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Valinomycin (Synonyms: NSC 122023)

Catalog No.GC16948

Valinomycin is a dodecadepsipeptide antibiotic, which is obtained from several Streptomyces strains.

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Valinomycin Chemical Structure

Cas No.: 2001-95-8

Size Price Stock Qty
10mM (in 1mL DMSO)
$92.00
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10mg
$49.00
In stock
50mg
$185.00
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Sample solution is provided at 25 µL, 10mM.

Description of Valinomycin

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 of Valinomycin

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.

Chemical Properties of Valinomycin

Cas No. 2001-95-8 SDF
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
Canonical 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
Formula C54H90N6O18 M.Wt 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 Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Valinomycin

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1 mg 5 mg 10 mg
1 mM 0.8998 mL 4.4992 mL 8.9983 mL
5 mM 0.18 mL 0.8998 mL 1.7997 mL
10 mM 0.09 mL 0.4499 mL 0.8998 mL
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In vivo Formulation Calculator (Clear solution) of Valinomycin

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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3. All of the above co-solvents are available for purchase on the GlpBio website.

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Average Rating: 5 ★★★★★ (Based on Reviews and 28 reference(s) in Google Scholar.)

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