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Merck

V0627

Valinomycin

≥90% (HPLC),≥98% (TLC), K+-selective ionophore , powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C54H90N6O18
Numéro CAS:
2001-95-8
Poids moléculaire :
1111.32
NACRES:
NA.77
PubChem Substance ID:
24900697
UNSPSC Code:
12352200
EC Number:
217-896-6
MDL number:
MFCD00005114
Beilstein/REAXYS Number:
78657
Assay:
≥90% (HPLC)
≥98% (TLC)
Form:
powder
Quality level:
300
Storage condition:
(Keep container tightly closed in a dry and well-ventilated place.)

Principaux documents

Voir toute la documentation
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Nom du produit

Valinomycin, ≥98% (TLC), ≥90% (HPLC)

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

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

≥90% (HPLC)
≥98% (TLC)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white

solubility

DMSO: ≥50 mg/mL
H2O: insoluble

antibiotic activity spectrum

Gram-positive bacteria
parasites
viruses

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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Catégories apparentées

Application

Valinomycin has been used:
  • to equilibrate intracellular pH and extracellular pH of 5 (and 6-)-carboxyfluorescein succinimidyl ester (cFSE) in Escherichia coli strain B23
  • as an ionophore to equilibrate intracellular pH and extracellular pH of lactic acid bacteria (LAB) strains
  • to establish the desired pH for acid-base transition and formation of K+-valinomycin diffusion potential

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 selectively transfers alkali metal ions via biological and synthetic membranes. The formation of a metal ion-peptide complex contributes to this ion-transporting. Valinomycin can create stable complexes with potassium, rubidium, and cesium (K+, Rb+, and Cs+) .

General description

Chemical structure: peptide
Valinomycin is a cyclic peptide, which contains d-valine, d-α-hydroxyvaleric acid, l-valine, and l-lactic acid in the sequential order of cyclo-[(l-Val-d-Hyv-d-Val-l-Lac)3].
Valinomycin, a nonribosomal peptide (NRP), is proposed to have a structure of a 24-membered cyclic peptide cyclo-(d-α-hydroxyisovaleryl-d-valyl-l-lactyl-l-valyl)2. It exhibits antitumor properties and plays a major role as a mitophagy activator. Initially isolated as an antibiotic compound, valinomycin has demonstrated antibacterial activity against Mycobacterium tuberculosis. Moreover, it has been identified as a potent antiviral agent against a wide spectrum of viruses, including human coronavirus, bunyavirus, enterovirus, and flavivirus.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Packaging

10MG,25MG,100MG,500MG

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral

Classe de stockage

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000497043
0000497041
0000497040
0000497040
0000497041

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

The nonribosomal peptide valinomycin: From discovery to bioactivity and biosynthesis
Huang S, et al.
Microorganisms, 9, 780-780 (2021)
Chitosan disrupts membrane permeability of lactic acid bacteria
Pan C, et al.
Journal of Experimental Microbiology and Immunology, 15, 7-14 (2011)
The effect of a fullerene water suspension on the growth, cell viability, and membrane integrity of Escherichia coli B23.
Aquino A, et al.
Journal of Experimental Microbiology and Immunology, 14, 13-20 (2010)
Jun-Ichi Kishikawa et al.
eLife, 9 (2020-07-09)
V-ATPase is an energy converting enzyme, coupling ATP hydrolysis/synthesis in the hydrophilic V1 domain, with proton flow through the Vo membrane domain, via rotation of the central rotor complex relative to the surrounding stator apparatus. Upon dissociation from the V1
Hannah R Schwartz et al.
Cell reports, 31(12), 107800-107800 (2020-06-25)
When evaluating anti-cancer drugs, two different measurements are used: relative viability, which scores an amalgam of proliferative arrest and cell death, and fractional viability, which specifically scores the degree of cell killing. We quantify relationships between drug-induced growth inhibition and
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