Wenwen Sun , Yuanfeng Qi , Le Wang , Yunpeng Tan , Xiao Zhang , Junfeng Wang , Yingbo Li
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引用次数: 0
Abstract
Boronic acid analogs are crucial in modern organic chemistry and drug development, serving as versatile reagents and intermediates with significant therapeutic applications. This area has gained increased interest with the recent development of the drug 4-boron-L-phenylalanine (L-BPA) for boron neutron capture therapy (BNCT). Fluorescent probe technology offers an essential pathway for imaging drugs in vitro and in vivo, providing high sensitivity with great spatial and temporal resolution for both disease diagnosis and drug development. In this paper, we designed and investigated three fluorescent probes—W-1-NN, W-2-NS and W-3-NO—for sensing 4-boron-L-phenylalanine (L-BPA). Among these, only W-1-NN reacts with L-BPA, resulting in a spectral blue-shift change. This probe can “ratiometrically” and specifically detect L-BPA among various metals, with a limit of detection (LOD) of 7.11 μM. Mechanistic studies revealed that the addition of L-BPA disrupts the inherent ESIPT mechanism of W-1-NN in protonic solutions, resulting in the appearance of a new peak at 372 nm. Additionally, theoretical computational studies have also demonstrated that the complexation of W-1-NN with L-BPA triggers a change in the resonance structure, resulting in a larger energy gap and causing a blue shift in the spectrum. Furthermore, W-1-NN has been successfully applied to the detection of L-BPA in human urine. Therefore, the template probe with N/O as the target and the introduction of N atoms can specifically detect L-BPA. This template probe lays the foundation for the detection of L-BPA, and provides great possibilities for the future realization of the template probe to be connected with different fluorophores to make it emit at long wavelengths to reach the target of the near-infrared.
期刊介绍:
Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (SAA) is an interdisciplinary journal which spans from basic to applied aspects of optical spectroscopy in chemistry, medicine, biology, and materials science.
The journal publishes original scientific papers that feature high-quality spectroscopic data and analysis. From the broad range of optical spectroscopies, the emphasis is on electronic, vibrational or rotational spectra of molecules, rather than on spectroscopy based on magnetic moments.
Criteria for publication in SAA are novelty, uniqueness, and outstanding quality. Routine applications of spectroscopic techniques and computational methods are not appropriate.
Topics of particular interest of Spectrochimica Acta Part A include, but are not limited to:
Spectroscopy and dynamics of bioanalytical, biomedical, environmental, and atmospheric sciences,
Novel experimental techniques or instrumentation for molecular spectroscopy,
Novel theoretical and computational methods,
Novel applications in photochemistry and photobiology,
Novel interpretational approaches as well as advances in data analysis based on electronic or vibrational spectroscopy.