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G2536

Sigma-Aldrich

Ganciclovir

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

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C9H13N5O4
Numer CAS:
82410-32-0
Masa cząsteczkowa:
255.23
Numer MDL:
MFCD00870588
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
24278453
NACRES:
NA.77

product name

Ganciclovir, ≥99% (HPLC), powder

Poziom jakości

300

Próba

≥99% (HPLC)

Postać

powder

kolor

white

rozpuszczalność

0.1 M HCl: 10 mg/mL

ε (współczynnik ekstynkcji)

12.0 at 256 nm at 1 mM

spektrum działania antybiotyku

viruses

Tryb działania

DNA synthesis | interferes

inicjator

Roche

temp. przechowywania

2-8°C

ciąg 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)

Klucz InChI

IRSCQMHQWWYFCW-UHFFFAOYSA-N

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Opis ogólny

Chemical structure: nucleoside

Zastosowanie

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

Działania biochem./fizjol.

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.

Cechy i korzyści

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.

Uwaga dotycząca przygotowania

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.
This page may contain text that has been machine translated.

Piktogramy

Health hazard
GHS08

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H340,H361fd

Zwroty wskazujące środki ostrożności

P201 - P202 - P280 - P308 + P313 - P405 - P501

Klasyfikacja zagrożeń

Muta. 1B - Repr. 2

Kod klasy składowania

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

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

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

Certyfikaty analizy (CoA)

Poszukaj Certyfikaty analizy (CoA), wpisując numer partii/serii produktów. Numery serii i partii można znaleźć na etykiecie produktu po słowach „seria” lub „partia”.

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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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