Fluoroquinolones are extensively used antibiotics that are generally prescribed as hydrochloride salts because the neutral forms display low solubility due to their zwitterionic character. Starting from the hydrochloride salts of ciprofloxacin (CiHCl) or (S,S)-moxifloxacin (MoHCl) and 4-hydroxybenzoic acid (4HBA) as a cocrystal former, two cocrystalline solids, CiHCl−4HBA and MoHCl−4HBA, were obtained in a salt/ coformer stoichiometric ratio of 1:1. The cocrystalline phases were identified by X-ray powder diffraction analysis and further characterized by IR spectroscopy, thermogravimetric analysisdifferential scanning calorimetry, and single crystal X-ray diffraction analysis. The novel solid phases could be formed using different methodologies, namely, solution-mediated phase transformation, solvent drop grinding, crystallization by solvent evaporation, and reaction crystallization. Pharmaceutically relevant properties such as phase stability, thermodynamic solubility, and dissolution rate were examined. All cocrystalline phases remained stable when suspended in acidic aqueous solutions and did not transform upon accelerated temperature/relative humidity exposition for 30 days. Interestingly, opposite trends in the thermal stability, solubility, and dissolution rate of the cocrystals were exhibited by the different fluoroquinolones in comparison to the parent starting salts. Upon heating, the CiHCl−4HBA cocrystal releases first the coformer before decomposing and displayed a lower solubility and dissolution rate in comparison to CiHCl•1.34H 2 O. By contrast, the MoHCl−4HBA cocrystal melts in a single-phase transition process and showed enhanced solubility and dissolution rate when compared to the parent moxifloxacin salt. The similar composition of the cocrystals and the structural resemblance of the fluoroquinolones examined herein allowed for a detailed vis-a-vis comparison between the supramolecular structures in the solid-state and the physicochemical properties. The incorporation of 4HBA in the crystal lattice caused changes in the number, type, and strength of the intermolecular interactions between the ionic components (chloride and fluoroquinolinium cations), which could be related to the solubility and dissolution rate properties. While the cocrystal CiHCl−4HBA retained essential features of the supramolecular assembly found also for the starting hydrochloride and gave an overall three-dimensional hydrogen bonded network with the cocrystal former, MoHCl−4HBA showed a singular two-dimensional assembly, with linear chains formed between the 4HBA molecules and chloride ions through O−H•••Cl − •••H−O hydrogen bonds in place of the usual chargedassisted N + −H•••Cl − interactions.
Chitosan membranes are widely applied for tissue engineering; however, a major drawback is their low resistance in aqueous phases and therefore the structure collapses impeding their long-term use. Although there is extensive research, because of chitosan’s importance as a biomaterial, studies involving chitosan-based membranes are still needed. Herein, a detailed investigation of diverse chemical routes to cross-link fibers in situ by electrospinning process is described. In case of using genipin as cross-linker, a close relationship with the content and the mean diameter values is reported, suggesting a crucial effect over the design of nanostructures. Also, the physical resistance is enhanced for the combination of two types of methods, such as chemical and physical methods. Cross-linked fibers upon exposure to long wave ultraviolet A (UVA light) change their morphology, but not their chemical composition. When they are incubated in aqueous phase for 70 days, they show an extensive improvement of their macrostructural integrity which makes them attractive candidates for tissue engineering application. As a result, the thermal properties of these materials reveal less crystallinity and higher temperature of degradation.
A cocrystal of the antihypertensive drug chlorthalidone (CTD) with caffeine (CAF) was obtained (CTD-CAF) by the slurry method, for which a 2:1 stoichiometric ratio was found by powder and single-crystal X-ray diffraction analysis. Cocrystal CTD-CAF showed a supramolecular organization in which CAF molecules are embedded in channels of a 3D network of CTD molecules. The advantage of the cocrystal in comparison to CTD is reflected in a threefold solubility increase and in the dose/solubility ratios, which diminished from near-unit values for D0D to 0.29 for D0CC. Furthermore, dissolution experiments under non-sink conditions showed improved performance of CTD-CAF compared with pure CTD. Subsequent studies showed that CTD-CAF cocrystals transform to CTD form I where CTD precipitation inhibition could be achieved in the presence of pre-dissolved polymer HPMC 80–120 cPs, maintaining supersaturation drug concentrations for at least 180 min. Finally, dissolution experiments under sink conditions unveiled that the CTD-CAF cocrystal induced, in pH-independent manner, faster and more complete CTD dissolution when compared to commercial tablets of CTD. Due to the stability and dissolution behavior of the novel CTD-CAF cocrystal, it could be used to develop solid dosage forms using a lower CTD dose to obtain the same therapeutic response and fewer adverse effects.
Novel fluorescent dendrimers of first, second, and third generation bearing a conjugated oligo(phenylenevinylene) (OPV) core and peripherial allyl chains as dendrons have been synthesized by a convergent method. The compounds have been fully characterized by 1H, 13C NMR, FTIR, UV-vis, and fluorescence spectroscopy, MALDI-TOF or FAB+ mass spectroscopy and elemental analysis. All dendrimers showed in solution a blue fluorescence with a maximum wavelength at 444-446 nm and can be deposited as thin films emitting in the blue-green region. The most homogeneous films were obtained for the second generation dendrimer which also exhibits the higher quantum yield in solution. These properties make it a possible candidate for application in organic light emitting diodes (OLEDs).
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