Hygromycin B
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| Systematic (IUPAC) name | |
| (3' R,3aS,4S,4' R,5' R,6R,6' R,7S,7aS)-4-{[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-[(1S)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 31282-04-9  |
| ATC code | None |
| PubChem | CID 35766 |
| ChemSpider | 32900 |
| ChEMBL | CHEMBL1276484  |
| Synonyms | O-6-Amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1-2-3)-O-β-D-talopyranosyl(1-5)-2-deoxy-N3-methyl-D-streptamine |
| Chemical data | |
| Formula | C20H37N3O13 |
| Mol. mass | 527.53 g/mol (563.5 with HCl) |
| SMILES | eMolecules & PubChem |
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Hygromycin B is an antibiotic produced by the bacterium Streptomyces hygroscopicus. It is an aminoglycoside that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis.[1]
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[edit] History
Hygromycin B was originally developed in the 1950s for use with animals and is still added into swine and chicken feed as an anthelmintic or anti-worming agent (product name: Hygromix). Hygromycin B is produced by Streptomyces hygroscopicus, a bacterium isolated in 1953 from a soil sample. Resistance genes were discovered in the early 1980s.[2][3] Mechanism of action: Hygromycin is active against both prokaryotic and eukaryotic cells. It acts by inhibiting polypeptide synthesis. It stabilizes the tRNA-ribosomal acceptor site, thereby inhibiting translocation.
[edit] Use in research
In the laboratory it is used for the selection and maintenance of prokaryotic and eukaryotic cells that contain the hygromycin resistance gene. The resistance gene is a kinase that inactivates hygromycin B through phosphorylation.[4] Since the discovery of hygromycin-resistance genes, hygromycin B has become a standard selection antibiotic in gene transfer experiments in many prokaryotic and eukaryotic cells. Based on impurity monitor method [5], four different kinds of impurities are discovered in commercial hygromycin B from different suppliers and toxicities of different impurities to the cell lines are described in the following external links.
[edit] External links
Information from hygromycin.net (InvivoGen)
Information from hygromycin-evopure.com
[edit] References
- ^ McGuire, Pettinger (1953), "Hygromycin I. Preliminary studies on the production and biological activity of a new antibiotic.", Antibiot. Chemother. 3: 1268–1278
- ^ Davies, Gritz; Davies, J (1983), "Plasmid-encoded hygromycin B resistance: the sequence of hygromycin B phosphotransferase gene and its expression in Escherichia coli and Saccharomyces cerevisiae.", Gene 25 (2-3): 179–88, doi:10.1016/0378-1119(83)90223-8, PMID 6319235
- ^ Burgett, Kaster; Burgett, SG; Rao, RN; Ingolia, TD (1983), "Analysis of a bacterial hygromycin B resistance gene by transcriptional and translational fusions and by DNA sequencing.", Nucleic Acids Res. 11 (19): 6895–911, doi:10.1093/nar/11.19.6895, PMC 326422, PMID 6314265
- ^ Rao RN, Allen NE, Hobbs JN, Alborn WE, Kirst HA, Paschal JW (1983), "Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli", Antimicrobial Agents and Chemotherapy 24 (5): 689–95, PMC 185926, PMID 6318654, http://aac.asm.org/cgi/content/abstract/24/5/689.
- ^ Kauffman, John (2009), "Analytical Strategies for Monitoring Residual Impurities Best methods to monitor product-related impurities throughout the production process.", BioPharm International 23: 1–3
