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V0627

Valinomycin

Name: Valinomycin
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₅₄H₉₀N₆O₁₈

CAS Number:

2001-95-8

Molecular Weight:

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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Product Name

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

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Related Categories

Antibiotics

Bioactive Small Molecules

Biochemicals

Cell Culture Supplements & Reagents

General description

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.

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].

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.

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

Regulatory Information

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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)

Mechanical inhibition of isolated Vo from V/A-ATPase for proton conductance.

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

On the nature of seizure dynamics.

Viktor K Jirsa et al.

Brain : a journal of neurology, 137(Pt 8), 2210-2230 (2014-06-13)

Seizures can occur spontaneously and in a recurrent manner, which defines epilepsy; or they can be induced in a normal brain under a variety of conditions in most neuronal networks and species from flies to humans. Such universality raises the

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Global Trade Item Number

SKU	GTIN
V0627-500MG	04061837429026
V0627-10MG	04061837429002
V0627-100MG	04061837428999
V0627-25MG	04061837429019

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