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Merck

SML1779

Nigericin sodium salt

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

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C40H67NaO11
Numéro CAS:
Poids moléculaire :
746.94
UNSPSC Code:
12352200
NACRES:
NA.77
Form:
solution
Quality level:
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Nom du produit

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

biological source

Streptomyces hygroscopicus

Quality Level

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

SMILES string

[Na+].[O-]C(=O)C(C1O[C@H](CC[C@@H]1C)C[C@H]2O[C@]3(OC(CC3C)(C4OC(CC4)(C5O[C@H](C[C@@H]5C)[C@H]6O[C@@]([C@@H](C[C@@H]6C)C)(O)CO)C)C)[C@@H]([C@@H](C2)OC)C)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

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Biochem/physiol Actions

Nigericin is a polyether ionophore which catalyzes the electroneutral exchange of alkali metal (K+) for H+ (antiport).
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).
The product can be stored at 2-8°C and is released with a 4 years suggested retest schedule. The solution is quite stable refrigerated and freezing is not necessary.
This product is a 5 mg/mL solution prepared in a 1:1 mixture of DMSO and Ethanol.

pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

Classe de stockage

3 - Flammable liquids

wgk

WGK 2

flash_point_f

78.8 °F

flash_point_c

26 °C


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Consulter la Bibliothèque de documents

G D Eytan et al.
The Journal of biological chemistry, 265(22), 12949-12954 (1990-08-05)
Reconstituted transhydrogenase-ATPase vesicles obtained with purified beef heart transhydrogenase and oligomycin-sensitive ATPase were investigated with respect to the mode of interaction between the two proton pumps, with special reference to the relative contributions of the membrane potential and proton gradient
S Ahmed et al.
The Biochemical journal, 212(1), 105-112 (1983-04-15)
Valinomycin, nigericin and trichlorocarbanilide were assessed for their ability to control the protonmotive force in Escherichia coli cells. Valinomycin, at high K+ concentrations, was found to decrease the membrane potential delta phi and indirectly to decrease the pH gradient delta
Calcium uptake and membrane potential in mitochondria.
H Rottenberg et al.
Biochemistry, 13(23), 4811-4817 (1974-11-05)
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
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

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