Chemistry:Nigericin
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| Preferred IUPAC name
(2R)-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-dimethyloxan-2-yl]-2,3′-dimethyl[2,2′-bioxolan]-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoic acid | |
| Other names
Polyetherin A, Azalomycin M, Helixin C, Helix C
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| Properties | |
| C40H68O11 | |
| Molar mass | 724.96132 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et. al),[1][2] and in 1968 the structure could be elucidated by X-ray crystallography.[3] 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, and 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. Its ability to induce K+ efflux also makes it a potent activator of the NLRP3 inflammasome[4][5]
References
- ↑ Harned, R. L.; Hidy, P. H.; Corum, C. J.; Jones, K. L. (December 1951). "Nigericin a new crystalline antibiotic from an unidentified Streptomyces". Antibiotics & Chemotherapy (Northfield, Ill.) 1 (9): 594–596. ISSN 0570-3123. PMID 24541690. https://pubmed.ncbi.nlm.nih.gov/24541690/.
- ↑ "Alkali metal cation release and respiratory inhibition induced by nigericin in rat liver mitochondria". Proc. Natl. Acad. Sci. U.S.A. 56 (2): 654–8. 1966. doi:10.1073/pnas.56.2.654. PMID 5229984. Bibcode: 1966PNAS...56..654G.
- ↑ "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31. 1968. doi:10.1016/0006-291X(68)90249-0. PMID 5696503.
- ↑ Mariathasan, S; Weiss, DS; Newton, K; McBride, J; O'Rourke, K; Roose-Girma, M; Lee, WP; Weinrauch, Y et al. (9 March 2006). "Cryopyrin activates the inflammasome in response to toxins and ATP.". Nature 440 (7081): 228–32. doi:10.1038/nature04515. PMID 16407890. Bibcode: 2006Natur.440..228M.
- ↑ Muñoz-Planillo, R; Kuffa, P; Martínez-Colón, G; Smith, BL; Rajendiran, TM; Núñez, G (27 June 2013). "K⁺ efflux is the common trigger of NLRP3 inflammasome activation by bacterial toxins and particulate matter.". Immunity 38 (6): 1142–53. doi:10.1016/j.immuni.2013.05.016. PMID 23809161.
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