Solid-Phase Synthesis of Peptide-Conjugated Perylene Diimide Bolaamphiphile and Its Application in Photodynamic Therapy

Young O. Kim, Sung Jun Park, Byeong Yeon Jung, Hyung Seok Jang, Seo Keong Choi, Jaehi Kim, Sehoon Kim, Yong Chae Jung, Dong Sik Shin, Yoon Sik Lee

Research output: Contribution to journalArticlepeer-review

Abstract

Here, we describe a rapid and efficient synthetic method of peptide-conjugated perylene diimide (P-PDI) using solid-phase peptide synthesis (SPPS). Due to severe insolubility of perylene dianhydride (PDA) as a starting material of perylene diimide (PDI), PDA was initially conjugated with amino acids to obtain soluble PDI derivatives. Target peptides were synthesized on a 2-chlorotrityl chloride resin using the SPPS method and then conjugated with the amino acid-appended PDI. Various conditions such as loading levels, reaction times and solvents were optimized for introducing the peptides to both sides of the amino acid-appended PDI. The final P-PDI was obtained with a maximum yield of 80% in 12 h. Its singlet oxygen-derived phototoxicity on cells was confirmed, which could be applicable to photodynamic therapy.

Original languageEnglish
Pages (from-to)5896-5902
Number of pages7
JournalACS Omega
Volume3
Issue number5
DOIs
Publication statusPublished - 2018 May 31

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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