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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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Osvaldo Correia et al.
The Journal of dermatological treatment, 19(4), 255-256 (2008-07-09)
Herpes zoster results from the reactivation of latent varicella-zoster virus (VZV) from the dorsal root ganglion of sensory nerves. It is rarely described in the pediatric population. We report the case of an 8-year-old immunocompetent boy with a painful lumbosacral
Tomoyuki Shiota et al.
Antiviral research, 91(2), 142-149 (2011-06-15)
Antiviral-resistant herpesvirus infection has become a great concern for immunocompromised patients. Herpes simplex virus type 1 (HSV-1) infections are treated with viral thymidine kinase (vTK)-associated drugs such as acyclovir (ACV), and most ACV-resistance (ACV(r)) is due to mutations in the
Liya Wang et al.
Nucleosides, nucleotides & nucleic acids, 27(6), 858-862 (2008-07-05)
Mitochondrial thymidine kinase (TK2) is responsible for phosphorylation of thymidine and deoxycytidine and plays a crucial role in mitochondrial DNA precursor synthesis. TK2 is expressed in all tissues at low levels complicating accurate determinations, especially in tissues with high cytosolic
Nils E Mikkelsen et al.
The FEBS journal, 275(9), 2151-2160 (2008-04-04)
The Drosophila melanogaster multisubstrate deoxyribonucleoside kinase (dNK; EC 2.7.1.145) has a high turnover rate and a wide substrate range that makes it a very good candidate for gene therapy. This concept is based on introducing a suicide gene into malignant
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.
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