Preparation and characterization of phospholipid-conjugated indocyanine green as a near-infrared probe

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7481-5. doi: 10.1016/j.bmcl.2012.10.044. Epub 2012 Oct 17.

Abstract

We have rationally designed and synthesized a novel near-infrared (NIR) photoactivating probe, designated by iDOPE, in which an indocyanine green (ICG) fluorophore is covalently conjugated with a phospholipid moiety, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), to incorporate into liposome bilayers. NIR irradiation showed that iDOPE retained the optical and fluorescence properties of ICG and demonstrated photoactivator characteristics: fluorescence emission at around 820 nm in a solvent, singlet oxygen production, and concentration-dependent heat generation. Additionally, iDOPE was incorporated into liposome bilayers and maintained stable liposomally formulated iDOPE (LP-iDOPE) over 1week under physiological conditions. We also observed the tumor-specific biodistribution of LP-iDOPE of in vivo xenografts. These findings suggest that LP-iDOPE might be a promising tool for NIR optical imaging, photodynamic therapy, and photothermal therapy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacokinetics
  • Humans
  • Indocyanine Green / chemistry*
  • Infrared Rays
  • Lipid Bilayers / chemistry
  • Lipid Bilayers / pharmacokinetics*
  • Liposomes / chemistry
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Neoplasms, Experimental / drug therapy*
  • Phosphatidylethanolamines / chemistry*

Substances

  • Fluorescent Dyes
  • Lipid Bilayers
  • Liposomes
  • Phosphatidylethanolamines
  • 1,2-dielaidoylphosphatidylethanolamine
  • Indocyanine Green