betadex and phthalocyanine

Two zinc(ii) phthalocyanines substituted with two and four permethylated β-cyclodextrin moieties at the α positions have been synthesised and immobilised on the surface of adamantane-modified silica nanoparticles through host-guest interactions. These molecular and supramolecular systems can catalyse the photooxygenation of 1-naphthol and 2-furoic acid in organic and aqueous media with high conversion efficiency and reaction yield, and photodegradation of 2-chlorophenol in water. Having a higher photostability and recyclability, the supramolecular nanosystems are particularly promising for these photocatalytic applications.

Topics: beta-Cyclodextrins; Catalysis; Chlorophenols; Coordination Complexes; Furans; Indoles; Isoindoles; Molecular Structure; Naphthols; Photochemical Processes; Solubility; Water; Zinc

In this communication we report on the synthesis and application of axially functionalized boron-subphthalocyanines (SubPC) which are able to form host-guest complexes with cyclodextrins. Here, a tert-butylphenyl substituted SubPC was investigated concerning its complexation with β-cyclodextrin (β-CD) and a β-cyclodextrin polymer. NMR-titrations showed the formation of a 1 : 1 complex with β-CD. These assemblies were analyzed for their cellular distribution as well as their phototoxicity towards HeLa cells.

Topics: beta-Cyclodextrins; Boron; Cell Survival; Cellulose; Cyclodextrins; HeLa Cells; Humans; Indoles; Isoindoles; Magnetic Resonance Spectroscopy; Microscopy, Fluorescence; Photosensitizing Agents; Reactive Oxygen Species

Near-infrared (NIR) light triggered photodynamic therapy (PDT), based on upconversion nanoparticles (UCNPs), has attracted great attention because of its high tissue penetration and low photodamage to living organisms. However, most UCNPs cannot be stably dispersed in aqueous solution and cannot carry photosensitive drugs directly. Besides, UCNP mediated PDT is a fluorescence resonance energy transfer (FRET) process from the UCNPs to the attached photosensitive drugs. So the drug and UCNPs must be stably connected and close enough. In this manuscript, carboxymethyl-β-cyclodextrin (COOH-β-CD) was used to connect UCNPs and adamantine modified phthalocyanine (Ad-ZnPc) through a self-assembly process followed by a host-guest interaction. COOH-β-CD can provide good water solubility of the system and short-distance linking between the UCNPs and Ad-ZnPc. Most importantly, the system has a strong NIR light triggered PDT activity toward cancer cells.

Topics: Adamantane; Antineoplastic Agents; beta-Cyclodextrins; Cell Line, Tumor; Drug Carriers; HeLa Cells; Humans; Indoles; Infrared Rays; Isoindoles; Models, Molecular; Molecular Conformation; Nanoparticles; Photosensitizing Agents; Solubility; Spectrometry, Fluorescence; Water

Porphyrins, phthalocyanines and subphthalocyanines are three attractive classes of chromophores with intriguing properties making them suitable for the design of artificial photosynthetic systems. The assembly of these components by a supramolecular approach is of particular interest as it provides a facile means to build multi-chromophoric arrays with various architectures and tuneable photophysical properties. In this paper, we show the formation of mixed host-guest supramolecular complexes that consist of a β-cyclodextrin-conjugated subphthalocyanine, a tetrasulfonated porphyrin and a series of silicon(IV) phthalocyanines substituted axially with two β-cyclodextrins via different spacers. We found that the three components form supramolecular complexes held by host-guest interactions in aqueous solution. Upon excitation of the subphthalocyanine part of the complex, the excitation energy is delivered to the phthalocyanine unit via excitation energy transfer and the porphyrin chromophore acts as an energy transfer bridge enabling this process. It was shown that photo-induced charge transfer also takes place. A sequential electron transfer process from the porphyrin unit to the phthalocyanine moiety and subsequently from the subphthalocyanine moiety to the porphyrin unit takes place, and the probability of this process is controlled by the linker between β-cyclodextrin and phthalocyanine. The lifetime of the charge-separated state was found to be 1.7 ns by transient absorption spectroscopy.

Topics: beta-Cyclodextrins; Electron Transport; Indoles; Isoindoles; Molecular Structure; Organosilicon Compounds; Porphyrins; Spectrometry, Fluorescence; Thermodynamics; Time Factors

A series of unsymmetrical silicon(IV) phthalocyanines with a permethylated β-cyclodextrin unit and a sugar or a diamino moiety as the axial substituents have been prepared. These compounds are highly photocytotoxic with IC(50) values as low as 21 nM, which is ca. sevenfold lower than those of the symmetrical bis(cyclodextrin) analogue.

Topics: Animals; beta-Cyclodextrins; HT29 Cells; Humans; Indoles; Isoindoles; Mice; Organometallic Compounds; Photochemotherapy; Photosensitizing Agents; Silicon

A stable 2 : 1 host-guest complex is formed between a beta-cyclodextrin-conjugated subphthalocyanine and a tetrasulfonated porphyrin in water. The complex exhibits an energy transfer property from the excited subphthalocyanine to the porphyrin core with an excitation energy transfer quantum yield of 0.38.

Topics: beta-Cyclodextrins; Energy Transfer; Indoles; Isoindoles; Light; Photosynthesis; Porphyrins; Spectrum Analysis; Water

A stable 1:1 host-guest complex is formed between a silicon(IV) phthalocyanine conjugated axially with two permethylated beta-cyclodextrin units and a tetrasulfonated porphyrin. The complex exhibits a light-harvesting property and works as an efficient photosensitizing system, killing HT29 human colon adenocarcinoma cells with an IC50 value of 0.09 microM. [structure: see text].

Topics: Adenocarcinoma; beta-Cyclodextrins; Cell Line, Tumor; Cell Proliferation; Colonic Neoplasms; Drug Screening Assays, Antitumor; Humans; Indoles; Isoindoles; Light; Molecular Structure; Organosilicon Compounds; Photochemotherapy; Porphyrins; Water