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

Enhanced fluorescent probe with high selectivity and sensitivity to hypochlorous acid

Fang Fang, Meixia Tan, Yihua Zhang, Lifen Chen, Houzheng Chen, Mei Lin, and Fang Ke

Fujian Dermatology and Venereology Research Institute, The First Affiliated Hospital, Fujian Medical University, Fuzhou, China

E-mail: kefang@mail.fjmu.edu.cn

Received: 26 July 2022  Accepted: 27 November 2022

Abstract:

Hypochlorous acid has important molecular functions in biological systems. The development of hypochlorous acid fluorescent probes has always been one of the research hotspots. In this study, a 7-hydroxy-4-methyl-2-oxo-2H-tryptamine-8-carboxaldehyde (HMOCC)-enhanced fluorescent probe was rationally synthesized as a simple and effective detection of hypochlorite (ClO⁻) in osteosarcoma cells (143B cells). The probe (HMOCC) exhibits high specificity, high fluorescence enhancement, low toxicity, and good selectivity for different reactive oxygen species (ROS) and low detection limit 0.00791 μM. The introduction of ClO⁻ makes the emission of HMOCC red-shift from 450 to 472 nm. Based on ESI–MS analysis and frontier molecular orbital calculations, a possible mechanism for fluorescence detection of ClO⁻ is proposed. Cytofluorescence imaging studies demonstrate that the probe has been successfully applied to image cancer cells and endogenous HOCl aggregation in living cells.

Keywords: Hypochlorous acid; Turn on fluorescent probe; Cancer cells

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02604-3

Chemical Papers 77 (4) 2309–2315 (2023)