N7143

Nigericin sodium salt

Name: Nigericin sodium salt
Brand: SIGMA

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

Synonym(s):

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

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All Photos(4)

About This Item

Empirical Formula (Hill Notation):

C₄₀H₆₇NaO₁₁

CAS Number:

28643-80-3

Molecular Weight:

746.94

NACRES:

NA.77

PubChem Substance ID:

24897813

UNSPSC Code:

12352200

MDL number:

MFCD00036825

Beilstein/REAXYS Number:

3892398

Product Name

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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Related Categories

Bioactive Small Molecules

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

GHS06

signalword

Danger

hcodes

H301,H319

pcodes

P264 - P280 - P301 + P310 - P305 + P351 + P338 - P337 + P313 - P405

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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000485847

0000485846

0000480935

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Development and optimization of an injectable formulation of copper diethyldithiocarbamate, an active anticancer agent.

Mohamed Wehbe et al.

International journal of nanomedicine, 12, 4129-4146 (2017-06-16)

Copper diethyldithiocarbamate (Cu(DDC)

Phosphorylation-dependent stimulation of prostanoid synthesis by nigericin in cerebral endothelial cells.

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

Development of endocytosis, degradative activity, and antigen processing capacity during GM-CSF driven differentiation of murine bone marrow.

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

Changes in the activity of defense mechanisms against induced acidosis during meiotic maturation in mouse oocytes.

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

The Role of the Primary Cilium in Sensing Extracellular pH.

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.

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