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Anti-Cancer Agents in Medicinal Chemistry

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ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

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Research Article

Design, Synthesis and Binding Affinity Evaluation of Cytochrome P450 1B1 Targeted Chelators

Author(s): Dongmei Chen, Qiqi Fan, Ting Xu, Jinyun Dong, Jiahua Cui, Zengtao Wang, Jie Wang, Qingqing Meng* and Shaoshun Li*

Volume 22, Issue 2, 2022

Published on: 05 April, 2021

Page: [261 - 269] Pages: 9

DOI: 10.2174/1871520621666210405091645

Price: $65

Abstract

Background: Cytochrome P450 1B1 (CYP1B1) is specifically expressed in a variety of tumors which makes it a promising imaging target of tumor.

Objective: We aimed to design and synthesize CYP1B1 targeted chelators for the potential application in positron emission tomography (PET) imaging of tumor.

Methods: 1,4,7-triazacyclononane-1,4-diiacetic acid (NODA) was connected to the CYP1B1 selective inhibitor we developed before through polyethylene glycol (PEG) linkers with different lengths. The inhibitory activities of chelators 6a-c against CYP1 family were evaluated by 7-ethoxyresorufin o-deethylation (EROD) assay. The manual docking between the chelators and the CYP1B1 was conducted subsequently. To determine the binding affinities of 6a-c to CYP1B1 in cells, we further performed a competition study at the cellular level.

Results: Among three chelators, 6a with the shortest linker showed the best inhibitory activity against CYP1B1. In the following molecular simulation study, protein-inhibitor complex of 6a showed the nearest F-heme distance which is consistent with the results of enzymatic assay. Finally, the cell based competitive assay proved the binding affinity of 6a-c to CYP1B1 enzyme.

Conclusion: We designed and synthesized a series of chelators which can bind to CYP1B1 enzyme in cancer cells.To our knowledge, this work is the first attempt to construct CYP1B1 targeted chelators for radiolabeling and we hope it will prompt the application of CYP1B1 imaging in tumor detection.

Keywords: Chelator, cytochrome P450 1B1, imaging agents, α-naphthoflavone derivative, radiopharmaceutical, PET.

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