The synthesis of some head to head linked DNA minor groove binders

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

doi:10.1016/S0040-4020(00)00432-4

The synthesis of some head to head linked DNA minor groove binders

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

^*Corresponding author for this work

Analytical, Measurements and Physical Chemistry

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

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.

Original language	English
Pages (from-to)	5225-5239
Number of pages	15
Journal	Tetrahedron
Volume	56
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4020(00)00432-4
Publication status	Published - 14 Jul 2000

Keywords

DNA
Lexitropsin dimer
Minor groove
Synthesis

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10.1016/S0040-4020(00)00432-4

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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, Lexitropsin dimer, Minor groove, Synthesis",

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T1 - The synthesis of some head to head linked DNA minor groove binders

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, Steven C.

AU - Wylie, William 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 - Lexitropsin dimer

KW - Minor groove

KW - Synthesis

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

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

M3 - Article

AN - SCOPUS:0034647767

SN - 0040-4020

VL - 56

SP - 5225

EP - 5239

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

The synthesis of some head to head linked DNA minor groove binders

Abstract

Keywords

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