Analysis of the microcrystalline inclusion compounds of triclosan with beta-cyclodextrin and its tris-O-methylated derivative
authors Ramos, AI; Braga, TM; Fernandes, JA; Silva, P; Ribeiro-Claro, PJ; Paz, FAA; Lopes, MFS; Braga, SS
nationality International
journal JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
author keywords Inclusion compounds; TRIMEB; beta-CD; Antimicrobial activity; Environmental bacteria
keywords MOLYBDENOCENE DICHLORIDE CP2MOCL2; CAMBRIDGE STRUCTURAL DATABASE; C-13 CHEMICAL-SHIFTS; ENOYL-ACP REDUCTASE; SOLID-STATE; PLASMODIUM-FALCIPARUM; CRYSTAL-STRUCTURES; COMPLEXES; CHEMISTRY; POLYMERS
abstract Solid 1:1 inclusion compounds of triclosan with native and permethylated 6-cyclodextrin (beta-CD and TRIMEB) were prepared by co-crystallisation and co-evaporation, respectively, and studied by FT-IR and C-13{H-1} CP/MAS NMR spectroscopies, thermogravimetric analysis, X-ray diffraction and theoretical calculations. Results showed that triclosan inclusion into TRIMEB afforded an amorphous solid, whilst beta-CD triclosan is composed of microcrystals belonging to two different phases. In the phase featuring larger crystals, X-ray diffraction was carried out and the beta-CD host units, packing head-to-head in infinite channels, were refined; the geometry for the included but highly disordered triclosan molecules was assessed by theoretical calculations. The bacterial growth inhibitory action of the inclusion compounds was studied in comparison to that of pure triclosan on Gram-negative (Salmonella, Escherichia) and Gram-positive strains (Bacillus, Listeria, Enterococcus and Staphylococcus) typically associated with human pathologies, and also on environmental bacteria isolated from different soil and water sources. The antimicrobial activities obtained in the present work showed that, of the two CD hosts, TRIMEB brings the most favourable carrier effect: it reduced the toxicity of triclosan against some of the environmental strains and afforded slightly higher action against virulent strains. (C) 2013 Elsevier B.V. All rights reserved.
publisher ELSEVIER SCIENCE BV
issn 0731-7085
year published 2013
volume 80
beginning page 34
ending page 43
digital object identifier (doi) 10.1016/j.jpba.2013.02.033
web of science category Chemistry, Analytical; Pharmacology & Pharmacy
subject category Chemistry; Pharmacology & Pharmacy
unique article identifier WOS:000318748900005
link http://www.sciencedirect.com/science/article/pii/S0731708513001015
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