Allaudeen H S, Chen M S, Lee J J, De Clercq E, Prusoff W H
J Biol Chem. 1982 Jan 25;257(2):603-6.
E-5-(2-Bromovinyl)-2'-deoxyuridine (BrvdUrd) and E-5-(2-iodovinyl)-2'-deoxyuridine (IvdUrd) are among the most potent and selective inhibitors of herpes simplex virus type 1 (HSV-1) replication. To elucidate the site of inhibition, we examined whether the halovinyl analogs are incorporated into DNA using two approaches. (i) In assays with purified DNA polymerases omitting dTTP from the reaction system, addition of either BrvdUTP or IvdUTP increased the polymerization reaction, indicating that these two analog triphosphates can be alternate substrates. (ii) When HSV-1-infected Vero cells were grown in the presence of either BrvdUrd or IvdUrd, there was an increase in the density of both the viral and cellular DNA. The viral DNA had 40% of its thymidine moiety substituted by IvdUrd when the concentration of [125I]IvdUrd was 24 microM (in the absence of added thymidine). At 30 microM BrvdUrd and 1 microM [2-14C]thymidine, the viral DNA had only 11% of its thymidine moiety substituted by BrvdUrd, presumably because of the presence of added thymidine. Following digestion of [125I]IvdUrd-substituted DNA with DNase 1, venom phosphodiesterase, and alkaline phosphatase, the radioactivity co-migrated with nonradioactive IvdUrd in thin layer chromatography. Under similar conditions, no detectable incorporation of either [125I]IvdUrd or BrvdUrd into mock-infected Vero cell DNA was observed. Thus, IvdUrd and BrvdUrd are incorporated into DNA of HSV-1 infected cells but not into DNA of uninfected cells.
E-5-(2-溴乙烯基)-2'-脱氧尿苷(BrvdUrd)和E-5-(2-碘乙烯基)-2'-脱氧尿苷(IvdUrd)是单纯疱疹病毒1型(HSV-1)复制最有效且最具选择性的抑制剂。为阐明抑制位点,我们采用两种方法检测卤乙烯类似物是否掺入DNA。(i)在反应体系中省略dTTP的纯化DNA聚合酶测定中,添加BrvdUTP或IvdUTP均可增加聚合反应,表明这两种类似物三磷酸酯可作为替代底物。(ii)当HSV-1感染的Vero细胞在BrvdUrd或IvdUrd存在下生长时,病毒和细胞DNA的密度均增加。当[125I]IvdUrd浓度为24μM(无添加胸苷)时,病毒DNA中40%的胸苷部分被IvdUrd取代。在30μM BrvdUrd和1μM [2-14C]胸苷存在下,病毒DNA中仅有11%的胸苷部分被BrvdUrd取代,可能是因为添加了胸苷。用DNase 1、蛇毒磷酸二酯酶和碱性磷酸酶消化[125I]IvdUrd取代的DNA后,放射性物质在薄层色谱中与非放射性IvdUrd共迁移。在类似条件下,未观察到[125I]IvdUrd或BrvdUrd掺入 mock感染的Vero细胞DNA中。因此,IvdUrd和BrvdUrd可掺入HSV-1感染细胞的DNA中,但不掺入未感染细胞的DNA中。