Open AccessSolid-Phase Synthesis of Peptide-Conjugated Perylene Diimide Bolaamphiphile and Its Application in Photodynamic Therapy
Author(s) -
YoungO Kim,
Sung Jun Park,
Byeong Yeon Jung,
Hyung-Seok Jang,
Seo Keong Choi,
Jaehi Kim,
Sehoon Kim,
Yong Chae Jung,
DongSik Shin,
Yoon-Sik Lee
Publication year - 2018
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.8b00040
Subject(s) - diimide , perylene , conjugated system , chemistry , peptide , combinatorial chemistry , singlet oxygen , photochemistry , peptide synthesis , yield (engineering) , solid phase synthesis , photodynamic therapy , polymer chemistry , organic chemistry , materials science , polymer , oxygen , biochemistry , molecule , metallurgy
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.
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