Cyclodextrin modulation of gallic acid in vitro antibacterial activity

The substitution of large spectrum antibiotics for natural bioactive molecules (especially polyphenolics) for the treatment of wound infections has come into prominence in the pharmaceutical industry. However, the use of such molecules depends on their stability during environmental stress and on their ability to reach the action site without losing biological properties. The application of cyclodextrins as a vehicle for polyphenolics protection has been documented and appears to enhance the properties of bioactive molecules. Therefore, the encapsulation of gallic acid, an antibacterial agent with low stability, by -cyclodextrin, (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin, was investigated. Encapsulation by -cyclodextrin was confirmed for pH 3 and 5, with similar stability parameters. The (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin interactions with gallic acid were only confirmed at pH 3. Among the three cyclodextrins, better gallic acid encapsulation were observed for (2-hydroxy) propyl--cyclodextrin, followed by -cyclodextrin and methyl--cyclodextrin. The effect of cyclodextrin encapsulation on the gallic acid antibacterial activity was also analysed. The antibacterial activity of the inclusion complexes was investigated here for the first time. According to the results, encapsulation of gallic acid by (2-hydroxy) propyl--cyclodextrin seems to be a viable option for the treatment of skin and soft tissue infections, since this inclusion complex has good stability and antibacterial activity.The authors are grateful for the FCT Strategic Project PEst-OE/EQB/LA0023/2013 and the Project "BioHealth-Biotechnology and Bioengineering approaches to improve health quality", Ref. NORTE-07-0124-FEDER-000027, co-funded by the "Programa Operacional Regional do Norte" (ON.2-O Novo Norte), QREN, FEDER. The authors also acknowledge the project "Consolidating Research Expertise and Resources on Cellular and Molecular Biotechnology at CEB/IBB", Ref. FCOMP-01-0124-FEDER-027462. This work is, also, funded by FEDER funds through the Operational Programme for Competitiveness Factors-COMPETE and National Funds through FCT-Foundation for Science and Technology under the project PEst-C/CTM/UI0264/2011. Additionally, the authors would like to thank the FCT for the grant for E. Pinho (SFRH/BD/62665/2009)

Adsorption properties of β- and hydroxypropyl-β-cyclodextrins cross-linked with epichlorohydrin in aqueous solution. A sustainable recycling strategy in textile dyeing process

β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) were used to prepare insoluble polymers using epichlorohydrin as a cross-linking agent and the azo dye Direct Red 83:1 was used as target adsorbate. The preliminary study related to adsorbent dosage, pH, agitation or dye concentration allowed us to select the best conditions to carry out the rest of experiments. The kinetics was evaluated by Elovich, pseudo first order, pseudo second order, and intra-particle diffusion models. The results indicated that the pseudo second order model presented the best fit to the experimental data, indicating that chemisorption is controlling the process. The results were also evaluated by Freundlich, Langmuir and Temkin isotherms. According to the determination coefficient (R 2 ), Freunlich gave the best results, which indicates that the adsorption process is happening on heterogeneous surfaces. One interesting parameter obtained from Langmuir isotherm is q max (maximum adsorption capacity). This value was six times higher when a β-CDs-EPI polymer was employed. The cross-linked polymers were fully characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), thermal gravimetric analysis (TGA). Also, morphology and particle size distribution were both assessed. Under optimized conditions, the β-CDs-EPI polymer seems to be a useful device for removing Direct Red 83:1 (close 90%), from aqueous solutions and industrial effluents. Complementarily, non-adsorbed dye was photolyzed by a pulsed light driven advanced oxidation process. The proposed methodology is environmental and economically advantageous, considering the point of view of a sustainable recycling economy in the textile dyeing process

Inclusion complexes of rosmarinic acid and cyclodextrins: stoichiometry, association constants, and antioxidant potential

The interaction between beta-cyclodextrin (beta-CD) and the polyphenol rosmarinic acid (RA) is here reported by H-1 NMR titration experiments. The formation of an aqueous soluble inclusion complex is confirmed and valuable information regarding mode of penetration of guest into beta-CD, stoichiometry, and stability of the complex is obtained. The analysis by the continuous variation method shows the undoubted formation of 1:1 beta-CD/RA complex. Additionally, the estimated apparent association constants reveal the importance of the asymmetry of the RA in the complexation; the incorporation of the catechol moiety closer to the carboxylic group is more favorable (K = 2,028 M-1) than from the other end of the RA molecule (K = 1,184 M-1). Finally, we have also investigated the antioxidant activity and storage stability of the beta-CD/RA complexed system; the presence of beta-CD was found to produce a remarkable enhancement on the antioxidant activity