A water-soluble pyrazino[2,3-]quinoxaline photosensitizer for high-efficiency one- and two-photon excited bioimaging and photodynamic therapy

• Published in: Chemical communications (Cambridge, England) England), 2020-05, Vol.56 (41), p.5544-5547
• Main Authors: Zhang, Li-Peng, Li, Xianqiang, Liu, Tianlong, Kang, Lin, Huang, Xing, Zhao, Yuxia
• Format: Article
• Language: English
• Subjects: Absorption cross sections; Animals; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Cell death; Cell Line, Tumor; Cell Proliferation - drug effects; Cell Survival - drug effects; Crystallography; Drug Screening Assays, Antitumor; Excitation; Fluorescence; HeLa Cells; Humans; Medical imaging; Mice; Molecular Structure; Optical Imaging; Photochemotherapy; Photodynamic therapy; Photon absorption; Photons; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - chemistry; Photosensitizing Agents - pharmacology; Quinoxalines; Quinoxalines - chemical synthesis; Quinoxalines - chemistry; Quinoxalines - pharmacology; Semiconductor lasers; Singlet oxygen; Solubility; Water - chemistry
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d0cc02285c

A water-soluble photosensitizer, PQs-PEG5, based on a novel pyrazino[2,3- g ]quinoxaline (PQ) prototype compound (PQs-5), was designed and synthesized. It has strong linear absorption within 400-600 nm and a desirable two-photon absorption cross section (100-1290 GM) within 740-1000 nm, and it exhibits both a high fluorescence quantum yield (∼0.55) and singlet oxygen quantum yield (∼0.47). By carrying out in vitro cell imaging and photodynamic therapy (PDT) experiments on PQs-PEG5 with HeLa and 4T1 cells, it was demonstrated that PQs-PEG5 can present outstanding bioimaging performance and PDT efficacies simultaneously. Under one-photon excitation (1PE) of a 635 nm diode laser (60 mW cm −2 , 5 min) or two-photon excitation (2PE) of an 820 nm fs laser (100 mW, 80 MHz, 140 fs, 5 min), PQs-PEG5 (10 μM) could cause HeLa and 4T1 cell death effectively, which indicated its great potential as a novel photosensitizer for both 1PE- and 2PE-PDT applications. A water-soluble pyrazino[2,3- g ]quinoxaline photosensitizer was synthesized and exhibited excellent performance for both one- and two photon excited bioimaging and photodynamic therapy.