Polymeric prodrug-functionalized polypropylene films for sustained release of salicylic acid

Int J Pharm. 2016 Sep 10;511(1):579-585. doi: 10.1016/j.ijpharm.2016.07.044. Epub 2016 Jul 21.

Abstract

Medical devices decorated with salicylic acid-based polymer chains (polymeric prodrug) that slowly release this anti-inflammatory and anti-biofilm drug at the implantation site were designed. A "grafting from" method was implemented to directly grow chains of a polymerizable derivative of salicylic acid (2-methacryloyloxy-benzoic acid, 2MBA) onto polypropylene (PP). PP was modified both at bulk and on the surface with poly(2MBA) by means of an oxidative pre-irradiation method ((60)Co source), in order to obtain a grafted polymer in which salicylic acid units were linked by means of labile ester bonds. The grafting percent depended on absorbed dose, reaction time, temperature and monomer concentration. The functionalized films were analyzed regarding structure (FTIR-ATR, SEM-EDX, fluorescence microscopy), temperature stability (TGA), interaction with aqueous medium (water contact angle and swelling), pH-responsive release and cytocompatibility (fibroblasts). In the obtained poly(2MBA)-grafted biomaterial, poly(2MBA) behaved as a polymeric prodrug that regulates salicylic acid release once in contact with aqueous medium, showing pH-dependent release rate.

Keywords: Grafting; Polymer-drug conjugate; Polypropylene; Salicylic acid release; pH-dependent release; γ-irradiation.

MeSH terms

  • Delayed-Action Preparations / chemistry
  • Delayed-Action Preparations / pharmacokinetics
  • Drug Liberation
  • Polymers / administration & dosage
  • Polymers / chemistry*
  • Polymers / pharmacokinetics
  • Polypropylenes / chemistry*
  • Polypropylenes / pharmacokinetics
  • Prodrugs / administration & dosage
  • Prodrugs / chemistry*
  • Prodrugs / pharmacokinetics
  • Salicylic Acid / chemistry*
  • Salicylic Acid / pharmacokinetics

Substances

  • Delayed-Action Preparations
  • Polymers
  • Polypropylenes
  • Prodrugs
  • Salicylic Acid