Synthesis of novel DNA binding agents: Indole-containing analogues of bis-netropsin

Abedawn I. Khalaf; Andrew R. Pitt; Martin Scobie; Colin J. Suckling; John Urwin; Roger D. Waigh; Robert V. Fishleigh; Stephen C. Young

doi:10.3184/030823400103167444

Synthesis of novel DNA binding agents: Indole-containing analogues of bis-netropsin

Abedawn I. Khalaf, Andrew R. Pitt, Martin Scobie, Colin J. Suckling^*, John Urwin, Roger D. Waigh, Robert V. Fishleigh, Stephen C. Young

^*Corresponding author for this work

Analytical, Measurements and Physical Chemistry

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

Abstract

Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bisnetropsin 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-methy-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	2
Journal	Journal of Chemical Research - Part S
Volume	2000
Issue number	6
DOIs	https://doi.org/10.3184/030823400103167444
Publication status	Published - Jun 2000

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@article{3449c3b28ee24ca7987a5dad56f1a61f,

title = "Synthesis of novel DNA binding agents: Indole-containing analogues of bis-netropsin",

abstract = "Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bisnetropsin 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-methy-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.",

author = "Khalaf, {Abedawn I.} and Pitt, {Andrew R.} and Martin Scobie and Suckling, {Colin J.} and John Urwin and Waigh, {Roger D.} and Fishleigh, {Robert V.} and Young, {Stephen C.}",

year = "2000",

month = jun,

doi = "10.3184/030823400103167444",

language = "English",

volume = "2000",

pages = "264--265",

journal = "Journal of Chemical Research - Part S",

issn = "0308-2342",

publisher = "Royal Society of Chemistry",

number = "6",

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TY - JOUR

T1 - Synthesis of novel DNA binding agents

T2 - Indole-containing analogues of bis-netropsin

AU - Khalaf, Abedawn I.

AU - Pitt, Andrew R.

AU - Scobie, Martin

AU - Suckling, Colin J.

AU - Urwin, John

AU - Waigh, Roger D.

AU - Fishleigh, Robert V.

AU - Young, Stephen C.

PY - 2000/6

Y1 - 2000/6

N2 - Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bisnetropsin 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-methy-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 bisnetropsin 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-methy-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.

UR - http://www.scopus.com/inward/record.url?scp=0033861554&partnerID=8YFLogxK

U2 - 10.3184/030823400103167444

DO - 10.3184/030823400103167444

M3 - Article

AN - SCOPUS:0033861554

SN - 0308-2342

VL - 2000

SP - 264

EP - 265

JO - Journal of Chemical Research - Part S

JF - Journal of Chemical Research - Part S

IS - 6

ER -

Synthesis of novel DNA binding agents: Indole-containing analogues of bis-netropsin

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