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SML2346

Sigma-Aldrich

Ganciclovir

≥99% (HPLC), DMSO solution, viral DNA elongation inhibitor

Synonym(s):

Ganciclovir ready made solution, 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one, 9-(1,3-Dihydroxy-2-propoxymethyl)guanine, DHPG

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About This Item

Empirical Formula (Hill Notation):
C9H13N5O4
CAS Number:
82410-32-0
Molecular Weight:
255.23
MDL number:
MFCD12197280
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Ganciclovir ready made solution, ≥99% (HPLC), 10 mM in DMSO

Assay

≥99% (HPLC)

form

DMSO solution

concentration

10 mM in DMSO

storage temp.

2-8°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)

InChI key

IRSCQMHQWWYFCW-UHFFFAOYSA-N

Application

Ganciclovir ready-made solution has been used in combination with resveratrol to study its effect on melanoma cells. It has also been used as a synthetic substrate for viral thymidine kinase to study its effects on human-inducible pluripotent stem cells.

Biochem/physiol Actions

Ganciclovir is a nucleoside guanosine analog that contains an active moiety, ganciclovir triphosphate. This active moiety can inhibit viral replication by interrupting the viral DNA during elongation. Ganciclovir is a potent agent in preventing cytomegalovirus (CMV) retinitis disease in human immunodeficiency virus (HIV) patients. It exhibits therapeutic effects against CMV disease involving the lungs, liver, and gastrointestinal tract. Ganciclovir can be enzymatically phosphorylated to an active triphosphate analog by herpes simplex virus thymidine kinase (HSV-TK) or host-encoded deoxyguanosine kinase. It has the potential to treat allogeneic bone marrow, kidney, heart, liver, and lung transplantations.

Other Notes

Ganciclovir ready made solution in DMSO is provided at 10mM concentration (2.55mg/mL). It is suggested to dilute the provided ready made solution to a working concentration of 2-100μM for cell culture applications.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340

Hazard Classifications

Muta. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Certificates of Analysis (COA)

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A Tseng et al.
The Canadian journal of infectious diseases = Journal canadien des maladies infectieuses, 7(3), 183-194 (1996-05-01)
To review the pharmacology and pharmacokinetics of intravenous, oral and intraocular ganciclovir, and to discuss the role of these various formulations in the management of cytomegalovirus (CMV) retinitis in AIDS patients. A MEDLINE search (1987 through November 1995) of English-language
Following universal prophylaxis with intravenous ganciclovir and cytomegalovirus immune globulin, valganciclovir is safe and effective for prevention of CMV infection following lung transplantation.
Zamora, et al.
American Journal of Transplantation : Official Journal of the American Society of Transplantation and the American Society of Transplant Surgeons, 4, 1635-1642 (2016)
Targeting of herpes simplex virus 1 thymidine kinase gene sequences into the OCT4 locus of human induced pluripotent stem cells.
Ou, et al.
PLoS ONE, 8, e81131-e81131 (2015)
P J Halloran et al.
Cancer research, 58(17), 3855-3865 (1998-09-10)
The mechanisms by which cytotoxic agents perturb the normal cell biology and cell cycle progression of cancer cells were explored using B16F10 cells genetically modified to express the Herpes Simplex Virus-thymidine kinase gene. Culture in the presence of the nucleoside
J S Cannon et al.
Journal of virology, 73(6), 4786-4793 (1999-05-11)
Human herpesvirus 8 (HHV-8) sensitivity to the nucleoside analog ganciclovir (GCV) suggests the presence of a virally encoded kinase that catalyzes the initial phosphorylation of GCV. Analysis of the HHV-8 genome identified two candidate kinases: proteins encoded by open reading
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