The synthesis of some indole-containing amino acids as linkers for the construction of DNA minor groove binders

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Khalaf, A.I. and Pitt, A.R. and Scobie, M. and Suckling, C.J. and Urwin, J. and Waigh, R.D. and Young, S.C. and Fishleigh, R.V. (2000) The synthesis of some indole-containing amino acids as linkers for the construction of DNA minor groove binders. International Journal of Chemical Research, 2000 (6). pp. 264-265. ISSN 0975-3699 (http://openurl.ingenta.com/content?genre=article&i...)

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Abstract

Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bis-netropsin analogues 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, 6-(2-carboxy-1-ethenyl)indole-2-carboxylic acid were prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido]dimethylaminopropane. Similarly indole-2,5-dicarboxylic acid was prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrple-2-carboxamido)pyrrole-2-carboxamido]propionamidine hydrochloride. The derivatives of 26-28 showed especially strong binding to AT rich regions as shown by footprinting studies.

ORCID iDs

Khalaf, A.I. ORCID logoORCID: https://orcid.org/0000-0001-9162-7527, Pitt, A.R., Scobie, M., Suckling, C.J., Urwin, J., Waigh, R.D., Young, S.C. and Fishleigh, R.V.;
CORE (COnnecting REpositories)