Synthesis of rhodamine 6G-based compounds for the ATRP synthesis of fluorescently labeled biocompatible polymers

Biomacromolecules. 2011 Jun 13;12(6):2225-34. doi: 10.1021/bm200311s. Epub 2011 May 2.

Abstract

Facile derivatization of rhodamine 6G in the 2' position by direct reaction with secondary amines is reported. If the secondary amine contains a hydroxy group, the hydroxyl-functional intermediate can be readily esterified to give either fluorescent initiators for atom transfer radical polymerization (ATRP) or a fluorescent methacrylic comonomer. In contrast to rhodamine dyes functionalized using primary amines, which are only fluorescent at low pH, these compounds are highly fluorescent at physiological pH. These new compounds were subsequently used to prepare a range of fluorescently labeled biocompatible polymers based on the biomimetic monomer, 2-(methacryloyloxy)ethyl phosphorylcholine (MPC), for biomedical studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis*
  • Biocompatible Materials / metabolism
  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / metabolism
  • Drug Delivery Systems / methods
  • Fluorescent Dyes / chemistry*
  • Methacrylates / chemistry
  • Molecular Imaging / methods
  • Phosphorylcholine / chemistry
  • Polymerization
  • Polymers / chemical synthesis*
  • Polymers / metabolism
  • Rhodamines / chemistry*
  • Rhodamines / metabolism
  • Spectrometry, Fluorescence

Substances

  • Biocompatible Materials
  • Fluorescent Dyes
  • Methacrylates
  • Polymers
  • Rhodamines
  • rhodamine 6G
  • Phosphorylcholine