Available from stock

Valinomycin

SKU: P0163

Category: Antibiotics

Synonyms: Potassium ionophore I, Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = alpha-Hydroxyisovaleric acid, Lac = Lactic acid, NSC 122023; 2001-95-8
CAS-Number: C₅₄H₉₀N₆O₁₈
Molecular Formula: 1111.32
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (HPLC)
Appearance: White to off-white powder

Properties

Solvents: DMSO (20 mg/ml), ethanol (20 mg/ml), water (insoluble)
Melting Point: 184-190 °C

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H300+H310
Precautionary statements: P262-P264-P280-P301+P310-P302+P352+P310-P361+P364
GHS Symbol: GHS06
Signal word: Danger
RIDADR: UN2811
Transportation: Packing Group I

Description: Valinomycin is a cyclododecadepsipeptide antibiotic originially isolated from Streptomyces strains and displays antibacterial efficacy. Valinomycin a neutral ionophore that selectively transfers alkali metal ions via biological and synthetic lipid membranes. Valinomycin is widely used as a selective potassium (K+)-selective ionophore (over Na+) and is an important research tool for membrane and membrane vesicles studies. As ionophore valinomycin has found application as a biosensor to detect potassium (K+) efflux. Valinomycin induces apoptosis in several cell types, including CHO cells, by stimulating potassium efflux and leading to phosphatidylserine membrane translocation, caspase-3 activation, inducing mitochondrial damage and oxidative stress. Valinomycin shows antitumor, antifungal, antiviral, insecticidal and antibacterial effects. Valinomycin as a mitophagy activator also plays a positive role in the treatment of Parkinson’s disease and Alzheimer’s disease. It was recently reported to have antiviral activity against several coronaviruses (FIPV, MERS-CoV, SARS-CoV, HCoV-OC43 or SARS-CoV2).
Smiles: 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 Key: FCFNRCROJUBPLU-UHFFFAOYSA-N
References: (1) L.A. Pioda, et al., Clin. Chim. Acta 29, 289 (1970) , (2) I.J. Furlong, et al., Cell Death Differ. 5, 214 (1998) , (3) R. Abdalah, et al., Neurosci. Lett. 405, 68 (2006) , (4) L. Rose & A.T.A. Jenkins, Bioelectrochem. 70, 387 (2007) , (5) M.A. Kroten, et al., Pol. J. Microbiol. 59, 3 (2010) , (6) B. Klein, et al., Apoptosis 16, 1101 (2011) , (7) K.-S. Chang, et al., Biosens. Bioelectronics 31, 137 (2011) , (8) X. Xiong, et al., Exp. Cell Res. 396, 112266 (2020) , (9) D. Zhang, et al., Biomed. J. 43, 414 (2020) (Review) , (10) S. Huang, et al., Microorganisms 9, 780 (2021) (Review) , (11) K. Gurukkalot & V. Rajendran, Curr. Microbiol. 80, 273 (2023) (Review)
InChi: 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

Valinomycin is a cyclododecadepsipeptide antibiotic originially isolated from Streptomyces strains and displays antibacterial efficacy. Valinomycin a neutral ionophore that selectively transfers alkali metal ions via biological and synthetic lipid membranes. Valinomycin is widely used as a selective potassium (K+)-selective ionophore (over Na+) and is an important research tool for membrane and membrane vesicles studies. As ionophore valinomycin has found application as a biosensor to detect potassium (K+) efflux. Valinomycin induces apoptosis in several cell types, including CHO cells, by stimulating potassium efflux and leading to phosphatidylserine membrane translocation, caspase-3 activation, inducing mitochondrial damage and oxidative stress. Valinomycin shows antitumor, antifungal, antiviral, insecticidal and antibacterial effects. Valinomycin as a mitophagy activator also plays a positive role in the treatment of Parkinson’s disease and Alzheimer’s disease. It was recently reported to have antiviral activity against several coronaviruses (FIPV, MERS-CoV, SARS-CoV, HCoV-OC43 or SARS-CoV2).

SKU: P0163 Category: Antibiotics

Additional information

Additional information

Synonyms	Potassium ionophore I, Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = alpha-Hydroxyisovaleric acid, Lac = Lactic acid, NSC 122023
Purity	≥95% (HPLC)
Appearance	White to off-white powder
CAS-Number	2001-95-8
Molecular Formula	C54H90N6O18
Molecular Weight	1111.32
Solvents	DMSO (20 mg/ml), ethanol (20 mg/ml), water (insoluble)
Melting Point	184-190 °C
Smiles	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 Key	FCFNRCROJUBPLU-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H300+H310
Precautionary statements	P262-P264-P280-P301+P310-P302+P352+P310-P361+P364
GHS Symbol	GHS06
Signal word	Danger
RIDADR	UN2811
Transportation	Packing Group I
References	(1) L.A. Pioda, et al., Clin. Chim. Acta 29, 289 (1970), (2) I.J. Furlong, et al., Cell Death Differ. 5, 214 (1998), (3) R. Abdalah, et al., Neurosci. Lett. 405, 68 (2006), (4) L. Rose & A.T.A. Jenkins, Bioelectrochem. 70, 387 (2007), (5) M.A. Kroten, et al., Pol. J. Microbiol. 59, 3 (2010), (6) B. Klein, et al., Apoptosis 16, 1101 (2011), (7) K.-S. Chang, et al., Biosens. Bioelectronics 31, 137 (2011), (8) X. Xiong, et al., Exp. Cell Res. 396, 112266 (2020), (9) D. Zhang, et al., Biomed. J. 43, 414 (2020) (Review), (10) S. Huang, et al., Microorganisms 9, 780 (2021) (Review), (11) K. Gurukkalot & V. Rajendran, Curr. Microbiol. 80, 273 (2023) (Review)
InChi	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
Quantity	25 mg, 100 mg, Bulk