53003-10-4 Usage
Description
Salinomycin is a polyether ionophore with a solid chemical structure, characterized by its broad-spectrum Gram-positive and anti-coccidial activity. It exhibits a high affinity for monovalent cations, particularly potassium, and has been recognized for its potential applications in various fields due to its unique properties.
Uses
Used in Veterinary Medicine:
Salinomycin is used as an antibacterial agent for controlling coccidia in animals, which are parasitic protozoa that cause coccidiosis, a disease affecting the intestinal tract. Its anti-coccidial activity helps in preventing and treating this condition in livestock.
Used in Animal Husbandry:
In the animal husbandry industry, Salinomycin is utilized for growth promotion in ruminants, such as cattle and sheep. Its use contributes to improved weight gain and overall health of these animals.
Used in Cancer Research:
Salinomycin has been shown to inhibit cancer stem cells, demonstrating a potency greater than that of taxol by more than 100 times. Although the exact mechanism of action is not yet fully understood, its potential in cancer treatment is being explored, particularly in targeting CD44+CD24mesenchymal-like subpopulations within breast carcinomas.
Used in Analytical Chemistry:
Salinomycin is employed as a standard in the development of LC-MS/MS methods for the detection of residual coccidiostats in egg and muscle samples. This application aids in ensuring the safety and quality of these food products by monitoring the presence of these substances.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 53003-10-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,0,0 and 3 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 53003-10:
(7*5)+(6*3)+(5*0)+(4*0)+(3*3)+(2*1)+(1*0)=64
64 % 10 = 4
So 53003-10-4 is a valid CAS Registry Number.
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
53003-10-4Relevant articles and documents
Antiproliferative Activity of Polyether Antibiotic - Cinchona Alkaloid Conjugates Obtained via Click Chemistry
Skiera, Iwona,Antoszczak, Micha?,Trynda, Justyna,Wietrzyk, Joanna,Boratyński, Przemys?aw,Kacprzak, Karol,Huczyński, Adam
, p. 911 - 917 (2015/10/06)
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
Pankiewicz, Rados?aw
, p. 464 - 470 (2013/10/22)
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
Huczyński, Adam,Janczak, Jan,Antoszczak, Micha?,Stefańska, Joanna,Brzezinski, Bogumil
experimental part, p. 197 - 203 (2012/10/07)
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).
