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Merck

H9773

Higromicina B from Streptomyces hygroscopicus

lyophilized powder, suitable for plant cell culture, BioReagent

Sinónimos:

Hygromycin

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Fórmula empírica (notación de Hill):
C20H37N3O13
Número CAS:
31282-04-9
Peso molecular:
527.52
NACRES:
NA.72
PubChem Substance ID:
329815270
UNSPSC Code:
12352207
EC Number:
250-545-5
MDL number:
MFCD06795479

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Nombre del producto

Higromicina B from Streptomyces hygroscopicus, suitable for plant cell culture, BioReagent, ≥60% (HPLC), lyophilized powder

InChI key

GRRNUXAQVGOGFE-XKIAHZFYSA-N

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

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

biological source

Streptomyces hygroscopicus

product line

BioReagent

form

lyophilized powder

purified by

ion-exchange chromatography

concentration

≥60% (HPLC)

technique(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

antibiotic activity spectrum

fungi

application(s)

agriculture

mode of action

protein synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Biochem/physiol Actions

Modo de acción: El producto actúa inhibiendo la síntesis de proteínas al inducir la lectura errónea de la plantilla de ARNm en procariotas, con la capacidad de inhibir la traducción.

Espectro antimicrobiano: La higromicina B actúa contra bacterias, hongos y células eucariotas superiores.
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.

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.

Disclaimer

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.

General description

Chemical structure: aminoglycoside
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.

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
GHS06

signalword

Danger

Hazard Classifications

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

Clase de almacenamiento

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000419073
0000419074
0000419075
0000419075
0000419073

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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
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