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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.

Item type: Article
ID code: 716
Keywords: indole dicarboxylic acids, synthesis DNA binding agents, indole-containing analogues, bis-netropsin, Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Unknown Department
Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
Related URLs:
    Depositing user: Allison Crawford
    Date Deposited: 11 Apr 2006
    Last modified: 16 Jul 2013 17:36
    URI: http://strathprints.strath.ac.uk/id/eprint/716

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