Nigericin

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Nigericin
Category Antibiotics
Catalog number BBF-02605
CAS 28380-24-7
Molecular Weight 724.96
Molecular Formula C40H68O11
Purity >98%

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Description

Nigericin, derived from S. hygroscopicus, is an antibiotic potassium ionophore. It exchanges K+ for H+ across biological membranes. Nigericin can be a NLRP3 activator that induces the release of IL-1β as a NALP3-dependent manner. Nigericin triggers eryptosis, an effect paralleled by ROS formation, and in part due to induction of oxidative stress. Nigericin triggers apoptosis.

Specification

Synonyms 2-[6-[[2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid; Antibiotic K178; Antibiotic X464; Azalomycin M; Helexin C, Polyetherin A
Storage Store at -20°C
IUPAC Name (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid
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
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
InChI Key DANUORFCFTYTSZ-SJSJOXFOSA-N
Source Streptomyces hygroscopicus

Properties

Appearance Colorless Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; mycobacteria; fungi
Boiling Point 779.91°C at 760 mmHg
Melting Point 183-185°C
Density 1.19±0.1 g/cm3
Solubility Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.

Reference Reading

1.The oxindole Syk inhibitor OXSI-2 blocks nigericin-induced inflammasome signaling and pyroptosis independent of potassium efflux.
Yaron JR1, Rao MY2, Gangaraju S2, Zhang L2, Kong X2, Su F2, Tian Y2, Glenn HL2, Meldrum DR3. Biochem Biophys Res Commun. 2016 Apr 8;472(3):545-50. doi: 10.1016/j.bbrc.2016.03.021. Epub 2016 Mar 9.
The inflammasome is a caspase-1-activating complex that is implicated in a growing number of acute and chronic pathologies. Interest has increased in identifying small molecular inhibitors of inflammasome signaling because of its role in clinically relevant diseases. It was recently reported that the protein tyrosine kinase, Syk, regulates pathogen-induced inflammasome signaling by phosphorylating a molecular switch on the adapter protein ASC. However, several aspects of the role of Syk in inflammasome signaling and the effects of its inhibition remain unclear. The aim of the present study is to explore in detail the effects of the oxindole Syk inhibitor OXSI-2 on various aspects of nigericin-induced inflammasome signaling. Our results indicate that OXSI-2 inhibits inflammasome assembly, caspase-1 activation, IL-1β processing and release, mitochondrial ROS generation, and pyroptotic cell death. Using a novel live cell potassium sensor we show that Syk inhibition with OXSI-2 has no effect on potassium efflux kinetics and that blockade of potassium efflux with extracellular potassium alters Syk phosphorylation.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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