Bioactive fluorinated derivative of amphotericin B

Nobuaki Matsumori; Yuichi Umegawa; Tohru Oishi; Michio Murata

doi:10.1016/j.bmcl.2005.05.058

Bioactive fluorinated derivative of amphotericin B

Bioorg Med Chem Lett. 2005 Aug 1;15(15):3565-7. doi: 10.1016/j.bmcl.2005.05.058.

Authors

Nobuaki Matsumori¹, Yuichi Umegawa, Tohru Oishi, Michio Murata

Affiliation

¹ Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.

PMID: 15963721
DOI: 10.1016/j.bmcl.2005.05.058

Abstract

The first stably fluorinated derivative of amphotericin B2 with a fluorine atom in the macrolide skeleton was synthesized using an electrophilic fluorination reagent, Selectfluor. The derivative 2 showed hemolytic, K+ permeable, and antifungal activities similar to those of AmB and thus was expected to be a powerful tool for NMR-based investigations on the mechanism of ion-channel formation by amphotericin B.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amphotericin B / chemistry
Amphotericin B / pharmacology*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Fluorine / chemistry*
Humans
Ion Channels / metabolism
Macrolides / chemistry
Macrolides / pharmacology
Magnetic Resonance Spectroscopy
Stereoisomerism

Substances

Antifungal Agents
Ion Channels
Macrolides
Fluorine
Amphotericin B