Rational Optimization of Mechanism-Based Inhibitors through Determination of the Microscopic Rate Constants of Inactivation

Rational Optimization of Mechanism-Based Inhibitors through Determination of the Microscopic Rate Constants of Inactivation
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DOI:
10.1021/jacs.7b00962
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发表时间:
2017-05-31
影响因子:
15
通讯作者:
Aldrich, Courtney C.
Aldrich, Courtney C.
中科院分区:
化学1区
文献类型:
--
作者:
Eiden, Carter G.;Maize, Kimberly M.;Aldrich, Courtney C.

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基于机制的抑制剂(MBIs)因其特异性强、抑制作用持续时间长而被广泛应用于化学、生物学和医学领域。MBIs的优化是复杂的,因为多步失活机制导致的时间依赖性抑制。全局动力学参数k(inact)和K-I已被用于表征MBIs,但它们提供的信息远少于通常假设的信息,如这些参数的推导和模拟所示。我们说明了一种替代的和更严格的方法MBI表征通过确定个别微观速率常数。动力学分析揭示了失活的限速步骤:二氢-(1,4)-吡啶酮1的PLP依赖性酶BioA。这一知识随后被应用于合理设计第二代抑制剂,支架具有接近最佳的最大失活速率(0.48 min(-1))。
Mechanism-based inhibitors, (MBIs) are widely employed in chemistry, biology, and :medicine because of their exquisite specificity and sustained-duration of :inhibition. Optimization of MBIs is complicated because of time-dependent inhibition resulting, from multistep inactivation mechanisms. The global kinetic parameters k(inact), and K-I have been used to characterize MBIs, 'but they provide far less information than is commonly assumed, as shown by derivation and simulation,of these parameters. We illustrate an alternative and more rigorous approach for MBI characterization through determination Of the individual microscopic rate constants. Kinetic analysis revealed the, rate-limiting step of inactivation :of the PLP-dependent enzyme BioA by dihydro-(1,4)-pyridone 1. This knowledge was subsequently applied to rationally design a second-generation inhibitor,scaffold with a nearly optimal maximum inactivation rate (0.48 min(-1)).