Configurationally restricted bismacrocyclic CXCR4 receptor antagonists

Gina C. Valks; Graeme McRobbie; Elizabeth A. Lewis; Timothy J. Hubin; Tina M. Hunter; Peter J. Sadler; Christophe Pannecouque; Erik De Clercq; Stephen J. Archibald

doi:10.1021/jm0607810

Configurationally restricted bismacrocyclic CXCR4 receptor antagonists

Gina C. Valks, Graeme McRobbie, Elizabeth A. Lewis, Timothy J. Hubin, Tina M. Hunter, Peter J. Sadler, Christophe Pannecouque, Erik De Clercq, Stephen J. Archibald^*

^*Corresponding author for this work

Imaging Chemistry & Biology

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Abstract

A zinc(II) containing configurationally restricted analogue of bismacrocyclic cyclam-type CXCR4 chemokine receptor antagonists has been synthesized and shown to adopt only one configuration in solution. The single crystal X-ray structure reveals favorable binding to acetate via a bidentate chelation that can be related to the proposed interaction with aspartate on the receptor protein surface. The zinc(II) complex is highly active against HIV infection in vitro.

Original language	English
Pages (from-to)	6162-6165
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	49
Issue number	21
DOIs	https://doi.org/10.1021/jm0607810
Publication status	Published - Oct 2006

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10.1021/jm0607810

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title = "Configurationally restricted bismacrocyclic CXCR4 receptor antagonists",

abstract = "A zinc(II) containing configurationally restricted analogue of bismacrocyclic cyclam-type CXCR4 chemokine receptor antagonists has been synthesized and shown to adopt only one configuration in solution. The single crystal X-ray structure reveals favorable binding to acetate via a bidentate chelation that can be related to the proposed interaction with aspartate on the receptor protein surface. The zinc(II) complex is highly active against HIV infection in vitro.",

author = "Valks, {Gina C.} and Graeme McRobbie and Lewis, {Elizabeth A.} and Hubin, {Timothy J.} and Hunter, {Tina M.} and Sadler, {Peter J.} and Christophe Pannecouque and {De Clercq}, Erik and Archibald, {Stephen J.}",

year = "2006",

month = oct,

doi = "10.1021/jm0607810",

language = "English",

volume = "49",

pages = "6162--6165",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

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T1 - Configurationally restricted bismacrocyclic CXCR4 receptor antagonists

AU - Valks, Gina C.

AU - McRobbie, Graeme

AU - Lewis, Elizabeth A.

AU - Hubin, Timothy J.

AU - Hunter, Tina M.

AU - Sadler, Peter J.

AU - Pannecouque, Christophe

AU - De Clercq, Erik

AU - Archibald, Stephen J.

PY - 2006/10

Y1 - 2006/10

N2 - A zinc(II) containing configurationally restricted analogue of bismacrocyclic cyclam-type CXCR4 chemokine receptor antagonists has been synthesized and shown to adopt only one configuration in solution. The single crystal X-ray structure reveals favorable binding to acetate via a bidentate chelation that can be related to the proposed interaction with aspartate on the receptor protein surface. The zinc(II) complex is highly active against HIV infection in vitro.

AB - A zinc(II) containing configurationally restricted analogue of bismacrocyclic cyclam-type CXCR4 chemokine receptor antagonists has been synthesized and shown to adopt only one configuration in solution. The single crystal X-ray structure reveals favorable binding to acetate via a bidentate chelation that can be related to the proposed interaction with aspartate on the receptor protein surface. The zinc(II) complex is highly active against HIV infection in vitro.

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U2 - 10.1021/jm0607810

DO - 10.1021/jm0607810

M3 - Article

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AN - SCOPUS:33750132891

SN - 0022-2623

VL - 49

SP - 6162

EP - 6165

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 21

ER -

Configurationally restricted bismacrocyclic CXCR4 receptor antagonists

Abstract

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