Determination of Anthraquinone-Tagged Amines Using High-Performance Liquid Chromatography with Online UV Irradiation and Luminol Chemiluminescence Detection

• Published in: Molecules (Basel, Switzerland) Switzerland), 2023-02, Vol.28 (5), p.2146
• Main Authors: Kishikawa, Naoya, El-Maghrabey, Mahmoud, Kawamoto, Ayaka, Ohyama, Kaname, Kuroda, Naotaka
• Format: Article
• Language: English
• Subjects: amine; Amines; Analysis; Anthraquinone; Anthraquinones; Biogenic amines; Biogenic Amines - analysis; Carbonyl compounds; Carbonyls; Chemiluminescence; Chloride; Chlorides; Chromatography; Chromatography, High Pressure Liquid - methods; derivatization; High performance liquid chromatography; Irradiation; Liquid chromatography; Luminescence; Luminol; Luminol - chemistry; Methods; Phenethylamine; Phenethylamines; Phosgene; Quinone; Quinones; Quinones - analysis; Reactive oxygen species; Reactive Oxygen Species - chemistry; Reagents; Tryptamine; Tryptamines; Ultraviolet radiation; UV irradiation
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28052146

Quinones are frequently used as derivatization reagents in HPLC analysis to improve detection sensitivity. In the present study, a simple, sensitive, and selective chemiluminescence (CL) derivatization strategy for biogenic amines, prior to their HPLC-CL analysis, was developed. The novel CL derivatization strategy was established based on using anthraquinone-2-carbonyl chloride as derivatizing agent for amines and then using the unique property of the quinones' moiety to generate reactive oxygen species (ROS) in response to UV irradiation. Typical amines such as tryptamine and phenethylamine were derivatized with anthraquinone-2-carbonyl chloride and then injected into an HPLC system equipped with an online photoreactor. The anthraquinone-tagged amines are separated and then UV-irradiated when they pass through a photoreactor to generate ROS from the quinone moiety of the derivative. Tryptamine and phenethylamine can be determined by measuring the chemiluminescence intensity produced by the reaction of the generated ROS with luminol. The chemiluminescence disappears when the photoreactor is turned off, suggesting that ROS are no longer generated from the quinone moiety in the absence of UV irradiation. This result indicates that the generation of ROS could be controlled by turning the photoreactor on and off. Under the optimized conditions, the limits of detection for tryptamine and phenethylamine were 124 and 84 nM, respectively. The developed method is successfully applied to determine the concentrations of tryptamine and phenethylamine in wine samples.