Analytical and Bioanalytical Chemistry

, Volume 386, Issue 3, pp 621–626

Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide

  • Yu Gabe
  • Tasuku Ueno
  • Yasuteru Urano
  • Hirotatsu Kojima
  • Tetsuo Nagano
Original Paper

DOI: 10.1007/s00216-006-0587-y

Cite this article as:
Gabe, Y., Ueno, T., Urano, Y. et al. Anal Bioanal Chem (2006) 386: 621. doi:10.1007/s00216-006-0587-y

Abstract

4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is a well-known fluorophore, with a high molar extinction coefficient and high fluorescence quantum efficiency (Φfl). Furthermore, its structure can be modified to change its excitation and emission wavelengths. However, little work has been done on the structural modification of fluorines at the B-4 position with other functional groups. We synthesized 4-methoxy-substituted BODIPY derivatives in satisfactory yields, and found that they exhibited improved solubility in aqueous solution. Moreover, their oxidation and reduction potentials were greatly decreased without any change in their absorbance and fluorescence properties. These features of 4-substituted BODIPYs may be useful for developing novel fluorescence probes based on the intramolecular photoinduced electron transfer (PeT) mechanism, because it is possible to optimize the PeT process precisely by modulating the electrochemical properties of the fluorophore. The value of this approach is exemplified by its application to the development of a highly sensitive and pH-independent fluorescence probe for nitric oxide.

Keywords

Fluorescence probe BODIPY Nitric oxide Photoinduced electron transfer 

Supplementary material

216_2006_587_MOESM1_ESM.doc (2 kb)
Supplementary data 1 (DOC 2.3 kb)
216_2006_587_MOESM2_ESM.doc (3 kb)
Supplementary data 2 (DOC 2.5 kb)
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Supplementary data 3 (DOC 1.08 kb)
216_2006_587_MOESM4_ESM.doc (2 kb)
Supplementary data 4 (DOC 1.5 kb)
216_2006_587_MOESM5_ESM.doc (1 kb)
Supplementary data 5 (DOC 1.3 kb)

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  • Yu Gabe
    • 1
    • 2
  • Tasuku Ueno
    • 1
    • 2
  • Yasuteru Urano
    • 1
    • 3
  • Hirotatsu Kojima
    • 1
    • 2
  • Tetsuo Nagano
    • 1
    • 2
  1. 1.Graduate School of Pharmaceutical SciencesThe University of TokyoBunkyo-kuJapan
  2. 2.CRESTJST AgencyKawaguchiJapan
  3. 3.PRESTOJST AgencyKawaguchiJapan

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