Nanomicelle with long-term circulation and enhanced stability of camptothecin based on mPEGylated alpha,beta-poly (L-aspartic acid)-camptothecin conjugate

Colloids Surf B Biointerfaces. 2010 Nov 1;81(1):297-303. doi: 10.1016/j.colsurfb.2010.07.019. Epub 2010 Jul 15.

Abstract

To enhance the stability and long-term circulation of camptothecin (CPT), mPEGylated alpha,beta-poly (L-aspartic acid)-CPT conjugates were synthesized, and used to fabricate nanomicelle. Firstly, alpha,beta-poly (L-aspartic acid) derivative (PAA-der) containing alkyne groups was synthesized via the ring-opening of PSI with propargyl amine. And then, azide-functionalized CPT derivatives (CPT-N(3)) and azide-terminated poly (ethylene glycol) methyl ether (mPEG-N(3)) were conjugated with PAA-der by click cycloaddition to give mPEG-graft-PAA-CPT conjugates. The formation of mPEG-graft-PAA-CPT nanomicelles was confirmed by fluorescence spectrophotoscopy and particle size measurements. It was found that all the nanomicelles showed spherical shapes with size about 178 nm. MPEG-graft-PAA-CPT nanomicelles showed good storage stability, even incubation at 37 degrees C for 60 days, and improved the stability of CPT lactone form in aqueous media. A steady release rate of CPT was kept for 72h, suggested the great potential of mPEG-graft-PAA-CPT nanomicelles as polymer prodrug of CPT.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacokinetics
  • Aspartic Acid / chemistry*
  • Camptothecin / chemistry*
  • Camptothecin / pharmacokinetics
  • Drug Compounding
  • Drug Stability
  • Micelles*
  • Microscopy, Electron, Transmission
  • Models, Chemical
  • Molecular Structure
  • Nanostructures
  • Particle Size
  • Polyethylene Glycols / chemistry*
  • Polymers / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Time Factors

Substances

  • Antineoplastic Agents, Phytogenic
  • Micelles
  • Polymers
  • Aspartic Acid
  • Polyethylene Glycols
  • monomethoxypolyethylene glycol
  • Camptothecin