Natural Antimicrobials Meet a Synthetic Antibiotic: Carvacrol/Thymol and Ciprofloxacin Cocrystals as a Promising Solid-State Route to Activity Enhancement

Crystal Growth & Design, Год журнала: 2020, Номер 20(10), С. 6796 - 6803

Опубликована: Авг. 21, 2020

The antibiotic ciprofloxacin (CIP) zwitterion has been cocrystallized via slurry and/or ball-milling with carvacrol (CAR) and thymol (THY), also known to exert antimicrobial activity, the aim of improving antibacterial activity ciprofloxacin. In case CAR, 1:4 cocrystal CIP·CAR4 appears be most stable phase, where intermediate phases CIP·CAR3 CIP·CAR2 have isolated by stepwise loss CAR. THY, 1:2 CIP·THY2 is stable, while CIP·THY4 easily loses THY yield bisadduct. All cocrystals were structurally characterized single crystal or powder diffraction: in both sheets CIP molecules are intercalated layers CAR respectively, that can released upon heating as followed DSC, TGA variable temperature XRPD. Preliminary experiments provide encouraging evidence enhanced against Escherichia coli (ATCC 25922) respect pure well physical mixtures thymol.

Язык: Английский

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On the Mechanism of Cocrystal Mechanochemical Reaction via Low Melting Eutectic: A Time-Resolved In Situ Monitoring Investigation

Crystal Growth & Design, Год журнала: 2022, Номер 22(7), С. 4260 - 4267

Опубликована: Июнь 1, 2022

Mechanochemistry has become a sustainable and attractive cost-effective synthetic technique, largely used within the frame of crystal engineering. Cocrystals, namely, crystalline compounds made different chemical entities same structure, are typically synthesized in bulk via mechanochemistry; however, whereas macroscopic aspects grinding becoming clear, fundamental principles that underlie mechanochemical cocrystallization at microscopic level remain poorly understood. Time-resolved situ (TRIS) monitoring approaches have opened door to exceptional detail regarding reactions. We here report clear example between two solid coformers proceeds through formation metastable low melting binary eutectic phase. The overall process been monitored by time-resolved synchrotron X-ray powder diffraction with customized ball milling setup, currently available μSpot beamline BESSY-II, Helmholtz-Zentrum Berlin. system phase were further characterized DSC, HSM, VT-XRPD.

Язык: Английский

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Self-assembled thymol-betaine co-crystals with controlled release and hygroscopic properties as green preservatives for aflatoxin prevention

Food Chemistry, Год журнала: 2024, Номер 456, С. 140037 - 140037

Опубликована: Июнь 8, 2024

Язык: Английский

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On the entropy cost of making solvates

Chemical Communications, Год журнала: 2020, Номер 56(38), С. 5127 - 5130

Опубликована: Янв. 1, 2020

We present a simple way of estimating the entropy cost solvate formation in crystals. The penalty making solvates can be as low <1 kJ mol-1 or high >9 and is entirely dependent on nature liquid component temperature formation. A link found between higher likelihood for solvent to make solvates.

Язык: Английский

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Systematic coformer contribution to cocrystal stabilization: energy and packing trends

CrystEngComm, Год журнала: 2020, Номер 22(43), С. 7341 - 7349

Опубликована: Янв. 1, 2020

CSD data mining and energy calculations show that coformer self-interactions might significantly contribute to the packing stabilization of cocrystals.

Язык: Английский

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