| Reference | 1. J Chromatogr A. 2005 Feb 25;1066(1-2):119-25. doi: 10.1016/j.chroma.2005.01.047.<br />
Fluorescence labeling method for aryl halides with 4-(4,5-diphenyl-1H-imidazol-2-yl)phenylboronic acid based on Suzuki coupling reaction.<br />
Kuroda N(1), Sugihara S, Sugihara Y, Wada M, Kishikawa N, Ohba Y, Nakashima K.<br />
Author information: (1)Graduate School of Biomedical Sciences, Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. [email protected]<br />
For the first time, fluorescence labeling methods for aryl halides with a fluorescent arylboronic acid was developed on the basis of a Suzuki coupling reaction. 4-(4,5-diphenyl-lH-imidazol-2-yl)phenylboronic acid (DPA) was used as a fluorescence labeling reagent. In order to explore its analytical performance, the reaction conditions were optimized using simple bromobenzene derivatives. The reactivity was then investigated with chloro- and iodobenzene derivatives, and also bromobenzene derivatives with different position of substituents. The order of reactivity with DPA: iodobenzene > bromobenzene more more than chlorobenzene derivatives, and p- > m- > o-substituted bromobenzenes. The detection limits of bromobenzene, 4-bromotoluene, and 4-bromoanisole ranged from 0.2 to 1.4 pmol/injection at a signal-to-noise ratio, (S/N) of 3. The applicability of the method to biological samples was also evaluated using clofibrate as the analyte. The reaction was found not only to proceed well but also to be selective for clofibrate even in the presence of plasma components. The method allowed the sensitive detection of clofibrate in human plasma with the detection limit of 170 pmol/mL (260 fmol/injection) at a S/N = 3. The proposed method is highly selective and sensitive and thus would be useful for labeling of aryl halides that do not have other functional groups that could be labeled by currently available fluorescent labeling reagents.<br />
DOI: 10.1016/j.chroma.2005.01.047 PMID: 15794562 [Indexed for MEDLINE]<br />
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2. Luminescence. 1999 Nov-Dec;14(6):361-4. doi: 10.1002/(SICI)1522-7243(199911/12)14:6<361::AID-BIO563>3.0.CO;2-J.<br />
New phenylboronic acid derivatives as enhancers of the luminol-H(2)O(2)-horseradish peroxidase chemiluminescence reaction.<br />
Kuroda N(1), Kawazoe K, Nakano H, Wada M, Nakashima K.<br />
Author information: (1)School of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.<br />
The preparation of three new types of phenylboronic acid derivatives and their evaluation as enhancers on the luminol-H(2)O(2)-horseradish peroxidase (HRP) chemiluminescence (CL) reaction are described. After optimizing the CL reaction conditions, the CL system was applied to the HRP determination. Among the three phenylboronic acid derivatives, i.e. 4-(4, 5-diphenyl-1H-imidazol-2-yl)phenylboronic acid (DPA), 4-[4(or 5)-(4-dimethylaminophenyl)-5(or 4)-phenyl-1H-imidazol-2-yl]phenylboronic acid (DAPA) and 4-[4, 5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid (DPPA), DPPA was found to be the most potent enhancer. The sensitivity obtained with DPPA was about 180 times higher than that without an enhancer. The detection limit of HRP obtained with DPPA was 0.15 ng/assay (ca. 3.5 fmol), which is comparable to that with 4-iodophenol under the conditions examined. All the phenylboronic acid derivatives examined had the effect of prolonging light emission compared to 4-iodophenol.<br />
Copyright 1999 John Wiley & Sons, Ltd.<br />
DOI: 10.1002/(SICI)1522-7243(199911/12)14:6<361::AID-BIO563>3.0.CO;2-J PMID: 10602309 [Indexed for MEDLINE]<br />
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3. Biomater Sci. 2019 Sep 1;7(9):3898-3905. doi: 10.1039/c9bm00884e. Epub 2019 Jul 18.<br />
A PEGylated alternating copolymer with oxidation-sensitive phenylboronic ester pendants for anticancer drug delivery.<br />
Zhang Y(1), He P(2), Liu X(3), Yang H(3), Zhang H(3), Xiao C(4), Chen X(5).<br />
Author information: (1)Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. [email protected] [email protected] and University of Chinese Academy of Sciences, 19A Yuquan road, Beijing 100049, P. R. China. (2)School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022, P. R. China. (3)Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. [email protected] [email protected]. (4)Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. [email protected] [email protected] and Jilin Biomedical Polymers Engineering Laboratory, Changchun, 130022, P. R. China. (5)Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. [email protected] [email protected] and University of Chinese Academy of Sciences, 19A Yuquan road, Beijing 100049, P. R. China and Jilin Biomedical Polymers Engineering Laboratory, Changchun, 130022, P. R. China.<br />
To target a response to a high oxidative stress environment of inflammatory or tumor sites, various reactive oxygen species (ROS) sensitive polymers have been developed as drug delivery systems. In this study, a novel oxidation sensitive copolymer, phenylboronic acid pinacol ester-functionalized methoxyl poly(ethylene glycol)-block-poly(phthalic anhydride-alter-glycidyl propargyl ether) (mPEG-b-P(PA-alt-GPBAe)), was designed and synthesized by ring-opening alternating copolymerization (ROAP) and click reaction. The copolymers could self-assemble into micelles in aqueous solution with an average size of 20.3 ± 9.3 nm, and are able to load hydrophobic anticancer drug (doxorubicin, DOX) with a high encapsulation efficiency of 75.2%. Interestingly, the encapsulated drug showed accelerated release in the trigger of H2O2, or at low pH values. The copolymers have low cytotoxicity indicated by the 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay towards 4T1 cells, which showed cell viabilities of more than 80% with treatment of our copolymers at concentrations up to 0.5 mg mL-1. The effective uptake of the drug-loaded micelles by 4T1 cells was investigated by confocal laser scanning microscopy (CLSM) and flow cytometry (FCM) analysis. Finally, compared with free DOX, the DOX-loaded nanoparticles exhibited a better antitumor effect and had lower systemic toxicity in 4T1 tumor-bearing mice. Therefore, this new kind of copolymer acting as a stimuli-responsive nanocarrier should represent a promising therapeutic platform for cancer therapy.<br />
DOI: 10.1039/c9bm00884e PMID: 31317137 [Indexed for MEDLINE]<br />
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4. Luminescence. 2014 Mar;29(2):118-21. doi: 10.1002/bio.2513. Epub 2013 Apr 30.<br />
Evaluation of lophine derivatives as L-012 (luminol analog)-dependent chemiluminescence enhancers for measuring horseradish peroxidase and H2O2.<br />
Ichibangase T(1), Ohba Y, Kishikawa N, Nakashima K, Kuroda N.<br />
Author information: (1)Research Institute of Pharmaceutical Sciences, Musashino University, Japan.<br />
8-Amino-5-chloro-7-phenylpyrido[3,4-d]pyridazine-1,4(2H,3H)dione (L-012) was recently synthesized as a new chemiluminescence (CL) probe; the light intensity and the sensitivity of L-012 are higher than those of other CL probes such as luminol. Previously, our group developed four lophine-based CL enhancers of the horseradish peroxidase (HRP)-catalyzed CL oxidation of luminol, namely 2-(4-hydroxyphenyl)-4,5-diphenylimidazole (HDI), 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole (HPI), 4-(4,5-diphenyl-1H-imidazol-2-yl)phenylboronic acid (DPA), and 4-[4,5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid (DPPA), and showed that DPPA was suitable for the photographic detection of HRP. In this study, we replaced luminol with L-012 and evaluated these as L-012-dependent CL enhancers. In addition, to detect HRP and/or H2O2 with higher sensitivity, each detection condition for the L-012-HRP-H2O2 enhanced CL was optimized. All the derivatives enhanced the L-012-dependent CL as well as luminol CL; HPI generated the highest enhanced luminescence. Under optimized conditions for HRP detection, the detection limit of HRP was 0.08 fmol. By contrast, the detection limit of HRP with the enhanced L-012-dependent CL using 4-iodophenol, which is a common enhancer of luminol CL, was 1.1 fmol. With regard to H2O2 detection, the detection limits for enhanced CL with HPI and 4-iodophenol were 0.29 and 1.5 pmol, respectively. Therefore, it is demonstrated that HPI is the most superior L-012-dependent CL enhancer.<br />
Copyright © 2013 John Wiley & Sons, Ltd.<br />
DOI: 10.1002/bio.2513 PMID: 23630098 [Indexed for MEDLINE]<br />
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5. Anal Bioanal Chem. 2006 Oct;386(3):719-24. doi: 10.1007/s00216-006-0755-0. Epub 2006 Sep 7.<br />
Determination of haloperidol and reduced haloperidol in human serum by liquid chromatography after fluorescence labeling based on the Suzuki coupling reaction.<br />
Kishikawa N(1), Hamachi C, Imamura Y, Ohba Y, Nakashima K, Tagawa Y, Kuroda N.<br />
Author information: (1)Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, 852-8521, Japan.<br />
A simultaneous method for the determination of haloperidol (HP) and its metabolite, reduced haloperidol (RHP), in human serum was developed by means of high-performance liquid chromatography (HPLC) with fluorescence detection. Suzuki coupling reaction with a fluorescent arylboronic acid, 4-(4,5-diphenyl-1H-imidazol-2-yl)phenylboronic acid (DPA), was employed to convert HP and RHP into highly fluorescent compounds. HP and RHP were extracted from human serum by liquid-liquid extraction with a mixture of n-hexane and isoamyl alcohol (99:1, v/v) and subsequently labeled by reaction with DPA. Separation of DPA derivatives of HP and RHP was performed on a silica column with a mixture of acetonitrile and H(2)O (90:10, v/v) containing triethylamine and acetic acid as a mobile phase. The proposed method allowed sensitive detection of HP and RHP in human serum with a detection limit (at a signal to noise ratio of 3) of 0.22 and 0.20 ng/mL, respectively. The applicability of the method for therapeutic drug monitoring (TDM) was demonstrated by analyzing human serum samples from schizophrenic patients receiving HP.<br />
DOI: 10.1007/s00216-006-0755-0 PMID: 16957915 [Indexed for MEDLINE]
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