Nigericin

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 Y
PubChem	34230
ChemSpider	10196461 Y
ChEBI	CHEBI:7569 N
ChEMBL	CHEMBL405862 Y
Jmol-3D images	Image 1
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
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 Y Key: DANUORFCFTYTSZ-SJSJOXFOSA-N YInChI=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
Properties
Molecular formula	C40H68O11
Molar mass	724.96132
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. Nigericin exhibits anti-HIV activity.

References

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=224422. 
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. 

External references

Commercial supplier of nigericin sodium

This systemic antibacterial-related article is a stub. You can help Wikipedia by expanding it.v · Categories: Antibiotics Ionophores Antibiotic stubs Wikimedia Foundation. 2010. Игры ⚽ Нужно решить контрольную? Jeremy Young Trevethin Community School Look at other dictionaries: nigericin — An ionophore capable of acting as a carrier for K+ or Rb+ or as an exchange carrier for H+ with K+. Originally used as an antibiotic. Has been used in investigating chemiosmosis and other transport systems …   Dictionary of molecular biology nigericin — noun An antibiotic, similar to monensin, obtained from Streptomyces hygroscopicus …   Wiktionary Ionophor — Ein Ionophor ist ein Molekül, das Ionen durch eine Membran transportiert. Einige Bakterien bilden Ionophore, also Moleküle, die die Permeabilität von Membranen für Ionen erhöhen. Oft haben solche Moleküle eine antibiotische Wirkung, da sie das… …   Deutsch Wikipedia Magnesium in biology — Magnesium is an essential element in biological systems. Magnesium occurs typically as the Mg2+ ion. It is an essential mineral nutrient for life[1][2][3] and is present in every cell type in every organism. For example, ATP (adenosine… …   Wikipedia Ionophore — An ionophore is a lipid soluble molecule usually synthesized by microorganisms to transport ions across the lipid bilayer of the cell membrane. There are two broad classifications of ionophores. # Small molecules (mobile ion carriers) that bind… …   Wikipedia Monensin — A IUPAC name 4 [2 [5 ethyl 5 [5 [6 hydroxy 6 (hydroxymethyl) 3,5 dimethyl oxan 2 yl] 3 methyl oxolan 2 yl]oxolan 2 yl] 9 hydroxy 2,8 d …   Wikipedia Lysyl oxidase — Lysyl oxidase, also known as LOX, is a human gene.cite web | title = Entrez Gene: LOX lysyl oxidase| url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene Cmd=ShowDetailView TermToSearch=4015| accessdate = ] PBB Summary section title = summary… …   Wikipedia Molecular switch — A molecular switch is a molecule that can be reversibly shifted between two or more stable states.[1] The molecules may be shifted between the states in response to changes in e.g. pH, light, temperature, an electrical current, microenvironment,… …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”