Self‐assembly of Amphiphilic Porphyrins To Construct Nanoparticles for Highly Efficient Photodynamic Therapy

• Published in: Chemistry : a European journal Vol. 27; no. 43; pp. 11195 - 11204
• Main Authors: Jiang, Meiyu, Wu, Jiasheng, Liu, Weimin, Ren, Haohui, Zhang, Wenjun, Lee, Chun‐Sing, Wang, Pengfei
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 02.08.2021; Wiley Subscription Services, Inc
• Subjects: amphiphilic; Aqueous solutions; Assembly; Blood circulation; Cell permeability; Chemistry; Chemistry, Multidisciplinary; Ethylene glycol; Hydrophobicity; Nanomaterials; Nanoparticles; Photodynamic therapy; Physical Sciences; Porphyrins; Science & Technology; self-assembly; Singlet oxygen; triphenylphosphine; Tumor cells; Tumors; Water circulation; triphenylphosphine; OXYGEN; self-assembly; YIELDS; nanoparticles; amphiphilic; photodynamic therapy; MITOCHONDRIA; STATE; WATER; nanoparticle; Self-assembly
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202101199

Hydrophobic photosensitizers greatly affect cell permeability and enrichment in tumors, but they cannot be used directly for clinical applications because they always aggregate in water, preventing their circulation in the blood and accumulation in tumor cells. As a result, amphiphilic photosensitizers are highly desirable. Although nanomaterial‐based photosensitizers can solve water solubility, they have the disadvantages of complicated operation, poor reproducibility, low drug loading, and poor stability. In this work, an efficient synthesis strategy is proposed that converts small molecules into nanoparticles in 100 % aqueous solution by molecular assembly without the addition of any foreign species. Three photosensitizers with triphenylphosphine units and ethylene glycol chains of different lengths, TPP−PPh3, TPP−PPh3−2PEG and TPP−PPh3−4PEG, were synthesized to improve amphiphilicity. Of the three photosensitizers, TPP−PPh3−4PEG is the most efficient (singlet oxygen yield: 0.89) for tumor photodynamic therapy not only because of its definite constituent, but also because its amphiphilic structure allows it to self‐assemble in water. Pull yourself together! Three photosensitizers with triphenylphosphine units and different lengths of ethylene glycol chains have been synthesized to improve amphiphilicity. Of the three photosensitizers, TPP−PPh3−4PEG is the most efficient (singlet oxygen yield: 0.89) for tumor photodynamic therapy not only because of its definite constituent, but also because its amphiphilic structure allows it to self‐assemble in water.