Equilibrium, structural and antibacterial characterization of moxifloxacin-β-cyclodextrin complex

Szabó, Zoltán‐István; Deme, Ruth; Mucsi, Zoltán; Rusu, Aura; Mare, Anca Delia; Fiser, Béla; Toma, Felicia; Sipos, Eszter; Tóth, Gergő

doi:10.1016/j.molstruc.2018.04.045

Cited by 31 publications

(22 citation statements)

References 28 publications

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“…However, this change was so small that it does not outweigh the benefit of the increased solubility of the HBA/M‐β‐CD complex. This change in antibacterial activity upon complexation is consistent with prior reports (Andrade et al, ; Duarte, Alves, Ferreira, Silva, & Domingues, ; Szabó et al, ). Of the positive controls, potassium sorbate did not show detectable antibacterial activity in the selected concentration range against all tested strains, while the antibacterial activity of penicillin and amoxicillin was lower than that of the inclusion complex in all tested strains except for B. cereus and S. paratyphi B .…”

Section: Resultssupporting

confidence: 92%

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Antibacterial activity of a hexahydro‐β‐acids/methyl‐β‐cyclodextrin inclusion complex against bacteria related to foodborne illness

Zhao

Liu

2019

Journal of Food Safety

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In this study, we investigated the antibacterial activity of hexahydro‐β‐acids/methyl‐β‐cyclodextrin inclusion complex (HBA/M‐β‐CD) and researched its antibacterial mechanism against Staphylococcus aureus and Enterobacter sakazakii. The result showed that bacteria had different sensitivities to HBA/M‐β‐CD with diameters of inhibition zones ranging from 7.8 ± 0.5 to 14.8 ± 0.7 mm and minimum inhibitory concentration (MIC) values from 16.25 to 65.00 μg/mL. Among these bacteria, S. aureus (G(+)) and E. sakazakii (G(−)) were most sensitive to HBA/M‐β‐CD, and MIC value is 16.25 and 32.50 μg/mL, respectively. Also, HBA/M‐β‐CD had potential inhibition effect on the bacterial growth of S. aureus and E. sakazakii. Moreover, the treatment with HBA/M‐β‐CD led to a release of cell contents into the culture medium, indicating damage to the plasma membrane. Scanning electron microscopy revealed permeabilization of S. aureus membranes, and shrinkage and roughening of E. sakazakii cells. HBA/M‐β‐CD also reduced the activity of succinate dehydrogenase (SDH) in bacterial cultures, indicating that HBA/M‐β‐CD interfere key enzyme metabolism. Practical Applications In the actual food system of western‐style ham sausage, HBA/M‐β‐CD revealed a great antibacterial effect to control the total bacteria count, and could stabilize the pH value. The result provided the theoretical and practical basis for the application of HBA/M‐β‐CD in foods.

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Section: Resultssupporting

confidence: 92%

“…Instead, E. sakazakii cells were seen to have shrunk, producing a ruffled appearance to their membranes. The difference in these two results is likely attributable to the difference in cell membrane structure between the gram‐positive S. aureus and the gram‐negative E. sakazakii (Sana, Datta, Biswas, & Sengupta, ; Szabó et al, ).…”

Section: Resultsmentioning

confidence: 99%

Antibacterial activity of a hexahydro‐β‐acids/methyl‐β‐cyclodextrin inclusion complex against bacteria related to foodborne illness

Zhao

Liu

2019

Journal of Food Safety

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“…Rhein‐β‐CD conjugates displayed a better inhibitory effect than Rhein against S. aqureus, Bacillus subtilis and E. coli (Liu, Lv, Liao, Zhao, & Yang, 2017). However, the encapsulation of β‐CD did not affect significantly the antibacterial activity of moxifloxacin (Szabo et al, 2018).…”

Section: Resultsmentioning

confidence: 99%

Development and physicochemical characterization of chitosan hydrochloride/sulfobutyl ether‐β‐cyclodextrin nanoparticles for cinnamaldehyde entrapment

Zhu

Guo

et al. 2020

J Food Biochem

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In this work, the cinnamaldehyde (CA) loaded nanoparticles were synthesized by directly cross‐linking chitosan hydrochloride (CSH) and sulfobutyl ether‐β‐cyclodextrin (SBE‐β‐CD). The CA/SBE‐β‐CD inclusion complex was firstly prepared, and its highest encapsulation efficiency (EE) was 86.34%. Field Emission Scanning Electron Microscope results indicated that the inclusion complex showed massive aggregates with a coarse and fluffy texture and irregular surface. Then, the inclusion complex interacted with CSH to form nanoparticles. The EE of CA in nanoparticles was improved. Atomic force microscopy showed the nanoparticles had regular and spherical morphology. Fourier transform infrared spectroscopy analysis demonstrated that CA was mainly encapsulated in the inner place of CSH/SBE‐β‐CD nanoparticles (CSNs). The enhanced thermal stability of the nanoparticles was found in differential scanning calorimeter. X‐ray diffraction implied that CA‐CSNs existed in the amorphous state. CA‐CSNs had excellent slow release property. Further, the bacteriostatic effect of CA‐CSNs was much better than that of CA and CSNs. All the results indicated that CSNs can be used as a promising carrier to encapsulate CA. Practical applications CA is an effective antimicrobial and generally recognized as Safe‐GRAS. CA also exhibits many other bioactivities and has been commonly used for digestive, cardiovascular and immune system diseases. However, CA is easy to be oxidized and volatilized during storage for poor water solubility. The nanoencapsulations display the capacities of enhancing solubility of bioactive compounds, protecting them from degradation, and prolonging their residence. In this manuscript, CA loaded nanoparticles were investigated. The results suggested that the nanoencapsulation could benefit for improving water solubility and stability of CA. This strategy could be helpful for its application and development in food preservation.

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“…Stability constants ( K ) of the inclusion complexes were calculated by non‐linear parameter fitting of Eq. to the δ obs versus [CD] T datasets using OriginPro 8 program based on previous works .…”

Section: Methodsmentioning

confidence: 99%

Chiral separation of rasagiline using sulfobutylether‐β‐cyclodextrin: capillary electrophoresis, NMR and molecular modeling study

et al. 2019

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Pressure‐assisted stereospecific capillary electrophoresis method was developed for the determination of enantiomeric purity of the antiparkinsonian agent (R)‐rasagiline. The optimized method, 50 mM glycine‐HCl buffer pH 2, supplied with 30 mM sulfobutylether‐β‐cyclodextrin, at 35°C, applying 12 kV in reversed polarity, and –8 mbar pressure (vacuum), short‐end injection with ‐25 mbar × 2 s, was successful for baseline separation of rasagiline enantiomers (Rs = 3.5 ± 0.1) in a short analysis time. The method was validated according to current guidelines and proved to be reliable, linear, precise and accurate for determination of 0.15% S‐enantiomer as chiral impurity in R‐rasagiline sample, as well as quantification of the eutomer. Method application was tested on a commercial tablet formulation. Determination of spatial structure of diastereomeric associates was based on 1H and 2D ROESY NMR, indicating that the aromatic moiety of the molecule can enter the cyclodextrin cavity. NMR titration and molecular modeling revealed that S‐rasagiline formed a more stable inclusion complex with sulfobutylether‐β‐cyclodextrin, than its antipode, which is in agreement with electrophoretic results.

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Equilibrium, structural and antibacterial characterization of moxifloxacin-β-cyclodextrin complex

Cited by 31 publications

References 28 publications

Antibacterial activity of a hexahydro‐β‐acids/methyl‐β‐cyclodextrin inclusion complex against bacteria related to foodborne illness

Antibacterial activity of a hexahydro‐β‐acids/methyl‐β‐cyclodextrin inclusion complex against bacteria related to foodborne illness

Development and physicochemical characterization of chitosan hydrochloride/sulfobutyl ether‐β‐cyclodextrin nanoparticles for cinnamaldehyde entrapment

Chiral separation of rasagiline using sulfobutylether‐β‐cyclodextrin: capillary electrophoresis, NMR and molecular modeling study

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