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
Category: Antibiotics
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).
Synonyms | Potassium ionophore I, Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = alpha-Hydroxyisovaleric acid, Lac = Lactic acid, NSC 122023 |
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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 |