A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity

Oliver Demmer; Andreas O. Frank; Franz Hagn; Margret Schottelius; Luciana Marinelli; Sandro Cosconati; Ruth Brack-Werner; Stephan Kremb; Hans Jürgen Wester; Horst Kessler

doi:10.1002/anie.201202090

A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity

Oliver Demmer, Andreas O. Frank, Franz Hagn, Margret Schottelius, Luciana Marinelli, Sandro Cosconati, Ruth Brack-Werner, Stephan Kremb, Hans Jürgen Wester, Horst Kessler

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

50 Scopus citations

Abstract

There can be only one: Using a peptoid motif obtained by shifting the arginine side chain of a pentapeptide previously developed by Fujii et al. to the neighboring nitrogen atom restricts the conformational freedom and yields a conformationally homogeneous peptide (see picture) with a 100-fold higher binding affinity to the chemokine receptor CXCR4 in the picomolar range. Its efficiency to inhibit HIV-1 infections is also demonstrated.

Original language	English
Pages (from-to)	8110-8113
Number of pages	4
Journal	Angewandte Chemie International Edition in English
Volume	51
Issue number	32
DOIs	https://doi.org/10.1002/anie.201202090
State	Published - 6 Aug 2012

Keywords

biological activity
drug design
medicinal chemistry
peptides
peptidomimetics

Access to Document

10.1002/anie.201202090

Cite this

@article{46e6aab86f944cd1a299629004ac95a9,

title = "A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity",

abstract = "There can be only one: Using a peptoid motif obtained by shifting the arginine side chain of a pentapeptide previously developed by Fujii et al. to the neighboring nitrogen atom restricts the conformational freedom and yields a conformationally homogeneous peptide (see picture) with a 100-fold higher binding affinity to the chemokine receptor CXCR4 in the picomolar range. Its efficiency to inhibit HIV-1 infections is also demonstrated.",

keywords = "biological activity, drug design, medicinal chemistry, peptides, peptidomimetics",

author = "Oliver Demmer and Frank, \{Andreas O.\} and Franz Hagn and Margret Schottelius and Luciana Marinelli and Sandro Cosconati and Ruth Brack-Werner and Stephan Kremb and Wester, \{Hans J{\"u}rgen\} and Horst Kessler",

year = "2012",

month = aug,

day = "6",

doi = "10.1002/anie.201202090",

language = "English",

volume = "51",

pages = "8110--8113",

journal = "Angewandte Chemie International Edition in English",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "32",

}

TY - JOUR

T1 - A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity

AU - Demmer, Oliver

AU - Frank, Andreas O.

AU - Hagn, Franz

AU - Schottelius, Margret

AU - Marinelli, Luciana

AU - Cosconati, Sandro

AU - Brack-Werner, Ruth

AU - Kremb, Stephan

AU - Wester, Hans Jürgen

AU - Kessler, Horst

PY - 2012/8/6

Y1 - 2012/8/6

N2 - There can be only one: Using a peptoid motif obtained by shifting the arginine side chain of a pentapeptide previously developed by Fujii et al. to the neighboring nitrogen atom restricts the conformational freedom and yields a conformationally homogeneous peptide (see picture) with a 100-fold higher binding affinity to the chemokine receptor CXCR4 in the picomolar range. Its efficiency to inhibit HIV-1 infections is also demonstrated.

AB - There can be only one: Using a peptoid motif obtained by shifting the arginine side chain of a pentapeptide previously developed by Fujii et al. to the neighboring nitrogen atom restricts the conformational freedom and yields a conformationally homogeneous peptide (see picture) with a 100-fold higher binding affinity to the chemokine receptor CXCR4 in the picomolar range. Its efficiency to inhibit HIV-1 infections is also demonstrated.

KW - biological activity

KW - drug design

KW - medicinal chemistry

KW - peptides

KW - peptidomimetics

UR - http://www.scopus.com/inward/record.url?scp=84864753795&partnerID=8YFLogxK

U2 - 10.1002/anie.201202090

DO - 10.1002/anie.201202090

M3 - Article

C2 - 22760863

AN - SCOPUS:84864753795

SN - 1433-7851

VL - 51

SP - 8110

EP - 8113

JO - Angewandte Chemie International Edition in English

JF - Angewandte Chemie International Edition in English

IS - 32

ER -

A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this