Impact of C4'-O-Alkyl Linker on in Vivo Pharmacokinetics of Near-Infrared Cyanine/Monoclonal Antibody Conjugates

Mol Pharm. 2015 Sep 8;12(9):3303-11. doi: 10.1021/acs.molpharmaceut.5b00472. Epub 2015 Aug 18.

Abstract

Near-infrared (NIR) fluorophores have several advantages over visible-light fluorophores, including superior tissue penetration and lower autofluorescence. We recently accessed a new class of readily synthesized NIR cyanines containing a novel C4'-O-alkyl linker, which provides both high chemical stability and excellent optical properties. In this study, we provide the first in vivo analysis of this new class of compounds, represented by the tetrasulfonate FNIR-774 (Frederick NIR 774). Monoclonal antibody (mAb) conjugates of FNIR-774 were compared to conjugates of the commercially available dye (IRDye800CW (IR800)), one of the most widely used NIR fluorophores for clinical translation. Both dyes were conjugated to panitumumab (pan) or cetuximab (cet) with ratios of 1:2 or 1:5. Conjugates of both dyes demonstrated similar quenching capacity, stability, and brightness in target cells in vitro. In contrast, in vivo imaging in mice showed different pharmacokinetics between pan-FNIR-774 (1:5) and pan-IR800 (1:5), or cet-FNIR-774 (1:5) and cet-IR800 (1:5). Particularly at the higher labeling density, mAb-FNIR-774 conjugates showed superior specific accumulation in tumors compared with mAb-IR800 conjugates. Thus, FNIR-774 conjugates showed superior in vivo pharmacokinetics compared with IR800 conjugates, independent of the mAb. These results suggest that FNIR-774 is a promising fluorescent probe for NIR optical imaging.

Keywords: cyanine; in vivo imaging; monoclonal antibody (mAb) conjugates; near-infrared (NIR) fluorophores.

Publication types

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

MeSH terms

  • Alkylation
  • Animals
  • Antibodies, Monoclonal / chemistry
  • Antibodies, Monoclonal / pharmacokinetics*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics*
  • BALB 3T3 Cells
  • Breast Neoplasms / drug therapy
  • Breast Neoplasms / metabolism
  • Breast Neoplasms / pathology*
  • Carbocyanines / chemistry*
  • Cells, Cultured
  • Cetuximab / chemistry
  • Cetuximab / metabolism*
  • Female
  • Flow Cytometry
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacokinetics*
  • Mice
  • Mice, Nude
  • Microscopy, Fluorescence
  • Panitumumab
  • Spectroscopy, Near-Infrared
  • Tissue Distribution

Substances

  • Antibodies, Monoclonal
  • Antineoplastic Agents
  • Carbocyanines
  • Fluorescent Dyes
  • Panitumumab
  • Cetuximab