B9647
(E)-5-(2-Bromovinyl)-2′-deoxyuridine
Synonym(s):
BVdU
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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:
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
SMILES string
O=C(C(/C=C/Br)=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O
InChI key
ODZBBRURCPAEIQ-PIXDULNESA-N
form
powder
storage temp.
2-8°C
Quality Level
Gene Information
human ... HV1S(3365)
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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
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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
Determination of (E)-5-(2-bromovinyl)-2?-deoxyuridine in plasma and urine by capillary electrophoresis
Jan Olgemoller, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 726, 261-268 (1999)
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
José M Baena-Cañada et al.
Nature reviews. Clinical oncology, 7(1), 55-58 (2009-12-24)
A 66-year-old woman with metastatic mammary carcinoma, who was being treated with capecitabine, contracted a herpes zoster infection that was treated with the antiviral drug brivudin. A drug-drug interaction between brivudin and capecitabine caused medullar aplasia, serious toxic effects to
Christophe Caillat et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(44), 16900-16905 (2008-10-31)
Unlike most DNA viruses, poxviruses replicate in the cytoplasm of host cells. They encode enzymes needed for genome replication and transcription, including their own thymidine and thymidylate kinases. Some herpes viruses encode only 1 enzyme catalyzing both reactions, a peculiarity
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