Silicon Tetrapyrazinoporphyrazine Derivatives-Incorporated Carbohydrate-Based Block Copolymer Micelles for Photodynamic Therapy

Jong Min Park, Chang Young Jung, Woo Dong Jang, Jae Yun Jaung

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Developing nonaggregated photosensitizers (PSs) for efficient photodynamic therapy (PDT) using polymeric micelles (PMs) has been challenging. In this study, axially substituted nonaggregated silicon tetrapyrazinoporphyrazine (SiTPyzPz) derivatives in carbohydrate-based block glycopolymer-based PMs were designed and used as PSs for PDT. To achieve the nonaggregated PSs, SiTPyzPz was axially substituted with trihexylsiloxy (THS) groups to form SiTPyzPz-THS, which exhibited highly monomeric behaviors in organic solvents. Moreover, three block copolymers were prepared via reversible addition-fragmentation chain transfer (RAFT) polymerization. Each copolymer comprised hydrophobic polystyrene blocks and loadable SiTPyzPz-THS, and one or two consisted of two possible hydrophilic blocks, polyethylene glycol or poly(glucosylethyl methacrylate). The self-assembly of SiTPyzPz-THS and the block copolymers in aqueous solvents induced the formation of spherical PMs with core-shell or core-shell-corona structures. The SiTPyzPz-THS in the PMs exhibited monomeric state, intense fluorescence emission, and outstanding singlet oxygen generation; moreover, it did not form aggregates. During the in vitro test, which was performed to investigate the PDT efficiency, the PMs, which consisted of poly(glucosylethyl methacrylate) shells, exhibited high photocytotoxicity and cellular internalization ability. Consequently, the PM systems of nonaggregated PSs and carbohydrate-based block copolymers could become very promising materials for PDT owing to their photophysicochemical properties and considerable selectivity against cancer cells.

Original languageEnglish
Pages (from-to)1988-2000
Number of pages13
JournalACS Applied Bio Materials
Issue number3
Publication statusPublished - 2021 Mar 15

Bibliographical note

Funding Information:
This work was supported by the Mid-Career Researcher Program (2017R1A2A1A17069537) funded by the National Research Foundation (NRF) of Korea, Technology Innovation Program (No. 10052798) funded by the Ministry of Trade, Industry & Energy of Korea, and the Postdoc Researcher Supporting Program (Project No. 2020-12-0026) funded by Yonsei University.

Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biomaterials
  • Biomedical Engineering
  • Biochemistry, medical


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