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(E)-5-(2-bromovinyl)uridine Requires Phosphorylation by the Herpes Simplex Virus (Type 1)-induced Thymidine Kinase to Express Its Antiviral Activity

(E)-5-(2-bromovinyl)uridine Requires Phosphorylation by the Herpes Simplex Virus (Type 1)-induced Thymidine Kinase to Express Its Antiviral Activity

R Bernaerts, C Desgranges, E De Clercq

Biochem Pharmacol. 1989 Jun 15;38(12):1955-61.

PMID: 2545207

Abstract:

(E)-5-(2-Bromovinyl)uridine (BVUrd), the riboside counterpart of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdUrd), effected a dose-dependent inhibition of viral progeny formation and viral DNA synthesis in herpes simplex virus type 1 (HSV-1, strain KOS)-infected human (E6SM) diploid fibroblast cells. BVUrd was directly phosphorylated in HSV-1-infected cells, presumably by the virus-encoded thymidine kinase (TK), since (i) BVUrd was not phosphorylated by extracts of cells infected with a HSV-1 strain deficient in TK expression and (ii) the phosphorylation was inhibited by a polyclonal anti-HSV-1 antibody. Within the HSV-1-infected cells, BVUrd was incorporated into the viral DNA as BVdUMP (BVdUrd 5'-monophosphate). This incorporation may account for the antiviral action of BVUrd, and implies that, following its initial phosphorylation by the viral TK, BVUrd is converted to its 2'-deoxy counterpart, most likely at the 5'-diphosphate level (BVUDP----BVdUDP).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP69304478	(E)-5-(2-Bromovinyl)-2′-deoxyuridine		69304-47-8	Price

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