700-nm Zwitterionic Near-Infrared Fluorophores for Dual-Channel Image-Guided Surgery

Mol Imaging Biol. 2016 Feb;18(1):52-61. doi: 10.1007/s11307-015-0870-4.

Abstract

Purpose: The purpose of this study was to develop a family of 700-nm zwitterionic pentamethine indocyanine near-infrared fluorophores that would permit dual-channel image-guided surgery.

Procedures: Three complementary synthetic schemes were used to produce novel zwitterionic chemical structures. Physicochemical, optical, biodistribution, and clearance properties were compared to Cy5.5, a conventional pentamethine indocyanine now used for biomedical imaging.

Results: ZW700-1a, ZW700-1b, and ZW700-1c were synthesized, purified, and analyzed extensively in vitro and in vivo. All molecules had extinction coefficients ≥199,000 M(-1) cm(-1), emission ≥660 nm, and stability ≥99 % after 24 h in warm serum. In mice, rats, and pigs, ≥80 % of the injected dose was completely eliminated from the body via renal clearance within 4 h. Either alone or conjugated to a tumor targeting ligand, ZW700-1a permitted dual-channel, high SBR, and simultaneous imaging with 800-nm NIR fluorophores using the FLARE® imaging system.

Conclusions: Novel 700-nm zwitterionic NIR fluorophores enable dual-NIR image-guided surgery.

Keywords: Image-guided surgery; Near-infrared fluorescence; Optical imaging; Signal-to-background ratio.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Death
  • Cell Line, Tumor
  • Female
  • Fluorescence
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / toxicity
  • Humans
  • Hydrogen-Ion Concentration
  • Intraoperative Care
  • Mice, Nude
  • Optical Imaging / methods*
  • Optical Phenomena*
  • Spectroscopy, Near-Infrared
  • Surgery, Computer-Assisted / methods*
  • Sus scrofa
  • Tissue Distribution

Substances

  • Fluorescent Dyes