Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds

Novel boron-containing drugs have recently been suggested as a new class of pharmaceuticals. However, the majority of current boron-detection techniques require expensive facilities and/or tedious pretreatment methods. Thus, to develop a novel and convenient detection method for boron-based pharmaceuticals, imine-type boron-chelating-ligands were previously synthesized for use in a fluorescent sensor for boronic acid containing compounds. However, the fluorescence quantum yield of the imine-type sensor was particularly low, and the sensor was easily decomposed in aqueous media. Thus, in this paper, we report the development of a novel, convenient, and stable fluorescent boron-sensor based on O- and N-chelation (i.e., 2-(pyridine-2yl)phenol), and a corresponding method for the quantitative and qualitative detection of boronic acid-containing compounds using this commercially available sensor is presented.

[1]  M. H. Lee,et al.  Four-coordinate boron compounds derived from 2-(2-pyridyl)phenol ligand as novel hole-blocking materials for phosphorescent OLEDs , 2009 .

[2]  P. Elliott,et al.  Role of the proteasome and NF-kappaB in streptococcal cell wall-induced polyarthritis. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[3]  J. Engbersen,et al.  Carbohydrate-interactive pDNA and siRNA gene vectors based on boronic acid functionalized poly(amido amine)s. , 2013, Journal of controlled release : official journal of the Controlled Release Society.

[4]  Rohan Yadav,et al.  A rationally designed peptidomimetic biosensor for sialic acid on cell surfaces. , 2015, Chemical communications.

[5]  J. Adams.  Development of the proteasome inhibitor PS-341. , 2002, The oncologist.

[6]  S. Miyatake,et al.  Boron neutron capture therapy for clear cell sarcoma (CCS): biodistribution study of p-borono-L-phenylalanine in CCS-bearing animal models. , 2011, Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine.

[7]  B. Wang,et al.  Boronic acid compounds as potential pharmaceutical agents , 2003, Medicinal research reviews.

[8]  V. Dembitsky,et al.  Boron containing compounds as protease inhibitors. , 2012, Chemical reviews.

[9]  M. Matsui,et al.  Synthesis and fluorescence properties of novel pyrazine-boron complexes bearing a β-iminoketone ligand. , 2011, Organic letters.

[10]  Y. Yamaguchi,et al.  Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine , 2008 .

[11]  Yi Xia,et al.  Therapeutic potential of boron-containing compounds. , 2009, Future medicinal chemistry.

[12]  J. Finch,et al.  Spotlight on tavaborole for the treatment of onychomycosis , 2015, Drug design, development and therapy.

[13]  R. Barth,et al.  The Chemistry of Neutron Capture Therapy , 1998 .

[14]  K. Ono,et al.  Detection of boronic acid derivatives in cells using a fluorescent sensor. , 2015, Organic & biomolecular chemistry.

[15]  Hiroshi Fukuda,et al.  TREATMENT OF MALIGNANT MELANOMA BY SINGLE THERMAL NEUTRON CAPTURE THERAPY WITH MELANOMA-SEEKING 10B-COMPOUND , 1989, The Lancet.

[16]  Yanqin Li,et al.  A mixed pyridine–phenol boron complex as an organic electroluminescent material , 2000 .

[17]  Y. Ohta,et al.  Visualization of Boronic Acid Containing Pharmaceuticals in Live Tumor Cells Using a Fluorescent Boronic Acid Sensor , 2016 .

[18]  Y. Chujo,et al.  Synthesis of Methyl-Substituted Main-Chain-Type Organoboron Quinolate Polymers and Their Emission Color Tuning , 2008 .

[19]  Kamalika Mukherjee,et al.  Rapid formation of a stable boron-nitrogen heterocycle in dilute, neutral aqueous solution for bioorthogonal coupling reactions. , 2015, Chemical communications.

[20]  T. Aida,et al.  Boronic Acid-Appended Molecular Glues for ATP-Responsive Activity Modulation of Enzymes. , 2016, Journal of the American Chemical Society.

[21]  M. Kalesse,et al.  Synthesis and pharmacology of proteasome inhibitors. , 2013, Angewandte Chemie.