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Antibiotic K178

Names

[ CAS No. ]:
28380-24-7

[ Name ]:
Antibiotic K178

[Synonym ]:
Nigericin
HELIXIN C
2H-Pyran-2-acetic acid, tetrahydro-6-[[(2S,4R,5R,9R,10R)-9-methoxy-2,4,10-trimethyl-2-[(2S,3'R)-octahydro-2,3'-dimethyl-5'-[(3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-α,3-dimethyl-, sodium salt, (αS,3R)- (1:1)
Sodium (2S)-2-[(3R)-6-{[(2S,4R,5R,9R,10R)-2-{(2S,3'R)-5'-[(3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoate
ANTIBIOTIC K178
NIGERICIN NA
AZALOMYCIN M
2H-Pyran-2-acetic acid, tetrahydro-6-[[(2S,4R,5R,9R,10R)-9-methoxy-2,4,10-trimethyl-2-[(2S,3'R)-octahydro-2,3'-dimethyl-5'-[(3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl ;][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-α,3-dimethyl-, sodium salt, (αS,3R)- (1:1)
POLYETHERIN A
Helix c
x-464

Biological Activity

[Description]:

Nigericin is an antibiotic derived from Streptomyces hygroscopicus that act as a K+/H+ ionophore, promoting K+/H+ exchange across mitochondrial membranes[1].Nigericin can be a NLRP3 activator that induces the release of IL-1β as a NALP3-dependent manner[2]. Nigericin triggers eryptosis, an effect paralleled by ROS formation, and in part due to induction of oxidative stress. Nigericin triggers apoptosis[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[Target]

K+/H+ ionophore[1]


[References]

[1]. Zotova L, et al. Novel components of an active mitochondrial K(+)/H(+) exchange. J Biol Chem. 2010 May 7;285(19):14399-414.

[2]. Mariathasan S, et al.Cryopyrin activates the inflammasome in response to toxins and ATP.Nature. 2006 Mar 9;440(7081):228-32.

[3]. Bissinger R, et al. Triggering of Suicidal Erythrocyte Death by the Antibiotic Ionophore Nigericin. Basic Clin Pharmacol Toxicol. 2016 May;118(5):381-9.

Chemical & Physical Properties

[ Density]:
1.19g/cm3

[ Boiling Point ]:
779.9ºC at 760mmHg

[ Melting Point ]:
245-255ºC

[ Molecular Formula ]:
C40H68O11

[ Molecular Weight ]:
746.943

[ Flash Point ]:
226.9ºC

[ Exact Mass ]:
746.458130

[ PSA ]:
145.20000

[ LogP ]:
4.37090

[ Index of Refraction ]:
1.543

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QT6825000
CHEMICAL NAME :
Nigericin
CAS REGISTRY NUMBER :
28380-24-7
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C40-H68-O11
MOLECULAR WEIGHT :
725.08

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,477,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 1,594,1951

Safety Information

[ Hazard Codes ]:
T: Toxic;

[ RIDADR ]:
UN 3462 6

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Precursor & DownStream

Precursor

DownStream

Related Compounds