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The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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

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

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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.