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Merck

A5361

Sigma-Aldrich

Alamethicin, Ready Made Solution from Trichoderma viride

5 mg/mL in DMSO

Synonym(e):

U-22324

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About This Item

CAS-Nummer:
EG-Nummer:
UNSPSC-Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

Qualitätsniveau

Form

DMSO solution

Konzentration

5 mg/mL in DMSO

Wirkungsspektrum von Antibiotika

Gram-positive bacteria

Wirkungsweise

cell membrane | interferes

Versandbedingung

wet ice

Lagertemp.

−20°C

InChI

1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54+,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1

InChIKey

LGHSQOCGTJHDIL-SLKIUSOBSA-N

Allgemeine Beschreibung

Alamethicin belongs to the peptaibol family of antimicrobial peptides. It is mainly composed of hydrophobic amino acids. It possess a helical structure with a movable hinge region at Gly-11 position.

Anwendung

Alamethicin 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.
Alamethicin, Ready Made Solution from Trichoderma viride has been used :
  • In the uridine 5′-diphospho-glucuronosyltransferase activity assay.
  • To determine the Na, K-ATPase activity in permeabilized bovine nonpigmented epithelium cells.
  • In methylcrotonyl-CoA carboxylase activity assay.

Biochem./physiol. Wirkung

Alamethicin is a 20-amino acid channel-forming peptide antibiotic isolated from the fungus Trichoderma viride. Alamethicin consists of several isoforms, for which structural information has been published. Alamethicin forms voltage-dependent channels across lipid bilayer membranes. The Alamethicin channel is built by a bundle of helical monomers forming a water filled transmembrane pore. The conductivity level of the channel is determined by the number of associated helical monomers (3-12), which generates a non aligned supermolecular structure with an aqueous core through which ions can cross lipid membranes. Alamethicin catalyzes the exchange of protons for monovalent cations with little difference in affinities and has the ability to transport cations through biological and artificial lipid membranes. Alamethicin can be used for the permeabilization of mitochondria without affecting the outer or inner membranes.

Physikalische Form

The product contains a mixture of alamethicin isoforms. It is supplied as a 5 mg/mL, 0.2 μm filtered solution in DMSO.

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flammpunkt (°F)

188.6 °F - closed cup

Flammpunkt (°C)

87 °C - closed cup


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Die Dokumentenbibliothek aufrufen

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Cell Metabolism, 25(4), 838-855 (2017)
Structure and alignment of the membrane-associated peptaibols ampullosporin A and alamethicin by oriented 15N and 31P solid-state NMR spectroscopy
Salnikov ES, et al.
Biophysical Journal, 96(1), 86-100 (2009)
Digoxin derivatives with selectivity for the alpha2beta3 isoform of Na, K-ATPase potently reduce intraocular pressure
Katz A, et al.
Proceedings of the National Academy of Sciences of the USA, 112(44), 13723-13728 (2015)
Piotr Pieta et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(52), 21223-21227 (2012-12-14)
We present direct visualization of pores formed by alamethicin (Alm) in a matrix of phospholipids using electrochemical scanning tunneling microscopy (EC-STM). High-resolution EC-STM images show individual peptide molecules forming channels. The channels are not dispersed randomly in the monolayer but

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