To examine the versatility of the trans-bisglycoconjugation architecture for 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TFPP) derivative-based photodynamic therapy (PDT), 25 porphyrin derivatives bearing d-glucopyranose moieties were prepared, and their in vitro photocytotoxicities were examined. trans-Bisglycoconjugated TFPP derivatives exerted the best photocytotoxicity among TFPP derivatives in the same category, regardless of the central metal ion and the type of glycoconjugation. trans-Bisglycoconjugated free-base TFPP bearing β-d-glucopyranosylthio groups (trans-H22SGlc) was found to be the most potent photosensitizer, not only in HeLa cells (EC50 < 5 nM), but also in highly metastatic cancer cell lines such as B16-BL6 melanoma cells (EC50 < 10 nM). UV–vis and dynamic light-scattering measurements suggested that trans-bisglycoconjugated TFPP derivatives formed relatively large J-aggregates in an aqueous solution. trans-Bisglycoconjugated TFPP derivatives exhibited greater uptake by HeLa cells than those with different glycoconjugation patterns, with the exception of Zn(II) complexes. trans-Bisglycoconjugated TFPP derivatives efficiently generated hydrogen peroxide and hydroxyl radical by a type I photoreaction, while no significant differences were found in the efficiency of singlet oxygen generation by a type II photoreaction. These unique characteristics of trans-bisglycoconjugated TFPP derivatives support the conclusion that trans-bisglycoconjugation is a highly efficient and robust architecture for TFPP-based PDT development.
The tribological properties between taut hair fibers in wet conditions were investigated to evaluate the tangling/detangling performance of shampoo formulations during washing (particularly rinsing). A new setup for friction measurements between taut hair fibers was established. Using the setup, tribological properties of hair fibers treated with two shampoo formulations, whose tangling performances were different, were investigated. The base formulation for the shampoos was the same; the only difference was the type of amino-modified silicones used as conditioning agents. Shampoo (Sp) A (poor detangling performance) incudes water-insoluble silicone, and Sp B (excellent detangling performance) includes water-soluble silicone. The tribological behaviors between taut hair fibers treated with the diluted solutions of the Sp were very different; the Sp A-treated hair exhibited stick-slip sliding, whereas the Sp B-treated hair exhibited smooth sliding. This difference presumably comes from the different coacervation behaviors in the diluted solutions and resulting structure of conditioning film formed on hair surfaces. The smooth sliding (ideal for detangling) of Sp B-treated hair comes from the two-layer structure of the conditioning film on hair; positively charged amino-modified silicone dissolved in water adsorbed immediately on negatively charged hair surface, followed by the physical adsorption of coacervates on the adsorbed silicone layer. The outer coacervate layer is easily removed during sliding, and smooth sliding comes from the low friction of the silicone layer. The relationship between the type of amino-modified silicones, conditioning film formation on the surface, and tribological properties was discussed, which gives insights into designing Sp formulations with excellent detangling performance.
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