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HIGHLY SENSITIVE METHOD FOR THE DETERMINATION OF ARYLHALIDES BY USING A FLUORESCENT ARYLBORONIC ACID AS A LABELING REAGENT

Research Project

Project/Area Number 13672256
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Physical pharmacy
Research InstitutionNAGASAKI UNIVERSITY

Principal Investigator

KURODA Naotaka  GRADUATE SCHOOL OF BIOMEDICAL SCIENCES, COURSE OF PHSRMSCEUTICAL SCIENCES, DEPARTMENT OF ENVIRONMENTAL AND PHARMACEUTICAL SCIENCES, PROFESSOR, 大学院・医歯薬学総合研究科, 教授 (50234612)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsFLUORESCENT LABELING REAGENT / HPLC / ARYLBORONIC ACID / ARYL HALIDES / FLUORESCENCE DETECTION / CLOFIBRATE
Research Abstract

Derivatization of aryl halides with a fluorescent arylboronic acid, 4-(4,5-diphenyl-1H-imidazol-2-yl) phenylboronic acid (DPA), based on Suzuki coupling reaction was investigated. Several bromobenzenes were chosen as analytes and their derivatization conditions with DPA were optimized. This reaction proceeded well in the presence of palladium (II) acetate, 2-(dicyclohexylphosphino) biphenyl and potassium fluoride by the use of dioxin as a solvent. Resultant fluorescent derivatives were separated on a reversed-phase HPLC and detected at 410 nm wife excitation at 320 nm. Calibration curves were linear up to 100 pool/injection with detection limits of sub and lower pmol levels. Labeling efficiencies were investigated using various aryl iodides and chlorides in addition to aryl bromides. Effects of subsistents position of aryl bromides on the reactivity with DPA were also examined using bromotoluene and bromoanisole.
To evaluate the scope and limitation of analytical performance of the derivatization method, applicability to biological samples was examined with clofibrate in human plasma. Clofibtare spiked to plasma sample (50 μl) was extracted with liquid-liquid extraction using ethyl acetate, and then applied to the labeling reaction, followed by HPLC separation. For the efficient label of clofibrate, a mixture of water and N,N-dimethylformamide, and potassium hydroxide were used in place of dioxane and potassium fluoride, respectively, for the labeling of bromobenzenes. The calibration curve of clofibrate spiked into human plasma were linear (r=0.998) over the range of 1-400 mol/ml and the detection limit was 170 pmol/ml (280 fool/injection) at a signal to noise ratio of 3.
The method for the determination of clofibrate was highly sensitive and the proposed method should be useful for the analysis of other pharmaceuticals involving aryl halide moiety.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] S.Sugihara, et al.: "Derivatization of aryl halides with a newly developed fluorescent arylboronic acid"Analytical Sciences. 17 Supplement. i1261-i1262 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N.Kuroda, et al.: "Application of enhanced luminol chemiluminescence reaction using 4-[4,5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid to photographic detection of horseradish peroxidase on a membrane"Luminescence. 16(2). 167-172 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] O.Al-Dirbashi, et al.: "Drugs of abuse in a non-conventional sample ; detection of methamphetamine and its main metabolite, amphetamine in abusers' clothes by HPLC with UV and fluorescence detection"Biomedical Chromatography. 15. 457-463 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Sun, et al.: "Determination of bisphenol A in rat brain by microdialysis and column switching high-performance liquid chromatography with fluorescence detection"Biomedical Chromatography. 16. 319-326 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N.Kuroda, et al.: "Measurement of bisphenol A levels in human blood serum and ascitic fluid by HPLC using a fluorescent labeling reagent"J.Pharm.Biomed.Anal.. 30. 1743-1749 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Wada, et al.: "Determination of organic peroxides by liquid chromatography with on-line post-column ultraviolet irradiation and peroxyoxalate chemiluminescence detection"J.Chromatography A. 987. 189-195 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Naotaka Kuroda, et al.: "Chemiluminescence Detection in Liquid Chromatography in "Chemiluminescence in Analytical Chemistry" ed.By W.R.G.Baeyens, et al."Marcel Dekker, Inc.. 34 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S. Sugihara, et al.: "Derivatization of aryl halides with a newly developed fluorescent arylboronic acid"Analytical Sciences. 17 Supplement. i1261-i1262 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N. Kuroda, et al.: "Application of enhanced luminol chemiluminescence reaction using 4-[4,5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid to photographic detection of horseradish peroxidase on a membrane"Luminescence. 16-2. 167-172 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] O. Al-Dirbashi, et al.: "Drugs of abuse in a non-conventional sample ; detection of methamphetamine and its main metabolite, amphetamine in abusers' clothes by HPLC with UV and fluorescence detection"Biomedical Chromatography. 15. 457-463 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y. Sun, et al.: "Determination of bisphenol A in rat brain by microdialysis and column switching high-performance liquid chromatography with fluorescence detection"Biomedical Chromatography. 16. 319-326 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N. Kuroda: "Measurement of bisphenol A levels in human blood serum and ascitic fluid by HPLC using a fluorescent labeling reagent"J. Pharm. Biomed. Anal.. 30. 1743-1749 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Wada: "Determination of organic peroxides by liquid chromatography with on-line post-column ultraviolet irradiation and peroxyoxalate chemiluminescence detection"J. Chromatography A. 987. 189-195 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Mitsuhiro Wada, et al.: "A simple HPLC-fluorescence detection of nitric oxide in cultivated plant cells by in situ derivatization with 2,3-diaminonaphthalene"Analytical Sciences. 18. 631-634 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Yen Sun, et al.: "Determination of bisphenol A in rat brain by microdialysis and column switching high-performance liquid chromatography with fluorescence detection"Biomedical Chromatography. 16. 319-326 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 和田光弘: "カタラーゼ活性の過シュウ酸エステル化学発光検出に基づく食品の細菌汚染評価に関する基礎的検討"分析化学. 51. 123-126 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Naotaka Kuroda, et al.: "Chemiluminescence Detection in Liquid Chromatography in "Chemiluminescence in Analytical Chemistry" ed. By W.R.G. Baeyens, et al."Marcel Dekker, Inc.. 34 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Naotaka Kuroda, et al.: "Application of an enhanced luminol chemiluminescence reaction using 4-[4, 5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid to photographic...."Luminescence. 16. 167-172 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yen Sun, et al.: "Simultaneous determination of phenolic xenoestrogens by solid-phase extraction and high-performance liquid chromatography with fluorescence.."Analytical Sciences. 17. 697-702 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Naotaka Kuroda, et al.: "Separation pf sympathomimetic amines of abuse and related compounds by micellar electrokinetic chromatography"Chemical and Pharmaceutical Bulletin. 49. 905-908 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Osama Y.Al-Dirbashi, et al.: "Drugs of abuse in a non-conventional sample ; detection of methamphetamine and its main metabolite, amphetamine in abusers' clothes by HPLC......."Biomedical Chromatography. 15. 457-463 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Naotaka Kuroda, et al.: "Chemiluminescence Detection in Liquid Chromatography in "Chemiluminescence in Analytical Chemistry" ed. By W.R.G. Baeyens, et al."Marcel Dekker, Inc.. 34 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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