59588-86-2

Alamethicin is used as a channel-forming ionophore that activates membrane enzymes, membrane channel-forming peptide. It is a 20-amino acid channel-forming peptide antibiotic that can function as a monovalent cation ionophore. Alamethicin has been used to develop methods for the routine assessment of potential new drug candidates to elicit their pharmacokinetic drug interactions.

These voltage-dependent, channel-forming, peptaibol antibiotics (MWAlamethicin F-30 = 1964.40; CAS 27061-78-5) from the soil fungus Trichoderma viride NRRL 3199 are membrane-active oligopeptides isolated from that exhibit anti-bacterial and anti-fungal properties. Peptaibols are amphipathic, usually highly helical in structure, and typically form voltage dependent ion channels that uncouple oxidative phosphorylation, often attended by in bacterial and fungal cell death. Alamethicin F-30 has the sequence Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib- Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phe-OH; Alamethicin F- 50 has the sequence Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly- Leu-Aib-Pro-Val-Aib Aib-Gln-Gln-Phe-OH; and Alamethicin II has the sequence Ac-Aib-Pro-Aib-Ala-Aib-Aib-Gln-Aib-Val-Aib-Gly-Leu-Aib- Pro-Val-Aib-Aib-Glu-Gln-Phe-OH. Note: The name “peptaibol” is derived from the prefix “pep-“, the central syllable “aib”, and the suffix “-ol” to designate its peptide structure, the presence of an a-aminoisobutyryl unit, and the C-terminal alcohol.