5-O-Mycaminosyltylonolide antibacterial derivatives: Design, synthesis and bioactivity

Akihiro Sugawara, Hitomi Maruyama, Sho Shibusawa, Hidehito Matsui, Tomoyasu Hirose, Ayumi Tsutsui, Robrecht Froyman, Carolin Ludwig, Johannes Koebberling, Hideaki Hanaki, Gerd Kleefeld, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


Tylosin is a 16-membered macrolide broad-spectrum antibiotic that has an important role in veterinary medicine, active against Gram-positive and a restricted range of Gram-negative bacteria. We synthesized 15 types of tylosin-related derivatives by chemical modification and evaluated them against mastitis pathogens. Among them, 20-deoxy-20-{N-methyl-N-[1-(3-quinolyl)-1H-1,2,3-triazol-4-yl]methylamino}-5-O-mycaminosyltylonolide 2f and 20-deoxy-20-{N-benzyl-N-[1-(3-quinolyl)-1H-1,2,3-triazol-4-yl]methylamino}-5-O-mycaminosyltylonolide 2k were found to not only expand their antibacterial impact to include Gram-negative bacteria, such as Escherichia coli and Klebsiella pneumoniae, but also to retain or increase antibacterial activity against Gram-positive bacteria, such as Staphylococcus aureus and Streptococcus uberis in comparison with the parent tylosin.

Original languageEnglish
Pages (from-to)878-887
Number of pages10
JournalJournal of Antibiotics
Issue number8
Publication statusPublished - 2017 Jul 1
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery


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