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Isothiocyanato Boron Dipyrromethenes—The First BODIPY Analogues of Fluorescein Isothiocyanate
Author(s) -
Malatesti Nela,
Hudson Robert,
Smith Karen,
Savoie Huguette,
Rix Katie,
Welham Kevin,
Boyle Ross W.
Publication year - 2006
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/2005-01-10-ra-769
Subject(s) - bodipy , fluorescein isothiocyanate , fluorescence , chemistry , isothiocyanate , fluorescein , quantum yield , ring (chemistry) , photochemistry , molar absorptivity , boron , monoclonal antibody , antibody , biochemistry , organic chemistry , biology , physics , quantum mechanics , optics , immunology
Two boron complexes of 5‐phenyldipyrromethenes bearing isothiocyanate groups on the phenyl ring have been synthesized for the first time. The utility of these new fluorescence probes for labeling biologically relevant proteins is demonstrated on two monoclonal antibodies that bind to antigens overexpressed on cancer cells. Spectral comparison of the two structures reveals significant photophysical differences, including bathochromically shifted excitation and emission bands, increased molar absorptivity and a large increase in fluorescence quantum yield of approximately 10 times. Differences in photophysical parameters are linked to hindered rotation of the phenyl ring in one of the probes.