The design, synthesis, and evaluation of organic dithienopyrrole-based D-π-A dyes for use as sensitizers in photodynamic therapy

Shinichiro Fuse, Keisuke Matsumura, Miori Takizawa, Shinichi Sato, Hiroyuki Nakamura

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Dithienopyrrole-based organic dyes that combine an electron-donating moiety (D), a π-conjugated bridge moiety (π), and an electron-accepting moiety (A) were designed and synthesized in short steps by previously developed one-pot Suzuki-Miyaura coupling approach. Absorption wavelengths of the dyes were readily tuned by altering the D and A moieties. The use of a strongly electron-withdrawing cyanopyridone acceptor enabled NIR absorption. A synthesized sensitizer, 2j, exerted potent phototoxicity mainly via a Type I mechanism in cells. A nitrogen atom in the dithienopyrrole ring serves as a connecting point for the introduction of functional building blocks that can improve the properties of sensitizers, which makes this D-π-A sensitizer a valuable template for the further development of sensitizers.

Original languageEnglish
Pages (from-to)3099-3104
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number18
DOIs
Publication statusPublished - 2018 Oct 1
Externally publishedYes

Keywords

  • CSZHBPSGFIRARQ-LFIBNONCSA-N
  • Dithienopyrrole
  • One-pot synthesis
  • Photodynamic therapy
  • Suzuki-Miyaura coupling

ASJC Scopus subject areas

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

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