Site-Specific Labeling of Cyanine and Porphyrin Dye-Stabilized Nanoemulsions with Affibodies for Cellular Targeting

J Am Chem Soc. 2018 Oct 24;140(42):13550-13553. doi: 10.1021/jacs.8b07866. Epub 2018 Oct 15.

Abstract

Recently, it has been shown that amphiphilic dyes such as Indocyanine Green (ICG) and Protoporphyrin IX (PpIX) can solubilize hydrophobic colloids and/or drugs by driving the formation of stable nanoemulsions. These nanoemulsions are unique in that they can be composed entirely of functional and clinically used materials; however, they lack bio-orthogonal chemical handles for the facile attachment of targeting ligands. The ability to target nanoparticles is desirable because it can lead to improved specificity and reduced side effects. Here, we describe variants of ICG and PpIX with azide handles that can be readily incorporated into dye-stabilized nanoemulsions and facilitate the attachment of targeting ligands via click-chemistry in a simple, scalable, and reproducible reaction. As a model system, an anti-Her2 affibody was site-specifically attached to both ICG and PpIX-stabilized nanoemulsions with encapsulated superparamagnetic iron oxide nanoparticles.

Publication types

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

MeSH terms

  • Cell Line
  • Click Chemistry
  • Coloring Agents / chemistry*
  • Drug Delivery Systems
  • Emulsions / chemistry*
  • Humans
  • Immunoconjugates / chemistry*
  • Indocyanine Green / chemistry*
  • Magnetite Nanoparticles / chemistry*
  • Magnetite Nanoparticles / ultrastructure
  • Models, Molecular
  • Protoporphyrins / chemistry*

Substances

  • Coloring Agents
  • Emulsions
  • Immunoconjugates
  • Magnetite Nanoparticles
  • Protoporphyrins
  • protoporphyrin IX
  • Indocyanine Green