Nigericin

Nigericin
Names
	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
Identifiers
CAS Number	28380-24-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7569 ;
ChEMBL	ChEMBL405862 ;
ChemSpider	10196461 ;
ECHA InfoCard	100.212.814
PubChem CID	34230;
UNII	RRU6GY95IS ;
CompTox Dashboard (EPA)	DTXSID9041079 ;
	InChI 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 Key: DANUORFCFTYTSZ-SJSJOXFOSA-N ; InChI=1/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 Key: DANUORFCFTYTSZ-SJSJOXFOBS;
	SMILES OC(=O)[C@H](C)[C@@H]1O[C@H](CC[C@@H]1C)C[C@H]6O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]3CC[C@](C)(O3)[C@@H]4O[C@H](C[C@@H]4C)[C@H]5O[C@@](O)(CO)[C@H](C)C[C@@H]5C)[C@H](C)[C@H](OC)C6;
Properties
Chemical formula	C40H68O11
Molar mass	724.973 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.
^ Graven SN, Estrada-O S, Lardy HA (1966). "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. Bibcode:1966PNAS...56..654G. doi:10.1073/pnas.56.2.654. PMC 224422. PMID 5229984.
^ Steinrauf LK, Pinkerton M, Chamberlin JW (1968). "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31. 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; Monack, DM; Dixit, VM (9 March 2006). "Cryopyrin activates the inflammasome in response to toxins and ATP". Nature. 440 (7081): 228–32. Bibcode:2006Natur.440..228M. doi:10.1038/nature04515. PMID 16407890.
^ 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. PMC 3730833. PMID 23809161.

[1] 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.

[pmid5229984-2] Graven SN, Estrada-O S, Lardy HA (1966). "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. Bibcode:1966PNAS...56..654G. doi:10.1073/pnas.56.2.654. PMC 224422. PMID 5229984.

[pmid5696503-3] Steinrauf LK, Pinkerton M, Chamberlin JW (1968). "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31. doi:10.1016/0006-291X(68)90249-0. PMID 5696503.

[4] Mariathasan, S; Weiss, DS; Newton, K; McBride, J; O'Rourke, K; Roose-Girma, M; Lee, WP; Weinrauch, Y; Monack, DM; Dixit, VM (9 March 2006). "Cryopyrin activates the inflammasome in response to toxins and ATP". Nature. 440 (7081): 228–32. Bibcode:2006Natur.440..228M. doi:10.1038/nature04515. PMID 16407890.

[5] 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. PMC 3730833. PMID 23809161.

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