Functional Imaging of CYP3A4 at Multiple Dimensions Using an AI-Driven High Performance Fluorogenic Substrate.

Journal: Small (Weinheim an der Bergstrasse, Germany)
PMID:

Abstract

Cytochrome P450 3A4 (CYP3A4) is a key mediator in xenobiotic metabolism and drug-drug interactions (DDI), developing orally active fluorogenic substrates for sensing and imaging of a target enzyme in biological systems remains challenging. Here, an artificial intelligence (AI)-driven strategy is used to construct a highly specific and orally active fluorogenic substrate for imaging CYP3A4 in complex biological systems. After the fusion of an AI-selected drug-like fragment with a CYP3A4-preferred fluorophore, three candidates are designed and synthesized. Among all evaluated candidates, NFa exhibits excellent isoform-specificity, ultra-high sensitivity, outstanding spatial resolution, favorable safety profiles, and acceptable oral bioavailability. Specifically, NFa excels at functional in situ imaging of CYP3A4 in living systems with exceptional endoplasmic reticulum (ER)-colocalization performance and high imaging resolution, while this agent can also replace hCYP3A4 drug-substrates for high-throughput screening of CYP3A4 inhibitors and for assessing DDI potential in vivo. With the help of NFa, a novel CYP3A4 inhibitor (D13) was discovered, and its anti-CYP3A4 effects are assessed in live cells, ex vivo and in vivo. Collectively, an AI-powered strategy is adapted for developing highly-specific and drug-like fluorogenic substrates, resulting in the first orally available tool (NFa) for sensing and imaging CYP3A4 activities, which facilitates CYP3A4-associated fundamental investigations and the drug discovery process.

Authors

  • Feng Zhang
    Institute of Food Safety, Chinese Academy of Inspection and Quarantine, Beijing 100176, China; Key Laboratory of Food Quality and Safety for State Market Regulation, Beijing 100176, China. Electronic address: fengzhang@126.com.
  • Lilin Song
    Liaoning Provincial Key Laboratory of Carbohydrates, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
  • Ruixuan Wang
    School of Computer Science and Engineering, Sun Yat-sen University, Guangzhou, P. R. China. wangruix5@mail.sysu.edu.cn.
  • Bei Zhao
    State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Shanghai Frontiers Science Center of TCM Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China.
  • Jian Huang
    Center for Informational Biology, University of Electronic Science and Technology of China, No. 2006, Xiyuan Ave, West Hi-Tech Zone, Chengdu 611731, P. R. China.
  • Luling Wu
    Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.
  • Yufan Fan
    State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Shanghai Frontiers Science Center of TCM Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China.
  • Hong Lin
    Wenzhou Medical University, Wenzhou, China.
  • Zhengtao Jiang
    State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Shanghai Frontiers Science Center of TCM Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China.
  • Xiaodi Yang
    Department of Microbiology and Parasitology, Anhui Key Laboratory of Infection and Immunity, Bengbu Medical College, Bengbu 233000, Anhui, China.
  • Hairong Zeng
    Shanghai University of Traditional Chinese Medicine, 201203 Shanghai City, China.
  • Xin Yang
    Department of Oral Maxillofacial-Head Neck Oncology, Ninth People's Hospital, College of Stomatology, Shanghai Jiao Tong University School of Medicine, National Clinical Research Center for Oral Diseases, Shanghai Key Laboratory of Stomatology & Shanghai Research Institute of Stomatology, Shanghai, China.
  • Tony D James
    Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.
  • Guangbo Ge
    Shanghai University of Traditional Chinese Medicine, 201203 Shanghai City, China.