20-Deoxysalinomycin
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| Category | Antibiotics |
| Catalog number | BBF-01356 |
| CAS | 64003-50-5 |
| Molecular Weight | 735.00 |
| Molecular Formula | C42H70O10 |
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Description
20-Deoxysalinomycin is produced by the strain of Streptomycesalbus. It mainly has the activity against gram-positive bacteria, especially against coccidia of poultry.
Specification
| Synonyms | Antibiotic SY 1 |
| IUPAC Name | 2-[6-[6-[3-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid |
| Canonical SMILES | CCC(C1CCC(C(O1)C(C)C(C(C)C(=O)C(CC)C2C(CC(C3(O2)C=CCC4(O3)CCC(O4)(C)C5CCC(C(O5)C)(CC)O)C)C)O)C)C(=O)O |
| InChI | InChI=1S/C42H70O10/c1-11-30(38(45)46)32-16-15-24(4)36(49-32)28(8)34(43)27(7)35(44)31(12-2)37-25(5)23-26(6)42(50-37)19-14-18-41(52-42)22-21-39(10,51-41)33-17-20-40(47,13-3)29(9)48-33/h14,19,24-34,36-37,43,47H,11-13,15-18,20-23H2,1-10H3,(H,45,46) |
| InChI Key | XLVIXTBNHCWLTO-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Synthesis and biological evaluation of 20-epi-amino-20-deoxysalinomycin derivatives
Yu Li, Qiuyan Shi, Jiajia Shao, Yaping Yuan, Zhigang Yang, Shizhen Chen, Xin Zhou, Shijun Wen, Zhong-Xing Jiang Eur J Med Chem. 2018 Mar 25;148:279-290. doi: 10.1016/j.ejmech.2018.02.004. Epub 2018 Feb 5.
To improve the druggability of salinomycin, a 20-epi-amino-20-deoxysalinomycin derivatives library was synthesized with high efficacy from which a few salinomycin derivatives with high potency and selectivity were identified through comprehensive cytotoxicity assay, including a fluorine-19 magnetic resonance sensitive tool molecule. Using a K-ras cellular model, salinomycin and its derivatives showed different molecular mode of action from literature reports. These results would be valuable for developing salinomycin-based cancer therapy.
2. Trypanocidal and cell swelling activity of 20-deoxysalinomycin
Dietmar Steverding, Daniel Strand, Adam Huczyński Exp Parasitol. 2022 Dec;243:108414. doi: 10.1016/j.exppara.2022.108414. Epub 2022 Oct 21.
The naturally occurring polyether ionophore salinomycin was previously found to display promising anti-proliferative activity against bloodstream forms of Trypanosoma brucei. Here, we report the evaluation of 20-deoxysalinomycin, a naturally occurring homolog to salinomycin, for trypanocidal and cell swelling activity. The concentration of 20-deoxysalinomycin required to reduce the growth rate of bloodstream-form trypanosomes by 50% was determined to be 0.12 μM and found to be 8 times more trypanocidal than that of salinomycin. Moreover, 20-deoxysalinomycin and salinomycin displayed similar cytotoxic activity against human HL-60 cells. Measured as the ratio of cytotoxic to trypanocidal activity, 20-deoxysalinomycin thus exhibits a four-fold higher selectivity compared to salinomycin. The stronger trypanocidal activity of 20-deoxysalinomycin is attributed to an enhanced ability to induce cell swelling in trypanosomes. The findings support 20-deoxysalinomycin as a useful lead in the rational development of new and improved anti-trypanosomal drugs.
3. Semisynthesis of SY-1 for investigation of breast cancer stem cell selectivity of C-ring-modified salinomycin analogues
Xiaoli Huang, Björn Borgström, Linda Månsson, Lo Persson, Stina Oredsson, Cecilia Hegardt, Daniel Strand ACS Chem Biol. 2014 Jul 18;9(7):1587-94. doi: 10.1021/cb5002153. Epub 2014 May 29.
Salinomycin, a naturally occurring polyether ionophore was recently found to selectively reduce the proportion of CD44(+)/CD24(-) cells, a phenotype associated with breast cancer stem cells. Subsequent studies from our group showed that chemical modification of the allylic C20 hydroxyl of salinomycin, located at the C-ring, can enhance the activity of derivatives against breast cancer cells over 5-fold compared to the native structure. Access to C-ring-modified salinomycin analogues is thus of interest from both a mechanistic and a synthetic perspective. Here, we report efficient strategies for gram scale synthesis of the natural product SY-1 (20-deoxy salinomycin), and a saturated analogue, 18,19-dihydro SY-1, for a comparative in vitro investigation of the biological profiles of these compounds with that of salinomycin. Across several assays, the deoxygenated structures required higher concentrations to elicit similar cellular responses to that of salinomycin. Similarly to salinomycin, SY-1 or 18,19-dihydro SY-1 treatment was found to reduce the proportion of CD44(+)/CD24(-) cells with essentially complete selectivity up to ~IC25. Importantly, the proportion of CD44(+)/CD24(-) cells showed a pronounced U-shaped dose response curve for salinomycin and its derivatives, but not for paclitaxel. The concentration for maximum response in this assay followed differences in IC50 for salinomycin and its analogues, which emphasizes the importance of taking concentration dependence into account when comparing effects on the CD44(+)/CD24(-) phenotype. Small differences in the global conformation within the triad of compounds investigated together with differences in activity across assays emphasize the importance of substitution at C20 for the activity of salinomycin and its derivatives.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
