Molecular parameters for the anti-human immunodeficiency virus activity of T22 ([Tyr5,12, Lys7]-polyphemusin II)

A. Otaka, H. Tamamura, Y. Terakawa, M. Masuda, Takaki Koide, T. Murakami, H. Nakashima, K. Matsuzaki, K. Miyajima, T. Ibuka, M. Waki, A. Matsumoto, N. Yamamoto, N. Fujii

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Abstract

T22 ([Tyr5,12, Lys7]-polyphemusin II) was found to exhibit strong anti-human immunodeficiency virus (HIV) activity and exert its effects on a virus-cell fusion process. In the present study, the all-D enantiomer of T22 and its related compounds were synthesized to examine the molecular parameters required for the interaction of T22 with membrane components of cells or viruses in order to exert this anti-HIV activity. The anti-HIV activity of these analogs was investigated in comparison with their membrane permeability with aspect to large unilamellar vesicles (LUVs). The all-D enantiomer of T22 exhibited a 20-fold lower anti-HIV activity compared with T22, whereas they both showed the same membrane permeability. No positive correlation between anti-HIV activity and membrane permeability was observed. These results suggest that the anti-HIV activity of T22 is mediated through the interaction with chiral component(s) of the cell or virus.

Original languageEnglish
Pages (from-to)1669-1672
Number of pages4
JournalBiological and Pharmaceutical Bulletin
Volume17
Issue number12
Publication statusPublished - 1994
Externally publishedYes

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Keywords

  • Anti-human immunodeficiency virus peptide
  • Chiral component
  • Polyphemusin
  • T22
  • Tachyplesin

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology, Toxicology and Pharmaceutics(all)

Cite this

Otaka, A., Tamamura, H., Terakawa, Y., Masuda, M., Koide, T., Murakami, T., Nakashima, H., Matsuzaki, K., Miyajima, K., Ibuka, T., Waki, M., Matsumoto, A., Yamamoto, N., & Fujii, N. (1994). Molecular parameters for the anti-human immunodeficiency virus activity of T22 ([Tyr5,12, Lys7]-polyphemusin II). Biological and Pharmaceutical Bulletin, 17(12), 1669-1672.