345700

Ganciclovir

A nucleoside analog structurally related to Acyclovir.

• Synonyme(s) : Ganciclovir, 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine
• Formule empirique (notation de Hill): C₉H₁₃N₅O₄
• Numéro CAS: 82410-32-0
• Poids moléculaire : 255.23
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Pureté: ≥98% (HPLC)
• Forme: solid
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; desiccated
• Couleur: white
• Solubilité: 0.1 M HCl: 5 mg/mL
• Conditions d'expédition: ambient
• Température de stockage: −20°C
• 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

A nucleoside analog structurally related to Acyclovir (Cat. No. 114798). Acts as a prodrug that is activated by phosphorylation. Has been used in the study of “suicide” gene therapy in cancer research. Upon expression of a viral suicide gene encoding herpes simplex virus, thymidine kinase (TK), the non-toxic prodrug ganciclovir, is converted to an active phosphorylated analog that can be incorporated into the DNA of replicating eukaryotic cells, causing death of the malignant dividing cell. Causes an irreversible cell cycle arrest at the G₂/M checkpoint. Has also been used to study the loss of telomeres and to evaluate sensitivity of viruses to antiviral agents.

A nucleoside analog that is structurally related to Acyclovir (Cat. No. 114798). Acts as a pro-drug that is activated by phosphorylation. It has been used in the study of "suicide gene therapy" in cancer research. Upon expression of a viral suicide gene encoding herpes simplex virus thymidine kinase (TK), the non-toxic pro-drug is converted to the phosphorylated active analog and is incorporated into the DNA of replicating eukaryotic cells, causing death of the dividing malignant cells. Causes an irreversible cell cycle arrest at the G₂/M checkpoint. Has also been used to study the loss of telomers and to evaluate the sensitivity of viruses to anti-viral agents.

Actions biochimiques/physiologiques

Cell permeable: yes

Primary Target
Acts as a prodrug that is activated by phosphorylation

Product does not compete with ATP.

Reversible: no

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Autres remarques

Aghi, M., et al. 2000. J. Gene Med.2, 148.
Qiao, J., et al. 2000. Hum. Gene Ther.11, 1569.
Cannon, J.S., et al. 1999. J. Virol.73, 4786.
Rubsam, L.Z., et al. 1999. Cancer Res.59, 669.
Sprung, C.N., et al. 1999. Proc. Natl. Acad. Sci. USA96, 6781.
Yamasaki, H., et al. 1999. C.R. Acad. Sci. III322, 151.
Halloran, P.J., and Fenton, R.G. 1998. Cancer Res.58, 3855.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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