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28643-80-3

28643-80-3 structure
28643-80-3 structure
  • Name: Nigericin sodium salt
  • Chemical Name: Nigericin sodium salt
  • CAS Number: 28643-80-3
  • Molecular Formula: C40H67NaO11
  • Molecular Weight: 746.943
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-06-15 16:42:56
  • Modify Date: 2024-01-03 11:25:58
  • Nigericin sodium salt is an antibiotic from Streptomyces hygroscopicus that works by acting as an H+, K+, and Pb2+ ionophore.
Name Nigericin sodium salt
Synonyms Nigericin,Natrium-Salz
2H-Pyran-2-acetic acid, tetrahydro-6-[[(2S,4R,5R,7R,9R,10R)-9-methoxy-2,4,10-trimethyl-2-[(2S,2'R,3'S,5R,5'R)-octahydro-2,3'-dimethyl-5'-[(2S,3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimet ;hyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-α,3-dimethyl-, sodium salt, (αR,2R,3S,6R)- (1:1)
nigericin.Na
nigericin monosodium salt
Leelamine hydrochloride
Polyetherin A,Azalomycin M,Helixin C,Antibiotic K178,Antibiotic X-464
Sodium (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,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
nigericin sodium
Nigericinsodiumsalt
sodium nigericin
Antibiotic K178,Antibiotic X464,Azalomycin M,Helexin C,Polyetherin A
Sodium (2R)-2-[(3S,6R)-6-[[(2S,4R,5R,7R,9R,10R)-2-[(5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl]-3-methyloxan-2-yl]propanoate
Nigericin sodium salt
Antibiotic K178 Antibiotic X464 Azalomycin M Helexin C Polyetherin A
Nigericin (sodium salt)
Description Nigericin sodium salt is an antibiotic from Streptomyces hygroscopicus that works by acting as an H+, K+, and Pb2+ ionophore.
Related Catalog
In Vitro Nigericin (0.1 µM) decreases inhibits proliferation and clonogenicity of H460 lung cancer cells in a dose dependent manner. Nigericin inhibits migration and invasion of H460 lung cancer cells[1]. Nigericin (0.1-10 nM) has apparently a dual effect on cell volume, that is a shrinking effect at lower Nigericin concentrations and a swelling effect at higher concentrations. Nigericin (0.1-1 nM) significantly decreases cytosolic pH (pHi), and slightly increases the pHi at 5 and 10 nM[2]. Nigericin exhibits higher toxicity on S18 cells than S26 cells, with IC50 of 2.03±0.55 μM and 4.77±2.35 μM, respectively. Nigericin can selectively kill cancer stem cells in NPC in vitro. Nigericin dramatically reduces the migration ability of S18 and HONE-1 cells[3]. Nigericin exhibits gteat toxicity for the HT29 and SW116 cell line with IC50 of 12.92±0.25 μmol and 15.86±0.18 μmol. Nigericin also shows a decreased ability to form colonies under anchorage-independent conditions in a standard soft agar assay[4].
In Vivo Ngericin (4 mg/kg, i.p.) significantly reduces tumor growth and acts synergistically with the chemotherapeutic agent DDP, as shown by the tumor volumes. Nigericin markedly decreases Bmi-1 in vivo. Overexpression of Bmi-1 partially restores CSC content and metastatic ability of NPC cells under Nigericin treatment. The downregulation of Bmi-1 may be involved in the inhibitory effect of Nigericin on CSCs in NPC[3].
Cell Assay For RCCs, cells (appr 2000 cells/well) are plated in 96-well cell-culture microplates and incubated over nigericinht in complete media (CM)-RPMI 1640 supplemented with 5% FBS, 2 mM l-glutamine, 100 U/mL penicillin, and 100 mg/mL streptomycin to allow them to adhere. Cells are then exposed to the appropriate concentration of drug or vehicle for 72 h. For PPSS, cells (appr 500 cells/well) are plated in 96-well cell-culture microplates incubated over Nigericinht in CM to allow them to adhere and then maintained in serum-free media for 7-8 days and then treated with the appropriate concentration of drug or vehicle for 72 h in SFM. Cell viability for cells growing under RCCs and PPSS are evaluated by the MTT assay. The absorbance of solubilized formazan is read at 570 nm using ELISA (enzyme-linked immunosorbent assay) reader. In all cases, the highest concentration of DMSO is used in the control and this concentration is maintained below 0.001% (v/v). This DMSO concentration does not show any significant antiproliferative effect on the cell line in a short-term assay.
Animal Admin Mice[3] The S18 cells are injected near the scapula of the nude mice. Nine days after injection, the mice are randomly divided into four groups with six animals each (control, DDP, Nigericin and DDP combined with Nigericin). DDP (2.5 mg/kg) is injected intraperitoneally for five continuous days and nigericin (4 mg/kg) is administrated intraperitoneally every two days. Tumor length and width are measured with a vernier caliper every other day. Tumor volume is calculated using the formula V=0.5×(length×width2). The body weights of the mice are recorded every two days. Mice are humanely euthanized when the tumor volume reach 2000 mm3.
References

[1]. Yakisich JS, et al. Nigericin decreases the viability of multidrug-resistant cancer cells and lung tumorspheres and potentiates the effects of cardiac glycosides. Tumour Biol. 2017 Mar;39(3):1010428317694310

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

[3]. Deng CC, et al. Nigericin selectively targets cancer stem cells in nasopharyngeal carcinoma. Int J Biochem Cell Biol. 2013 Sep;45(9):1997-2006

[4]. Zhou HM, et al. Suppression of colorectal cancer metastasis by nigericin through inhibition of epithelial-mesenchymal transition. World J Gastroenterol. 2012 Jun 7;18(21):2640-8
Density 1.19g/cm3
Boiling Point 779.9ºC at 760mmHg
Molecular Formula C40H67NaO11
Molecular Weight 746.943
Flash Point 226.9ºC
Exact Mass 746.458130
PSA 145.20000
LogP 4.37090
Vapour Pressure 4.26E-28mmHg at 25°C
Storage condition 2-8°C
Water Solubility Soluble in chloroform, methanol or ethanol

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QT6840000
CHEMICAL NAME :
Nigericin, monosodium salt
CAS REGISTRY NUMBER :
28643-80-3
LAST UPDATED :
198910
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C40-H68-O11.Na
MOLECULAR WEIGHT :
748.07

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
48 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 30,77-5,1977 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 27,81A,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 27,81A,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 27,81A,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 33,47,1986
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H315-H319-H335
Precautionary Statements P261-P301 + P310-P305 + P351 + P338
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R25;R36/37/38
Safety Phrases S26-S36/37/39-S45
RIDADR UN 3462
WGK Germany 3
RTECS QT6840000
Packaging Group III
Hazard Class 6.1(b)
HS Code 29419090

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