A novel strategy for bioconjugation: synthesis and preliminary evaluation with amphotericin B

Andreas Zumbuehl; Pasquale Stano; Marc Sohrmann; Mathias Peter; Peter Walde; Erick M Carreira

doi:10.1039/b701953j

A novel strategy for bioconjugation: synthesis and preliminary evaluation with amphotericin B

Org Biomol Chem. 2007 May 7;5(9):1339-42. doi: 10.1039/b701953j. Epub 2007 Mar 23.

Authors

Andreas Zumbuehl¹, Pasquale Stano, Marc Sohrmann, Mathias Peter, Peter Walde, Erick M Carreira

Affiliation

¹ Laboratorium für Organische Chemie, ETH Hönggerberg, 8093, Zürich, Switzerland.

PMID: 17464400
DOI: 10.1039/b701953j

Abstract

A novel linker strategy is presented based on a double reductive amination of a dialdehyde to the amine of the amphotericin B mycosamine sugar and the biological activity of a series of conjugates is compared to the native amphotericin B.

MeSH terms

Amides / chemistry
Amination
Amphotericin B / analogs & derivatives*
Amphotericin B / chemistry
Amphotericin B / pharmacology*
Antifungal Agents / chemistry*
Antifungal Agents / pharmacology*
Biotin / chemistry
Liposomes / metabolism
Phosphatidylcholines / metabolism
Potassium / metabolism
Potentiometry

Substances

Amides
Antifungal Agents
Liposomes
Phosphatidylcholines
Biotin
Amphotericin B
Potassium
1-palmitoyl-2-oleoylphosphatidylcholine