Hygromycin B

Hygromycin B
Clinical data
Trade names	Hygromix
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, HYG
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	527.524 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 other 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 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]}

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.^[7]

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.^[8]

References

^ Pittenger RC, Wolfe RN, Hoehn MM, Marks PN, Daily WA, McGUIRE JM (December 1953). "Hygromycin. I. Preliminary studies on the production and biologic activity of a new antibiotic". Antibiotics & Chemotherapy. 3 (12): 1268–1278. PMID 24542808.
^ Gritz L, Davies J (November 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): 179–188. doi:10.1016/0378-1119(83)90223-8. PMID 6319235.
^ Kaster KR, Burgett SG, Rao RN, Ingolia TD (October 1983). "Analysis of a bacterial hygromycin B resistance gene by transcriptional and translational fusions and by DNA sequencing". Nucleic Acids Research. 11 (19): 6895–6911. doi:10.1093/nar/11.19.6895. PMC 326422. PMID 6314265.
^ "Hygromycin B". TOKU-E. Retrieved 2024-06-28.
^ Rao RN, Allen NE, Hobbs JN, Alborn WE, Kirst HA, Paschal JW (November 1983). "Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli". Antimicrobial Agents and Chemotherapy. 24 (5): 689–695. doi:10.1128/aac.24.5.689. PMC 185926. PMID 6318654.
^ Kauffman JS (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 MM, 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. S2CID 84495391. Retrieved November 17, 2014.
^ Jones EE, Stewart A, Whipps JM (March 2003). "Use of Coniothyrium minitans transformed with the hygromycin B resistance gene to study survival and infection of Sclerotinia sclerotiorum sclerotia in soil" (PDF). Mycological Research. 107 (Pt 3): 267–276. doi:10.1017/S0953756203007457. PMID 12825495.

[discovery-1] Pittenger RC, Wolfe RN, Hoehn MM, Marks PN, Daily WA, McGUIRE JM (December 1953). "Hygromycin. I. Preliminary studies on the production and biologic activity of a new antibiotic". Antibiotics & Chemotherapy. 3 (12): 1268–1278. PMID 24542808.

[res1-2] Gritz L, Davies J (November 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): 179–188. doi:10.1016/0378-1119(83)90223-8. PMID 6319235.

[res2-3] Kaster KR, Burgett SG, Rao RN, Ingolia TD (October 1983). "Analysis of a bacterial hygromycin B resistance gene by transcriptional and translational fusions and by DNA sequencing". Nucleic Acids Research. 11 (19): 6895–6911. doi:10.1093/nar/11.19.6895. PMC 326422. PMID 6314265.

[4] "Hygromycin B". TOKU-E. Retrieved 2024-06-28.

[pmid6318654-5] Rao RN, Allen NE, Hobbs JN, Alborn WE, Kirst HA, Paschal JW (November 1983). "Genetic and enzymatic basis of hygromycin B resistance in Escherichia coli". Antimicrobial Agents and Chemotherapy. 24 (5): 689–695. doi:10.1128/aac.24.5.689. PMC 185926. PMID 6318654.

[impurities-6] Kauffman JS (2009). "Analytical Strategies for Monitoring Residual Impurities Best methods to monitor product-related impurities throughout the production process". BioPharm International. 23: 1–3.

[pazuki-7] Pazuki A, Asghari J, Sohani MM, 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. S2CID 84495391. Retrieved November 17, 2014.

[8] Jones EE, Stewart A, Whipps JM (March 2003). "Use of Coniothyrium minitans transformed with the hygromycin B resistance gene to study survival and infection of Sclerotinia sclerotiorum sclerotia in soil" (PDF). Mycological Research. 107 (Pt 3): 267–276. doi:10.1017/S0953756203007457. PMID 12825495.

[1]