Hygromycin B

Hygromycin B
Clinical data
Other names	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
AHFS/Drugs.com	International Drug Names
ATC code	none;
Identifiers
	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;
CAS Number	31282-04-9 ;
PubChem CID	35766;
ChemSpider	32900 ;
UNII	3XQ2233B0B;
ChEMBL	ChEMBL1276484 ;
CompTox Dashboard (EPA)	DTXSID7041045 ;
ECHA InfoCard	100.045.935
Chemical and physical data
Formula	C20H37N3O13
Molar mass	527.53 g/mol (563.5 with HCl) g·mol−1
3D model (JSmol)	Interactive image;
Melting point	160 to 180 °C (320 to 356 °F) (decomp.)
	SMILES 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 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 ; Key:GRRNUXAQVGOGFE-KPBUCVLVSA-N ;
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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

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 translation.

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.

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.[6]

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References

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
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, doi:10.1128/aac.24.5.689, PMC 185926, PMID 6318654.
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
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.

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[discovery-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

[res1-2] 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

[res2-3] 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

[pmid6318654-4] 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.

[impurities-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

[pazuki-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.