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

A.I. Khalaf; A.R. Pitt; M. Scobie; C.J. Suckling; J. Urwin; R.D. Waigh; S.C. Young; R.V. Fishleigh

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

A.I. Khalaf, A.R. Pitt, M. Scobie, C.J. Suckling, J. Urwin, R.D. Waigh, S.C. Young, R.V. Fishleigh

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	264-265
Number of pages	1
Journal	International Journal of Chemical Research
Volume	2000
Issue number	6
Publication status	Published - 1 Jun 2000

Keywords

indole dicarboxylic acids
synthesis DNA binding agents
indole-containing analogues
bis-netropsin

Cite this

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

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.",

keywords = "indole dicarboxylic acids, synthesis DNA binding agents, indole-containing analogues, bis-netropsin",

author = "A.I. Khalaf and A.R. Pitt and M. Scobie and C.J. Suckling and J. Urwin and R.D. Waigh and S.C. Young and R.V. Fishleigh",

year = "2000",

month = jun,

day = "1",

language = "English",

volume = "2000",

pages = "264--265",

journal = "International Journal of Chemical Research",

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TY - JOUR

T1 - The synthesis of some indole-containing amino acids as linkers for the construction of DNA minor groove binders

AU - Khalaf, A.I.

AU - Pitt, A.R.

AU - Scobie, M.

AU - Suckling, C.J.

AU - Urwin, J.

AU - Waigh, R.D.

AU - Young, S.C.

AU - Fishleigh, R.V.

PY - 2000/6/1

Y1 - 2000/6/1

N2 - 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.

AB - 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.

KW - indole dicarboxylic acids

KW - synthesis DNA binding agents

KW - indole-containing analogues

KW - bis-netropsin

UR - http://openurl.ingenta.com/content?genre=article&issn=0308-2342&volume=2000&issue=6&spage=264&epage=265

M3 - Article

SN - 0975-3699

VL - 2000

SP - 264

EP - 265

JO - International Journal of Chemical Research

JF - International Journal of Chemical Research

IS - 6

ER -

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

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