Nigericin

Nigericin (sodium salt)

Molecular Formula:

C40H67O11∙Na

CAS number:

28643-80-3 (sodium salt)

Fermentek product code:

Source:

Streptomyces hygroscopicus

Brand/grade:

For research

Specifications

Appearance:

White powder

Purity by HPLC:

≥98% ; refer to CoA for more data

Purity By TLC:

≥98% ; refer to CoA for more data

Solubility test:

Clear colorless solution at 10mg/ml of Dichloromethane

Chemical identification

Names and identifiers:

Polyetherin A; Azalomycin M; Helixin C ;

RTECS QT6825000

EU number:

608-231-4

Description:

Nigericin is a polyether antibiotic which affects ion transport and ATPase activity in mitochondria.

Nigericin is produced by Streptomyces hygroscopicus. Nigericin, an ionophore and antibiotic, is supplied as a sodium salt.

Nigericin is one of the compounds successfully tested as a feed additive, displaying a significant effect on milk production in cattle. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumor cell lines and some viruses, including HIV.

Molecular weight:

746.93

InChl Key:

MOYOTUKECQMGHE-NTQCAYBPSA-M

Canonical SMILES:

CC1CCC(OC1C(C)C(=O)[O-])CC2CC(C(C3(O2)C(CC(O3)(C)C4CCC(O4)(C)C5C(CC(O5)C6C(CC(C(O6)(CO)O)C)C)C)C)C)OC.[Na+]

Isomeric SMILES:

C[[email protected]]1CC[[email protected]@H](OC1[[email protected]@H](C)C(=O)[O-])C[[email protected]@H]2C[[email protected]]([[email protected]]([[email protected]@]3(O2)[[email protected]@H](C[[email protected]@](O3)(C)C4CC[[email protected]@](O4)(C)C5[[email protected]](C[[email protected]@H](O5)[[email protected]@H]6[[email protected]](C[[email protected]]([[email protected]@](O6)(CO)O)C)C)C)C)C)OC.[Na+]

Further Information

Solubility ( literature ):

DMSO, Ethanol, petrol ether. Not soluble in water

Storage, handling:

Store in a freezer upon arrival, at -10°C to -25°C

Open carefully – Lyophilized solid under vacuum

Expiration time:

Retest time:

Applications:

Disrupts the membrane potential and stimulates ATPase activity in mitochondria.

Disclaimer:

For Research use only

Not for Human or Drug use

Not extracted from humans or animals

Refer to MSDS for further safety and handling instructions

Composition

Ingredient type:

Fermentek product

Supply related information

Supply related comments:

Customs: Other Antibiotics-29419000

Shipped at ambient temperature

Shipped in amber-glass vials

Publications

Nigericin, a new crystalline antibiotic from an unidentified streptomyces. Harned r.l. et al., Antibiot. Chemother. 1951, 1, 594.
The structure of nigericin. Steinrauf l.k. et al., biochem. Biophys. Res. Commun. 1968, 33, 29.
Nigericin-induced na+/h+ and k+/h+ exchange in synaptosomes: effect on [3h]gaba release. Rodriguez r. & sitges m., Neurochem. Res. 1996, 21, 889.
Nigericin inhibits accumulation of the steroidogenic acute regulatory protein but not steroidogenesis. King s.r. et al., Mol. Cell. Endocrinol. 2000, 166, 147.
Nigericin inhibits insulin-stimulated glucose transport in 3t3-l1 adipocytes. Chu c.y. et al., j. Cell. Biochem. 2002, 85, 83.
Inhibitory effects of polyethers on human immunodeficiency virus replication. Nakamura m., Antimicrob. Ag. Chemother. 1992, 36, 492.
Teratogenic effects of nigericin, a carboxylic ionophore ; vedel-macrander gc; hood rd ; teratology 33:47-51,1986
Altered membrane permeability to monovalent cations as a teratogenic mechanism: Teratogenic effects of nigericin, a carboxylic ionophore vedel gc; hood rd teratology 27(2):81a,1983
Export of a single drug molecule in two transport cycles by a multidrug efflux pump; Eitan Bibi at al., ; Nature communications; DOI: 10.1038/ncomms5615

Special Info

Available since:

1997

Other Fields

Title:

More about

Value:

Nigericin f.a.; cas 28380-24-7 rtecs QT6825000, mouse oral ld50=190 mg/kg