Elucidating the mode of action for thiophene-based organic D-π-A sensitizers for use in photodynamic therapy

Shinichiro Fuse, Miori Takizawa, Shinichi Sato, Shigetoshi Okazaki, Hiroyuki Nakamura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Photodynamic therapy (PDT) is a non-invasive, selective, and cost-effective cancer therapy. The development of readily accessible templates that allow rapid structural modification for further improvement of PDT remains important. We previously reported thiophene-based organic D-π-A sensitizers consisted of an electron-donating (D) moiety, a π-conjugated bridge (π) moiety, and an electron-accepting (A) moiety as valuable templates for a photosensitizer that can be used in PDT. Our preliminary structure-activity relationship study revealed that the structure of the A moiety significantly influences its phototoxicity. In this study, we evaluated the photoabsorptive, cellular uptake, and photo-oxidizing abilities of D-π-A sensitizers that contained different A moieties. The level of phototoxicity of the D-π-A sensitizers was rationalized by considering those three abilities. In addition, we observed the ability of amphiphilic sensitizers containing either a carboxylic acid or an amide in an A moiety to form aggregates that penetrate cells mainly via endocytosis.

Original languageEnglish
Pages (from-to)315-321
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume27
Issue number2
DOIs
Publication statusPublished - 2019 Jan 15
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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