H9773

Sigma-Aldrich

Hygromycin B from Streptomyces hygroscopicus

suitable for plant cell culture, BioReagent, ≥60% (HPLC), lyophilized powder

Empirical Formula (Hill Notation):
C20H37N3O13
CAS Number:
Molecular Weight:
527.52
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.72
Pricing and availability is not currently available.

Quality Level

biological source

Streptomyces hygroscopicus

product line

BioReagent

assay

≥60% (HPLC)

form

lyophilized powder

purified by

ion-exchange chromatography

application(s)

cell culture | plant: suitable

color

faintly brown to brown
white to beige

 

(1) 7.1, (2) 8.8

solubility

H2O: soluble 50 mg/mL
ethanol: soluble
methanol: soluble

Featured Industry

Agriculture

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

fungi

storage temp.

2-8°C

SMILES string

CN[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@@H]3O[C@]4(O[C@H]([C@H](N)CO)[C@H](O)[C@H](O)[C@H]4O)O[C@H]23)[C@@H]1O

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

InChI key

GRRNUXAQVGOGFE-XKIAHZFYSA-N

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General description

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.
Chemical structure: aminoglycoside

Application

Hygromycin B is an aminoglycoside antibiotic isolated from Streptomyces hygroscopicus. It has been used to study protein synthesis at the level of the 70S ribosome translocation and mRNA template misreading, as an antiviral agent by selectively penetrating cells rendered permeable by virus infection and inhibiting translation, and as a selection agent for hygromycin resistance gene transformed cells. It is recommended for use as a selection agent at 100-800 μg/mL, specifically at 100 μg/mL for prokaryotes, 200 μg/mL for lower eukaryotes and 150-400 μg/mL for higher eukaryotes.

Hygromycin B from Streptomyces hygroscopicus is used for gene cloning and ectopic expression. It is also used in MS medium for the in vitro screening of transgenic plants.

Biochem/physiol Actions

Hygromycin B is used in mutagenesis or for selection of gene expression and complementation constructs in C. jejuni. It is also adopted as a marker in other approaches for manipulating, introducing or deleting DNA in C. elegans. It can be inactivated by Aminoglycoside 4-phosphotransferase-Ia (APH(4)-Ia)/Hygromycin B phosphotransferase (Hph) through phosphorylation. The amino function of this antibiotic may be involved in a general acid-base catalysis performed by the ribozyme, acting as proton acceptors/donors.
Mode of Action: The product acts by inhibiting protein synthesis by inducing the misreading of the m-RNA template in the prokaryote, with the potency to inhibit translation.

Antimicrobial Spectrum: Hygromycin B acts against bacteria, fungi and higher eukaryotic cells.

Caution

Hygromycin B products should be stored as supplied at 2-8°C, and the dry solid is table for at least 5 years if stored at 2-8°C. It is stable at 37°C for 30 days. (For solutions) This solution is stable as supplied for two years if stored at 2-8°C.

Preparation Note

This product is purified by ion exchange chromatography. Hygromycin B is soluble in water at concentrations >50 mg/mL, and also soluble in methanol or ethanol. Solutions should be sterilized by filtration, not by autoclaving. Additionally, Hygromycin B solutions have been reported to lose activity on freezing, and since they are stable refrigerated, freezing should be avoided.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

RIDADR

UN3462 - class 6.1 - PG 1 - Toxins, extracted from living sources, solid, n.o.s., HI: all (not BR)

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Andrew Cameron et al.
PloS one, 9(4), e95084-e95084 (2014-04-23)
Campylobacter jejuni genetic manipulation is restricted by the limited number of antibiotic resistance cassettes available for use in this diarrheal pathogen. In this study, two antibiotic resistance cassettes were developed, encoding for hygromycin B and apramycin resistance, for use in...
Hany A El-Shemy et al.
Current issues in molecular biology, 11 Suppl 1, i21-i28 (2009-02-06)
The green fluorescent protein (GFP) of jellyfish (Aequorea victoria) has significant advantages over other reporter genes, because expression can be detected in living cells without any substrates. Recently, epigenetic phenomena are important to consider in plant biotechnology experiments for elucidate...
Daisuke Iino et al.
Journal of structural biology, 183(1), 76-85 (2013-06-12)
Aminoglycoside 4-phosphotransferase-Ia (APH(4)-Ia)/Hygromycin B phosphotransferase (Hph) inactivates the aminoglycoside antibiotic hygromycin B (hygB) via phosphorylation. The crystal structure of the binary complex of APH(4)-Ia with hygB was recently reported. To characterize substrate recognition by the enzyme, we determined the crystal...
Yajun Xi et al.
Methods in molecular biology (Clifton, N.J.), 581, 53-59 (2009-09-22)
Switchgrass (Panicum virgatum L.) is a highly productive warm-season C4 species that is being developed into a dedicated biofuel crop. This chapter describes a protocol that allows the generation of transgenic switchgrass plants by Agrobacterium tumefaciens-mediated transformation. Embryogenic calluses induced...
M Dutt et al.
Plant cell reports, 29(11), 1251-1260 (2010-08-17)
A method for the genetic transformation of several citrus cultivars is described, including cultivars observed to be recalcitrant to conventional epicotyl-mediated transformation. Embryogenic cell suspension cultures, established from unfertilized ovules were used as target tissues for Agrobacterium-mediated transformation. Several modifications...
Articles
Protein synthesis is a complex, multi-step process involving many enzymes as well as conformational alignment. However, the majority of antibiotics that block bacterial protein synthesis interfere with the processes at the 30S subunit or 50S subunit of the 70S bacterial ribosome.
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Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic
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