A4665

Alamethicin from Trichoderma viride

≥98% (HPLC)

• Sinônimo(s): Antibiotic U-22324
• Número CAS: 27061-78-5
• Beilstein: 5213858
• Número MDL: MFCD00151517
• Código UNSPSC: 12352209
• ID de substância PubChem: 24890893
• NACRES: NA.77

Propriedades

• Nível de qualidade: 300
• Ensaio: ≥98% (HPLC)
• Formulário: powder
• espectro de atividade do antibiótico: Gram-positive bacteria
• Modo de ação: cell membrane | interferes
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: CC(C)C[C@H](NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H](NC(=O)C(C)(C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]1CCCN1C(=O)C(C)(C)NC(C)=O)C(C)C)C(=O)NC(C)(C)C(=O)N2CCC[C@H]2C(=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(N)=O)C(=O)N[C@@H](CO)Cc3ccccc3
• 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
• chave InChI: LGHSQOCGTJHDIL-SLKIUSOBSA-N

Descrição

Descrição geral

Alamethicin is an antibiotic and a cytolytic peptide capable of forming an amphipathic α-helical structure in biological membranes.[1] It is a linear peptaibol, made up of 20 amino acid residues. It belongs to the class of Nonribosomal peptides (NRP) and is loaded with alpha-amino isobutyric acid.[2]

Aplicação

Alamethicin from Trichoderma viride has been used:

• to examine the effect of glutamate transporters on the Na⁺/K⁺-ATPase dependent extracellular K⁺ transient during neuronal activity[3]
• to investigate the formation of anion-permeable channels in planar lipid bilayers by magainin I obtained from Xenopus skin[1]
• to study the permeability of root apical meristem and epidermis and cellulase induced resistance to Alamethicin in Arabidopsis thaliana[2]
• to study the cytotoxic effects of the phycotoxin okadaic acid and mycotoxins on human intestinal (HT-29) and neuroblastoma (SH-SY5Y) cell lines[4]
• to analyze the structural variations and biological activity of peptaibols obtained from the Longibrachiatum clade belonging to the genus of filamentous fungi Trichoderma[5]

Ações bioquímicas/fisiológicas

Alamethicin is responsible for eliciting resistance in plants and is harmful to them by causing lesions and rapid death associated with ribosomal ribonucleic acid (rRNA) cleavage. It can cause permeability of the apical meristem and epidermis in A. thaliana roots. Alamethicin leads to the coiling of tendrils in Bryonia dioica induced by jasmonates.[5]

Qualidade

A mixture of alamethicin homologs

Sequência

Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH₂)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH₂)-phenylalaninol

Informações de segurança

• Pictogramas: GHS06
• Palavra indicadora: Danger
• Frases de perigo: H301
• Declarações de precaução: P264 - P270 - P301 + P310 - P405 - P501
• Classificações de perigo: Acute Tox. 3 Oral
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges