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SML1779

Sigma-Aldrich

Nigericin sodium salt

from Streptomyces hygroscopicus, ≥98% (HPLC), solution, polyether ionophore

Synonym(s):

3B2-6379, Antibiotic K178, Antibiotic X464, Azalomycin M, HE331800, Helexin C, Polyetherin A, sodium;2-[(3S,6R)-6-[[(5R,6R,7R,9R)-2-[5-[(3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoate

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About This Item

Empirical Formula (Hill Notation):
C40H67NaO11
CAS Number:
28643-80-3
Molecular Weight:
746.94
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Nigericin sodium salt Ready Made Solution, 5 mg/mL (DMSO:ethanol 1:1)

biological source

Streptomyces hygroscopicus

Quality Level

200

form

solution

concentration

5 mg/mL (DMSO:ethanol 1:1)

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell membrane | interferes

shipped in

ambient

storage temp.

2-8°C

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-KKCUGXASSA-M

Related Categories

Biochem/physiol Actions

Nigericin is a polyether ionophore which catalyzes the electroneutral exchange of alkali metal (K+) for H+ (antiport). Nigericin transports monovalent cations across membranes with the following specificity: K+ >Rb+ >Cs+ >>Na+ and thus, disrupts membrane potential and stimulates ATPase activity in mitochondria.
Nigericin kills bacteria by facilitating the diffusion of ions across membranes.
Low concentration (0.5 μM) of Nigericin rapidly decreases pHi, causing stimulation of PG production 1.5- to 2-fold in cerebral microvascular endothelial cells and arresting of DNA synthesis in Erlich acites carcinoma cells. Treatment of Hela cells, after entry of poliovirus, with nigericin, prevents the inhibition of host protein synthesis by poliovirus. Nigericin is also widely used in studies of the consequences of changes in membrane potential in variable systems.

Preparation Note

Nigericin sodium salt ready made solution is provided at 6.7 mM concentration. The solution can be further diluted with a desired solvent to a working concentration (0.5-10 μM).

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

WGK

WGK 2

Flash Point(F)

78.8 °F

Flash Point(C)

26 °C

Regulatory Information

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A A Guffanti et al.
Journal of general microbiology, 114(1), 201-206 (1979-09-01)
At an external pH of 3.5, nigericin (which catalyses an electroneutral H+/K+ exchange) abolished the transmembrane proton gradient (delta pH) of Bacillus acidocaldarius, causing a rapid acidification of the cytoplasm from approximately pH 6.0 to pH 3.5. A pronounced loss
Mayu Sugiyama et al.
Biochimica et biophysica acta, 1660(1-2), 24-30 (2004-02-06)
A novel gene transfer system utilizing polycation liposomes (PCLs), obtained by modifying liposomes with cetyl polyethylenimine (PEI), was previously developed (Gene Ther. 7 (2002) 1148). PCLs show notable transfection efficiency with low cytotoxicity. However, the mechanism of PCL-mediated gene transfer
Hachiro Konaka et al.
The EMBO journal, 42(20), e112573-e112573 (2023-09-04)
Mitochondrial DNA (mtDNA) leakage into the cytoplasm can occur when cells are exposed to noxious stimuli. Specific sensors recognize cytoplasmic mtDNA to promote cytokine production. Cytoplasmic mtDNA can also be secreted extracellularly, leading to sterile inflammation. However, the mode of
L B Margolis et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(17), 6626-6629 (1989-09-01)
Acidification of the cytoplasm of Ehrlich ascites carcinoma cells to pH 6.3 arrests DNA synthesis in these cells. Such an effect can be achieved by incubating the cells at pH 6.2 or by adding low concentrations of the K+/H+ antiporter
Michael G Gänzle et al.
Applied and environmental microbiology, 69(2), 1305-1307 (2003-02-07)
The mode of action of reutericyclin was determined with fluorescent dyes that probed the permeability of the cytoplasmic membrane by large molecules, protons, and potassium. A comparison of reutericyclin activity with those of nisin, nigericin, and valinomycin demonstrated that reutericyclin
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