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N7143

Sigma-Aldrich

Nigericin sodium salt

≥98% (TLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C40H67NaO11
Numéro CAS:
28643-80-3
Poids moléculaire :
746.94
Numéro Beilstein :
3892398
Numéro MDL:
MFCD00036825
Code UNSPSC :
12352200
ID de substance PubChem :
24897813
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces hygroscopicus

Niveau de qualité

300

Pureté

≥98% (TLC)

Forme

powder

Spectre d'activité de l'antibiotique

Gram-positive bacteria

Mode d’action

cell membrane | interferes

Température de stockage

2-8°C

Chaîne SMILES 

[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

Clé InChI

MOYOTUKECQMGHE-PDEFJWSRSA-M

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Description générale

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.

Actions biochimiques/physiologiques

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

Autres remarques

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H319

Classification des risques

Acute Tox. 3 Oral - Eye Irrit. 2

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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Consulter la Bibliothèque de documents

Mohamed Wehbe et al.
International journal of nanomedicine, 12, 4129-4146 (2017-06-16)
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Adesola C Olatunde et al.
PloS one, 13(5), e0196591-e0196591 (2018-05-11)
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
Nardhy Gomez-Lopez et al.
Biology of reproduction, 100(5), 1306-1318 (2019-01-01)
Sterile intra-amniotic inflammation is commonly observed in patients with spontaneous preterm labor, a syndrome that commonly precedes preterm birth, the leading cause of perinatal morbidity and mortality worldwide. However, the mechanisms leading to sterile intra-amniotic inflammation are poorly understood and
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
Leonid Tarassishin et al.
PloS one, 9(7), e103432-e103432 (2014-07-24)
Glioblastoma is the most frequent and malignant form of primary brain tumor with grave prognosis. Mounting evidence supports that chronic inflammation (such as chronic overactivation of IL-1 system) is a crucial event in carcinogenesis and tumor progression. IL-1 also is
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