G2536

Ganciclovir

≥99% (HPLC), powder, viral DNA elongation inhibitor

• Synonyme(s) : 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one, 9-(1,3-Dihydroxy-2-propoxymethyl)guanine, DHPG
• Formule empirique (notation de Hill) : C₉H₁₃N₅O₄
• CAS Number: 82410-32-0
• Poids moléculaire : 255.23
• Numéro MDL: MFCD00870588
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278453
• Nomenclature NACRES : NA.77

Propriétés

• Product Name: Ganciclovir, ≥99% (HPLC), powder
• Niveau de qualité: 300
• Essai: ≥99% (HPLC)
• Forme: powder
• Couleur: white
• Solubilité: 0.1 M HCl: 10 mg/mL
• ε (coefficient d'extinction): 12.0 at 256 nm at 1 mM
• Spectre d'activité de l'antibiotique: viruses
• Mode d’action: DNA synthesis | interferes
• Auteur: Roche
• Température de stockage: 2-8°C
• Chaîne SMILES: NC1=Nc2c(ncn2COC(CO)CO)C(=O)N1
• InChI: 1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
• Clé InChI: IRSCQMHQWWYFCW-UHFFFAOYSA-N

Description

Description générale

Chemical structure: nucleoside

Application

Ganciclovir is used in molecular biology for selection against random recombination events when homologous recombination of a gene of interest is required.

Actions biochimiques/physiologiques

Ganciclovir is a pro-drug nucleoside analog that is activated by phosphorylation. It is useful in the study of gene therapy in cancer research.
Upon expression of a viral suicide gene encoding thymidine kinase, the non-toxic pro-drug is converted to a phosphorylated active analog and is incorporated into the DNA of replicating eukaryotic cells, causing death of the malignant dividing cell. The cell cycle is irreversibly arrested at the G2-M checkpoint. Gap junction involvement in the ganciclovir bystander effect has been studied. Ganciclovir has been used to study loss of telomeres and to evaluate sensitivity of viruses to antiviral treatments.

Caractéristiques et avantages

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Notes préparatoires

Ganciclovir is soluble in 0.1 M HCl (10 mg/ml), DMSO (5 mg/ml), water (2 mg/ml), hot methanol, and ethanol (<1 mg/ml).
This product should be stored desiccated at 2-8 °C. Under these conditions the product is stable for 3 years.

Ganciclovir is tested for solubility in 0.1M HCl at 10 mg/mL. The compound is also soluble in DMSO at 5 mg/mL.

Informations sur la sécurité

• Pictogrammes: GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H340,H361fd
• Conseils de prudence: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Classification des risques: Muta. 1B - Repr. 2
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges