Chemistry Biology Interface Graduate Training Program and Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Baltimore, Maryland 21218, United States.
Chem Res Toxicol. 2020 Nov 16;33(11):2903-2913. doi: 10.1021/acs.chemrestox.0c00413. Epub 2020 Nov 5.
The reversible generation and capture of certain electrophilic quinone methide intermediates support dynamic reactions with DNA that allow for migration and transfer of alkylation and cross-linking. This reversibility also expands the possible consequences that can be envisioned when confronted by DNA repair processes and biological machines. To begin testing the response to such an encounter, quinone methide-based modification of DNA has now been challenged with a helicase (T7 bacteriophage gene protein four, T7gp4) that promotes 5' to 3' translocation and unwinding. This model protein was selected based on its widespread application, well characterized mechanism and detailed structural information. Little over one-half of the cross-linking generated by a bisfunctional quinone methide remained stable to T7gp4 and did not suppress its activity. The helicase likely avoids the topological block generated by this fraction of cross-linking by its ability to shift from single- to double-stranded translocation. The remaining fraction of cross-linking was destroyed during T7gp4 catalysis. Thus, this helicase is chemically competent to promote release of the quinone methide from DNA. The ability of T7gp4 to act as a Brownian ratchet for unwinding DNA may block recapture of the QM intermediate by DNA during its transient release from a donor strand. Most surprisingly, T7gp4 releases the quinone methide from both the translocating strand that passes through its central channel and the excluded strand that was typically unaffected by other lesions. The ability of T7gp4 to reverse the cross-link formed by the quinone methide does not extend to that formed irreversibly by the nitrogen mustard mechlorethamine.
某些亲电醌甲基化物中间体的可逆生成和捕获支持与 DNA 的动态反应,允许烷基化和交联的迁移和转移。这种可逆性还扩展了在面对 DNA 修复过程和生物机器时可以想象的可能后果。为了开始测试对这种相遇的反应,现在已经用解旋酶(T7 噬菌体基因蛋白四,T7gp4)挑战了基于醌甲基化物的 DNA 修饰,该酶促进 5'到 3'易位和解旋。选择这种模型蛋白是基于其广泛的应用、特征良好的机制和详细的结构信息。只有一半以上的双功能醌甲基化物交联物对 T7gp4 稳定且不抑制其活性。该解旋酶可能通过从单链到双链易位的能力来避免该交联物部分产生的拓扑阻塞。在 T7gp4 催化过程中,剩余的交联物被破坏。因此,这种解旋酶在化学上能够促进醌甲基化物从 DNA 中释放。T7gp4 作为解旋 DNA 的布朗棘轮的能力可能会阻止 QM 中间体在从供体链短暂释放期间被 DNA 重新捕获。最令人惊讶的是,T7gp4 从穿过其中心通道的易位链和通常不受其他损伤影响的排除链释放醌甲基化物。T7gp4 逆转醌甲基化物形成的交联的能力不能扩展到氮芥氮芥不可逆形成的交联。