94675

Valinomycin

≥99.0% (TLC)

• Sinónimos: Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)₃: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid
• Fórmula empírica (notación de Hill): C₅₄H₉₀N₆O₁₈
• Número de CAS: 2001-95-8
• Peso molecular: 1111.32
• Beilstein: 78657
• Número CE: 217-896-6
• Número MDL: MFCD00005114
• Código UNSPSC: 12352200
• ID de la sustancia en PubChem: 329770374
• NACRES: NA.32

Propiedades

• Nivel de calidad: 200
• Ensayo: ≥99.0% (TLC)
• Formulario: powder
• mp: 187-190 °C
• espectro de actividad antibiótica: mycobacteria
• Modo de acción: cell membrane | interferes
• temp. de almacenamiento: 2-8°C
• cadena 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
• Clave InChI: FCFNRCROJUBPLU-RPUZOQEISA-N

Descripción

Descripción general

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).

Aplicación

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.

Acciones bioquímicas o fisiológicas

K⁺-selective ionophore which uncouples oxidative phosphorylation.

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.

Otras notas

Review

Información de seguridad

• Pictogramas: GHS06
• Palabra de señalización: Danger
• Frases de peligro: H300 + H310
• Consejos de prudencia: P262 - P264 - P280 - P301 + P310 - P302 + P352 + P310 - P361 + P364
• Clasificaciones de peligro: Acute Tox. 1 Dermal - Acute Tox. 1 Oral
• Código de clase de almacenamiento: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges