Hygromycin B

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Hygromycin B
Hygromycin b.svg
Clinical data
Other namesO-6-Amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1-2-3)-O-β-D-talopyranosyl(1-5)-2-deoxy-N3-methyl-D-streptamine
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.935 Edit this at Wikidata
Chemical and physical data
FormulaC20H37N3O13
Molar mass527.53 g/mol (563.5 with HCl) g·mol−1
3D model (JSmol)
Melting point160 to 180 °C (320 to 356 °F) (decomp.)
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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]

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 translation.

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.

Use in plant research[edit]

Hygromycin resistance gene is frequently used as a selectable marker in research on plants. In rice Agrobacterium-mediated transformation system, hygromycin is used at about 30–75 mg L−1, with an average of 50 mg L−1. The use of hygromycin at 50 mg L−1 demonstrated highly toxic to non-transformed calli. Thus, it can be efficiently used to select transformants.[6]

References[edit]

  1. ^ McGuire, Pettinger (1953), "Hygromycin I. Preliminary studies on the production and biological activity of a new antibiotic.", Antibiot. Chemother., 3 (12): 1268–1278, PMID 24542808
  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
  6. ^ Pazuki, A; Asghari, J; Sohani, M; Pessarakli, M & Aflaki, F (2014). "Effects of Some Organic Nitrogen Sources and Antibiotics on Callus Growth of Indica Rice Cultivars" (PDF). Journal of Plant Nutrition. 38 (8): 1231–1240. doi:10.1080/01904167.2014.983118. Retrieved November 17, 2014.