94675

Valinomycin

≥99.0% (TLC), K+ ionophore, powder

• 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
• NACRES: NA.32
• PubChem Substance ID: 329770374
• UNSPSC Code: 12352200
• EC Number: 217-896-6
• MDL number: MFCD00005114
• Beilstein/REAXYS Number: 78657
• Assay: ≥99.0% (TLC)
• Form: powder

Eigenschaften

• Produktname: Valinomycin, ≥99.0% (TLC)
• Quality Segment: 200
• assay: ≥99.0% (TLC)
• form: powder
• mp: 187-190 °C
• antibiotic activity spectrum: mycobacteria
• mode of action: cell membrane | interferes
• storage temp.: 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
• InChI key: FCFNRCROJUBPLU-RPUZOQEISA-N

Beschreibung

General description

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).[1]

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.

Biochem/physiol Actions

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.

Sicherheitshinweise

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H310
• pcodes: P262 - P264 - P280 - P301 + P310 - P302 + P352 + P310 - P361 + P364
• Hazard Classifications: Acute Tox. 1 Dermal - Acute Tox. 1 Oral
• Lagerklasse: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges