Two- and three-photon excitable quaternized imidazo[1,2-a]pyridines as mitochondrial imaging and potent cancer therapy agents

Eiji Hase; Hiroki Takanari; Keita Hoshi; Masaki Okamoto; Atsushi Tabata; Hideaki Nagamune; Takeo Minamikawa; Takeshi Yasui; Yasushi Yoshida; Keiji Minagawa; Yasuhiko Kawamura; Yasushi Imada; Fumitoshi Yagishita

doi:10.1039/D0OB01585G

Two- and three-photon excitable quaternized imidazo[1,2-a]pyridines as mitochondrial imaging and potent cancer therapy agents†

Eiji Hase,^ab Hiroki Takanari,^bc Keita Hoshi,^d Masaki Okamoto,^d Atsushi Tabata,^e Hideaki Nagamune,^e Takeo Minamikawa,^ab Takeshi Yasui,^ab Yasushi Yoshida,^f Keiji Minagawa,^d Yasuhiko Kawamura,^d Yasushi Imada

^d and Fumitoshi Yagishita

*^abd

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* Corresponding authors

^a Department of Post-LED Photonics Research, Institute of Post-LED Photonics, Tokushima University, 2-1 Minamijosanjima, Tokushima 770-8506, Japan
E-mail: yagishitaf@tokushima-u.ac.jp

^b Research Cluster on “Multi-scale Vibrational Microscopy for Comprehensive Diagnosis and Treatment of Cancer”, Tokushima University, Tokushima 770-8506, Japan

^c Department of Interdisciplinary Researches for Medicine and Photonics, Institute of Post-LED Photonics, Tokushima University, Tokushima 770-8503, Japan

^d Department of Applied Chemistry, Tokushima University, Tokushima 770-8506, Japan

^e Department of Bioscience and Bioindustry, Tokushima University, Tokushima 770-8513, Japan

^f Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan

Abstract

We have synthesized a series of quaternized imidazo[1,2-a]pyridines in three steps from commercially available reagents. These compounds exhibit blue fluorescence emission at around 425 nm with good quantum yields. In addition, one specific compound was found to work as not only a two- and three-photon excitable mitochondria imaging agent, but also a therapeutic agent upon continuous irradiation conditions.

This article is part of the themed collection: Chemical Biology in OBC

Organic & Biomolecular Chemistry

Two- and three-photon excitable quaternized imidazo[1,2-a]pyridines as mitochondrial imaging and potent cancer therapy agents†

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Two- and three-photon excitable quaternized imidazo[1,2-a]pyridines as mitochondrial imaging and potent cancer therapy agents

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