Nigericin sodium salt

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Synomyms: Nigericin, Helexin C, Polyetherin A, Azalomycin M, Antibiotic X464, Antibiotic K178

IUPAC Name:

Sodium 2-[(3S,6R)-6-[[(5R,6R,7R,9R)-3-[5-[(3S,5R)-5-[(2S,3S,5R, 6R)-6-hydroxy-6-(hydroxymethyl)-3, 5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7- methoxy-1,3,6-trimethyl-4, 10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoate

Functional Activity:

Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Nigericin acts as an H⁺, K⁺, Pb²⁺ ionophore. Most commonly it is an antiporter of H⁺ and K⁺. Polyether ionophore which disrupts membrane potential and stimulates ATPase activity in mitochondria. Ion selectivity is K⁺> Rb⁺≥Cs⁺>> Na⁺.

In the past nigericin was used as an antibiotic active against gram positive bacteria. It inhibits the Golgi functions in Eukaryotic cells. Nigericin exhibits anti-HIV activity.

Technical Data:

M.Wt: 746.94

Formula: C₄₀H₆₇ NaO₁₁

Solubility: Soluble in water, DMSO, and ethanol

Purity: >98%

Storage: Dessicate at 4°C

CAS No.: 28643-80-3

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References for Nigericin:

1. Fruth, I. A. and Arrizabalaga, G. Toxoplasma gondii: induction of egress by the potassium ionophore nigericin. Int J Parasitol, 37: 1559-1567, 2007.

2. Harvey, B. M., Mironenko, T., Sun, Y., Hong, H., Deng, Z., Leadlay, P. F., Weissman, K. J., and Haydock, S. F. Insights into polyether biosynthesis from analysis of the nigericin biosynthetic gene cluster in Streptomyces sp. DSM4137. Chem Biol, 14: 703-714, 2007.

3. Pelegrin, P. and Surprenant, A. Pannexin-1 couples to maitotoxin- and nigericin-induced interleukin-1beta release through a dye uptake-independent pathway. J Biol Chem, 282: 2386-2394, 2007.

4. Kucejova, B., Kucej, M., Petrezselyova, S., Abelovska, L., and Tomaska, L. A screen for nigericin-resistant yeast mutants revealed genes controlling mitochondrial volume and mitochondrial cation homeostasis. Genetics, 171: 517-526, 2005.

5. Hamidinia, S. A., Tan, B., Erdahl, W. L., Chapman, C. J., Taylor, R. W., and Pfeiffer, D. R. The ionophore nigericin transports Pb2+ with high activity and selectivity: a comparison to monensin and ionomycin. Biochemistry, 43: 15956-15965, 2004.

6. Hentze, H., Lin, X. Y., Choi, M. S., and Porter, A. G. Critical role for cathepsin B in mediating caspase-1-dependent interleukin-18 maturation and caspase-1-independent necrosis triggered by the microbial toxin nigericin. Cell Death Differ, 10: 956-968, 2003.

Certificate of Analysis/MSDS is available upon request with lot number