A thiol-reactive fluorescence probe based on donor-excited photoinduced electron transfer: Key role of ortho substitution

被引:284
作者
Matsumoto, Takuya [1 ]
Urano, Yasuteru [1 ]
Shoda, Takuji [1 ]
Kojima, Hirotatsu [1 ]
Nagano, Tetsuo [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ol071352e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We designed and synthesized a novel thiol-reactive fluorescence probe based on the BODIPY fluorophore. The fluorescence of this probe is strongly quenched by donor-excited photoinduced electron transfer (d-PeT) from BODIPY to maleimide, but after reaction with thiol, the fluorescence of BODIPY is restored, affording a 350-fold intensity increase.
引用
收藏
页码:3375 / 3377
页数:3
相关论文
共 18 条
  • [1] [Anonymous], 2005, INVITROGEN MOL PROBE
  • [2] BODIPY-based hydroxyaryl derivatives as fluorescent pH probes
    Baruah, M
    Qin, WW
    Basaric, N
    De Borggraeve, WM
    Boens, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) : 4152 - 4157
  • [3] de Silva AP, 1998, TETRAHEDRON LETT, V39, P5077
  • [4] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe
    Gabe, Y
    Urano, Y
    Kikuchi, K
    Kojima, H
    Nagano, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) : 3357 - 3367
  • [5] Synthesis and characterization of dimaleimide fluorogens designed for specific labeling of proteins
    Girouard, S
    Houle, MH
    Grandbois, A
    Keillor, JW
    Michnick, SW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 559 - 566
  • [6] FLUORESCENCE AND STRUCTURES OF PROTEINS AS MEASURED BY INCORPORATION OF FLUOROPHORE .4. SYNTHESIS AND FLUORESCENCE CHARACTERISTICS OF N-PARA-(2-BENZIMIDAZOLYL)PHENYL) MALEIMIDE
    KANAOKA, Y
    MACHIDA, M
    ANDO, K
    SEKINE, T
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1970, 207 (02) : 269 - &
  • [7] 3′-(2,4-Dinitirobenzenesulfonyl)-2′,7′-dimethyl-fluorescein as a fluorescent probe for selenols
    Maeda, H
    Katayama, K
    Matsuno, H
    Uno, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) : 1810 - 1813
  • [8] Alkynylpyrenes as improved pyrene-based biomolecular probes with the advantages of high fluorescence quantum yields and long absorption/emission wavelengths
    Maeda, H
    Maeda, T
    Mizuno, K
    Fujimoto, K
    Shimizu, H
    Inouye, M
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) : 824 - 831
  • [9] Creation of superior carboxyfluorescein dyes by blocking donor-excited photoinduced electron transfer
    Mineno, Tomoko
    Ueno, Tasuku
    Urano, Yasuteru
    Kojima, Hirotatsu
    Nagano, Tetsuo
    [J]. ORGANIC LETTERS, 2006, 8 (26) : 5963 - 5966
  • [10] FLUORESCENT STAINING OF MICROFILAMENTS WITH HEAVY-MEROMYOSIN LABELED WITH N-(7-DIMETHYLAMINO-4-METHYLCOUMARINYL) MALEIMIDE
    NAMIHISA, T
    TAMURA, K
    SAIFUKU, K
    IMANARI, H
    KURODA, H
    KANAOKA, Y
    OKAMOTO, Y
    SEKINE, T
    [J]. JOURNAL OF HISTOCHEMISTRY & CYTOCHEMISTRY, 1980, 28 (04) : 335 - 338