WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406668
CAS#: 28380-24-7
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.
MedKoo Cat#: 406668
Name: Nigericin
CAS#: 28380-24-7
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
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 Key: MOYOTUKECQMGHE-PDEFJWSRSA-M
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
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.
