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Key Documents

A5361

Sigma-Aldrich

Alamethicin, Ready Made Solution from Trichoderma viride

5 mg/mL in DMSO

Synonyme(s) :

U-22324

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About This Item

Numéro CAS:
Numéro CE :
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Niveau de qualité

Forme

DMSO solution

Concentration

5 mg/mL in DMSO

Spectre d'activité de l'antibiotique

Gram-positive bacteria

Mode d’action

cell membrane | interferes

Conditions d'expédition

wet ice

Température de stockage

−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

Clé InChI

LGHSQOCGTJHDIL-SLKIUSOBSA-N

Description générale

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.

Application

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.

Actions biochimiques/physiologiques

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.

Forme physique

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

188.6 °F - closed cup

Point d'éclair (°C)

87 °C - closed cup


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Inhibition of UDP-glucose dehydrogenase by 6-thiopurine and its oxidative metabolites: Possible mechanism for its interaction within the bilirubin excretion pathway and 6TP associated liver toxicity
Weeramange CJ, et al.
Journal of Pharmaceutical and Biomedical Analysis, 151, 106-115 (2018)
SIRT4 is a lysine deacylase that controls leucine metabolism and insulin secretion
Anderson KA, et al.
Cell Metabolism, 25(4), 838-855 (2017)
Ako Matsui et al.
Journal of radiation research, 61(1), 1-13 (2019-12-18)
Human oxidation resistance 1 (OXR1) was identified as a protein that decreases genomic mutations in Escherichia coli caused by oxidative DNA damage. However, the mechanism by which OXR1 defends against genome instability has not been elucidated. To clarify how OXR1

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