ISSN 0975-3699

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Mol. modeling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bisnetropsin analogs with a good fit to the minor groove of DNA. To test this hypothesis, 2-carboxyindole-6-acetic acid, indole-2,6-dicarboxylic acid, 6-(2-carboxyethyl)indole-2-carboxylic acid, and 6-(2-carboxy-1-ethenyl)indole-2-carboxylic acid were prepd. and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido]dimethylaminopropane. Similarly, indole-2,5-dicarboxylic acid was prepd. and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido]propionamidine hydrochloride. Some derivs. showed esp. strong binding at AT rich regions as shown by footprinting studies.