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Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold.

Abstract：

:The CXC chemokine receptor 7 (CXCR7)/ACKR3 is a chemokine receptor that recognizes stromal cell-derived factor 1 (SDF-1)/CXCL12 and interferon-inducible T-cell α chemoattractant (I-TAC)/CXCL11. Here, we report the development of novel CXCR7-selective ligands with a cyclic pentapeptide scaffold through an SAR study of CXC chemokine receptor 4 (CXCR4) selective antagonist FC131 [cyclo(-d-Tyr-l-Arg-l-Arg-l-Nal-Gly-), Nal = 3-(2-naphthyl)alanine]. Substitution of Gly with l-Pro switched the receptor preference of the peptides from CXCR4 to CXCR7. The SAR study led to the identification of a potent CXCR7 ligand, FC313 [cyclo(-d-Tyr-l-Arg-l-MeArg-l-Nal-l-Pro-)], which recruits β-arrestin to CXCR7. Investigations via receptor mutagenesis and molecular modeling experiments suggest a possible binding mode of the cyclic pentapeptide CXCR7 agonist.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Oishi S,Kuroyanagi T,Kubo T,Montpas N,Yoshikawa Y,Misu R,Kobayashi Y,Ohno H,Heveker N,Furuya T,Fujii N

doi

10.1021/acs.jmedchem.5b00216

subject

Has Abstract

pub_date

2015-07-09 00:00:00

pages

5218-25

issue

13

eissn

0022-2623

issn

1520-4804

journal_volume

58

pub_type

杂志文章

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