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Merck

N7143

Nigericin sodium salt

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C40H67NaO11
Número CAS:
28643-80-3
Peso molecular:
746.94
NACRES:
NA.77
PubChem Substance ID:
24897813
UNSPSC Code:
12352200
MDL number:
MFCD00036825
Beilstein/REAXYS Number:
3892398

Nombre del producto

Nigericin sodium salt, ≥98% (TLC)

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

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 key

MOYOTUKECQMGHE-PDEFJWSRSA-M

biological source

Streptomyces hygroscopicus

assay

≥98% (TLC)

form

powder

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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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.

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+.

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.

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

Clase de almacenamiento

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

wgk

WGK 3

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
0000485847
0000485847
0000485846
0000485846
0000480935

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Mohamed Wehbe et al.
International journal of nanomedicine, 12, 4129-4146 (2017-06-16)
Copper diethyldithiocarbamate (Cu(DDC)
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
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
Kimberly F Atkinson et al.
Cells, 8(7) (2019-07-25)
Biosensors on the membrane of the vascular endothelium are responsible for sensing mechanical and chemical signals in the blood. Transduction of these stimuli into intracellular signaling cascades regulate cellular processes including ion transport, gene expression, cell proliferation, and/or cell death.
Seref Erdogan et al.
Theriogenology, 75(6), 1057-1066 (2011-01-12)
Previous work has indicated that although activity of the HCO₃⁻/Cl⁻exchanger (AE), which regulates intracellular alkalosis, is high in the germinal vesicle (GV) stage, the oocyte is inhibited as it progresses through meiotic maturation. In this study, we aimed to investigate
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Product Information Sheet - N7143

Product Information Sheet

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