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Near‐Infrared Fluorescent 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene Probes for One‐ and Two‐Photon Fluorescence Bioimaging
Author(s) -
Kim Bosung,
Yue Xiling,
Sui Binglin,
Zhang Xinfu,
Xiao Yi,
Bondar Mykhailo V.,
Sawada Junko,
Komatsu Masanobu,
Belfield Kevin D.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500664
Subject(s) - fluorescence , chemistry , two photon excitation microscopy , nanoprobe , fluorophore , biocompatibility , colocalization , photochemistry , fluorescence lifetime imaging microscopy , bodipy , absorption (acoustics) , biophysics , fluorescence microscope , nanoparticle , ex vivo , in vitro , nanotechnology , materials science , biochemistry , optics , organic chemistry , microbiology and biotechnology , physics , composite material , biology
Abstract Two new two‐photon absorbing near‐infrared (NIR) emitting 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene (BODIPY) derivatives, DDC and SDC, were designed for one‐ and two‐photon fluorescence microscopy imaging. Linear and nonlinear photophysical properties, including UV/Vis absorption, fluorescence, excitation anisotropy, photostability, and two‐photon absorption cross sections, of the dyes were investigated to assess the potential of using the new probes as bioimaging agents. Cell viability and colocalization studies of DDC with Lysotracker Red, in COS 7 and HCT 116 cells demonstrated not only low toxicity but also selective targeting of lysosomes. SDC was encapsulated in silica‐based nanoparticles for in vitro and ex vivo fluorescence bioimaging. The nanoparticles were modified with an RGD peptide to target α V β 3 integrin. The nanoprobe exhibited good biocompatibility and highly selective uptake in α V β 3 integrin‐overexpressing cancers.