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N7143

Sigma-Aldrich

Nigericin sodium salt

From Streptomyces hygroscopicus, ≥98% (TLC), Ionophore, powder

Synonym(s):

Antibiotic K178, Antibiotic X464, Azalomycin M, Helexin C, Polyetherin A

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About This Item

Empirical Formula (Hill Notation):
C40H67NaO11
CAS Number:
28643-80-3
Molecular Weight:
746.94
Beilstein/REAXYS Number:
3892398
MDL number:
MFCD00036825
UNSPSC Code:
12352200
PubChem Substance ID:
24897813
NACRES:
NA.77

Key Documents

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Product Name

Nigericin sodium salt, ≥98% (TLC)

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

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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.
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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
128M4034V
079M4051V
14190104
029M4022V

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Dendritic cells (DC) are sentinels of the immune system, alerting and enlisting T cells to clear pathogenic threats. As such, numerous studies have demonstrated their effective uptake and proteolytic activities coupled with antigen processing and presentation functions. Yet, less is
H Parfenova et al.
The American journal of physiology, 277(4 Pt 1), C728-C738 (1999-10-12)
Nigericin decreases intracellular pH (pH(i)) and stimulates prostanoid (PG) synthesis in endothelial cells from cerebral microvessels of newborn pigs. Nigericin-induced PG production was abolished by protein tyrosine kinase (PTK) inhibitors and amplified by phorbol 12-myristate 13-acetate (PMA) or protein tyrosine
Nina Raben et al.
Methods in enzymology, 453, 417-449 (2009-02-17)
Lysosomes are the final destination of the autophagic pathway. It is in the acidic milieu of the lysosomes that autophagic cargo is metabolized and recycled. One would expect that diseases with primary lysosomal defects would be among the first systems
Saskia F Erttmann et al.
Nature communications, 10(1), 3493-3493 (2019-08-04)
Hydrogen peroxide (H2O2) has a major function in host-microbial interactions. Although most studies have focused on the endogenous H2O2 produced by immune cells to kill microbes, bacteria can also produce H2O2. How microbial H2O2 influences the dynamics of host-microbial interactions
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