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Merck
CN

B9647

(E)-5-(2-Bromovinyl)-2′-deoxyuridine

别名:

BVdU

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关于此项目

经验公式(希尔记法):
C11H13BrN2O5
化学文摘社编号:
分子量:
333.14
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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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

SMILES string

O=C(C(/C=C/Br)=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O

InChI key

ODZBBRURCPAEIQ-PIXDULNESA-N

form

powder

storage temp.

2-8°C

Quality Level

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Lior Nissim et al.
Molecular systems biology, 6, 444-444 (2010-12-24)
Precise discrimination between similar cellular states is essential for autonomous decision-making scenarios, such as in vivo targeting of diseased cells. Discrimination could be achieved by delivering an effector gene expressed under a highly active context-specific promoter. Yet, a single-promoter approach
Tomoyuki Shiota et al.
Antiviral research, 91(2), 142-149 (2011-06-15)
Antiviral-resistant herpesvirus infection has become a great concern for immunocompromised patients. Herpes simplex virus type 1 (HSV-1) infections are treated with viral thymidine kinase (vTK)-associated drugs such as acyclovir (ACV), and most ACV-resistance (ACV(r)) is due to mutations in the
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
(E)-5-(2-Bromovinyl)-2'-Deoxyuridine (BVDU)
Clercq E, et al.
Medical Research Engineering, 25(1), 1-20 (2005)
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.

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