A novel method for the synthesis of the PEG-crosslinked chitosan with a pH-independent swelling behavior

In this study, a simple method was developed to crosslink chitosan using poly(ethylene glycol) (PEG) with different molecular weights. Crosslinking of chitosan was confirmed by various spectral analyses. The differential scanning calorimetric (DSC) study indicated that the rigid crystalline structure of chitosan was decreased after crosslinking with PEG. The PEG-crosslinked chitosan (PEG-Ch) showed a pH-independent swelling behavior: swelled in both the simulated stomach (pH 1.1) and intestinal (pH 7.4) solutions. The swelling ratio of PEG-Ch increased significantly with a higher molecular weight of PEG used. In contrast, chitosan dissolved completely in a simulated stomach solution and showed a comparatively less swelling in a simulated intestinal solution. Thus, the prepared PEG-Ch could be a better biomaterial than chitosan in the development of orally sustained drug-delivery devices.     

Synthesis and crystal structures of novel calix[4]azacrowns

A series of novel 1,3‐altemate calix[4]arene azacrowns having mono and bis crown ethers on the lower rim of the calix[4]arene framework were synthesized. Solid‐state structures confirmed the three dimensional conformation of compounds 1–3.     

Depigmenting activity and low cytotoxicity of alkoxy benzoates or alkoxy cinnamte in cultured melanocytes

To obtain effective and safe topical depigmenting agents, we synthesized hydroxybenzoates, alkoxybenzoates, and 3,4,5-trimethoxycinnamate containing a thymol moiety and screened then for high-level inhibitory activity against melanin synthesis in cultured melanocytes. Eight compounds were tested for their depigmenting effect and cytotoxicity using a murine melanocyte cell line. We found that 3,4,5-trialkoxybenzoates and 3,4,5-trimethoxycinnamate, synthesized by conjugating 3,4,5-trialkoxybenzoic acids and 3,4,5-trimethoxycinnmic acid with thymol, showed a potent depigmenting effect and low cytotoxicity. Compound 4h, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate, showed the most potent depigmenting effect (IC50=10 microM) with low cytotoxicity (IC50=200 microM).