Novel 12-membered non-antibiotic macrolides from erythromycin A; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents

Akihiro Sugawara, Akito Sueki, Tomoyasu Hirose, Kenichiro Nagai, Hiroaki Gouda, Shuichi Hirono, Hideaki Shima, Kiyoko S. Akagawa, Satoshi Õmura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

Herein, we report the design and synthesis of the novel 12-membered non-antibiotic macrolide (8R,9S)-8,9-dihydro-6,9-epoxy-8,9- anhydropseudoerythromycin A (EM900), which was found to be a potent anti-inflammatory and/or immunomodulatory agent, capable of promoting monocyte to macrophage differentiation. This molecule shows improved acid stability, does not exhibit any anti-bacterial activity and has relatively low cytotoxicity against THP-1 cells. In addition, one of its analogues, (8R,9S)-4″,13-O- diacetyl-8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM911), was found to be twice as effective as EM900.

Original languageEnglish
Pages (from-to)3373-3376
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number11
DOIs
Publication statusPublished - 2011 Jun 1
Externally publishedYes

Keywords

  • (8R,9S)-8,9-Dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM900)
  • 14-Membered non-antibiotic macrolide
  • Anti-inflammatory agent
  • Diffuse panbronchiolitis
  • Immunomodulatory agent

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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