Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer

Bioconjug Chem. 2019 Jan 16;30(1):169-183. doi: 10.1021/acs.bioconjchem.8b00820. Epub 2018 Dec 14.

Abstract

Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Animals
  • Antibodies, Monoclonal / chemistry
  • Boron Compounds / chemistry*
  • Cell Line, Tumor
  • Fluorescent Dyes / chemistry*
  • Heterografts
  • Humans
  • Mice
  • Neoplasms / diagnostic imaging*
  • Optical Imaging / methods*
  • Polyethylene Glycols / chemistry*
  • Porphyrins / chemistry*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Antibodies, Monoclonal
  • Boron Compounds
  • Fluorescent Dyes
  • Porphyrins
  • bacteriochlorin
  • Polyethylene Glycols