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Reactive Oxygen Species-Sensitive Nanophotosensitizers of Aminophenyl Boronic Acid Pinacol Ester Conjugated Chitosan-G-Methoxy Poly(ethylene Glycol) Copolymer for Photodynamic Treatment of Cancer

Reactive Oxygen Species-Sensitive Nanophotosensitizers of Aminophenyl Boronic Acid Pinacol Ester Conjugated Chitosan-G-Methoxy Poly(ethylene Glycol) Copolymer for Photodynamic Treatment of Cancer

Young-Il Jeong, Taeyeon Kim, Eun Ju Hwang, Sang Woo Kim, Kai-Christian Sonntag, Do Hoon Kim, Jae Woong Koh

Biomed Mater. 2020 Jun 11.

PMID: 32526727

Abstract:

The aim of this study is to prepare reactive oxygen species (ROS)-sensitive nanophotosensitizers for targeted delivery of chlorin e6 (Ce6) and photodynamic therapy of tumor. For this purpose, thiodipropionic acid (TDPA) was conjugated with phenyl boronic acid pinacol ester (PBAP) (TDPA-PBAP conjugates) and then TDPA-PBAP conjugates were attached to the chitosan backbone of chitosan-g-methoxy poly(ethylene glycol) (ChitoPEG) copolymer (ChitoPEG-PBAP). Ce6-incorporated ChitoPEG-PBAP nanophotosensitizers have a ROS-sensitive manner in vitro. The size of ChitoPEG-PBAP nanoparticles increased or disintegrated in the responsive manner against H2O2 concentration. Ce6 release rate from ChitoPEG-PBAP nanophotosensitizers also increased by adding H2O2. These results indicated that nanophotosensitizers have sensitivity against ROS and showed triggered Ce6 release behavior. ChitoPEG-PBAP nanophotosensitizers can be more efficiently internalized into cancer cells compared to Ce6 alone and then produce ROS with a more efficient manner. Furthermore, ChitoPEG-PBAP nanophotosensitizers suppressed the viability of cancer cells in vitro and tumor growth in vivo with higher efficacy compared to Ce6 alone. Furthermore, ChitoPEG-PBAP nanophotosensitizers were efficiently delivered to irradiated tumor tissues, indicating that ChitoPEG-PBAP nanophotosensitizers can be delivered to the tumor with ROS-sensitive manner. We suggest that ChitoPEG-PBAP nanophotosensitizer is a promising candidate for PDT of cancers.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793389	(4-methoxycarbonylmethylphenyl)boronic acid pinacol ester			Price

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