94675

Valinomycin

≥99.0% (TLC)

• Synonyme(s) : Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)₃: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid
• Formule empirique (notation de Hill): C₅₄H₉₀N₆O₁₈
• Numéro CAS: 2001-95-8
• Poids moléculaire : 1111.32
• Numéro Beilstein : 78657
• Numéro CE : 217-896-6
• Numéro MDL: MFCD00005114
• Code UNSPSC : 12352200
• ID de substance PubChem : 329770374
• Nomenclature NACRES : NA.32

Propriétés

• Niveau de qualité: 200
• Pureté: ≥99.0% (TLC)
• Forme: powder
• Pf: 187-190 °C
• Spectre d'activité de l'antibiotique: mycobacteria
• Mode d’action: cell membrane | interferes
• Température de stockage: 2-8°C
• Chaîne SMILES: CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
• InChI: 1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1
• Clé InChI: FCFNRCROJUBPLU-RPUZOQEISA-N

Description

Description générale

Chemical structure: peptide

Valinomycin is a neutral cyclic dodecadepsi-peptide antibiotic, that has a 36-member ring.Valinomycin consists of twelve stereogenic centers that are made of three repeating sequences of a tetramer of D-α-hydroxyisovalericacid-D-valine-L-lactate-L-valine. It shows antibacterial, antitumor, antifungal, antiviral, and insecticidal properties. Valinomycin exerts its antiviral activity against human coronavirus OC43 (HCoV-OC43), severe acute respiratory syndrome coronavirus (SARS-CoV), and middle-east respiratory syndrome coronavirus (MERS-CoV).

Application

Valinomycin has been used as an internal standard in the cytotoxicity assay for the detection of cereulide produced by emetic Bacillus cereus. It has also been used in the measurement of the electrogenicity of bile salt/H⁺ antiport in Escherichia coli.

Actions biochimiques/physiologiques

K⁺-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.

Valinomycin affects the ion transport behavior of mitochondrial systems.

Autres remarques

Review

Informations sur la sécurité

• Pictogrammes: GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H300 + H310
• Conseils de prudence: P262 - P264 - P280 - P301 + P310 - P302 + P352 + P310 - P361 + P364
• Classification des risques: Acute Tox. 1 Dermal - Acute Tox. 1 Oral
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges