Enhancement of the Aggregation-Induced Emission by Hydrogen Bond for Visualizing Hypochlorous Acid in an Inflammation Model and a Hepatocellular Carcinoma Model

• Published in: Analytical chemistry (Washington) Vol. 92; no. 3; pp. 2830 - 2838
• Main Authors: Han, Xiaomin, Ma, Yufan, Chen, Yuzhi, Wang, Xuefei, Wang, Zhuo
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 04.02.2020
• Subjects: Agglomeration; Animals; Carcinoma, Hepatocellular - chemically induced; Carcinoma, Hepatocellular - diagnostic imaging; Chemistry; Disease Models, Animal; Emission; Female; Fluorescence; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; HeLa Cells; Hepatocellular carcinoma; Humans; Hydrogen Bonding; Hydrogen bonds; Hydrophobicity; Hypochlorous acid; Hypochlorous Acid - analysis; Inflammation - chemically induced; Inflammation - diagnostic imaging; Inflammatory diseases; Lipopolysaccharides; Liver cancer; Liver Neoplasms - chemically induced; Liver Neoplasms - diagnostic imaging; Mice; Mice, Inbred Strains; Models, Molecular; Molecular Structure; Optical Imaging; Organic chemistry; Probes; RAW 264.7 Cells; Reaction products; Reactive oxygen species
• DOI: 10.1021/acs.analchem.9b05347
• ISSN: 0003-2700

As an important reactive oxygen species, hypochlorous acid (HClO) is produced in various physiological processes. The abnormal rise of the HClO level is associated with a large number of inflammatory diseases. In this work, we develop a simple, aqueous-soluble aggregration-induced emission (AIE) probe for sensing HClO with significant aggregation-induced fluorescence (>1000 times). Two probes, CH3O–TPE–Py+–N+ (COTN) and OH–TPE–Py+–N+ (HOTN) (TPE, tetraphenylethylene), are synthesized for sensing HClO by the cleavage of the Py+–N+ group; the reaction products are CH3O–TPE–CHO (COT) and OH–TPE–CHO (HOT), respectively. The hydrophobicity of the probes is changed with the increased aggregation-induced emission. During the process, HOTN shows significantly better response than COTN. The slightly different chemical structures of COTN and HOTN result in a significant response to HClO. The theoretical calculation data support the theory that the hydrogen bond contributes to the excellent sensitivity for HClO. On the basis of the good response to HClO in vitro, HOTN is used to image inflammation and hepatocellular carcinoma in vivo because these diseases always produce high HClO levels.