(E)-5-(2-Bromovinyl)-2′-deoxyuridine

Name: (E)-5-(2-Bromovinyl)-2′-deoxyuridine
Brand: SIGMA

别名:

BVdU

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所有图片(1)

About This Item

经验公式（希尔记法）:

C₁₁H₁₃BrN₂O₅

CAS Number:

69304-47-8

分子量:

333.14

MDL编号:

MFCD00058585

UNSPSC代码:

12352200

PubChem化学物质编号:

24278280

NACRES:

NA.77

表单

powder

质量水平

200

储存温度

2-8°C

SMILES字符串

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

基因信息

human ... HV1S(3365)

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应用

(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

生化/生理作用

(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.