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Issue 23, 2008
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Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore

Tomohiro Tanaka,a  Hiroshi Tsutsumi,*a  Wataru Nomura,a  Yasuaki Tanabe,a  Nami Ohashi,a  Ai Esaka,b  Chihiro Ochiai,a  Jun Sato,a  Kyoko Itotani,a  Tsutomu Murakami,c  Kenji Ohba,c  Naoki Yamamoto,c  Nobutaka Fujiib  and  Hirokazu Tamamura*a 
Author affiliations

* Corresponding authors

a Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Chiyoda-ku, Tokyo, Japan
E-mail: tsutsumi.mr@tmd.ac.jp, tamamura.mr@tmd.ac.jp
Fax: 813 5280 8039
Tel: 813 5280 8036

b Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan

c AIDS Research Center, National Institute of Infectious Diseases, Shinjuku-ku, Tokyo, Japan

Abstract

A highly potent CXCR4 antagonist 2 [cyclo (-D-Tyr1-Arg2-Arg3-Nal4-Gly5-)] has previously been identified by screening cyclic pentapeptide libraries that were designed based on pharmacophore residues of a 14-residue peptidic CXCR4 antagonist 1. In the present study, D-Tyr and Arg in peptide 2 were replaced by a bicyclic aromatic amino acid and a cationic amino acid, respectively, and their binding activity for CXCR4 was evaluated for identification of the novel pharmacophore.

Graphical abstract: Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore

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Publication details

The article was received on 14 Jul 2008, accepted on 28 Aug 2008 and first published on 17 Oct 2008


Article type: Paper
DOI: 10.1039/B812029C
Citation: Org. Biomol. Chem., 2008,6, 4374-4377
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    Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore

    T. Tanaka, H. Tsutsumi, W. Nomura, Y. Tanabe, N. Ohashi, A. Esaka, C. Ochiai, J. Sato, K. Itotani, T. Murakami, K. Ohba, N. Yamamoto, N. Fujii and H. Tamamura, Org. Biomol. Chem., 2008, 6, 4374
    DOI: 10.1039/B812029C

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