Half‐Curcumin‐Based Chemiluminescence Probes and Their Applications in Detecting Quasi‐Stable Oxidized Proteins

• Published in: Angewandte Chemie International Edition Vol. 63; no. 40; pp. e202409896 - n/a
• Main Authors: Yang, Jun, Zhu, Biyue, Zhang, Jing, Liang, Steven H., Shen, Shiqian, Ran, Chongzhao
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.10.2024; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Acetylacetone; Aging; Alzheimer's disease; Amino acids; Chemiluminescence; Chemistry; Chemistry, Multidisciplinary; Curcumin; Disease control; In vitro methods and tests; in vivo imaging; In vivo methods and tests; liquid biopsy; Neurodegenerative diseases; Physical Sciences; Proteins; Quasi-stable oxidized proteins; Reactive nitrogen species; Reactive oxygen species; Science & Technology; Taurine; ELECTROGENERATED CHEMILUMINESCENCE; in vivo imaging; OXIDATIVE STRESS; Quasi-stable oxidized proteins; chemiluminescence; ALZHEIMERS-DISEASE; HYPOCHLOROUS ACID; CROSS-LINKING; TAURINE CHLORAMINE; IRIDIUM(III) COMPLEXES; FREE-RADICAL THEORY; AMYLOID-BETA; HYDROGEN-PEROXIDE; liquid biopsy; curcumin
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.202409896

Numerous methods have been reported for detecting ROS/RNS in vitro and in vivo; however, detecting methods for the secondary products of the reactive oxygen species (ROS)/reactive nitrogen species (RNS) reactions, particularly quasi‐stable oxidized products, have been much less explored. In this report, we observed that half‐curcumins could generate chemiluminescence (CL). In contrast to other chemiluminescence scaffolds, the distinguishing feature of a half‐curcumin is the formation of a carbanion intermediate of its acetylacetone moiety, opening unique avenues for applications. In this study, we designed a series of half‐curcumins CRANAD‐Xs and found that CRANAD‐164 could be used to detect quasi‐stable oxidized proteins (QSOP) in vivo and in patient serum samples. We illustrated that CRANAD‐164 could be used to monitor the responses of taurine, an amino acid with newly reported anti‐aging capacity, in an inflammatory mouse model. Remarkably, we further demonstrated that the QSOP levels were much higher in the disease serum samples, including Alzheimer's disease (AD), compared to the samples from healthy controls. Moreover, our results revealed that the sera chemiluminescence intensities were higher in aged healthy controls compared to young healthy subjects, suggesting that CRANAD‐164 can be used to monitor the increase of QSOP during aging. Half‐curcumin analogue, CRANAD‐164, was developed as a novel chemiluminescence probe. It is sensitive to quasi‐stable oxidized proteins with strong chemiluminescence emission, which could be exploited for in vivo liver imaging and in vitro blood tests.