Nigericin sodium

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MedKoo CAT#: 406668

CAS#: 28643-80-3 (sodium)

Description: Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation was described in the 1950s, and in 1968 the structure could be elucidated by X-ray crystallography. The structure and properties of nigericin are similar to the antibiotic monensin. Commercially it is obtained as a byproduct, or contaminant, at the fermentation of Geldanamycin. It is also called Polyetherin A, Azalomycin M, Helixin C, Antibiotic K178, Antibiotic X-464. Nigericin acts as an H+, K+, Pb2+ ionophore. Most commonly it is an antiporter of H+ and K+. In the past nigericin was used as an antibiotic active against gram positive bacteria. It inhibits the Golgi functions in Eukaryotic cells. Nigericin exhibits anticancer and anti-HIV activity.

Chemical Structure

Nigericin sodium
CAS# 28643-80-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 406668
Name: Nigericin sodium
CAS#: 28643-80-3 (sodium)
Chemical Formula: C40H68O11
Exact Mass: 724.47616
Molecular Weight: 724.9
Elemental Analysis: C, 64.32; H, 9.04; Na, 3.08; O, 23.56

Price and Availability

Size Price Availability Quantity
5.0mg USD 385.0 2 Weeks
10.0mg USD 650.0 2 Weeks
50.0mg USD 1650.0 2 Weeks
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Related CAS #: 28380-24-7 (free)   28643-80-3 (sodium)    

Synonym: Antibiotic K178, Antibiotic X464, Azalomycin M, Helexin C, Polyetherin A

IUPAC/Chemical Name: sodium (R)-2-((2R,3S,6R)-6-(((2S,4R,5R,7R,9R,10R)-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoate


InChi Code: InChI=1S/C40H68O11.Na/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34;/h21-35,41,44H,11-20H2,1-10H3,(H,42,43);/q;+1/p-1/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+;/m0./s1

SMILES Code: C[C@H]([C@H]1[C@@H](C)CC[C@H](C[C@H](C[C@@H](OC)[C@H]2C)O[C@]32[C@H](C)C[C@@](C)([C@@H]4O[C@](C)([C@@H]5O[C@@H]([C@@H]6[C@@H](C)C[C@@H](C)[C@@](CO)(O)O6)C[C@@H]5C)CC4)O3)O1)C(O[Na])=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 724.9 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Bilen S, Biswas G, Otsuyama S, Kono T, Sakai M, Hikima J. Inflammatory responses in the Japanese pufferfish (Takifugu rubripes) head kidney cells stimulated with an inflammasome-inducing agent, nigericin. Dev Comp Immunol. 2014 Oct;46(2):222-30. doi: 10.1016/j.dci.2014.04.010. Epub 2014 Apr 24. PubMed PMID: 24768998.

2: Deng CC, Liang Y, Wu MS, Feng FT, Hu WR, Chen LZ, Feng QS, Bei JX, Zeng YX. Nigericin selectively targets cancer stem cells in nasopharyngeal carcinoma. Int J Biochem Cell Biol. 2013 Sep;45(9):1997-2006. doi: 10.1016/j.biocel.2013.06.023. Epub 2013 Jul 4. PubMed PMID: 23831840.

3: Zhou HM, Dong TT, Wang LL, Feng B, Zhao HC, Fan XK, Zheng MH. Suppression of colorectal cancer metastasis by nigericin through inhibition of epithelial-mesenchymal transition. World J Gastroenterol. 2012 Jun 7;18(21):2640-8. doi: 10.3748/wjg.v18.i21.2640. PubMed PMID: 22690072; PubMed Central PMCID: PMC3370000.

4: Lim J, Lee Y, Kim HW, Rhyu IJ, Oh MS, Youdim MB, Yue Z, Oh YJ. Nigericin-induced impairment of autophagic flux in neuronal cells is inhibited by overexpression of Bak. J Biol Chem. 2012 Jul 6;287(28):23271-82. doi: 10.1074/jbc.M112.364281. Epub 2012 Apr 5. PubMed PMID: 22493436; PubMed Central PMCID: PMC3390606.

5: Stout-Delgado HW, Vaughan SE, Shirali AC, Jaramillo RJ, Harrod KS. Impaired NLRP3 inflammasome function in elderly mice during influenza infection is rescued by treatment with nigericin. J Immunol. 2012 Mar 15;188(6):2815-24. doi: 10.4049/jimmunol.1103051. Epub 2012 Feb 10. PubMed PMID: 22327078; PubMed Central PMCID: PMC3294083.

6: Sturz GR, Phan TH, Mummalaneni S, Ren Z, DeSimone JA, Lyall V. The K+-H+ exchanger, nigericin, modulates taste cell pH and chorda tympani taste nerve responses to acidic stimuli. Chem Senses. 2011 May;36(4):375-88. doi: 10.1093/chemse/bjq146. Epub 2011 Jan 21. PubMed PMID: 21257734; PubMed Central PMCID: PMC3151661.

7: Myskiw C, Piper J, Huzarewich R, Booth TF, Cao J, He R. Nigericin is a potent inhibitor of the early stage of vaccinia virus replication. Antiviral Res. 2010 Dec;88(3):304-10. doi: 10.1016/j.antiviral.2010.10.001. Epub 2010 Oct 15. PubMed PMID: 20951746.

8: Mashima T, Okabe S, Seimiya H. Pharmacological targeting of constitutively active truncated androgen receptor by nigericin and suppression of hormone-refractory prostate cancer cell growth. Mol Pharmacol. 2010 Nov;78(5):846-54. doi: 10.1124/mol.110.064790. Epub 2010 Aug 13. PubMed PMID: 20709811.

9: Cui J, Li C, Wang C, Li Y, Zhang L, Zhang L, Xiu X, Li Y, Wei N. Nigericin-mediated liposome loading of topotecan: is nigericin a potential drug release regulator? Int J Pharm. 2010 Oct 31;399(1-2):31-6. doi: 10.1016/j.ijpharm.2010.07.050. Epub 2010 Aug 1. PubMed PMID: 20678563.

10: Fruth IA, Arrizabalaga G. Toxoplasma gondii: induction of egress by the potassium ionophore nigericin. Int J Parasitol. 2007 Dec;37(14):1559-67. Epub 2007 Jun 9. PubMed PMID: 17618633; PubMed Central PMCID: PMC2221775.

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