Synthesis of BODIPY FL-tethered ridaifen-B, RID-B-BODIPY, and its localization in cancer cells

Takatsugu Murata; Kyoka Komukai; Yuta Semba; Eri Murata; Fumi Sato; Tomohiro Takano; Kaho Tsuchiya; Chihiro Matsuda; Anju Sakai; Amane Yoneoka; Shunsuke Takahashi; Yukitoshi Nagahara; Isamu Shiina

doi:10.3389/fchem.2024.1451468

Synthesis of BODIPY FL-tethered ridaifen-B, RID-B-BODIPY, and its localization in cancer cells

Front Chem. 2024 Aug 23:12:1451468. doi: 10.3389/fchem.2024.1451468. eCollection 2024.

Affiliations

¹ Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
² Division of Life Science and Engineering, College of Science and Engineering, Tokyo Denki University, Saitama, Japan.

Abstract

We synthesized ridaifen-B boron dipyrromethene (RID-B-BODIPY) using 2-methyl-6-nitro benzoic anhydride (MNBA)-mediated dehydration condensation reaction between amino alkyl-tethered RID and BODIPY FL. Comparative experiments between dicyclohexylcarbodiimide (DCC) and MNBA for their coupling reactions demonstrated that MNBA is an effective condensation reagent for amines and BODIPY FL. A cell staining study with RID-B-BODIPY showed intracellular localization of BODIPY FL fluorescence, attributed to the RID-B structure, indicating the successful development of a tool for analyzing intracellular molecular behavior efficiently.

Keywords: BODIPY; BODIPY FL; MNBA; dehydration condensation; ridaifen.

Grants and funding

The author(s) declare that financial support was received for the research, authorship, and/or publication of this article. This work was partially supported by the Research Institute for Science and Technology (RIST) at the Tokyo University of Science.