Bright, Color-Tunable Fluorescent Dyes in the Vis/NIR Region: Establishment of New "Tailor-Made" Multicolor Fluorophores Based on Borondipyrromethene

被引:226
作者
Umezawa, Keitaro [1 ]
Matsui, Akihiro [1 ]
Nakamura, Yuki [1 ]
Citterio, Daniel [1 ]
Suzuki, Koji [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
boron; dyes/pigments; fluorescent probes; imaging agents; RESTRICTED AZA-BODIPY; IN-VIVO; QUANTUM YIELDS; PHOTODYNAMIC THERAPY; HIGHLY FLUORESCENT; PROBES; TUMORS; BORON; COMPLEXES; ANALOGS;
D O I
10.1002/chem.200801906
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of high-performance fluorophores named Keio Fluors (KFL), which are based on borondipyrromethene (BODIPY), are reported. The KFL dyes cover a wide spectral range from the yellow (547 nm) to the near-infrared (NIR, 738 nm) region, and their emission wavelength could be easily and subtly controlled based on simple molecular modifications only, without losing their optical properties. This "tailor-made" synthetic strategy for tuning the emission wavelength enabled the creation of fourteen KFL dyes with well-controlled emission colors (yellow, orange, red, far-red, and NIR). Moreover, these KFL dyes also retain their excellent optical properties, such as spectral bands sharper than quantum dots, high extinction coefficients (140000-316000M (1)cm(-1)), and high quantum yields (0.56-0.98), without any critical solvent polarity dependent decrease of their brightness. These advantageous characteristics make the KFL dyes potentially Useful as new candidates of fluorescent standard dyes to substitute or to complement existing long-wavelength fluorescent dyes, such as cyanines, oxazines, rhodamines, or other BODIPY dyes.
引用
收藏
页码:1096 / 1106
页数:11
相关论文
共 43 条
  • [31] Shah M., 1990, HETEROATOM CHEM, V1, P389, DOI 10.1002/hc.520010507
  • [32] Boron-diindomethene (BDI) dyes and their tetrahydrobicyclo precursors -: en route to a new class of highly emissive fluorophores for the red spectral range
    Shen, Z
    Röhr, H
    Rurack, K
    Uno, H
    Spieles, M
    Schulz, B
    Reck, G
    Ono, N
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (19) : 4853 - 4871
  • [33] Tsien R. Y., 2006, HDB BIOL CONFOCAL MI
  • [34] The chemistry of fluorescent bodipy dyes: Versatility unsurpassed
    Ulrich, Gilles
    Ziessel, Raymond
    Harriman, Anthony
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) : 1184 - 1201
  • [35] Bright, color-tunable fluorescent dyes in the visible-near-infrared region
    Umezawa, Keitaro
    Nakamura, Yuki
    Makino, Hiroshi
    Citterio, Daniel
    Suzuki, Koji
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) : 1550 - +
  • [36] Corrected emission spectra and quantum yields for a series of fluorescent compounds in the visible spectral region
    Velapoldi, RA
    Tonnesen, HH
    [J]. JOURNAL OF FLUORESCENCE, 2004, 14 (04) : 465 - 472
  • [37] Synthesis and optical properties of a new class of pyrromethene-BF2 complexes fused with rigid bicyclo rings and benzo derivatives
    Wada, M
    Ito, S
    Uno, H
    Murashima, T
    Ono, N
    Urano, T
    Urano, Y
    [J]. TETRAHEDRON LETTERS, 2001, 42 (38) : 6711 - 6713
  • [38] In vivo imaging of tumors with protease-activated near-infrared fluorescent probes
    Weissleder, R
    Tung, CH
    Mahmood, U
    Bogdanov, A
    [J]. NATURE BIOTECHNOLOGY, 1999, 17 (04) : 375 - 378
  • [39] A clearer vision for in vivo imaging
    Weissleder, R
    [J]. NATURE BIOTECHNOLOGY, 2001, 19 (04) : 316 - 317
  • [40] Preparation of BODIPY probes for multicolor fluorescence imaging studies of membrane dynamics
    Yamada, K
    Toyota, T
    Takakura, K
    Ishimaru, M
    Sugawara, T
    [J]. NEW JOURNAL OF CHEMISTRY, 2001, 25 (05) : 667 - 669