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94675

Valinomycin

Name: Valinomycin
Brand: SIGMA

≥99.0% (TLC), K+ ionophore, powder

Sinónimos:

Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)₃: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid

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Fórmula empírica (notación de Hill):

C₅₄H₉₀N₆O₁₈

Número CAS:

2001-95-8

Peso molecular:

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

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Propiedades

Nombre del producto

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

Descripción

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).

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.

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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

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c