Near-Infrared Fluorescent 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Probes for One- and Two-Photon Fluorescence Bioimaging

Bosung Kim, Xiling Yue, Binglin Sui, Xinfu Zhang, Yi Xiao, Mykhailo V. Bondar, Junko Sawada, Masanobu Komatsu, Kevin Belfield

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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 αVβ3 integrin. The nanoprobe exhibited good biocompatibility and highly selective uptake in αVβ3 integrin-overexpressing cancers.

Original languageEnglish (US)
Pages (from-to)5563-5571
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number25
DOIs
StatePublished - Sep 1 2015

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene
  • Click chemistry
  • Fluorescence spectroscopy
  • Fluorescent bioimaging
  • Fluorescent probes

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