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H7772

Sigma-Aldrich

Hygromycin B from Streptomyces hygroscopicus

lyophilized powder

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Synonym(s):
Hygrovetine
Empirical Formula (Hill Notation):
C20H37N3O13
CAS Number:
Molecular Weight:
527.52
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces hygroscopicus

Quality Level

form

lyophilized powder

purified by

ion-exchange chromatography

color

faintly brown to brown
white to beige

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

viruses

Mode of action

protein synthesis | interferes

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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1 of 4

This Item
H9773H5527H0654
form

lyophilized powder

form

lyophilized powder

form

-

form

-

color

faintly brown to brown, white to beige

color

faintly brown to brown, white to beige

color

yellow-brown to orange

color

brown-yellow, light orange to dark orange, light yellow to dark yellow

solubility

H2O: 50 mg/mL

solubility

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

solubility

-

solubility

-

antibiotic activity spectrum

viruses

antibiotic activity spectrum

fungi

antibiotic activity spectrum

viruses

antibiotic activity spectrum

viruses

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

General description

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..

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 stable for at least 5 years if stored at 2-8°C. It is stable at 37°C for 30 days.

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

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Séverine Lorrain et al.
The Plant cell, 16(8), 2217-2232 (2004-07-23)
The hypersensitive response (HR) is a programmed cell death that is commonly associated with plant disease resistance. A novel lesion mimic mutant, vad1 (for vascular associated death1), that exhibits light conditional appearance of propagative HR-like lesions along the vascular system
Claudine Balagué et al.
The Plant cell, 15(2), 365-379 (2003-02-05)
The hypersensitive response (HR) in plants is a programmed cell death that is commonly associated with disease resistance. A novel mutation in Arabidopsis, hlm1, which causes aberrant regulation of cell death, manifested by a lesion-mimic phenotype and an altered HR
Senthilkumar Padmanaban et al.
Plant physiology, 144(1), 82-93 (2007-03-06)
Guard cell movement is induced by environmental and hormonal signals that cause changes in turgor through changes in uptake or release of solutes and water. Several transporters mediating these fluxes at the plasma membrane have been characterized; however, less is
Sung Ki Cho et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(40), 15629-15634 (2008-09-24)
Abscission is a developmental program that results in the active shedding of infected or nonfunctional organs from a plant body. Here, we establish a signaling pathway that controls abscission in Arabidopsis thaliana from ligand, to receptors, to downstream effectors. Loss
Ben-Jiang Ma et al.
PLoS pathogens, 7(9), e1002200-e1002200 (2011-09-13)
The HIV-1 gp41 envelope (Env) membrane proximal external region (MPER) is an important vaccine target that in rare subjects can elicit neutralizing antibodies. One mechanism proposed for rarity of MPER neutralizing antibody generation is lack of reverted unmutated ancestor (putative

Articles

Inhibition of Protein Synthesis by Antibiotics

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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