Synthesis of Structurally Defined Cationic Polythiophenes for DNA Binding and Gene Delivery

ACS Appl Mater Interfaces. 2018 Feb 7;10(5):4519-4529. doi: 10.1021/acsami.7b17948. Epub 2018 Jan 24.

Abstract

Water-soluble conjugated polymers (WCPs) have prospective applications in the field of bioimaging, disease diagnosis, and therapy. However, the use of WCPs with controllability and regioregularity for bioapplications have scarcely been reported. In this work, we synthesized polythiophenes containing ester side chains (P3ET) via Kumada catalyst-transfer polycondensation (KCTP) and confirmed a quasi-"living" chain-growth mechanism. In addition, we obtained cationic regioregular polythiophenes (cPTs) by aminolysis of P3ET with varied chain lengths, and studied DNA binding capability and gene delivery performance. Benefiting from photocontrolled generation of intracellular reactive oxygen species (ROS), the cationic polythiophenes successfully delivered DNA into tumor cells without additional polymer species.

Keywords: Kumada catalyst-transfer polycondensation; gene delivery; photochemical internalization; regioregular polythiophenes; water-soluble conjugated polymers.

MeSH terms

  • Cations
  • DNA
  • Polymers / chemistry*
  • Prospective Studies
  • Thiophenes / chemistry*

Substances

  • Cations
  • Polymers
  • Thiophenes
  • polythiophene
  • DNA