Citation: Leichen Wang, Anqing Mei, Na Li, Xiaohong Ruan, Xu Sun, Yu Cai, Jinjun Shao, Xiaochen Dong. Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy[J]. Chinese Chemical Letters, ;2024, 35(6): 108974. doi: 10.1016/j.cclet.2023.108974 shu

Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy

Leichen Wang ^a ,
Anqing Mei ^a ,
Na Li ^a ,
Xiaohong Ruan ^a ,
Xu Sun ^a ,
Yu Cai ^c ,
Jinjun Shao ^{a, *,} ,
Xiaochen Dong ^{a, b, *,}

a.
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), Nanjing 211800, China
b.
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China
c.
Center for Rehabilitation Medicine, Rehabilitation & Sports Medicine Research Institute of Zhejiang Province, Department of Rehabilitation Medicine, Zhejiang Provincial People's Hospital (Affiliated People's Hospital, Hangzhou Medical College), Hangzhou 310014, China

iamjjshao@njtech.edu.cn

iamxcdong@njtech.edu.cn

Received Date: 29 June 2023
Revised Date: 23 August 2023
Accepted Date: 24 August 2023
Available Online: 26 August 2023

Figures(6)

Introducing heavy halogen atoms into organic small molecules is a practical strategy for efficient singlet oxygen (¹O₂) generation. Generally, bromine or iodine atoms are introduced on the aza-boron-dipyrromethene (aza-BODIPY) core, rather than on the periphery aryl rings for efficient ¹O₂ generation. Herein, an aza-BODIPY dye NBDPBr with unexpected bromination on the periphery aryl rings was synthesized for photoacoustic (PA) imaging-guided synergistic photothermal therapy (PTT) and photodynamic therapy (PDT) in tumor cells. Owing to unexcepted bromination at the periphery aryl rings, NBDPBr demonstrated an outstanding singlet oxygen quantum yield of 66% which was superior to similar brominated photosensitizers previously reported. After encapsulation with amphiphilic polymer F-127, hydrophilic NBDPBr nanoparticles (NPs) were fabricated and exhibited an excellent photothermal conversion efficiency (η) of 43.0% under 660 nm photoirradiation. In vivo PA imaging results demonstrated that NBDPBr NPs could specifically accumulate at tumor sites and realized the maximum tumor retention at 7 h post-injection. All the in vitro and in vivo results indicated the significant potence of NBDPBr with unexpected bis-bromination for PA imaging-guided synergetic PDT/PTT.
- Unexpected bromination,
- Aza-BODIPY,
- Photodynamic therapy,
- Photothermal therapy,
- Synergetic therapy
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