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H3274

Sigma-Aldrich

Hygromycin B from Streptomyces hygroscopicus

powder, BioReagent, suitable for cell culture, suitable for insect cell culture

Empirical Formula (Hill Notation):
C20H37N3O13
CAS Number:
Molecular Weight:
527.52
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Quality Level

biological source

Streptomyces hygroscopicus

product line

BioReagent

assay

≥60% (HPLC)

form

powder

application(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

color

faintly brown to brown
white to beige

 

(1) 7.1, (2) 8.8

mp

160-180 °C

solubility

H2O: 50 mg/mL (As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 30 days.)

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

Chemical structure: aminoglycoside
Aminoglycosides are the most widely used class of antibiotics that target ribosome. Hygromycin B is an aminocyclitol antibiotic. The organism, S. hygroscopicus contains phosphotransferase (HPH) activity, which phosphorylates hygromycin B helping in autoimmunity against the toxic effects of the drug.

Application

Hygromycin B antibiotic was used for hygro resistance effect in the following cells:
  • transfected 293T cells with mixture of plasmids at 160 μg/ml.
  • MCF-7ALOX12 cells at 150 μg/ml.
  • MSCV Luciferase PGK-hygro plasmid.
  • STAT3 Reporter HeLa Stable Cell Line (stably transfected with Luciferase gene under the control of STAT3 promoter) maintained in DMEM supplemented with 10% FBS.
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.

Biochem/physiol Actions

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

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

J M Pardo et al.
Journal of general microbiology, 131(6), 1289-1298 (1985-06-01)
Hygromycin B, an aminocyclitol antibiotic that strongly inhibits both 70S and 80S ribosomes, is synthesized by Streptomyces hygroscopicus. Ribosomes from this Gram-positive mycelial bacterium are inhibited in vitro by the antibiotic. In contrast, the streptomycete is highly resistant to the...
Nils Elfving et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(20), 8245-8250 (2011-05-04)
Development in plants is controlled by abiotic environmental cues such as day length, light quality, temperature, drought, and salinity. These signals are sensed by a variety of systems and transmitted by different signal transduction pathways. Ultimately, these pathways are integrated...
Maria A Borovinskaya et al.
RNA (New York, N.Y.), 14(8), 1590-1599 (2008-06-24)
Aminoglycosides are one of the most widely used and clinically important classes of antibiotics that target the ribosome. Hygromycin B is an atypical aminoglycoside antibiotic with unique structural and functional properties. Here we describe the structure of the intact Escherichia...
Alessio Colombo et al.
Neurobiology of disease, 33(3), 518-525 (2009-01-27)
Secretion of Amyloid-beta peptide (Abeta) circulating oligomers and their aggregate forms derived by processing of beta-amyloid precursor protein (APP) are a key event in Alzheimer's disease (AD). We show that phosphorylation of APP on threonine 668 may play a role...
Ayodele Akintayo et al.
The Journal of biological chemistry, 295(41), 14053-14064 (2020-08-09)
The membrane-bound, long form of MGAT4D, termed MGAT4D-L, inhibits MGAT1 activity in transfected cells and reduces the generation of complex N-glycans. MGAT1 is the GlcNAc-transferase that initiates complex and hybrid N-glycan synthesis. We show here that Drosophila MGAT1 was also...

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