Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied <i>N</i>-Acyl Moieties
Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH<sub>2</sub> enhance cytotoxicity.
Authors
- Eiichi N. Kodama (ORCID: https://orcid.org/0000-0002-6622-2752)
- Kenichi Matsuda (ORCID: https://orcid.org/0000-0002-9269-688X)
- Yoshiki Hiramatsu
- Hironori Hayashi (ORCID: https://orcid.org/0000-0002-5892-0040)
- Rokusuke Yoshikawa (ORCID: https://orcid.org/0000-0002-7444-6895)
- Jiro Yasuda (ORCID: https://orcid.org/0000-0001-9928-5621)
- Toshiyuki Wakimoto (ORCID: https://orcid.org/0000-0003-2917-1797)
- Kei Fujita
- Rintaro Ichihara
- Shinya Niikura
- Anna M. Strasser
Institutions
- Tohoku University (JP)
- Hokkaido University (JP)
- Hokkaido Pharmaceutical University (JP)
- Infectious Diseases Institute (UG)
- Tohoku Medical Megabank Organization (JP)
- Nagasaki University (JP)
Publication Details
- Journal
- Chemical and Pharmaceutical Bulletin
- Published
- 2024-09-19
- DOI
- https://doi.org/10.1248/cpb.c24-00533
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.23
Funders
- Japan Foundation for Applied Enzymology
- Ministry of Education, Culture, Sports, Science and Technology
- Hokkaido University
- Japan Society for the Promotion of Science
- Japan Science and Technology Agency
- Global Institution for Collaborative Research and Education, Hokkaido University
- ACT-X