Investigation into the influence of an acrylic acid acceptor in organic D-π-A sensitizers against phototoxicity

Shinichiro Fuse, Wataru Moriya, Shinichi Sato, Hiroyuki Nakamura

Research output: Contribution to journalArticle

Abstract

Photodynamic therapy (PDT) is a non-invasive, selective, and cost-effective cancer therapy. We previously reported that thiophene-based organic D-π-A sensitizers consist of an electron-donating (D) moiety, a π-conjugated bridge (π) moiety, and an electron-accepting (A) moiety, and are readily accessible and stable templates for photosensitizers that could be used in PDT. In addition, acrylic acid acceptor-containing photosensitizers exert a high level of phototoxicity. This study was an investigation into 1) the possibility of increasing phototoxicity by introducing another carboxyl group or by replacing a carboxyl group with a pyridinium group, and 2) the importance of an alkene in the acrylic acid acceptor for phototoxicity. A review of the design, synthesis, and evaluation of sensitizers revealed that neither dicarboxylic acid nor pyridinium photosensitizers enhance phototoxicity. An evaluation of a photosensitizer without an alkene in the acrylic acid moiety revealed that the alkene was not indispensable in the pursuit of phototoxicity. The obtained results provided new insight into the design of ideal D-π-A photosensitizers for PDT.

Original languageEnglish
Article number115558
JournalBioorganic and Medicinal Chemistry
Volume28
Issue number13
DOIs
Publication statusPublished - 2020 Jul 1
Externally publishedYes

Keywords

  • Endocytosis
  • Organic dye
  • Photodynamic therapy
  • Sensitizer
  • Singlet oxygen

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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