Umbelliferone Decorated Water-soluble Zinc(II) Phthalocyanines - In Vitro Phototoxic Antimicrobial Anti-cancer Agents.

In this contribution we report on the synthesis, characterization and application of water-soluble zinc(II) phthalocyanines, which are decorated with four or eight umbelliferone moieties for photodynamic therapy (PDT). These compounds are linked peripherally to zinc(II) phthalocyanine by a triethylene glycol linker attached to pyridines, leading to cationic pyridinium units, able to increase the water solubility of the system. Beside their photophysical properties they were analyzed concerning their cellular distribution in human hepatocyte carcinoma (HepG2) cells as well as their phototoxicity towards HepG2 cells, Gram-positive (S. aureus strain 3150/12 and B. subtilis strain DB104) and Gram-negative bacteria (E. coli strain UTI89 and E. coli strain Nissle 1917). At low light doses and concentrations, they exhibit superb antimicrobial activity against Gram-positive bacteria as well as anti-tumor activity against HepG2. They are even capable to inactivate Gram-negative bacteria, whereas the dark toxicity remains low. These unique water-soluble compounds can be regarded as all-in-one type photosensitizers with broad applications ranges in the future.

Host-guest complexes - Boosting the performance of photosensitizers.

In this review, we will show the diversity of supramolecular host-guest complexes of cyclodextrins, cucurbit[n]urils, calix[n]- and pillar[n]arenes with photosensitizers, like porphyrins and phthalocyanines. Host-guest complexes are one of the main building blocks in supramolecular chemistry. For example, they have been widely used to encapsulate hydrophobic drug molecules to enhance the bioavailability in the human body. In these days of multiresistant bacteria and difficulties in cancer therapy, supramolecular host-guest systems with photosensitizers for the photodynamic therapy(PDT) gain more and more interest. In general, photosensitizers with a (large) conjugated aromatic π-system are used, which tend to π-πstacking in aqueous media suppressing the cell toxicity by singletoxygen production quenching. This can be overcome by the formation of host-guest complexes. Besides that, encapsulation of the photosensitizers in host molecules can enhance the solubility, increase cellular uptake, lead to hydrogels, rotaxanes, and switchable systems.

Lipofection with estrone-based luminophores featuring aggregation-induced emission properties.

In this communication we present the use of a novel class of luminophores with aggregation-induced emission (AIE) properties based on the steroid estrone. These molecules were equipped with cationic residues yielding amphiphiles suitable for lipofection. To this end, self-assembled luminescent structures were formed in aqueous media and mixed with a red-fluorescent protein expressing plasmid, yielding lipoplexes with increased emission intensity. These luminescent lipoplexes were able to efficiently transfect HeLa and HEK 293T cells and were able to be tracked due to the aggregation induced-emission properties.

Alkylated Aromatic Thioethers with Aggregation-Induced Emission Properties-Assembly and Photophysics.

In this contribution, we present the synthesis and self-assembly of alkylated thioethers with interesting photophysical properties. To this end, the emission, absorption and excitation spectra in organic solvents and as aggregates in water were measured as well as the corresponding photoluminescence quantum yields and lifetimes. The aggregates in aqueous media were visualized and measured using transmission electron microscopy. Besides that, crystal structures of selected compounds allowed a detailed discussion of the structure-property relationship. Furthermore, the mesomorphic behavior was investigated using polarized optical microscopy (POM) as well as differential scanning calorimetry (DSC).