1. Effect of Methyl-β-Cyclodextrin on the antimicrobial activity of a new series of poorly water-soluble benzothiazoles
- Author
-
Alessia Catalano, Delia Mandracchia, Carlo Franchini, Adriana Trapani, Giuseppe Tripodo, Antonio Carrieri, Ernesto Mesto, Brigida Immacolata Pia Schiavone, Antonio Rosato, Annalisa Mercurio, Filomena Corbo, Alessia Carocci, and Emanuela Schingaro
- Subjects
Models, Molecular ,Staphylococcus aureus ,Polymers and Plastics ,Molecular model ,Drug Compounding ,Microbial Sensitivity Tests ,Poloxamer ,02 engineering and technology ,010402 general chemistry ,Antimicrobial agents ,Methyl-β-Cyclodextrin ,PF-127 ,X-ray powder diffraction ,Molecular modelling ,01 natural sciences ,Surface-Active Agents ,Differential scanning calorimetry ,Enterococcus faecalis ,Escherichia coli ,Materials Chemistry ,Benzothiazoles ,Dissolution ,chemistry.chemical_classification ,Cyclodextrin ,beta-Cyclodextrins ,Organic Chemistry ,021001 nanoscience & nanotechnology ,Antimicrobial ,Combinatorial chemistry ,Anti-Bacterial Agents ,0104 chemical sciences ,Membrane ,Solubility ,chemistry ,0210 nano-technology ,Antibacterial activity ,Powder diffraction ,Bacillus subtilis - Abstract
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.
- Published
- 2019