345700

Ganciclovir

A nucleoside analog structurally related to Acyclovir.

• Sinónimos: Ganciclovir, 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine
• Fórmula empírica (notación de Hill): C₉H₁₃N₅O₄
• Número de CAS: 82410-32-0
• Peso molecular: 255.23
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• Análisis: ≥98% (HPLC)
• formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; desiccated
• color: white
• solubilidad: 0.1 M HCl: 5 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: −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)
• Clave InChI: IRSCQMHQWWYFCW-UHFFFAOYSA-N

Descripción

Descripción general

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.

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
Acts as a prodrug that is activated by phosphorylation

Product does not compete with ATP.

Reversible: no

Envase

Packaged under inert gas

Advertencia

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitución

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

Otras notas

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.

Información legal

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

Información de seguridad

• Pictogramas: GHS08
• Palabra de señalización: Danger
• Frases de peligro: H340,H361fd
• Consejos de prudencia: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Clasificaciones de peligro: Muta. 1B - Repr. 2
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable