53003-10-4

Basic information

• Product Name: Salinomycin
• Synonyms: SALINOMYCIN SODIUM;SALINOMYCIN SODIUM SALT;coxistac;SALINOMYCIN GRANULE;Salinomycin Premix 12%;SALINOMYCIN FROM STREPTOMYCES ALBUS;SALINOMYCIN 90%;SV sodium salt,2,5 salinomycin hydrate
• CAS NO: 53003-10-4
• Molecular Formula: C₄₂H₇₀O₁₁
• Molecular Weight: 772.98
• EINECS: 258-290-1
• Product Categories: Interferes with Cell Membrane Permeability (Ionophores)Voltage-gated Ion Channels;IonophoresSpectrum of Activity;Antibacterial;Antibiotics;Antibiotics A to;Antibiotics N-SAntibiotics;Chemical Structure Class;L - ZAntibiotics;Mechanism of Action;Monovalent Ion Channels;Polyethers;KOKCISAN;Inhibitors
• Mol File: 53003-10-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 112.5-113.5 °C(lit.)
• Boiling Point: 839.2 °C at 760 mmHg
• Flash Point: >110°(230°F)
• Appearance: white or light yellow crystalline powder
• Density: 1.18 g/cm³
• Vapor Pressure: 1.04E-32mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: insoluble in H2O; ≥142.2 mg/mL in EtOH; ≥91.8 mg/mL in DMSO
• PKA: 6.4 (DMF)
• Water Solubility: Soluble in methanol. Insoluble in water
• Stability: Stable, but may be heat sensitive - keep cool. Incompatible with strong oxidizing agents.
• Merck: 13,8415
• CAS DataBase Reference: Salinomycin(CAS DataBase Reference)
• NIST Chemistry Reference: Salinomycin(53003-10-4)
• EPA Substance Registry System: Salinomycin(53003-10-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 45-36-26
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: VO8620000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 53003-10-4(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 53003-10-4 differently. You can refer to the following data:
1. antibacterial
2. Salinomycin is a polyether ionophore with broad spectrum Gram positive and anti-coccidial activity. Salinomycin has a high affinity for monovalent cations, particularly potassium. Salinomycin is used to control coccidia in animals and for growth promotion in ruminants. Recently, salinomycin has been shown to inhibit cancer stem cells and is >100 times more potent than taxol. While the mechanism of action is unknown, it was noted that among the 60,000 compounds screened, another monovalent ionophore, nigericin, and a chloride channel inhibitor, avermectin, were also active.
3. Salinomycin was used as a standard in the development of LC-MS/MS method for detection of residual coccidiostats in egg and muscle samples. It was used to screen out CD44+CD24- mesenchymal-like subpopulation within breast carcinomas.

General Description

Chemical structure: polyether

Biological Activity

salinomycin (sal), which is a polyether ionophore antibiotic from streptomyces albus, has been proven to be able to kill different types of human cancer cells, most likely via interfering with abc drug transporters, the wnt/β-catenin signaling pathway, or other pathways.

Biochem/physiol Actions

Salinomycin produced by Streptomyces albus is a carboxylic polyether ionophore with antibiotic and anti-cancer properties. It induces cell death in some types of cancer cells such as breast, lung, gastric cancer, leukemia and osteosarcoma. Salinomycin inhibits multidrug resistance protein 1 and induces apoptosis by the generation of reactive oxygen species that cause DNA damage and inactivation of Stat3. Use of salinomycin as antibiotic results in lowered spermatozoa count and motility and decreased steroidogenesis in mice.

in vitro

several hepatocellular carcinoma (hcc) cell lines were treated with sal. results showed that sal inhibited proliferation and decreased pcna levels. cell cycle analysis showed that sal caused cell cycle arrest in different phases. sal induced apoptosis as characterized by an increase in the bax/bcl-2 ratio. compared to control, β-catenin expression was down-regulated by sal treatment significantly. the ca2+ concentration in hcc cells was examined by flow cytometry and it was found that higher ca2+ concentrations were observed in sal treatment groups [1].

in vivo

the in vivo anti-tumor effect of sal was verified using the hepatoma orthotopic tumor model and results showed that the liver tumor size in sal-treated groups decreased. immunohistochemistry and tunel staining also demonstrated that sal could in vivo inhibit proliferation and induced apoptosis [1].

IC 50

7.7, 13.7 and 10.4 μm for hepg2, smmc-7721 and bel-7402 cell line, respectively (after 24h treatment)

references

[1] wang f,he l,dai wq,xu yp,wu d,lin cl,wu sm,cheng p,zhang y,shen m,wang cf,lu j,zhou yq,xu xf,xu l,guo cy. salinomycin inhibits proliferation and induces apoptosis of human hepatocellular carcinoma cells in vitro and in vivo. plos one.2012;7(12):e50638.

InChI:InChI=1/C42H70O11.Na/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33;/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47);/q;+1/p-1/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41?,42-;/m0./s1

Upstream product

• 120330-27-0 salinomycin 
• 120297-98-5 Methanesulfonic acid (2S,5S)-2-((S)-1-benzyloxymethyl-propyl)-2-hydroxy-5-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester 
• 113643-40-6 <(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran>-2-methanol 
• 126394-12-5 (2S,5S,6S)-5-Benzyloxy-5-ethyl-heptane-1,2,6-triol 
• 126394-13-6 methyl <(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran>-2-carboxylate 
• 110672-03-2 <(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-2-dimethoxyphosphonoethan-1-one 
• 110653-60-6 (2R,4S,5S,6S,7R)-6-ethyl-5,7-isopropylidenedioxy-2,4-dimethylnonanal 
• 120269-74-1 (2R,3R,6S)-6-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxy)-heptane-1,3,6-triol 
• 108470-05-9 5-O-benzyl-2,4-dideoxy-3-O-formyl-2,4-di-C-methyl-L-lyxose 
• 113643-46-2 (R)-4-[(2S,5S,7S,9S,10S,12R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one 
• 113643-46-2 (R)-4-[(2S,5R,7S,9S,10S,12R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one 
• 120269-90-1 C₅₈H₈₆O₁₃ 
• 120269-86-5 (2S,5R,6R,10R,12S,13S,14S,15R)-2,6-bis(tert-butyldimethylsilyloxy)-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-13,15-isopropylidenedioxy-10,12-dimethylheptadec-7-yn-9-one 
• 120297-96-3 (2S,5R,6R,10R,12S,13S,14S,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-2,5-bis(tert-butyldimethylsilyloxy)-13,15-isopropylidenedioxy-6-(4-methoxybenzyloxy)-10,12-dimethylheptadec-7-yn-9-one 

Downstream Products

• 1388822-10-3 C₄₈H₇₅NO₁₀ 
• 1388822-18-1 C₄₉H₇₇NO₁₀ 

Relevant articles and documents

Antiproliferative Activity of Polyether Antibiotic - Cinchona Alkaloid Conjugates Obtained via Click Chemistry

A series of eight new conjugates of salinomycin or monensin and Cinchona alkaloids were obtained by the Cu(I)-catalysed 1,3-dipolar Huisgen cycloaddition (click chemistry) of respective N-propargyl amides of salinomycin or monensin with four different Cinchona alkaloid derived azides. In vitro antiproliferative activity of these conjugates evaluated against three cancer cell lines (LoVo, LoVo/DX, HepG2) showed that four of the compounds exhibited high antiproliferative activity (IC50 below 3.00 μm) and appeared to be less toxic and more selective against normal cells than two standard anticancer drugs.

Spectroscopic and computational study of a new isomer of salinomycin

A new derivative of polyether ionophore salinomycin was obtained as a result of a rearrangement catalysed by sulphuric acid in two-phase medium of water/methylene chloride solution. The new isomer was fully characterized by multinuclear 2D NMR, NOESY and MALDI-TOF. The properties of the new compound were additionally study by semiempirical (PM5) and DFT (B3LYP) methods. A potential mechanism of the rearrangement was also proposed.

X-ray, FT-IR, NMR and PM5 structural studies and antibacterial activity of unexpectedly stable salinomycin-benzotriazole intermediate ester

The unexpectedly stable benzotriazole ester of salinomycin (SAL-HOBt) - an intermediate product of the amidation reaction of salinomycin has been isolated and structurally characterised (using a single crystal) by X-ray, FT-IR, NMR and semiempirical methods. The results of the X-ray and spectroscopic studies demonstrated that this intermediate ester exist in the solid state and in solution exclusively as the stable O-acyl form. The molecular structure of SAL-HOBt is stabilised by relatively weak intramolecular hydrogen bonds. The PM5 calculation of possible structures of SAL-HOBt has shown that the O-acyl form is more energetically favourable than its N-oxide-N-acyl isomers. The antimicrobial tests show that SAL-HOBt is active against Gram-positive bacteria and clinical isolates methicillin-resistant Staphylococcus aureus (MIC = 1-2 μg/ml).