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Merck

SML1779

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:
Molecular Weight:
746.94
UNSPSC Code:
12352200
NACRES:
NA.77
Form:
solution
Quality level:
Technical Service
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Product Name

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

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.


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pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

78.8 °F

flash_point_c

26 °C



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