WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H540319
CAS#: 28380-24-7 (free acid)
Description: Nigericin is a cationic ionophore that inhibits Golgi function and suppresses growth of gram positive bacteria. It also prevents viral activation and triggers activation of the NALP3 inflammasome. 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. Its ability to induce K+ efflux also makes it a potent activator of the NLRP3 inflammasome.
Hodoodo Cat#: H540319
Name: Nigericin free acid
CAS#: 28380-24-7 (free acid)
Chemical Formula: C40H68O11
Exact Mass: 724.48
Molecular Weight: 724.973
Elemental Analysis: C, 66.27; H, 9.45; O, 24.28
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 28380-24-7 (free acid) 28643-80-3 (sodium)
Synonym: Nigericin; Azalomycin M; Helixin C; Polyetherin A
IUPAC/Chemical Name: (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)propanoic acid
InChi Key: DANUORFCFTYTSZ-SJSJOXFOSA-N
InChi Code: InChI=1S/C40H68O11/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)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
SMILES Code: CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@@H](O2)[C@@H](C)C(O)=O)O[C@]3(O[C@@]([C@H]4CC[C@]([C@@H]5O[C@H](C[C@@H]5C)[C@H]6O[C@@]([C@H](C)C[C@@H]6C)(O)CO)(C)O4)(C)C[C@H]3C)[C@@H]1C
Appearance: TBD
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
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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 724.97 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Zhu S, Yue X, Huang K, Li X, Gouife M, Nawaz M, Ma R, Jiang J, Jin S, Xie J. Nigericin treatment activates endoplasmic reticulum apoptosis pathway in goldfish kidney leukocytes. Fish Shellfish Immunol. 2023 Feb 15;134:108616. doi: 10.1016/j.fsi.2023.108616. Epub ahead of print. PMID: 36796597.
2: Zhu X, Hong A, Sun X, Wang W, He G, Luo H, Wu Z, Xu Q, Hu Z, Wu X, Huang D, Li L, Zhao X, Deng X. Nigericin is effective against multidrug resistant gram- positive bacteria, persisters, and biofilms. Front Cell Infect Microbiol. 2022 Dec 20;12:1055929. doi: 10.3389/fcimb.2022.1055929. PMID: 36605124; PMCID: PMC9807916.
3: Niu Q, Liu Y, Zheng Y, Tang Z, Qian Y, Qi R, Shen J, Zhao P. Co-delivery of nigericin and decitabine using hexahistidine-metal nanocarriers for pyroptosis- induced immunotherapeutics. Acta Pharm Sin B. 2022 Dec;12(12):4458-4471. doi: 10.1016/j.apsb.2022.11.002. Epub 2022 Nov 4. PMID: 36562000; PMCID: PMC9764131.
4: Deryabin PI, Shatrova AN, Borodkina AV. Targeting Multiple Homeostasis- Maintaining Systems by Ionophore Nigericin Is a Novel Approach for Senolysis. Int J Mol Sci. 2022 Nov 17;23(22):14251. doi: 10.3390/ijms232214251. PMID: 36430735; PMCID: PMC9693507.
5: Guo H, Zhang Q, Li R, Seshadri VD. Nigericin Abrogates Maternal and Embryonic Oxidative Stress in the Streptozotocin-Induced Diabetic Pregnant Rats. Appl Biochem Biotechnol. 2023 Feb;195(2):801-815. doi: 10.1007/s12010-022-04100-6. Epub 2022 Oct 3. PMID: 36190644.
6: Wei J, Ma M, Guo S, Xu Y, Xie J, Pan G, Zhou Z. Characterization of Pathway- Specific Regulator NigR for High Yield Production of Nigericin in Streptomyces malaysiensis F913. Antibiotics (Basel). 2022 Jul 13;11(7):938. doi: 10.3390/antibiotics11070938. PMID: 35884192; PMCID: PMC9312159.
7: Taechowisan T, Klomluam K, Chuen-Im T, S Phutdhawong W. Synergistic Antibacterial Activity of 1-Methyl Ester-Nigericin and Methyl 5-(Hydroxymethyl) Furan-2-Carboxylate Against Proteus spp. Pak J Biol Sci. 2022 Jan;25(4):304-312. doi: 10.3923/pjbs.2022.304.312. PMID: 35638524.
8: Cao J, Li L, Yao Y, Xing Y, Ma H. Dehydroepiandrosterone exacerbates nigericin-induced abnormal autophagy and pyroptosis via GPER activation in LPS- primed macrophages. Cell Death Dis. 2022 Apr 19;13(4):372. doi: 10.1038/s41419-022-04841-6. PMID: 35440074; PMCID: PMC9018772.
9: Díaz-Cruz GA, Liu J, Tahlan K, Bignell DRD. Nigericin and Geldanamycin Are Phytotoxic Specialized Metabolites Produced by the Plant Pathogen Streptomyces sp. 11-1-2. Microbiol Spectr. 2022 Apr 27;10(2):e0231421. doi: 10.1128/spectrum.02314-21. Epub 2022 Feb 28. PMID: 35225656; PMCID: PMC9045263.
10: Yang Z, Xie J, Fang J, Lv M, Yang M, Deng Z, Xie Y, Cai L. Nigericin exerts anticancer effects through inhibition of the SRC/STAT3/BCL-2 in osteosarcoma. Biochem Pharmacol. 2022 Apr;198:114938. doi: 10.1016/j.bcp.2022.114938. Epub 2022 Jan 31. PMID: 35114189.
11: Ye X, Liu X, Wei W, Yu H, Jin X, Yu J, Li C, Xu B, Guo X, Mao J. Volume- activated chloride channels contribute to lipopolysaccharide plus nigericin- induced pyroptosis in bone marrow-derived macrophages. Biochem Pharmacol. 2021 Nov;193:114791. doi: 10.1016/j.bcp.2021.114791. Epub 2021 Sep 25. PMID: 34582774.
12: Zhou B, Wang C, Liu X, Wu B, Li J, Yao S, Zhang S. Combination of nigericin with cisplatin enhances the inhibitory effect of cisplatin on epithelial ovarian cancer metastasis by inhibiting slug expression via the Wnt/β-catenin signalling pathway. Oncol Lett. 2021 Oct;22(4):700. doi: 10.3892/ol.2021.12961. Epub 2021 Aug 3. PMID: 34457055; PMCID: PMC8358618.
13: Qin N, Xu G, Wang Y, Zhan X, Gao Y, Wang Z, Fu S, Shi W, Hou X, Wang C, Li R, Liu Y, Wang J, Zhao H, Xiao X, Bai Z. Bavachin enhances NLRP3 inflammasome activation induced by ATP or nigericin and causes idiosyncratic hepatotoxicity. Front Med. 2021 Aug;15(4):594-607. doi: 10.1007/s11684-020-0809-2. Epub 2021 Apr 28. PMID: 33909257.
14: Mitrović I, Grahovac J, Hrustić J, Jokić A, Dodić J, Mihajlović M, Grahovac M. Utilization of waste glycerol for the production of biocontrol agents nigericin and niphimycin by Streptomyces hygroscopicus: bioprocess development. Environ Technol. 2022 Aug;43(19):3000-3013. doi: 10.1080/09593330.2021.1913241. Epub 2021 Apr 18. PMID: 33820481.
15: Gao Y, Xu G, Ma L, Shi W, Wang Z, Zhan X, Qin N, He T, Guo Y, Niu M, Wang J, Bai Z, Xiao X. Icariside I specifically facilitates ATP or nigericin-induced NLRP3 inflammasome activation and causes idiosyncratic hepatotoxicity. Cell Commun Signal. 2021 Feb 11;19(1):13. doi: 10.1186/s12964-020-00647-1. PMID: 33573688; PMCID: PMC7879676.
16: Gao G, Liu F, Xu Z, Wan D, Han Y, Kuang Y, Wang Q, Zhi Q. Evidence of nigericin as a potential therapeutic candidate for cancers: A review. Biomed Pharmacother. 2021 May;137:111262. doi: 10.1016/j.biopha.2021.111262. Epub 2021 Jan 25. PMID: 33508621.
17: Garcia-Princival IMR, Princival JL, Dias da Silva E, de Arruda Lima SM, Carregosa JC, Wisniewski A Jr, de Lucena CCO, Halwass F, Alves Franca JA, Ferreira LFGR, Hernandes MZ, Saraiva KLA, Peixoto CA, Baratte B, Robert T, Bach S, Gomes DC, Guedes Paiva PM, Marchand P, Rodrigues MDD, Gonçalves da Silva T. Streptomyces hygroscopicus UFPEDA 3370: A valuable source of the potent cytotoxic agent nigericin and its evaluation against human colorectal cancer cells. Chem Biol Interact. 2021 Jan 5;333:109316. doi: 10.1016/j.cbi.2020.109316. Epub 2020 Dec 4. PMID: 33285127.
18: Sahu AK, Said MS, Hingamire T, Gaur M, Khan A, Shanmugam D, Barvkar VT, Dharne MS, Bharde AA, Dastager SG. Approach to nigericin derivatives and their therapeutic potential. RSC Adv. 2020 Nov 26;10(70):43085-43091. doi: 10.1039/d0ra05137c. PMID: 35514935; PMCID: PMC9058090.
19: Petersen LM, Beitz E. The Ionophores CCCP and Gramicidin but Not Nigericin Inhibit Trypanosoma brucei Aquaglyceroporins at Neutral pH. Cells. 2020 Oct 21;9(10):2335. doi: 10.3390/cells9102335. PMID: 33096791; PMCID: PMC7589649.
20: Xu Z, Gao G, Liu F, Han Y, Dai C, Wang S, Wei G, Kuang Y, Wan D, Zhi Q, Xu Y. Molecular Screening for Nigericin Treatment in Pancreatic Cancer by High- Throughput RNA Sequencing. Front Oncol. 2020 Jul 31;10:1282. doi: 10.3389/fonc.2020.01282. PMID: 32850392; PMCID: PMC7411259.
