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 ;
ChemSpider	10196461 ;
ECHA InfoCard	100.212.814
PubChem CID	34230;
	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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/12 23:33:38」(JST)

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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.

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. PMC 224422 . PMID 5229984. doi:10.1073/pnas.56.2.654.
^ Steinrauf LK, Pinkerton M, Chamberlin JW (1968). "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31. PMID 5696503. doi:10.1016/0006-291X(68)90249-0.

External links

Commercial supplier of nigericin sodium

English Journal

Static magnetic field (SMF) sensing of the P723/P689 photosynthetic complex.

Bhattacharya A1, Chakraborty M, Raja SO, Ghosh A, Dasgupta M, Dasgupta AK.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.Photochem Photobiol Sci.2014 Dec 12;13(12):1719-29. doi: 10.1039/c4pp00295d. Epub 2014 Oct 15.
Moderate intensity SMF have been shown to act as a controller of the protic potential in the coherent milieu of the thylakoid membranes. SMF of the order of 60-500 mT induces memory-like effect in photosystem I (PSI, P723) emission with a correlated oscillation of photosystem II (PSII, P689) fluores
PMID 25314902

Mdm31 protein mediates sensitivity to potassium ionophores but does not regulate mitochondrial morphology or phospholipid trafficking in Schizosaccharomyces pombe.

Ivan B1, Lajdova D, Abelovska L, Balazova M, Nosek J, Tomaska L.
Yeast (Chichester, England).Yeast.2014 Dec 5. doi: 10.1002/yea.3062. [Epub ahead of print]
Mdm31p is an inner mitochondrial membrane (IMM) protein with unknown function in Saccharomyces cerevisiae. Mutants lacking Mdm31p contain only few giant spherical mitochondria with disorganized internal structure, altered phospholipid composition, and disturbed ion homeostasis accompanied by increas
PMID 25483891

Pyroptosis of resident macrophages differentially orchestrates inflammatory responses to Staphylococcus aureus in resistant and susceptible mice.

Accarias S1, Lugo-Villarino G, Foucras G, Neyrolles O, Boullier S, Tabouret G.
European journal of immunology.Eur J Immunol.2014 Dec 4. doi: 10.1002/eji.201445098. [Epub ahead of print]
The relationship between Staphylococcus aureus and innate immunity is highly complex and requires further investigation to be deciphered. Intraperitoneal challenge of C57BL/6 and DBA/2 mice, resistant and susceptible to the infection, respectively, resulted in different patterns of cytokine producti
PMID 25472006

Japanese Journal

Diversity and mechanisms of alkali tolerance in lactobacilli

Sawatari Yuki,Yokota Atsushi
Applied and Environmental Microbiology 73(12), 3909-3915, 2007-06
… However, the pH contributed to alkali tolerance, as the pHmax values of several strains decreased with the addition of nigericin, which dissipates pH. Although neutral external-pH values resulted in the highest glycolysis activity in the presence of nigericin regardless of alkali tolerance, substantial glucose utilization was still detected in the alkali-tolerant strains, even in a pH range of between 8.0 and 8.5, at which the remaining strains lost most activity. …
NAID 120000968181

The Extracellular pH Dependency of Transport Activity by Human Oligopeptide Transporter 1 (hPEPT1) Expressed Stably in Chinese Hamster Ovary (CHO) Cells : A Reason for the Bell-Shaped Activity versus pH(Biopharmacy)

FUJISAWA Yuki,TATEOKA Ryoko,NARA Toshifumi,KAMO Naoki,TAIRA Takahiro,MIYAUCHI Seiji
Biological & pharmaceutical bulletin 29(5), 997-1005, 2006-05-01
… The pH profile of the transport activity vs. pH was measured in the presence of nigericin/monensin. …
NAID 110005602229

Related Pictures

[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. PMC 224422 . PMID 5229984. doi:10.1073/pnas.56.2.654.

[pmid5696503-2] Steinrauf LK, Pinkerton M, Chamberlin JW (1968). "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31. PMID 5696503. doi:10.1016/0006-291X(68)90249-0.

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