Lophine derivatives as versatile analytical tools

Abstract

Lophine (2,4,5-triphenylimidazole) derivatives as versatile analytical tools in biomedical sciences are described. Chemiluminescence (CL) and fluorescence (FL) properties of the lophine derivatives are first demonstrated including the CL reaction mechanism, effects of substituents on CL yields, FL spectral behaviors, etc. Next, analytical applications to the determination of metal ions such as cobalt (II) and chromium (VI) are discussed. Finally, the application studies of lophine derivatives as CL and FL reagents for the determination of organic substances in biological materials are presented. Among the derivatives, 2-(4-hydrazinocarbonylphenyl)-4,5-diphenylimidazole (HCPI) and 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoyl chloride (DIB-Cl) are studied, with their excellent properties as labeling reagents for fatty acids and amines and/or phenols, respectively, in high-performance liquid chromatography. The utility of boronic acid derivatives as CL enhancers is also discussed in this review.

Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction

“…Stock solutions of alprenolol, IS and DIBI were prepared in DMAc and stored at 4 ºC. Pd(OAc) 2 and TEA were dissolved in DMAc and water, respectively, just before use.…”

“…Then, the concentration of TEA was studied over a range of 20-60 mM and 50 mM of TEA was selected because it gave maximum peak heights. The effect of Pd(OAc) 2 concentration was investigated over a range of 5-40 µM, and the maximum peak height of alprenolol was observed at 20 µM; 20 µM of Pd(OAc) 2 was selected. The reaction temperature was selected at 100 ºC because the peak heights increased with increasing the temperature.…”

“…Many fluorescent labeling reagents have been developed for a various functional groups such as amine, phenol, thiol, aldehyde and carbonyl groups [1][2][3][4]. Although the fluorescent labeling reagents are frequently applied to the drug analysis in biological fluids, there are drawbacks as follows: (1) fluorescent labeling technique cannot be applied to compounds which do not possess derivatizable functional groups, (2) fluorescent labeling reagent reacts with co-existing biological substances and the resultant products can interfere with the detection of target analyte.…”

Interaction of Fluorescent 2-(1-Methoxynaphthalen-4-Yl)-1-(4-Methoxyphenyl)-4, 5-Diphenyl-1H-Imidazole with Pristine Zno, Cu-Doped Zno and Ag-Doped Zno Nanoparticles

“…Not due to any cobalt oxide phase formation or any metallic Co isolation the observed nature of ferromagnetism was intrinsic. Heterocyclic imidazole moieties have also attracted significant attention because of their unique optical properties [4] and for their use in preparing functionalized materials [5]. Nanoparticles can be used as drug carriers because they have enormous surface area and due to their submicron size they can efficiently be taken up by the cells [6].…”

Peroxyoxalate chemiluminescence detection for the highly sensitive determination of fluorescence-labeled chlorpheniramine with Suzuki coupling reaction

“…Its superior selectivity in analysis is derived from minimal interferences because most of biological components are not reacted with phenylboronic acid, in addition to improved sensitivity brought about by the elimination of a halogen atom, which sometimes leads to unexpected quenching of fluorescence (FL) [6]. Lophine derivatives have been identified to possess excellent FL properties [7], so we have designed a boronic acid derivative of lophine, 4-(4,5-diphenyl-1H-imidazole-2-yl) phenyl boronic acid (DPA) [8]. In one of our previous reports, we demonstrated the analytical applicability of Suzuki coupling reaction for the labeling of aryl halides [6].…”