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Effect of Methyl-β-Cyclodextrin on the antimicrobial activity of a new series of poorly water-soluble benzothiazoles

Trapani, Adriana, Catalano, Alessia, Carocci, Alessia, Carrieri, Antonio, Mercurio, Annalisa, Rosato, Antonio, Mandracchia, Delia, Tripodo, Giuseppe, Schiavone, Brigida Immacolata Pia, Franchini, Carlo, Mesto, Ernesto, Schingaro, Emanuela, Corbo, Filomena
Carbohydrate polymers 2019 v.207 pp. 720-728
Fourier transform infrared spectroscopy, X-ray diffraction, antibacterial properties, differential scanning calorimetry, dispersions, molecular models, water solubility
The antibacterial activity of the S-unsubstituted- and S-benzyl-substituted-2-mercapto-benzothiazoles 1-4 has been evaluated after complexation with Methyl-β-Cyclodextrin (Me-β-CD) or incorporation in solid dispersions based on Pluronic® F-127 and compared with that of the pure compounds. This with the aim to gain further insights on the possible mechanism(s) involved in the CD-mediated enhancement of antimicrobial effectiveness, a promising methodology to overcome the microbial resistance issue. Together with Differential Scanning Calorimetry, FT-IR spectroscopy and X-ray Powder Diffraction investigations, a molecular modeling study focused on compounds 2 and 4 showed that the S-unsubstituted compound 2/Me-β-CD complex should be more stable than S-benzyl-substituted 4/Me-β-CD. Only for 1/Me-β-CD or, particularly, 2/Me-β-CD complexes, the antibacterial effectiveness was enhanced in the presence of selected bacterial strains. The results herein presented support the mechanisms focusing on the interactions of the bacterial membrane with CD complexes more than those focusing on the improvement of dissolution properties consequent to CD complexation.