TY - JOUR
T1 - Near-Infrared Fluorescent 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Probes for One- and Two-Photon Fluorescence Bioimaging
AU - Kim, Bosung
AU - Yue, Xiling
AU - Sui, Binglin
AU - Zhang, Xinfu
AU - Xiao, Yi
AU - Bondar, Mykhailo V.
AU - Sawada, Junko
AU - Komatsu, Masanobu
AU - Belfield, Kevin D.
N1 - Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/9/1
Y1 - 2015/9/1
N2 - 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 αVβ3 integrin. The nanoprobe exhibited good biocompatibility and highly selective uptake in αVβ3 integrin-overexpressing cancers.
AB - 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 αVβ3 integrin. The nanoprobe exhibited good biocompatibility and highly selective uptake in αVβ3 integrin-overexpressing cancers.
KW - 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene
KW - Click chemistry
KW - Fluorescence spectroscopy
KW - Fluorescent bioimaging
KW - Fluorescent probes
UR - http://www.scopus.com/inward/record.url?scp=84939652952&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84939652952&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201500664
DO - 10.1002/ejoc.201500664
M3 - Article
AN - SCOPUS:84939652952
SN - 1434-193X
VL - 2015
SP - 5563
EP - 5571
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 25
ER -