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 Broach, John O. Trent, Zi xuan Wang, Stephen C. Peiper

Research output: Contribution to journalArticle

170 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3251-3253
Number of pages3
JournalAngewandte Chemie - International Edition
Volume42
Issue number28
DOIs
StatePublished - Jul 28 2003

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Lead compounds
Chemokines
Peptides
Conformations
4-fluorobenzoyl-TN-14003
3-(2-naphthyl)alanine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Fujii, Nobutaka ; Oishi, Shinya ; Hiramatsu, Kenichi ; Araki, Takanobu ; Ueda, Satoshi ; Tamamura, Hirokazu ; Otaka, Akira ; Kusano, Shuichi ; Terakubo, Shigemi ; Nakashima, Hideki ; Broach, James ; Trent, John O. ; Wang, Zi xuan ; Peiper, Stephen C. / Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries. In: Angewandte Chemie - International Edition. 2003 ; Vol. 42, No. 28. pp. 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, J, 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

Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries. / Fujii, Nobutaka; Oishi, Shinya; Hiramatsu, Kenichi; Araki, Takanobu; Ueda, Satoshi; Tamamura, Hirokazu; Otaka, Akira; Kusano, Shuichi; Terakubo, Shigemi; Nakashima, Hideki; Broach, James; Trent, John O.; Wang, Zi xuan; Peiper, Stephen C.

In: Angewandte Chemie - International Edition, Vol. 42, No. 28, 28.07.2003, p. 3251-3253.

Research output: Contribution to journalArticle

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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

AU - Trent, John O.

AU - Wang, Zi xuan

AU - Peiper, Stephen C.

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