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Progress in Chemistry 2023, Vol. 35 Issue (2): 189-205 DOI: 10.7536/PC220731   Next Articles

• Review •

Development and Application of Dioxetane-based Chemiluminescent Probes

Anchen Fu1(), Yanjia Mao2, Hongbo Wang2, Zhijuan Cao1   

  1. 1 School of Pharmacy, Fudan University,Shanghai 201203, China
    2 China State Institute of Pharmaceutical Industry, Incubation Center for S&T Achievements,Shanghai 201203, China
  • Received: Revised: Online: Published:
  • Contact: *e-mail:zjcan@fudan.edu.cn
  • Supported by:
    Shanghai Agriculture Science and Technology Support Project(21N31900500); Shanghai Municipal Health Commission Project(202140016); project of Basic Medicine funded by Minhang Hospital, Fudan University(2021MHJC10)
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Optical analysis is non-destructive, real-time with a specific spatial resolution, which has been developed as an essential technology to study the occurrence, development, diagnosis, and treatment of diseases. It contains fluorescent (FL), bioluminescent (BL) and chemiluminescent (CL) methods. Among them, CL probes with an adamantane-dioxetane chemiluminescence (AD-CL) scaffold attracted much attention. Recently, significant improvement on these probes has been achieved with the elimination of external light source, low phototoxicity, high sensitivity, and a facile system without additional reagents, such as oxidants. Until now, the CL probes were further developed with special modifications and new synthesis routes based on the AD-CL scaffold, realizing the detection and optical imaging of various biomolecules in living systems with enhanced properties. Herein, the recent research progress on AD-CL probes has been reviewed. The review is divided into two parts. The first part will mainly introduce the molecular modification strategy of AD-CL probes and the second part will focus on their application in several cases.

Contents

1 Introduction

2 Modification of AD-CL probes

2.1 Intramolecular modification of AD-CL probes

2.2 Supramolecular modification of AD-CL probes

3 Application of AD-CL probes

3.1 Application on small molecules detection

3.2 Application on macromolecules detection

3.3 Application on pathogenic and drug-resistance bacteria detection

3.4 Other application

4 Conclusion and outlook

Key words: dioxetane, chemiluminescence, probes, molecular design, optical imaging
Fig.1 The activation pathway of the AD-CL probe
Fig.2 Molecular modification of AD-CL probes: (A) Increase the intensity of CL-introduce the electron-withdrawing group; (B) elongate the wavelength of CL-introduce near-infrared/fluorescent molecules; (C) speed up the CL reaction-introduce the phenoxy group
Fig.3 (A) Multiple AD-CL structures connected by the linking group; (B) the domino-cascaded AD-CL structure
Fig.4 Using CRET strategy (A) and materials (B) to increase the CL intensity and prolong the CL wavelength of AD-CL probes: (a) Surfactant-fluorophore molecular system; (b) β-cyclodextrin-fluorophore supramolecular system; (c) the application of nanoprecipitation technology with amphiphilic substances
Fig.5 (A) AD-CL probe for single oxygen detection and its mechanism; (B) AD-CL probe for detection of small molecules; (C) the schematic principle of dual-lock CL probe for detection
Fig.6 (A) The schematic principle of the probe for protease detection based on CRET strategy; (B) AD-CL probes for detection of macromolecules
Fig.7 Visualization of Prodrug 1 and Prodrug 2 for monitoring drug progression in vivo
Fig.8 AD-CL probes for the detection of pathogenic and drug-resistant bacteria
Fig.9 (A,B)CL-FL duplex probes
Table 1 Applications of AD-CL probes
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