Self-Assembled BODIPY Derivative with A-D-A Structure as Organic Nanoparticles for Photodynamic/Photothermal Cancer Therapy

Guojing Li; Mengqian Yang; Qilong Sha; Li Li; Xiaogang Luo; Fengshou Wu

doi:10.3390/ijms232214473

Self-Assembled BODIPY Derivative with A-D-A Structure as Organic Nanoparticles for Photodynamic/Photothermal Cancer Therapy

Int J Mol Sci. 2022 Nov 21;23(22):14473. doi: 10.3390/ijms232214473.

Authors

Guojing Li¹, Mengqian Yang¹, Qilong Sha¹, Li Li¹, Xiaogang Luo^{1

2}, Fengshou Wu^{1

3}

Affiliations

¹ Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430072, China.
² School of Materials Science and Engineering, Zhengzhou University, Zhengzhou 450001, China.
³ Key Laboratory of Novel Biomass-Based Environmental and Energy Materials in Petroleum and Chemical Industry, Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430072, China.

Abstract

Organic nanomaterials have attracted considerable attention in the area of photodynamic and photothermal therapy, owing to their outstanding biocompatibility, potential biodegradability, well-defined chemical structure, and easy functionalization. However, it is still a challenge to develop a single organic molecule that obtains both photothermal and photodynamic effects. In this contribution, we synthesized a new boron-dipyrromethene (BODIPY)-based derivative (DPBDP) with an acceptor-donor-acceptor (A-D-A) structure by coupling 3,6-di(2-thienyl)-2,5-dihydropyrrolo [3,4-c] pyrrole-1,4-dione (DPP) and BODIPY. To enhance the hydrophilicity of the BODIPY derivative, the polyethylene glycol (PEG) chains were introduced to the meso- position of BODIPY core. The amphiphilic DPBDP was then self-assembled into related nanoparticles (DPBDP NPs) with improved hydrophilicity and enhanced absorbance in the NIR region. DPBDP NPs could simultaneously generate the singlet oxygen (¹O₂) and heat under the irradiation of a single laser (690 nm). The ¹O₂ quantum yield and photothermal conversion efficiency (PCE) of DPBDP NPs were calculated to be 14.2% and 26.1%, respectively. The biocompatibility and phototherapeutic effect of DPBDP NPs were evaluated through cell counting kit-8 (CCK-8) assay. Under irradiation of 690 nm laser (1.0 W/cm²), the half maximal inhibitory concentration (IC₅₀) of DPBDP NPs was calculated to be 16.47 µg/mL. Thus, the as-prepared DPBDP NPs could be acted as excellent candidates for synergistic photodynamic/photothermal therapy.

Keywords: BODIPY; nanoparticles; photodynamic therapy; photothermal therapy; self-assembly.

MeSH terms

Boron
HeLa Cells
Humans
Nanoparticles* / chemistry
Neoplasms* / drug therapy

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
dipyrromethene
Boron

Grants and funding

This work was supported by Key Project of Scientific Research Project of Hubei Provincial Department of Education (grant no. D20201504), the Opening Project of Hubei Key Laboratory of Novel Reactor and Green Chemical Technology (grant no. NRG202103), Outstanding Young and Middle-aged Scientific Innovation Team of Colleges and Universities of Hubei Province: “Biomass chemical technologies and materials” (grant no. T201908), and the Innovation Project of Key Laboratory of Novel Biomass-Based Environmental and Energy Materials in Petroleum and Chemical Industry (grant no. 2022BEEA06).