Hygromycin B

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Hygromycin B
Hygromycin b.svg
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
Legal status ?
Identifiers
CAS number 31282-04-9 YesY
ATC code None
PubChem CID 35766
ChemSpider 32900 YesY
ChEMBL CHEMBL1276484 N
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)
 N (what is this?)  (verify)

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]

History[edit]

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[edit]

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.

Use in research[edit]

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.

References[edit]

  1. ^ McGuire, Pettinger (1953), "Hygromycin I. Preliminary studies on the production and biological activity of a new antibiotic.", Antibiot. Chemother. 3: 1268–1278 
  2. ^ 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 
  3. ^ 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 
  4. ^ 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, doi:10.1128/aac.24.5.689, PMC 185926, PMID 6318654. 
  5. ^ 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 

External links[edit]