ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Novel hemicyanine dyes with a large Stokes shift and strong fluorescence: mitochondrial-targeted imaging

Ci-Qin Li, Zhao Hui Sun, Kun-Jie Bian, Qing-Guang Zhang, and Li-Wei Zou

Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai, China

E-mail: zqg362322@163.com

Received: 28 August 2023  Accepted: 1 November 2023

Abstract:

Hemicyanine dyes have a donor-π-acceptor (D-π-A) system that offers potential applications in mitochondrial-targeted analysis. However, there are currently few hemicyanide dyes with good fluorescent properties such as NIR and large Stokes shifts. In this study, a series of hemicyanine dyes were synthesized and evaluated for their fluorescence properties and cytotoxicity as well as mitochondria-targeted imaging. The fluorescent probe HC-7 exhibited near-infrared fluorescence emission (685 nm) with a large Stokes shift (115 nm). It is highly resistant to temperature, pH, and light, has high stability, and shows excellent mitochondrial targeting capabilities. These findings highlight the potential of hemicyanine dyes for improved fluorescence-based mitochondrial imaging and analysis, which facilitate the practical application of hemicyanine dyes in biomedical systems.

Keywords: Hemicyanine dyes; Stokes shift; Near-infrared fluorescence; Mitochondrial imaging

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03195-3

Chemical Papers 78 (3) 1687–1697 (2024)