GLPBio

Valinomycin

Catalog No.: GC16948Purity:>98.00%Synonyms: NSC 122023
Valinomycin is a dodecadepsipeptide antibiotic, which is obtained from several Streptomyces strains.

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Valinomycin
Cas No.: 2001-95-8
10mM (in 1mL DMSO)In Stock
$92.00
1
10mgIn Stock
$49.00
1
50mgIn Stock
$185.00
1

Citations

1 publicationsPublications from researchers using this product

Description

Valinomycin is a dodecadepsipeptide antibiotic, which is obtained from several Streptomyces strains. Valinomycin functions as a potassium-specific transporter and promotes the movement of K+ through lipid membranes. Excessive K+ efflux is an ionic mechanism underlying apoptosis.It can be used as uncoupling agent to induce depolarization[1-3].

Valinomycin(1-100µM;12-24 h) treated CHO cells underwent an apoptotic event due to potassium efflux[4]. Valinomycin (2 nM) induced energy-dependent mitochondrial swelling, cytochrome c release, cytosolic NADH/cytochrome c oxidation and apoptosis[5]. Neurite formation and membrane changes of mouse neuroblastoma cells induced by valinomycin(100 µM) [6].

Incorporation of valinomycin into multilamellar liposomes composed of dimyristoyl phosphatidyl choline:cholesterol:phosphatidyl serine (10:4:1 M ratio) results in a profound reduction in toxicity with maintainence of antitumor efficacy in mice, the LD50 for liposome incorporated valinomycin (MVL-VM) is in excess of 50 mg/kg[7].

References:
[1]. Varma S, Sabo D, ,et,al. K+/Na+ selectivity in K channels and valinomycin: over-coordination versus cavity-size constraints. J Mol Biol. 2008 Feb 8;376(1):13-22. doi: 10.1016/j.jmb.2007.11.059. Epub 2007 Nov 28. PMID: 18155244; PMCID: PMC2390915.
[2]. Daniele RP, Holian SK. A potassium ionophore (valinomycin) inhibits lymphocyte proliferation by its effects on the cell membrane. Proc Natl Acad Sci U S A. 1976 Oct;73(10):3599-602. doi: 10.1073/pnas.73.10.3599. PMID: 1068473; PMCID: PMC431165.
[3]. Berezin SK. Valinomycin as a Classical Anionophore: Mechanism and Ion Selectivity. J Membr Biol. 2015 Aug;248(4):713-26. doi: 10.1007/s00232-015-9784-y. Epub 2015 Mar 4. PMID: 25736817.
[4]. Abdalah R, Wei L, ,et,al. Valinomycin-induced apoptosis in Chinese hamster ovary cells. Neurosci Lett. 2006 Sep 11;405(1-2):68-73. doi: 10.1016/j.neulet.2006.06.055. Epub 2006 Jul 20. PMID: 16857314.
[5]. Lofrumento DD, La Piana G, ,et,al. Valinomycin induced energy-dependent mitochondrial swelling, cytochrome c release, cytosolic NADH/cytochrome c oxidation and apoptosis. Apoptosis. 2011 Oct;16(10):1004-13. doi: 10.1007/s10495-011-0628-7. PMID: 21739274.
[6]. Koike T. Neurite formation and membrane changes of mouse neurobalstoma cells induced by valinomycin. Biochim Biophys Acta. 1978 Jun 2;509(3):429-39. doi: 10.1016/0005-2736(78)90237-7. PMID: 656419.
[7]. Daoud SS, Juliano RL. Reduced toxicity and enhanced antitumor effects in mice of the ionophoric drug valinomycin when incorporated in liposomes. Cancer Res. 1986 Nov;46(11):5518-23. PMID: 3756900.

Protocol

Cell experiment [1]:

Cell lines

CHO cells

Preparation method

Valinomycin is added into the culture medium.

Reaction Conditions

1-100μM;12-24 h

Applications

100 μM valinomycin caused 77% and 86% cell death at 12 h and 24 h, respectively.

References:

[1]. Abdalah R, Wei L,et,al. Valinomycin-induced apoptosis in Chinese hamster ovary cells. Neurosci Lett. 2006 Sep 11;405(1-2):68-73. doi: 10.1016/j.neulet.2006.06.055. Epub 2006 Jul 20. PMID: 16857314.

Product Documents

Purity:>98.00%Appearance:A solid

Chemical Properties

CAS No.
2001-95-8
Synonyms
NSC 122023
Chemical Name
(3S,6R,9R,12S,15S,18S,21R,24R,27R,30R,33R,36S)-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecaone
SMILES
O=C([C@@H](C(C)C)OC([C@@H](C(C)C)NC1=O)=O)N[C@@H](C(O[C@H](C)C(N[C@@H](C(O[C@H](C(N[C@H](C(O[C@@H](C)C(N[C@@H](C(O[C@@H](C(N[C@H](C(O[C@H]1C)=O)C(C)C)=O)C(C)C)=O)C(C)C)=O)=O)C(C)C)=O)C(C)C)=O)C(C)C)=O)=O)C(C)C
Molecular Formula
C54H90N6O18
Molecular Weight
1111.32
Solubility
DMF: 30 mg/ml,DMSO: 5 mg/ml,Ethanol: 10 mg/ml
Storage
Store at -20°C,protect from light
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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