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

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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

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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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, 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