B9647
(E)-5-(2-Bromovinyl)-2′-deoxyuridine
Synonym(s):
BVdU
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C11H13BrN2O5
CAS Number:
Molecular Weight:
333.14
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Form:
powder
Quality level:
form
powder
Quality Level
storage temp.
2-8°C
SMILES string
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
InChI key
ODZBBRURCPAEIQ-PIXDULNESA-N
Gene Information
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
Biochem/physiol Actions
(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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
新产品
This item has
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Mia Bjerke et al.
Nucleosides, nucleotides & nucleic acids, 29(1), 1-13 (2010-04-15)
Thymidine kinase 2 (TK2) is a mitochondrial deoxyribonucleoside kinase that phosphorylates several nucleoside analogs used in anti-viral and anti-cancer therapy. A fibroblast cell line with decreased TK2 activity was investigated in order to obtain insights in the effects of TK2
Alexandre Mottu et al.
Journal of hepatology, 51(5), 967-969 (2009-08-21)
Brivudin is licensed in several European countries for the treatment of herpetic infections, and is considered safe (approximately 1% of patients with transient elevation of liver enzymes) in large multicenter trials. We report a case of acute brivudin hepatitis documented
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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B9647-10MG | 04061832631080 |
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service