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G2536

Sigma-Aldrich

Ganciclovir

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

Sinônimo(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

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About This Item

Fórmula empírica (Notação de Hill):
C9H13N5O4
Número CAS:
82410-32-0
Peso molecular:
255.23
Número MDL:
MFCD00870588
Código UNSPSC:
12352200
ID de substância PubChem:
24278453
NACRES:
NA.77

product name

Ganciclovir, ≥99% (HPLC), powder

Nível de qualidade

300

Ensaio

≥99% (HPLC)

forma

powder

cor

white

solubilidade

0.1 M HCl: 10 mg/mL

ε (coeficiente de extinção)

12.0 at 256 nm at 1 mM

espectro de atividade do antibiótico

viruses

Modo de ação

DNA synthesis | interferes

originador

Roche

temperatura de armazenamento

2-8°C

cadeia de caracteres 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)

chave InChI

IRSCQMHQWWYFCW-UHFFFAOYSA-N

Procurando produtos similares? Visita Guia de comparação de produtos

Descrição geral

Chemical structure: nucleoside

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Nota de preparo

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.

Pictogramas

Health hazard
GHS08

Palavra indicadora

Danger

Frases de perigo

H340,H361fd

Classificações de perigo

Muta. 1B - Repr. 2

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Aciclovir European Pharmacopoeia (EP) Reference Standard

A0220000

Aciclovir

(S)-3,5-Dihydroxyphenylglycine hydrate &#8805;98% (HPLC), powder

Sigma-Aldrich

D3689

(S)-3,5-Dihydroxyphenylglycine hydrate

Penciclovir

Sigma-Aldrich

P0035

Penciclovir

Valganciclovir Hydrochloride Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1626

Valganciclovir Hydrochloride

Zhanguo Gao et al.
Biomolecules, 11(10) (2021-10-24)
Duchenne muscular dystrophy (DMD), caused by the loss of dystrophin, remains incurable. Reduction in muscle regeneration with DMD is associated with the accumulation of fibroadipogenic progenitors (FAPs) differentiating into myofibroblasts and leading to a buildup of the collagenous tissue aggravating
Sunwen Chou
Reviews in medical virology, 18(4), 233-246 (2008-04-03)
Mutations in the human CMV UL97 kinase gene are a major mechanism of viral resistance to two anti-CMV drugs, ganciclovir (GCV) and maribavir (MBV). GCV, the most widely used and established therapy for CMV, is a substrate for the UL97
C N Sprung et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(12), 6781-6786 (1999-06-09)
The addition of new telomeres to the ends of broken chromosomes, termed chromosome healing, has been extensively studied in unicellular organisms; however, its role in the mammalian cell response to double-strand breaks is unknown. A system for analysis of chromosome
J K McGavin et al.
Drugs, 61(8), 1153-1183 (2001-07-24)
Ganciclovir is a nucleoside guanosine analogue which incorporates ganciclovir triphosphate (the active moiety) into DNA during elongation, thereby inhibiting viral replication. Comparative studies of pre-emptive and prophylactic ganciclovir therapies in bone marrow transplant (BMT) recipients have shown similar rates of
L Z Rubsam et al.
Cancer research, 59(3), 669-675 (1999-02-11)
The ability of herpes simplex virus type 1 thymidine kinase (HSV-TK)-expressing cells incubated with ganciclovir (GCV) to induce cytotoxicity in neighboring HSV-TK-negative (bystander) cells has been well documented. Although it has been suggested that this bystander cell killing occurs through
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