Crawford McKenna C, Tripu Deepika R, Barritt Samuel A, Jing Yihang, Gallimore Diamond, Kales Stephen C, Bhanu Natarajan V, Xiong Ying, Fang Yuhong, Butler Kamaria A T, LeClair Christopher A, Coussens Nathan P, Simeonov Anton, Garcia Benjamin A, Dibble Christian C, Meier Jordan L
Chemical Biology Laboratory, National Cancer Institute, Frederick, MD, USA.
Department of Pathology, Cancer Research Institute, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, MA, USA.
bioRxiv. 2023 May 16:2023.05.15.540887. doi: 10.1101/2023.05.15.540887.
The human acetyltransferase paralogs EP300 and CREBBP are master regulators of lysine acetylation whose activity has been implicated in various cancers. In the half-decade since the first drug-like inhibitors of these proteins were reported, three unique molecular scaffolds have taken precedent: an indane spiro-oxazolidinedione (A-485), a spiro-hydantoin (iP300w), and an aminopyridine (CPI-1612). Despite increasing use of these molecules to study lysine acetylation, the dearth of data regarding their relative biochemical and biological potencies makes their application as chemical probes a challenge. To address this gap, here we present a comparative study of drug-like EP300/CREBBP acetyltransferase inhibitors. First, we determine the biochemical and biological potencies of A-485, iP300w, and CPI-1612, highlighting the increased potency of the latter two compounds at physiological acetyl-CoA concentrations. Cellular evaluation shows that inhibition of histone acetylation and cell growth closely aligns with the biochemical potencies of these molecules, consistent with an on-target mechanism. Finally, we demonstrate the utility of comparative pharmacology by using it to investigate the hypothesis that increased CoA synthesis caused by knockout of PANK4 can competitively antagonize binding of EP300/CREBBP inhibitors and demonstrate proof-of-concept photorelease of a potent inhibitor molecule. Overall, our study demonstrates how knowledge of relative inhibitor potency can guide the study of EP300/CREBBP-dependent mechanisms and suggests new approaches to target delivery, thus broadening the therapeutic window of these preclinical epigenetic drug candidates.
人类乙酰转移酶旁系同源物EP300和CREBBP是赖氨酸乙酰化的主要调节因子,其活性与多种癌症有关。自首次报道这些蛋白质的类药物抑制剂以来的五年里,三种独特的分子支架占据了主导地位:茚满螺恶唑烷二酮(A-485)、螺乙内酰脲(iP300w)和氨基吡啶(CPI-1612)。尽管越来越多地使用这些分子来研究赖氨酸乙酰化,但关于它们相对生化和生物学效力的数据匮乏,这使得它们作为化学探针的应用面临挑战。为了填补这一空白,我们在此展示了一项关于类药物EP300/CREBBP乙酰转移酶抑制剂的比较研究。首先,我们确定了A-485、iP300w和CPI-1612的生化和生物学效力,突出了后两种化合物在生理乙酰辅酶A浓度下效力的增加。细胞评估表明,对组蛋白乙酰化和细胞生长的抑制与这些分子的生化效力密切相关,这与靶向机制一致。最后,我们通过比较药理学来研究PANK4基因敲除导致的辅酶A合成增加可竞争性拮抗EP300/CREBBP抑制剂结合这一假说,并展示了一种强效抑制剂分子的光释放概念验证,从而证明了比较药理学的实用性。总体而言,我们的研究展示了相对抑制剂效力的知识如何指导对EP300/CREBBP依赖性机制的研究,并提出了新的靶向递送方法,从而拓宽了这些临床前表观遗传药物候选物的治疗窗口。