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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.)
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Nom du produit

Valinomycin, ≥98% (TLC), ≥90% (HPLC)

Quality Level

300

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

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

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.

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+) .

Packaging

10MG,25MG,100MG,500MG

Other Notes

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

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Skull and crossbones
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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
0000549546
0000515482
0000549546
0000515482
0000497043

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Contenu apparenté

The nonribosomal peptide valinomycin: From discovery to bioactivity and biosynthesis
Huang S, et al.
Microorganisms, 9, 780-780 (2021)
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)
Chitosan disrupts membrane permeability of lactic acid bacteria
Pan C, et al.
Journal of Experimental Microbiology and Immunology, 15, 7-14 (2011)
Afficher tous les articles scientifiques apparentés