59588-86-2

Basic information

• Product Name: ALAMETHICIN
• Synonyms: alamethicinf30;alamethicingamma;alamethicini;f-50;U-22324;ANTIBIOTIC U-22324;ALMETHICIN;ALAMETHACIN
• CAS NO: 59588-86-2
• Molecular Formula: C₉₂H₁₅₀N₂₂O₂₅
• Molecular Weight: 1964.31
• Mol File: 59588-86-2.mol

Chemical Properties

• Melting Point: 267-270℃
• Appearance: Tan or light brown solid
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO and ethanol.
• Water Solubility: Soluble in DMSO and ethanol
• CAS DataBase Reference: ALAMETHICIN(CAS DataBase Reference)
• NIST Chemistry Reference: ALAMETHICIN(59588-86-2)
• EPA Substance Registry System: ALAMETHICIN(59588-86-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 3462 6.1/PG 3
• WGK Germany: 3
• RTECS: AY1900000
• F: 10-21
• HazardClass: 6.1
• Hazardous Substances Data: 59588-86-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Alamethicin is used as a channel-forming ionophore for activating membrane enzymes. Its ability to form channels in biological membranes has made it a valuable tool in the study of ion transport and membrane protein function. This application aids in the development of new drug candidates and the assessment of their pharmacokinetic drug interactions.
Used in Drug Delivery Systems:
Alamethicin's membrane channel-forming properties have been explored for use in drug delivery systems. By creating temporary pores in cell membranes, alamethicin can potentially enhance the uptake of therapeutic agents, improving their bioavailability and efficacy.
Used in Antimicrobial Applications:
As a peptide antibiotic, alamethicin exhibits antimicrobial activity against a range of pathogens, including bacteria and fungi. Its ability to disrupt cell membranes and interfere with essential cellular processes makes it a promising candidate for the development of new antimicrobial agents, particularly in the context of increasing antibiotic resistance.

Enzyme inhibitor

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.

Upstream product

• 76939-45-2 C₉₉H₁₅₆N₂₂O₂₅ 

Relevant articles and documents

Solid-Phase Synthesis of the Peptaibol Alamethicin U-22324 by Using a Double-Linker Strategy

The facile Fmoc (Fluorenylmethoxycarbonyl) solid-phase synthesis of the α-helical-channel-forming peptaibol alamethicin U-22324 is described. A late-stage reduction by using a new double-linker method was used to introduce the C-terminal alcohol. Furthermore, we also report the synthesis of an alamethicin analogue with a C-terminal carboxylic acid.

A SOLID-SUPPORTED HYDROXY AMINO ACID AND A SOLID-SUPPORTED AMINO ALCOHOL

There is provided a solid-supported hydroxy amino acid or a solid-supported amino alcohol of Formula (I) as defined herein. There is further provided a method of making the solid-supported hydroxy amino acid or the solid-supported amino alcohol. There is further provided a method of making a peptide alcohol by using the solid-supported hydroxy amino acid or the solid-supported amino alcohol. There is also provided a peptide alcohol, obtained by using the solid-supported hydroxy amino acid or the solid-supported amino alcohol. There is also provided a stapled peptide alcohol and medical uses thereof.

SOLUTION PHASE SYNTHESIS OF ALAMETHICIN I

The total synthesis of alamethicin I by solution phase methods is reported.