An AceDAN–porphyrin(Zn) dyad for fluorescence imaging and photodynamic therapy via two-photon excited FRET

Abstract

A FRET based AceDAN–porphyrin(Zn) dyad was designed to generate red emission and singlet oxygen (1O2) simultaneously, which were utilized successfully for two-photon excited fluorescence imaging and PDT of cancer cells.

Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines

“…In recent literature, functional porphyrins were specified as potential fluorescent probes for TPE fluorescence imaging of various tumoral cells. Thus, 2-acetyl-6-dimethyl-aminonaphthalene-porphyrin dyads, characterized by intramolecular fluorescence resonance energy transfer process (FRET) from the aminonaphthalene donor to the porphyrin acceptor unit, were employed for TPE fluorescence imaging of lung cancer A549 cells under the irradiation with a 740 nm femtosecond laser [34,35]. Mesoporous silica nanocomposites containing the photosensitizer 5,10,15,20-tetrakis-(1-methyl-4-pyridinio)porphyrin-tetra-(p-toluenesulfonate) were employed for targeted TPE-FLIM of human breast carcinoma cell line MCF-7 and the human lung cancer A549 cell line [36].…”

“…Thus, 2-acetyl-6-dimethyl-aminonaphthalene-porphyrin dyads, characterized by intramolecular fluorescence resonance energy transfer process (FRET) from the aminonaphthalene donor to the porphyrin acceptor unit, were employed for TPE fluorescence imaging of lung cancer A549 cells under the irradiation with a 740 nm femtosecond laser. [34,35] Mesoporous silica nanocomposites containing the photosensitizer 5,10,15,20-tetrakis-(1-methyl-4-pyridinio)porphyrin-tetra-(ptoluenesulfonate) were employed for targeted TPE-FLIM of human breast carcinoma cell line MCF-7 and the human lung cancer A549 cell line [36]. A non-covalent complex of lipid-coated semiconductor CdSe/ZnS quantum dots with a partially hydrogenated porphyrin (chlorin e6) photosensitizer was imaged within plasma membrane and intracellular compartments of living HeLa cells [37].…”

Photophysical Exploration of Zn(II) Polypyridine Photosensitizers in Two-Photon Photodynamic Therapy: Insights from Theory

“…13 However, the development of these organic molecules acting as PSs in TP-PDT are limited by the small δ and a low intersystem crossing (ISC) efficiency. 15,16 In recent years, transition-metal complexes taken as PSs have attracted extensive attention due to their excellent properties. Compared with nonmetal organic molecule PSs, transition-metal complexes as PSs have large spin−orbital coupling, large Stokes shift, and good photophysical and photochemical stability.…”

“…In general, the large two-photon cross-section (δ) is an important factor in determining whether PSs can be used in TP-PDT. Organic molecules, especially hematoporphyrin and phthalocyanine, are common PSs in the early stage. , However, the development of these organic molecules acting as PSs in TP-PDT are limited by the small δ and a low intersystem crossing (ISC) efficiency. , In recent years, transition-metal complexes taken as PSs have attracted extensive attention due to their excellent properties. Compared with nonmetal organic molecule PSs, transition-metal complexes as PSs have large spin–orbital coupling, large Stokes shift, and good photophysical and photochemical stability. , Among transition-metal complexes as PSs, Ru­(II) complexes have emerged as star PSs because of the high 1 O 2 yield and good photophysical and photochemical stability. , However, at the current stage, most Ru­(II) PSs also suffer from the disadvantages of a shorter excitation wavelength and poor solubility in water; these complexes have some limitations in the deep treatment of tumors and hence affect the therapeutic effect seriously. , In 2020, Johannes Karges group synthesized a series of Ru­(II) polypyridine complexes with large δ and proved that molecule 7 has the potential to be a highly efficient PS in TP-PDT.…”