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B9647

Sigma-Aldrich

(E)-5-(2-Bromovinyl)-2′-deoxyuridine

Synonyme(s) :

BVdU

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About This Item

Formule empirique (notation de Hill):
C11H13BrN2O5
Numéro CAS:
69304-47-8
Poids moléculaire :
333.14
Numéro MDL:
MFCD00058585
Code UNSPSC :
12352200
ID de substance PubChem :
24278280
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

200

Température de stockage

2-8°C

Chaîne SMILES 

O=C(C(/C=C/Br)=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O

InChI

1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1

Clé InChI

ODZBBRURCPAEIQ-PIXDULNESA-N

Informations sur le gène

human ... HV1S(3365)

Application

(E)-5-(2-Bromovinyl)-2′-deoxyuridine (BVdU) has been used:
  • as a substrate for thymidine kinase 1 to study its effects on cancer cells by a dual-promoter integrator approach
  • as a bromovinyl nucleoside analog to study its effects on varicella-zoster virus replication in a mouse model
  • as a nucleoside analog prodrug to study its effects on transduced cells

Actions biochimiques/physiologiques

(E)-5-(2-Bromovinyl)-2′-deoxyuridine(BVdU) is a thymidine analog and a well-known inhibitor of Herpes simplex virus type 1 (HSV-1) and Varicella zoster virus (VZV) infections. It shows a minimal effect on HSV-2. BVdU shows therapeutic effects against herpetic keratitis, recurrent herpes labialis, and herpes zoster. BVdU undergoes phosphorylation at its 5’-diphosphate and further to 5’-triphosphate by the virus-encoded thymidine kinase, this results in BVdU acting as a competitive inhibitor to the viral DNA polymerase.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Vineet Kumar et al.
Bioorganic & medicinal chemistry letters, 18(20), 5640-5642 (2008-09-18)
Nucleoside-based antiviral drugs have been synthesized using imidazolium-based ionic liquids as reaction medium. The ionic liquids were proved to be better solvents for all the nucleoside in terms of solubility and reaction medium as compared to conventional molecular solvents.
(E)-5-(2-Bromovinyl)-2'-Deoxyuridine (BVDU)
Clercq E, et al.
Medical Research Engineering, 25(1), 1-20 (2005)
Jörg-Christian Heinrich et al.
Journal of cancer research and clinical oncology, 137(9), 1349-1361 (2011-08-13)
Several reports describe the importance of the chaperone HSP27 (HSPB1) in cancer progression, and the demand for drugs that modulate HSPB1-activity is increasing rapidly. We reported earlier that RP101 (Bromovinyldeoxyuridine, BVDU, Brivudine) improves the efficacy of chemotherapy in pancreatic cancer.
Leonardo D'Aiuto et al.
Schizophrenia bulletin, 41(1), 123-132 (2014-03-14)
Herpes simplex virus, type 1 (HSV-1) commonly produces lytic mucosal lesions. It invariably initiates latent infection in sensory ganglia enabling persistent, lifelong infection. Acute HSV-1 encephalitis is rare and definitive evidence of latent infection in the brain is lacking. However
Lior Nissim et al.
Molecular systems biology, 6, 444-444 (2010-12-24)
Precise discrimination between similar cellular states is essential for autonomous decision-making scenarios, such as in vivo targeting of diseased cells. Discrimination could be achieved by delivering an effector gene expressed under a highly active context-specific promoter. Yet, a single-promoter approach
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