Nigericin

Nigericin
Names
	IUPAC name (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,7R,9R,10R)- 2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy- 6-(hydroxymethyl)-3,5-dimethyl-2-tetrahydropyranyl]-3-methyl- 2-tetrahydrofuranyl]-5-methyl-2-tetrahydrofuranyl]-9-methoxy- 2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl]-3-methyl- 2-tetrahydropyranyl]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;
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	724.96132 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation was described in the 1950s,[1] and in 1968 the structure could be elucidated by X-ray crystallography.[2] 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. Its ability to induce K⁺ efflux also makes it a potent activator of the NLRP3 inflammasome[3][4]

References

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. 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. 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.

External links

Commercial supplier of nigericin sodium

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[pmid5229984-1] 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. doi:10.1073/pnas.56.2.654. PMC 224422. PMID 5229984.

[pmid5696503-2] 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.

[3] 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. doi:10.1038/nature04515. PMID 16407890.

[4] 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.