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94675

Sigma-Aldrich

Valinomycin

≥99.0% (TLC)

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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
Beilstein:
78657
EC Number:
217-896-6
MDL number:
MFCD00005114
UNSPSC Code:
12352200
PubChem Substance ID:
329770374
NACRES:
NA.32

Quality Level

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

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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 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.

Other Notes

Review

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Topics in Current Chemistry, 128, 175-175 (1985)
Dong Zhang et al.
Biomedical journal, 43(5), 414-423 (2020-10-06)
Human coronaviruses (HCoVs), including severe acute respiratory syndrome coronavirus (SARS-CoV), Middle East respiratory syndrome coronavirus (MERS-CoV), and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), have been resulting in global epidemics with heavy morbidity and mortality. Unfortunately, there are currently no
Transmembrane voltage sensor
Membrane Science and Technology, 7, 847-886 (2003)
The molecular structure and some transport properties of valinomycin
Pinkerton M, et al.
Biochemical and Biophysical Research Communications, 35(4), 512-518 (1969)
Measurement of the Electrogenicity of Bile Salt/H+ Antiport in Escherichia coli
Holdsworth S R and Law C J
Molecular Microbiology (2014)
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