B9647

(E)-5-(2-Bromovinyl)-2′-deoxyuridine

• Synonyme(s) : BVdU
• Formule empirique (notation de Hill) : C₁₁H₁₃BrN₂O₅
• CAS Number: 69304-47-8
• Poids moléculaire : 333.14
• Numéro MDL: MFCD00058585
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278280
• Nomenclature NACRES : NA.77

Propriétés

• 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)

Description

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.

Informations sur la sécurité

• 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)