Three structurally similar antibiotics of the cephalosporin (CEPH) class, namely, cephalexin (CPX), cephradine (CFD), and cefaclor (CFC), have been co-crystallized with thymol (THY) via different preparation techniques, yielding the hydrated co-crystals CPX·THY·2.5H2O form I and form II, CFD·THY·2.5H2O, and CFC·THY·4H2O. All co-crystals were structurally characterized by single crystal and/or powder X-ray diffraction. In all co-crystals, except in the case of the elusive metastable form I of CPX·THY·2.5H2O, the CEPH molecules interact with thymol only via water bridges; i.e., there is no direct hydrogen bonding between CEPH molecules and THY. Preliminary antimicrobial experiments via measurements of minimal inhibitory concentration (MIC) provide clear-cut evidence that the association with thymol increases the resistance of both Gram-negative and Gram-positive bacteria to the antibiotic with respect to pure CEPH as well as to physical mixtures of CEPH with thymol.

Inhibition of the Antibiotic Activity of Cephalosporines by Co-Crystallization with Thymol

Fiore C.;Shemchuk O.;Sambri V.;Grepioni F.;Braga D.
2022

Abstract

Three structurally similar antibiotics of the cephalosporin (CEPH) class, namely, cephalexin (CPX), cephradine (CFD), and cefaclor (CFC), have been co-crystallized with thymol (THY) via different preparation techniques, yielding the hydrated co-crystals CPX·THY·2.5H2O form I and form II, CFD·THY·2.5H2O, and CFC·THY·4H2O. All co-crystals were structurally characterized by single crystal and/or powder X-ray diffraction. In all co-crystals, except in the case of the elusive metastable form I of CPX·THY·2.5H2O, the CEPH molecules interact with thymol only via water bridges; i.e., there is no direct hydrogen bonding between CEPH molecules and THY. Preliminary antimicrobial experiments via measurements of minimal inhibitory concentration (MIC) provide clear-cut evidence that the association with thymol increases the resistance of both Gram-negative and Gram-positive bacteria to the antibiotic with respect to pure CEPH as well as to physical mixtures of CEPH with thymol.
Fiore C.; Baraghini A.; Shemchuk O.; Sambri V.; Morotti M.; Grepioni F.; Braga D.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/862094
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