Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries

Nobutaka Fujii; Shinya Oishi; Kenichi Hiramatsu; Takanobu Araki; Satoshi Ueda; Hirokazu Tamamura; Akira Otaka; Shuichi Kusano; Shigemi Terakubo; Hideki Nakashima; James A. Broach; John O. Trent; Zi xuan Wang; Stephen C. Peiper

doi:10.1002/anie.200351024

Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries

Nobutaka Fujii
, Shinya Oishi
, Kenichi Hiramatsu
, Takanobu Araki
, Satoshi Ueda
, Hirokazu Tamamura
, Akira Otaka
, Shuichi Kusano
, Shigemi Terakubo
, Hideki Nakashima
, James A. Broach
, John O. Trent
, Zi xuan Wang
, Stephen C. Peiper

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

201 Scopus citations

Abstract

Efficient downsizing of peptides: By combination of two orthogonal "conformation-based" and "sequence-based" libraries, the cyclic pentapeptide cyclo-(-L-Nal1-Gly2-D-Tyr3-L-Arg4-L-Arg5-) (Nal = L-3-(2-naphthyl)alanine; see overlay of the five lowest energy structures), which exhibited strong CXCR4 antagonistm (IC₅₀ = 4 nM) comparable to that of a 14-residue lead compound, T140, was discovered.

Original language	English (US)
Pages (from-to)	3251-3253
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	28
DOIs	https://doi.org/10.1002/anie.200351024
State	Published - Jul 28 2003

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1002/anie.200351024

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Fujii, N., Oishi, S., Hiramatsu, K., Araki, T., Ueda, S., Tamamura, H., Otaka, A., Kusano, S., Terakubo, S., Nakashima, H., Broach, J. A., Trent, J. O., Wang, Z. X., & Peiper, S. C. (2003). Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries. Angewandte Chemie - International Edition, 42(28), 3251-3253. https://doi.org/10.1002/anie.200351024

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title = "Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries",

abstract = "Efficient downsizing of peptides: By combination of two orthogonal {"}conformation-based{"} and {"}sequence-based{"} libraries, the cyclic pentapeptide cyclo-(-L-Nal1-Gly2-D-Tyr3-L-Arg4-L-Arg5-) (Nal = L-3-(2-naphthyl)alanine; see overlay of the five lowest energy structures), which exhibited strong CXCR4 antagonistm (IC50 = 4 nM) comparable to that of a 14-residue lead compound, T140, was discovered.",

author = "Nobutaka Fujii and Shinya Oishi and Kenichi Hiramatsu and Takanobu Araki and Satoshi Ueda and Hirokazu Tamamura and Akira Otaka and Shuichi Kusano and Shigemi Terakubo and Hideki Nakashima and Broach, \{James A.\} and Trent, \{John O.\} and Wang, \{Zi xuan\} and Peiper, \{Stephen C.\}",

year = "2003",

month = jul,

day = "28",

doi = "10.1002/anie.200351024",

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volume = "42",

pages = "3251--3253",

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Fujii, N, Oishi, S, Hiramatsu, K, Araki, T, Ueda, S, Tamamura, H, Otaka, A, Kusano, S, Terakubo, S, Nakashima, H, Broach, JA, Trent, JO, Wang, ZX & Peiper, SC 2003, 'Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries', Angewandte Chemie - International Edition, vol. 42, no. 28, pp. 3251-3253. https://doi.org/10.1002/anie.200351024

TY - JOUR

T1 - Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries

AU - Fujii, Nobutaka

AU - Oishi, Shinya

AU - Hiramatsu, Kenichi

AU - Araki, Takanobu

AU - Ueda, Satoshi

AU - Tamamura, Hirokazu

AU - Otaka, Akira

AU - Kusano, Shuichi

AU - Terakubo, Shigemi

AU - Nakashima, Hideki

AU - Broach, James A.

AU - Trent, John O.

AU - Wang, Zi xuan

AU - Peiper, Stephen C.

PY - 2003/7/28

Y1 - 2003/7/28

N2 - Efficient downsizing of peptides: By combination of two orthogonal "conformation-based" and "sequence-based" libraries, the cyclic pentapeptide cyclo-(-L-Nal1-Gly2-D-Tyr3-L-Arg4-L-Arg5-) (Nal = L-3-(2-naphthyl)alanine; see overlay of the five lowest energy structures), which exhibited strong CXCR4 antagonistm (IC50 = 4 nM) comparable to that of a 14-residue lead compound, T140, was discovered.

AB - Efficient downsizing of peptides: By combination of two orthogonal "conformation-based" and "sequence-based" libraries, the cyclic pentapeptide cyclo-(-L-Nal1-Gly2-D-Tyr3-L-Arg4-L-Arg5-) (Nal = L-3-(2-naphthyl)alanine; see overlay of the five lowest energy structures), which exhibited strong CXCR4 antagonistm (IC50 = 4 nM) comparable to that of a 14-residue lead compound, T140, was discovered.

UR - https://www.scopus.com/pages/publications/10744227507

UR - https://www.scopus.com/pages/publications/10744227507#tab=citedBy

U2 - 10.1002/anie.200351024

DO - 10.1002/anie.200351024

M3 - Article

C2 - 12876735

AN - SCOPUS:10744227507

SN - 1433-7851

VL - 42

SP - 3251

EP - 3253

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 28

ER -

Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries

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