55721-31-8 Usage
Description
Salinomycin is a polyether ionophore with antibiotic and anti-cancer properties. It is a white or light yellow crystalline powder with a slight specific smell and a melting point of 140-142 ℃. Salinomycin is soluble in acetone, chloroform, benzene, ethyl acetate, diethyl ether, and methanol, but almost insoluble in water.
Uses
Used in Animal Feed Industry:
Salinomycin is used as a coccidiostat for preventing coccidiosis in chickens. It is also effective against most Gram-positive bacteria and has an inhibitory effect on various insects. It is added to chicken feed at a rate of 50-60g/t and should be stopped during the laying period for 5 days.
Used in Pharmaceutical Industry:
Salinomycin is used as an ionophore agent, which has a high affinity for monovalent cations, particularly potassium. It has been shown to inhibit cancer stem cells and induce cell death in some types of cancer cells, such as breast, lung, gastric cancer, leukemia, and osteosarcoma. Salinomycin sodium, prepared from salinomycin, is the preferred formulation in animals to prevent coccidiosis and promote growth.
Used in Anticancer Applications:
Salinomycin displays selective toxicity for cancer stem cells and induces rapid mitochondrial hyperpolarization. It induces selective cytotoxicity to MCF-7 mammosphere cells via the hedgehog signaling pathway and reduces doxorubicin resistance of breast tumor cells by inhibiting drug efflux pump expression and activity. Additionally, it kills cancer stem cells by sequestering iron.
Chemical Properties:
Salinomycin is a brown solid with a slight specific smell. It has a melting point of 140-142 ℃ and is soluble in various organic solvents but almost insoluble in water. The oral LD50 values for rats, mice, and chickens are 70-100mg/kg, 50mg/kg, and 150mg/kg, respectively.
production method
It is produced by fermentation of white Streptomyces (Streptomyces albus).
References
1) Gupta?et al. (2009),?Identification of selective inhibitors of cancer stem cells by high-throughput screening; Cell,?138?645
2) Manago?et al. (2015),?Early effects of the antineoplastic agent salinomycin on mitochondrial function; Cell Death Dis.,?6?e1930
3) Fu?et al. (2016),?Salinomycin induces selective cytotoxicity to MCF-7 mammosphere cells through targeting the Hedgehog signaling pathway;?Oncol. Rep.,?35?912
4)?Kim?et al.?(2015), Salinomycin enhances doxorubicin-induced cytotoxicity in multidrug resistant MCF-7/MDR human breast cancer cells via decreased efflux of doxorubicin;?Mol. Med. Rep.,?12(2)?1898
5) Mai et al. (2017)?Salinomycin kills cancer stem cells by sequestering iron in lysosomes; Nat. Chem.,?9?1025
Check Digit Verification of cas no
The CAS Registry Mumber 55721-31-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,5,7,2 and 1 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 55721-31:
(7*5)+(6*5)+(5*7)+(4*2)+(3*1)+(2*3)+(1*1)=118
118 % 10 = 8
So 55721-31-8 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
55721-31-8Relevant articles and documents
Structure–Activity Relationships in Salinomycin: Cytotoxicity and Phenotype Selectivity of Semi-synthetic Derivatives
Borgstr?m, Bj?rn,Huang, Xiaoli,Hegardt, Cecilia,Oredsson, Stina,Strand, Daniel
, p. 2077 - 2083 (2017)
The ionophore salinomycin has attracted attention for its exceptional ability to selectively reduce the proportion of cells with stem-like properties in cancer cell populations of varying origin. Targeting the tumorigenicity of such cells is of interest as they are implicated in recurrence, metastasis, and drug resistance. Structural derivatives of salinomycin are thus sought after, both as tools for probing the molecular mechanism(s) underlying the observed phenotype effects, and for improving selectivity and activity against cancer stem cells. Synthetic strategies for modification of each of the directly accessible functional groups of salinomycin are presented and the resulting library of analogues was investigated to establish structure–activity relationships, both with respect to cytotoxicity and phenotype selectivity in breast cancer cells. 20-O-Acylated derivatives stand out by exhibiting both improved selectivity and activity. Mechanistically, the importance of the ionophore properties of salinomycin is highlighted by a significant loss of activity by modifications directly interfering with either of the two primary ion coordinating motifs in salinomycin, the C11 ketone and the C1 carboxylate.