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Two prop-2-ynyloxybenzyloxy axially/peripherally substituted zinc/silicon phthalocyanines (YSiPc and YZnPc) were synthesized. They were encapsulated into an amphiphilic block copolymeric micelle polyethylene glycol monomethyl ether-polycaprolactone (MPEG5000–PCL2000) to form polymeric nanoparticles YSiPc@MPEG5000–PCL2000 and YZnPc@MPEG5000–PCL2000. The photophysical and photochemical properties of these polymeric nanoparticles were studied by UV/Vis and fluorescence spectroscopy. The cellular uptake and reactive oxygen species (ROS) production abilities of two polymeric nanoparticles in MCF-7 breast cancer cells were evaluated by confocal laser scanning imaging. YSiPc@MPEG5000–PCL2000 exhibited a higher cellular uptake, higher ROS generation ability as well as higher photodynamic efficacy against MCF-7 cells. YSiPc@MPEG5000–PCL2000 is a promising photosensitizer for photodynamic therapy. [ABSTRACT FROM AUTHOR]

Three nanohybrid materials (FCSiPc@PEG-Cu-Cy) using poly (ethylene glycol) copper-cysteamine (PEG-Cu-Cy) nanoparticles as a carrier to load three fluorocoumarin silicon(IV) phthalocyanines (FCSiPcs) were prepared. The morphologies of these nanohybrids were characterized by transmission electron microscopy (TEM). The interactions between PEG-Cu-Cy nanoparticles and three FCSiPcs were studied by UV/Vis and fluorescence spectroscopic methods. The photophysical and photochemical properties of these FCSiPcs were influenced by PEG-Cu-Cy nanoparticles and exhibited substituents dependent of phthalocyanines in nanohybrids. The fluorescence resonance energy transfer (FRET) occurred from FCSiPcs (donors) to PEG-Cu-Cy nanoparticles (acceptors). These nanohybrids may be potential photosensitizers for photodynamic therapy. [ABSTRACT FROM AUTHOR]

Two aluminum chloride phthalocyanines with pyridyloxy substitution at α/β positions were synthesized. Their structures were characterized by infrared spectroscopy, proton nuclear magnetic resonance as well as elemental analysis. Tetra-α(β)-(2-pyridyloxy) aluminum chloride phthalocyanines were encapsulated into a diblock copolymer methoxy-poly(ethylene glycol)-block-poly(L-lysine) through a cosolvent method. The morphologies and photophysical properties of phthalocyanines encapsulated in nanoparticles were studied by transmission electron microscope, ultraviolet-visible, and fluorescence spectroscopic methods. The photophysical properties of phthalocyanines encapsulated into nanoparticles exhibited substitution positions dependence. The phthalocyanines with substitution at α positions were found to be an excellent candidate for use as photosensitizers for treatment of cancer by photodynamic therapy. [ABSTRACT FROM AUTHOR]

The timely evasion of nanomedicines from lysosomes is essential to avert premature degradation under the acidic and hydrolytic conditions characteristic of these cellular compartments. However, the development of effective strategies has been hindered by the complexity of design material and the scarcity of practical methods. In this study, we have synthesized a novel nanoparticle, designated as TPA-BPAF-SiPc@AuNR@SiO 2. This nanoparticle was prepared by encapsulating near-infrared fluorinated triphenylamine-substituted silicon phthalocyanines (TPA-BPAF-SiPc) within mesoporous silica-coated gold nanorods (AuNR@SiO 2). TPA-BPAF-SiPc@AuNR@SiO 2 functions as a dual-function two-photon probe, facilitating photoactivated lysosome escape and targeting mitochondria. The inherent aggregation-induced emission (AIE) two-photon fluorescence of TPA-BPAF-SiPc is notably bright when encapsulated in AuNR@SiO 2 nanocarriers, a phenomenon not observed in polymer nanocarriers composed of 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DSPE-PEG 2000) or in THF/water mixtures. Upon irradiation, this nanoparticle autonomously escapes from lysosomes and selectively targets mitochondria, a process can be visually monitored in real-time through the two-photon AIE fluorescence of TPA-BPAF-SiPc. Moreover, upon activation, TPA-BPAF-SiPc@AuNR@SiO 2 produces a substantial quantity of reactive oxygen species (ROS) and induces hyperthermia effects, showcasing its potential for effective photodynamic therapy (PDT) in conjunction with synergistic hyperthermia. Flow cytometry data corroborate the induction of tumor cell death through both necrosis and apoptosis pathways by TPA-BPAF-SiPc@AuNR@SiO 2. This study underscores the potential of TPA-BPAF-SiPc@AuNR@SiO 2 as a multifunctional probe capable of enabling lysosome escape, mitochondria targeting, and two-photon fluorescence imaging-guided photothermal synergistic photodynamic therapy, specifically tailored for the treatment of breast cancer. • TPA-BPAF-SiPc@AuNR@SiO 2 was prepared by loading TPA-BPAF-SiPc into AuNR@SiO 2. • TPA-BPAF-SiPc@AuNR@SiO 2 functions as a two-photon probe for visualized lysosome escape and mitochondria targeting. • AIE fluorescence of TPA-BPAF-SiPc was observed within AuNR@SiO 2 but not in DSPE-PEG 2000 or THF/water mixtures. • Nanoplatform can realize photodynamic synergistic photothermal therapy in vitro treatment of breast cancer cells. [ABSTRACT FROM AUTHOR]

Two series of fluorinated and non-fluorinated dendritic silicon (IV) phthalocyanines with cyano/nitro/ester terminal functionalities have been synthesized. Their structures were characterized by elemental analysis, FT-IR, 1H NMR and ESI-MS. The effects of fluorinated groups and terminal functionalities properties on the photophysical properties, photoinduced intermolecular electron transfer and intramolecular energy transfer of silicon phthalocyanines were compared. In order to endow water soluble and biocompatibility to these silicon phthalocyanines, an amphiphilic diblock copolymer polyethylene glycol monomethyl ether–polycaprolactone was used to encapsulate these silicon phthalocyanines to form fluorinated and non-fluorinated dendritic silicon phthalocyanines nanoparticles. The binding model between the fluorinated dendritic silicon phthalocyanines nanoparticles and calf thymus DNA was studied by UV–Vis and fluorescence spectroscopic method. The photocleavage DNA activities of three fluorinated dendritic silicon phthalocyanines nanoparticles were compared and the possible cleavage mechanism was proposed. Image 1 • Fluorinated and non-fluorinated silicon phthalocyanines with cyano/nitro/ester terminal groups was synthesized • The photophysical properties of silicon phthalocyanines exhibited fluorinated substitution and terminal groups dependence. • Fluorinated silicon phthalocyanines nanoparticles bind at the outside negative phosphate of DNA via "positive charge". • MPEG@SiPc-F-COOCH 3 showed the most outstanding photo-degradation ability through produce singlet oxygen. [ABSTRACT FROM AUTHOR]