Inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin in solid phase

Bongiorno, David; Ceraulo̊, Leopoldo; Ferrugia, Mirella; Filizzola, Felice; Ruggirello, Angela; Liveri, Vincenzo Turco

doi:10.3998/ark.5550190.0006.e14

Cited by 20 publications

(12 citation statements)

References 19 publications

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“…Generally a shift in the frequency is observed due to the phenomenon. 26,27 Fig. 3(A) and (B) demonstrate the FT-IR spectra of the individual probes (2 and 3), g-CD and probe-CD complex.…”

Section: Evidence Of Hydrogen Bond Formation In the Guest-host Complexesmentioning

confidence: 99%

“Extra stabilisation” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state

Ghosh

Mandal

Das

et al. 2012

Phys. Chem. Chem. Phys.

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Two thiosemicarbazide and semicarbazide functionalized pyrene labeled Schiff base compounds have been synthesized. The pyrene moieties in the compounds result in formation of π-π coupled complexes in aqueous medium in the excited electronic state. Added γ-cyclodextrin allows incorporation of the pyrene head inside its less polar core and promotes hydrogen bonding of the thio and oxo groups of the compounds with its rim hydroxyl groups to "stabilise" the monomers. This is confirmed by FT-IR and absorption spectroscopy. The stabilised monomers lead to formation of stabilised excimers as monitored by steady state and time-resolved fluorescence spectroscopy through varying the experimental conditions. The proposed model for the stabilisation of the Schiff base monomers has been evidenced by comparing with the fluorescence spectroscopic changes of two control compounds. The present work reports a step ahead toward proposing a simple host-guest method to extra stabilise the pyrene based excimers that can be biologically utilised.

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“…Generally a shift in the frequency is observed due to the phenomenon. 26,27 Fig. 3(A) and (B) demonstrate the FT-IR spectra of the individual probes (2 and 3), g-CD and probe-CD complex.…”

Section: Evidence Of Hydrogen Bond Formation In the Guest-host Complexesmentioning

confidence: 99%

“Extra stabilisation” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state

Ghosh

Mandal

Das

et al. 2012

Phys. Chem. Chem. Phys.

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“…The broad-band obtained at the 3400−3300 cm −1 region may be due to the formation of extended noncovalent interactions among the carbonic group of the carboxyl group attached with the quarternized N atom of the heterocycle and O−H groups of the outer rim of β-CD (Scheme 3). 32 Additionally, the fact that there was no change in the IR peaks of the benzimidazole ring proves that the benzimidazolium part of ILs remains outside of the CD cavity. Moreover, a large shift of the alkyl −C−H stretching vibrational band frequency for −CH 3 and −CH 2 of the alkyl part in the case of B8 and B10 over the pure ILs indicates that the alkyl chains in ILs move in the inner cavity by van der Waals (vdW) noncovalent hydrophobic−hydrophobic interaction, in the hydrophobic interior of cyclodextrin.…”

Section: Ft-ir Analysismentioning

confidence: 83%

“…van der Waals forces of interactions, the liberation of CD strain energy, and geometric compatibility are significant factors for the complexation. For the current explored three systems, hydrophobic interaction for surface-active ILs [C 6 CFBim]Br, [C 8 CFBim]Br, and [C 10 CFBim]Br and β-CD can form channel-type structure. ,,− …”

Section: Resultsmentioning

confidence: 99%

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Insights into the Formations of Host–Guest Complexes Based on the Benzimidazolium Based Ionic Liquids−β-Cyclodextrin Systems

et al. 2021

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Inclusion complexation is one of the best strategies for developing a controlled release of a toxic drug without unexpected side effects from the very beginning of the administration to the target site. In this study, three benzimidazolium based ionic liquids (ILs) having bromide anion and cation bearing long alkyl chains, hexyl-([C 6 CFBim]Br), octyl-([C 8 CFBim]Br), and decyl-([C 10 CFBim]Br) were designed and synthesized as antibacterial drugs. Inclusion complexes (ICs) of studied ILs have been prepared by the combination of β-cyclodextrin (β-CD), considering these conjugations should enhance the benignity of ILs and make them potential candidates for the controlled drug release. Characterizations and structural analysis of studied ICs have been performed by 1 H NMR, 2D-ROESY NMR, FT-IR, HRMS, TGA, DSC, surface tension, ionic conductivity, dynamic light scattering (DLS), and isothermal titration calorimetry (ITC). Further, the morphology of the ICs has been analyzed by SEM and TEM. Furthermore, neat ILs and ICs have been treated against Escherichia coli and Bacillus subtilis to investigate their antibacterial activity, which confirms the prevention of bacterium growth and the shrinkage of the bacterial cell wall. The findings of this work provide the proof of concept that studied benzimidazolium based ILs-β-CD host−guest complexes should act as a potential candidate in controlled drug delivery and other biomedical applications.

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“…In addition, the peak at around 2900 cm −1 on PVA spectrum was observed due to CH/CH 2 bonding [48]. When the FT-IR spectrum of β–CD was observed in Figures 3, the broad peak around the wavelength of 3300 cm −1 (OH stretching) and the characteristic peaks of β–CD were observed at around 1000–1200 cm −1 assigned to the coupled C−C/C−O stretching vibrations and the asymmetric stretching vibration of the C−O−C glycosidic bridge [49,50].…”

Section: Resultsmentioning

confidence: 99%

Functionalized polyvinyl alcohol nanofiber webs containing β–cyclodextrin/Vitamin C inclusion complex

Okur

Sarıçam

Göcek

et al. 2019

Journal of Industrial Textiles

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In the present study, the electrospinning method was used to develop β–cyclodextrin functionalized polyvinyl alcohol nanofiber webs. The electrospinning parameters were adjusted in order to obtain uniform nanofiber webs by incorporation of varying concentrations of polyvinyl alcohol and β–cyclodextrin in the solutions. Subsequently, β–cyclodextrin/Vitamin C inclusion complexes were added into the polyvinyl alcohol solution, and adjusted parameters were used in the electrospinning process of functionalized polyvinyl alcohol nanofiber webs containing β–cyclodextrin/Vitamin C inclusion complexes. The formation of nanofiber webs was demonstrated by using Scanning Electron Microscopy. The presence of the inclusion complex in the functionalized electrospun polyvinyl alcohol nanofiber webs was proven by using ultraviolet–visible spectroscopy and Fourier Transform-Infrared Spectroscopy. Consequently, it was achieved to functionalize polyvinyl alcohol electrospun nanofiber webs by incorporating β–cyclodextrin/Vitamin C inclusion complex, which might be considered to have useful applications in cosmetics, personal-care products, and topical drug delivery.

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Inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin in solid phase

Cited by 20 publications

References 19 publications

“Extra stabilisation” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state

“Extra stabilisation” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state

Insights into the Formations of Host–Guest Complexes Based on the Benzimidazolium Based Ionic Liquids−β-Cyclodextrin Systems

Functionalized polyvinyl alcohol nanofiber webs containing β–cyclodextrin/Vitamin C inclusion complex

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