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
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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)
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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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Patrizia Vernole et al.
Mutation research, 664(1-2), 39-47 (2009-05-12)
Mismatch repair (MMR) has been shown to control homologous recombination (HR) by aborting strand exchange between divergent sequences. We previously demonstrated that MMR-deficient tumour cells are more resistant to chromosomal damage induced by bleomycin (BLM) during the G(2) phase, likely
Phu Hoang Anh Nguyen et al.
Japanese journal of infectious diseases, 73(6), 447-451 (2020-07-03)
Morphological changes in the structure of the herpes simplex virus 1 (HSV-1) viral thymidine kinase (vTK) polypeptide usually lead to conferring acyclovir (ACV) resistance. HSV-1 I4-2, in which a UAG stop codon is present at the 8th position between the
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)
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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