N7143

Nigericin sodium salt

≥98% (TLC)

• Synonym(s): Antibiotic K178, Antibiotic X464, Azalomycin M, Helexin C, Polyetherin A
• Empirical Formula (Hill Notation): C₄₀H₆₇NaO₁₁
• CAS Number: 28643-80-3
• Molecular Weight: 746.94
• Beilstein: 3892398
• MDL number: MFCD00036825
• UNSPSC Code: 12352200
• PubChem Substance ID: 24897813
• NACRES: NA.77

Properties

• biological source: Streptomyces hygroscopicus
• Quality Level: 300
• Assay: ≥98% (TLC)
• form: powder
• antibiotic activity spectrum: Gram-positive bacteria
• Mode of action: cell membrane | interferes
• storage temp.: 2-8°C
• SMILES string: [Na+].[H][C@@]1(CC[C@H](C)[C@@]([H])(O1)[C@@H](C)C([O-])=O)C[C@]2([H])C[C@@H](OC)[C@@H](C)[C@]3(O2)O[C@@](C)(C[C@H]3C)[C@@]4([H])CC[C@](C)(O4)[C@]5([H])O[C@]([H])(C[C@@H]5C)[C@@]6([H])O[C@@](O)(CO)[C@H](C)C[C@@H]6C
• InChI: 1S/C40H68O11.Na/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);/q;+1/p-1/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+;/m0./s1
• InChI key: MOYOTUKECQMGHE-PDEFJWSRSA-M

Description

General description

Chemical structure: polyether

Nigericin, a polyether ionophore, serves as a probe of ion transport across mitochondrial membranes. It catalyzes the overall electroneutral exchange of K+ for H+(1) and acts as a potassium efflux activator. It may enhance bactericidal action via inflammasome-independent mechanisms specific to NLRP3 (NOD-, LRR- and pyrin domain-containing protein 3). Nigericin is a linear molecule with rings of heterocyclic oxygen together with a hydroxyl group. In the membrane, the molecule cyclizes to form a structure like valinomycin. Nigericin forms a neutral complex while losing a proton when it binds a cation which can diffuse across the membrane as a mobile carrier. Nigericin in protonated noncomplexed form is also considered mobile.

Application

Nigericin sodium salt has been used to induce NLRP3 inflammasome activation in human macrophages. It has also been used as a bacterial toxin to trigger IL-1β secretion monocytes.

Biochem/physiol Actions

Polyether ionophore that disrupts membrane potential and stimulates ATPase activity in mitochondria. Ion selectivity is K⁺> Rb⁺≥ Cs⁺>> Na⁺.

Other Notes

As ion-selective electrode - an efficient K⁺-carrier.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301,H319
• Precautionary Statements: P264 - P280 - P301 + P310 - P305 + P351 + P338 - P337 + P313 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Eye Irrit. 2
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves