ChemicalBook--->CAS DataBase List--->28380-24-7

28380-24-7

28380-24-7 Structure

28380-24-7 Structure
IdentificationBack Directory
[Name]

NIGERICIN SODIUM SALT
[CAS]

28380-24-7
[Synonyms]

x-464
Helix c
HELIXIN C
NIGERICIN
Aids003767
Aids-003767
AZALOMYCIN M
NIGERICIN NA
POLYETHERIN A
Antibiotic M 2
ANTIBIOTIC K178
ANTIBIOTIC X-464
nigericin sodium
NIGERICIN, NA SALT
NIGERICIN APPOX. 95%
28643-80-3 (Sodium salt)
ANTIBIOTIC K178 SODIUM SALT
Nigericin from Streptomyces hygroscopicus
Antibiotic K178 sodium salt, Azalomycin M
nigericin sodium from streptomyces*hygroscopicus
NIGERICIN, SODIUM SALT, STREPTOMYCES HYGROSCOPICUS
Polyetherin A, AzaloMycin M, Helixin C, K 178, X 464
nigericin sodium salt from streptomyces hygroscopicus
(2R)-2-((3S)-6-{[2-((5S)-5-{(3S)-5-[(3S,5R,6R)-6-Hydroxy-6-(hydroxymethyl)-3,5-dimethylperhydro-2H-pyran-2-yl]-3-methyloxolan-2-yl}-5-methyloxolan-2-yl)(2S,4R,9R,10R)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methylperhydro-2H-pyran-2-yl)propanoic acid
[Molecular Formula]

C40H67NaO11
[MDL Number]

MFCD00036825
[MOL File]

28380-24-7.mol
[Molecular Weight]

746.94
Chemical PropertiesBack Directory
[Melting point ]

183.5-185°
[alpha ]

D24 +36.2° (c = 0.842 in CHCl3)
[Boiling point ]

779.9±60.0 °C(Predicted)
[density ]

1.19±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

chloroform: 10 mg/mL, clear, colorless
[form ]

Solid
[pka]

4.39±0.10(Predicted)
[color ]

White to off-white
[InChIKey]

DANUORFCFTYTSZ-ANZYULKNSA-N
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)
GHS06
[Signal word ]

Danger
[Hazard statements ]

H319-H335-H301-H315
[Precautionary statements ]

P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
[Hazard Codes ]

T,Xi
[Risk Statements ]

25-36/37/38
[Safety Statements ]

26-36/37/39-45-36
[RIDADR ]

UN 3462 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

QT6840000
[F ]

10
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29419090
[Toxicity]

LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned)
Hazard InformationBack Directory
[Uses]

Nigericin is a polyether antibiotic produced by Streptomyces, notably S. hygroscopicus, isolated in the 1950s. Its complex structure was finally elucidated in 1968. Nigericin is an ionophore, possessing very high affinity for monovalent cations such as Na+ and K+. Nigericin disrupts membrane potential and Golgi apparatus in mitochondria. Although nigericin can be isolated as the free acid (under acidic conditions), like most ionophores it is extracted into organic solvents and is most conveniently isolated as a salt. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumor cell lines and some viruses, including HIV. Nigericin is the most common member of the polyether class which are common false positives in in vitro screening bioassays using crude microbial extracts. They are thus important standards for dereplication.
[Uses]

Nigericin is a polyether antibiotic produced by Streptomyces, notably S. hygroscopicus, isolated in the 1950s. Its complex structure was finally elucidated in 1968. Nigericin is an ionophore, possessing very high affinity for monovalent cations such as Na+ and K+. Nigericin disrupts membrane potential and Golgi apparatus in mitochondria. Although nigericin can be isolated as the free acid (under acidic conditions), like most ionophores it is extracted into organic solvents and is most conveniently isolated as a salt. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumour cell lines and some viruses, including HIV. Nigericin is the most common member of the polyether class which are common false positives in in vitro screening bioassays using crude microbial extracts. They are thus important standards for dereplication.
[Definition]

ChEBI: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.
[in vivo]

Nigericin (1 mg/kg; i.p.; every 12 h for 3 D) reduces the infection of S. aureus USA300 in mice[4].
Nigericin (0.025 mg/kg; s.c.; every two days in 4 weeks) plus anti-PD-1 shows synergistic anti-cancer effect[6].

Animal Model:BALB/c Mice injected orthotopically with 4T1 cells[6]
Dosage:0.025 mg/kg
Administration:Subcutaneous injection (s.c.)
Result:Showed combination with anti-PD-1 antibody almost completely suppressed tumor growth.
Animal Model:Mice Infected with S. aureus USA300[4]
Dosage:1 mg/kg
Administration:Intraperitoneal injection (i.p.)
Result:Showed reduction in the bacterial burden to 1,000-10,000-fold in the major organs.
[IC 50]

NLRP3
Spectrum DetailBack Directory
[Spectrum Detail]

NIGERICIN SODIUM SALT(28380-24-7)1HNMR
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