Nigericin

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Nigericin

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	[28643-80-3]
PubChem	34230
SMILES	C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C @@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H ](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
Properties
Molecular formula	C₄₀H₆₈O₁₁
Molar mass	724.96132
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation was described in the 1950s^[1] but 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. Nigericin exhibits anti-HIV activity.

[edit] 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. 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.