94675

Valinomycin

≥99.0% (TLC), K+ ionophore, powder

• Synonym(s): Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)₃: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid
• Empirical Formula (Hill Notation): C₅₄H₉₀N₆O₁₈
• CAS Number: 2001-95-8
• Molecular Weight: 1111.32
• NACRES: NA.32
• PubChem Substance ID: 329770374
• UNSPSC Code: 12352200
• EC Number: 217-896-6
• MDL number: MFCD00005114
• Beilstein/REAXYS Number: 78657

Properties

• Product Name: Valinomycin, ≥99.0% (TLC)
• InChI key: FCFNRCROJUBPLU-RPUZOQEISA-N
• 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
• 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
• 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
• Quality Level: 200

Description

Application

Valinomycin has been used as an internal standard in the cytotoxicity assay for the detection of cereulide produced by emetic Bacillus cereus.[1] It has also been used in the measurement of the electrogenicity of bile salt/H⁺ antiport in Escherichia coli.[2]

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.[3]

General description

Chemical structure: peptide

Valinomycin is a neutral cyclic dodecadepsi-peptide antibiotic,[4] that has a 36-member ring.[5]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).[6]

Safety Information

• 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
• Storage Class: 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