Geneticin

Geneticin Basic information
Product Name:Geneticin
Synonyms:TRYPSIN INHIBITOR SOYBEAN REAGENT GRADE;G-418 disulfate,Geneticin;Geneticin Disulfate (G418), Antibiotic for Culture Media Use Only;Geneticin disulfate saltPotency ≥ 700 ug/mg (anhydrous basis);Antibiotic G418 Geneticin®;2-[4,6-diamino-3-[3-amino-4,5-dihydroxy-6-(1-hydroxyethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol,sulfuric acid;G 418 Sulfate, Sterile-Filtered Aqueous Solution, Cell Culture Tested;D-Streptamine, O-2-amino-2,7-dideoxy-D-glycero-α-D-gluco-heptopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-2-deoxy-, sulfate (1:2)
CAS:108321-42-2
MF:C20H42N4O14S
MW:594.63
EINECS:600-864-4
Product Categories:Antibiotic Explorer;antibiotic;Inhibitors;108321-42-2
Mol File:108321-42-2.mol
Geneticin Structure
Geneticin Chemical Properties
storage temp. 2-8°C
solubility H2O: 50 mg/mL
form white powder
color white to off-white
optical activity[α]/D (Specific Rotation: +104.4o (c=0.3% in H2O at 26oC))
Water Solubility soluble
Stability:Hygroscopic
InChIKeyQNQZPJLBGRQFDD-ZLRXUJDMSA-N
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/37/38-42/43
Safety Statements 22-24/25-36/37-23-36-26-45
WGK Germany 3
RTECS CB9378500
HS Code 29419090
MSDS Information
Geneticin Usage And Synthesis
DescriptionGeneticin (also known as G418, G418 sulfate) is an aminoglycoside antibiotic similar in structure to gentamicin B1, produced by Micromonospora rhodorangea. Geneticin blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells and is commonly used in laboratory research to select genetically engineered cells. Resistance to Geneticin is conferred by the neo gene from Tn5 encoding an aminoglycoside 3'-phosphotransferase, APH 3'II.
Chemical Propertieswhite to off-white powder
UsesGeneticin is an aminoglycoside antibiotic similar in structure to gentamicin used for selection and maintenance of prokaryotic and eukaryotic cells. Optimal concentrations for selection and maintenance vary by cell lines. Bacteria and algae require 5 μg/mL or less while animal cells may require 300-500 μg/mL. It is also used to membrane-permeant allosteric effector of hemoglobin therapeutic in cardiovascular diseases and cancer.
ApplicationGeneticin's most common application is in molecular biology as a selection agent. Geneticin(G418 sulfate) is toxic to bacteria, yeast, protozoa, helminths, and mammalian cells. Resistance is conferred by one of two dominant genes of bacterial origin which can be expressed in eukaryotic cells. G418 is water soluble and can be stored at room temperature for as long as 1 year. Aqueous solutions should be stored frozen. The amount of G418 required for selection will vary with each cell type and growth cycle. Although cells that are multiplying will be affected sooner than those that are not, cells that are in log phase will still require 3 to 7 days for selection. In general, the amount of G418 required for selection of mammalian cells is 400 mg/ml and 200 mg/ml for maintenance.
General DescriptionThe optimal concentration of G418 for selection of resistance will vary according to the organism and/or cell type under investigation. In general, the concentration of active drug required for selection is as follows: Dictyostelium sp.: 10-100 μg/ml Plant cells: 10-100 μg/ml Yeast cells: 0.5-1.0 μg/ml Mammalian cells: 0.1-2.0 μg/ml
Biochem/physiol ActionsMode of Action: G418 blocks polypeptide synthesis and protein elongation by inhibiting synthesis at the 70S and 80S ribosomes.Antimicrobial Spectrum: G418 selects for cells stably transfected with an iNOS promoter construct and neomycin resistance gene and shows activity against protozoa and helminthes.
storage+4°C
Mode of actionGeneticin works by blocking polypeptide synthesis by preventing the elongation step within eukaryotic cells.
Resistance: Resistance to Geneticin is conferred through the NPTll gene in plant cells and the NEO gene in mammalian cells, which encodes aminoglycoside 3'-phosphotransferase.
Action: Geneticin functions by causing a chain of nonsense mutations during translation, ultimately resulting in inhibition of polypeptide synthesis and protein elongation.
references[1] bar-nun s, shneyour y, beckmann js. g-418, an elongation inhibitor of 80 s ribosomes. biochim biophys acta. 1983, 741 (1): 123-7.
[2] julian davies and antonio jimenez. a new selective agent for eukaryotic cloning vectors. am. j. trop. med. hyg. 1980, 29 (5): 1089-1092.
[3] xianchao g. zhang, peter w. mason, edward j. dubovi, xiaodong xu, nigel bourne, randall w. renshaw, timothy m. block, and alexander v. birk. antiviral activity of geneticin against dengue virus. antiviral res. 2009 july, 83(1): 21–27.
Geneticin Preparation Products And Raw materials
(R)-2-Aminocyclohenanol Trans-4-aminocyclohexanol sulfate Sodium sulfate D-Glucosamine sulfate Cyclohexanol, 2-amino-, (1S,2S)- 3-Amino-cyclohexanol 4-Aminotetrahydropyran Geneticin 4-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-6-O-(3-deoxy-3-methylamino-β-L-arabinopyranosyl)-2-deoxy-D-streptamine 1,3-Diaminocyclohexane G418 TRANS-2-AMINOCYCLOHEXANOL HYDROCHLORIDE TRANS-1,2-CYCLOHEXANEDIOL 3-AMINO-4-METHYL-PENTAN-1-OL 3-Deoxy-D-arabinose (1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL GOLD COAST SOLUTION NO 1

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