Hygromycin B

Chemical compound From Wikipedia, the free encyclopedia

Hygromycin B is an antibiotic produced by the bacterium Streptomyces hygroscopicus. It is an aminoglycoside that kills bacteria, fungi and other eukaryotic cells by inhibiting protein synthesis.[1]

Trade namesHygromix
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, HYG
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Quick facts Clinical data, Trade names ...
Hygromycin B
Clinical data
Trade namesHygromix
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, HYG
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.935 Edit this at Wikidata
Chemical and physical data
FormulaC20H37N3O13
Molar mass527.524 g·mol−1
3D model (JSmol)
Melting point160 to 180 °C (320 to 356 °F) (decomp.)
  • O1[C@H]4[C@@H](OC12O[C@@H]([C@H](O)[C@@H](O)[C@H]2O)[C@@H](N)CO)[C@@H](O)[C@H](O[C@H]4O[C@@H]3[C@@H](O)[C@H](N)C[C@H](NC)[C@H]3O)CO
  • InChI=1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6+,7+,8-,9+,10-,11+,12-,13-,14-,15-,16+,17+,18-,19+,20?/m1/s1 checkY
  • Key:GRRNUXAQVGOGFE-KPBUCVLVSA-N checkY
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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 B, along with aminoglycosides, inhibits protein synthesis by strengthening the interaction of tRNA binding in the ribosomal A-site. Hygromycin B also prevents mRNA and tRNA translocation by an unknown mechanism.[4]

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.[5] 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,[6] 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.[citation needed]

Fungus Coniothyrium minitans was transformed with the hygromycin B resistance gene to improve the infection rates of Sclerotinia sclerotiorum, a fungal parasite of many crops.[7]

Use in plant research

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.[8]

References

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