94675

Valinomycin

≥99.0% (TLC)

• Synonym(e): [(D-Val-L-Lac-Val-D-HyV)(3)](cycl.) (L-Lac: L-Milchsäure, D-HyV: D-α-Hydroxy-isovaleriansäure)
• Empirische Formel (Hill-System): C₅₄H₉₀N₆O₁₈
• CAS-Nummer: 2001-95-8
• Molekulargewicht: 1111.32
• Beilstein: 78657
• EG-Nummer: 217-896-6
• MDL-Nummer: MFCD00005114
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 329770374
• NACRES: NA.32

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥99.0% (TLC)
• Form: powder
• mp (Schmelzpunkt): 187-190 °C
• Wirkungsspektrum von Antibiotika: mycobacteria
• Wirkungsweise: cell membrane | interferes
• Lagertemp.: 2-8°C
• SMILES String: 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
• InChIKey: FCFNRCROJUBPLU-RPUZOQEISA-N

Beschreibung

Allgemeine Beschreibung

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).

Anwendung

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.

Biochem./physiol. Wirkung

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.

Sonstige Hinweise

Review

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H300 + H310
• P-Sätze: P262 - P264 - P280 - P301 + P310 - P302 + P352 + P310 - P361 + P364
• Gefahreneinstufungen: Acute Tox. 1 Dermal - Acute Tox. 1 Oral
• Lagerklassenschlüssel: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges