Antibiotic K178

Names

[ 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

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.