B9647

(E)-5-(2-Bromovinyl)-2′-deoxyuridine

• Synonym(e): BVdU
• Empirische Formel (Hill-System): C₁₁H₁₃BrN₂O₅
• CAS-Nummer: 69304-47-8
• Molekulargewicht: 333.14
• MDL-Nummer: MFCD00058585
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24278280
• NACRES: NA.77

Eigenschaften

• Form: powder
• Qualitätsniveau: 200
• Lagertemp.: 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
• InChIKey: ODZBBRURCPAEIQ-PIXDULNESA-N
• Angaben zum Gen: human ... HV1S(3365)

Beschreibung

Anwendung

(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. Wirkung

(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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)