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
Recommended Products
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 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
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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.
Karoline Bleymehl et al.
Medical microbiology and immunology, 200(3), 193-202 (2011-03-05)
The treatment of varicella-zoster virus (VZV) reactivation is based on nucleoside analogues acyclovir (ACV) and bromevinyldeoxyuridine (BVdU) and a phosphonic acid derivative (PFA). Drug-resistant mutants of 3 wild-type (WT) VZV strains were obtained by exposure of human retinal pigment epithelial
(E)-5-(2-Bromovinyl)-2'-Deoxyuridine (BVDU)
Clercq E, et al.
Medical Research Engineering, 25(1), 1-20 (2005)
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
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.
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