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Merck

A5361

Alamethicin

from Trichoderma viride, ≥98% (HPLC), antibiotic, DMSO solution

Sinónimos:

U-22324

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Número CAS:
27061-78-5
MDL number:
MFCD00151517
UNSPSC Code:
12352200
EC Number:
200-664-3
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
DMSO solution
Quality level:
200

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Nombre del producto

Alamethicin, Ready Made Solution from Trichoderma viride, 5 mg/mL in DMSO

SMILES string

N2([C@@H](CCC2)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CO)Cc3ccccc3)C(=O)C(NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@H]1N(

InChI key

LGHSQOCGTJHDIL-SLKIUSOBSA-N

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

assay

≥98% (HPLC)

form

DMSO solution

concentration

5 mg/mL in DMSO

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell membrane | interferes

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

Categorías relacionadas

General description

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.

Biochem/physiol Actions

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.

Physical form

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

Clase de almacenamiento

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

wgk

WGK 2

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

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Certificados de análisis (COA)

Lot/Batch Number
0000148430
0000152805
0000284781
0000254795
0000152805

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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
Ako Matsui et al.
Genes and environment : the official journal of the Japanese Environmental Mutagen Society, 42(1), 29-29 (2020-12-10)
DNA damage is generated by various intrinsic and extrinsic sources such as reactive oxygen species (ROS) and environmental mutagens, and causes genomic alterations. DNA damage response (DDR) is activated to induce cell cycle arrest and DNA repair. Oxidation resistance 1
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)
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)
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Data Sheet - A5361

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