Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4

Shinya Oishi; Ryo Masuda; Barry Evans; Satoshi Ueda; Yukiko Goto; Hiroaki Ohno; Akira Hirasawa; Gozoh Tsujimoto; Zixuan Wang; Stephen C. Peiper; Takeshi Naito; Eiichi Kodama; Masao Matsuoka; Nobutaka Fujii

doi:10.1002/cbic.200700761

Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4

Shinya Oishi^*, Ryo Masuda, Barry Evans, Satoshi Ueda, Yukiko Goto, Hiroaki Ohno, Akira Hirasawa, Gozoh Tsujimoto, Zixuan Wang, Stephen C. Peiper, Takeshi Naito, Eiichi Kodama, Masao Matsuoka, Nobutaka Fujii

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

The design, synthesis, and bioevaluation of fluorescence- and biotin-labeled CXCR4 antagonists are described. The modification of D-Lys8 at an ε-amino group in the peptide antagonist Ac-TZ14011 derived from polyphemusin II had no significant influence on the potent binding of the peptide to the CXCR4 receptor. The application of the labeled peptides in flow cytometry and confocal microscopy studies demonstrated the selectivity of their binding to the CXCR4 receptor, but not to CXCR7, which was recently reported to be another receptor for stromal cell-derived factor 1 (SDF-1)/CXCL12.

Original language	English
Pages (from-to)	1154-1158
Number of pages	5
Journal	ChemBioChem
Volume	9
Issue number	7
DOIs	https://doi.org/10.1002/cbic.200700761
Publication status	Published - 2008 May 5
Externally published	Yes

Keywords

CXCR4 antagonists
Cell imaging
Chemokine receptors
Fluorescent probes
Peptides

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.200700761

Cite this

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title = "Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4",

abstract = "The design, synthesis, and bioevaluation of fluorescence- and biotin-labeled CXCR4 antagonists are described. The modification of D-Lys8 at an ε-amino group in the peptide antagonist Ac-TZ14011 derived from polyphemusin II had no significant influence on the potent binding of the peptide to the CXCR4 receptor. The application of the labeled peptides in flow cytometry and confocal microscopy studies demonstrated the selectivity of their binding to the CXCR4 receptor, but not to CXCR7, which was recently reported to be another receptor for stromal cell-derived factor 1 (SDF-1)/CXCL12.",

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doi = "10.1002/cbic.200700761",

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AU - Oishi, Shinya

AU - Masuda, Ryo

AU - Evans, Barry

AU - Ueda, Satoshi

AU - Goto, Yukiko

AU - Ohno, Hiroaki

AU - Hirasawa, Akira

AU - Tsujimoto, Gozoh

AU - Wang, Zixuan

AU - Peiper, Stephen C.

AU - Naito, Takeshi

AU - Kodama, Eiichi

AU - Matsuoka, Masao

AU - Fujii, Nobutaka

PY - 2008/5/5

Y1 - 2008/5/5

N2 - The design, synthesis, and bioevaluation of fluorescence- and biotin-labeled CXCR4 antagonists are described. The modification of D-Lys8 at an ε-amino group in the peptide antagonist Ac-TZ14011 derived from polyphemusin II had no significant influence on the potent binding of the peptide to the CXCR4 receptor. The application of the labeled peptides in flow cytometry and confocal microscopy studies demonstrated the selectivity of their binding to the CXCR4 receptor, but not to CXCR7, which was recently reported to be another receptor for stromal cell-derived factor 1 (SDF-1)/CXCL12.

AB - The design, synthesis, and bioevaluation of fluorescence- and biotin-labeled CXCR4 antagonists are described. The modification of D-Lys8 at an ε-amino group in the peptide antagonist Ac-TZ14011 derived from polyphemusin II had no significant influence on the potent binding of the peptide to the CXCR4 receptor. The application of the labeled peptides in flow cytometry and confocal microscopy studies demonstrated the selectivity of their binding to the CXCR4 receptor, but not to CXCR7, which was recently reported to be another receptor for stromal cell-derived factor 1 (SDF-1)/CXCL12.

KW - CXCR4 antagonists

KW - Cell imaging

KW - Chemokine receptors

KW - Fluorescent probes

KW - Peptides

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Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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