TY - JOUR
T1 - Silicon Tetrapyrazinoporphyrazine Derivatives-Incorporated Carbohydrate-Based Block Copolymer Micelles for Photodynamic Therapy
AU - Park, Jong Min
AU - Jung, Chang Young
AU - Jang, Woo Dong
AU - Jaung, Jae Yun
N1 - Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/3/15
Y1 - 2021/3/15
N2 - 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.
AB - 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.
KW - carbohydrate-based block copolymers
KW - photodynamic therapy
KW - polymeric micelles
KW - self-assembly
KW - silicon tetrapyrazinoporphyrazine
UR - http://www.scopus.com/inward/record.url?scp=85086837653&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85086837653&partnerID=8YFLogxK
U2 - 10.1021/acsabm.0c00256
DO - 10.1021/acsabm.0c00256
M3 - Article
C2 - 35014324
AN - SCOPUS:85086837653
SN - 2576-6422
VL - 4
SP - 1988
EP - 2000
JO - ACS Applied Bio Materials
JF - ACS Applied Bio Materials
IS - 3
ER -