The Synthesis of Some Head to Head Linked 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, W.A. Wylie

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA by footprinting showed high affinity for compounds derived from 2,7-dihydrophenanthrene dicarboxylic acid and a predominant selectivity for AT rich regions containing at least 4 AT pairs but with the ability to span up to two CG base pairs.
LanguageEnglish
Pages5225-5239
Number of pages14
JournalInternational Journal of Chemical Research
Volume56
Issue number29
DOIs
Publication statusPublished - 14 Jul 2000

Fingerprint

Dicarboxylic Acids
Binders
Phenanthrenes
AT Rich Sequence
Indoles
DNA
Dimers
Amino Acids

Keywords

  • DNA
  • minor groove
  • lexitropsin dimer
  • synthesis

Cite this

Khalaf, A.I. ; Pitt, A.R. ; Scobie, M. ; Suckling, C.J. ; Urwin, J. ; Waigh, R.D. ; Young, S.C. ; Fishleigh, R.V. ; Wylie, W.A. / The Synthesis of Some Head to Head Linked DNA Minor Groove Binders. In: International Journal of Chemical Research. 2000 ; Vol. 56, No. 29. pp. 5225-5239.
@article{807aca556cea42418b5e1b257a76efca,
title = "The Synthesis of Some Head to Head Linked DNA Minor Groove Binders",
abstract = "A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA by footprinting showed high affinity for compounds derived from 2,7-dihydrophenanthrene dicarboxylic acid and a predominant selectivity for AT rich regions containing at least 4 AT pairs but with the ability to span up to two CG base pairs.",
keywords = "DNA, minor groove, lexitropsin dimer, synthesis",
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 and W.A. Wylie",
year = "2000",
month = "7",
day = "14",
doi = "10.1016/S0040-4020(00)00432-4",
language = "English",
volume = "56",
pages = "5225--5239",
journal = "International Journal of Chemical Research",
issn = "0975-3699",
number = "29",

}

Khalaf, AI, Pitt, AR, Scobie, M, Suckling, CJ, Urwin, J, Waigh, RD, Young, SC, Fishleigh, RV & Wylie, WA 2000, 'The Synthesis of Some Head to Head Linked DNA Minor Groove Binders' International Journal of Chemical Research, vol. 56, no. 29, pp. 5225-5239. https://doi.org/10.1016/S0040-4020(00)00432-4

The Synthesis of Some Head to Head Linked DNA Minor Groove Binders. / Khalaf, A.I.; Pitt, A.R.; Scobie, M.; Suckling, C.J.; Urwin, J.; Waigh, R.D.; Young, S.C.; Fishleigh, R.V.; Wylie, W.A.

In: International Journal of Chemical Research, Vol. 56, No. 29, 14.07.2000, p. 5225-5239.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The Synthesis of Some Head to Head Linked 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.

AU - Wylie, W.A.

PY - 2000/7/14

Y1 - 2000/7/14

N2 - A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA by footprinting showed high affinity for compounds derived from 2,7-dihydrophenanthrene dicarboxylic acid and a predominant selectivity for AT rich regions containing at least 4 AT pairs but with the ability to span up to two CG base pairs.

AB - A series of head to head linked dimers of heterocyclic amino acids has been prepared for investigation of affinity and selectivity in binding to the minor groove of DNA. The selection of targets for synthesis was led by computer based design. Several novel dicarboxylic acid linkers including indoles, phenanthrenes, a fluorenone, and a bisbenzothiophene have been included. Analysis of binding to DNA by footprinting showed high affinity for compounds derived from 2,7-dihydrophenanthrene dicarboxylic acid and a predominant selectivity for AT rich regions containing at least 4 AT pairs but with the ability to span up to two CG base pairs.

KW - DNA

KW - minor groove

KW - lexitropsin dimer

KW - synthesis

UR - http://dx.doi.org/10.1016/S0040-4020(00)00432-4

U2 - 10.1016/S0040-4020(00)00432-4

DO - 10.1016/S0040-4020(00)00432-4

M3 - Article

VL - 56

SP - 5225

EP - 5239

JO - International Journal of Chemical Research

T2 - International Journal of Chemical Research

JF - International Journal of Chemical Research

SN - 0975-3699

IS - 29

ER -