Comparative Study of the Inclusion Properties of ß-Cyclodextrins for Ketoprofen And Ibuprofen in Solution and in The Solid State

Mura, Paola; Bettinetti, Giampiero; Manderioli, A.; Faucci, Maria Teresa; Bramanti, G; Setti, Massimo

doi:10.1007/978-94-011-5448-2_71

Cited by 18 publications

(28 citation statements)

References 4 publications

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“…28 For all the investigated systems, the obtained K C values are reported in Table 2, where assuming S 0 = 2.4×10 −4 M, 28 we can observe that the (R)-enantiomer gives more stable inclusion complexes with respect to the (S)-enantiomer and to the racemate. Moreover, the relative CD complex stability for the two IBP enantiomers must be related to the pharmacological property of this drug system, for which only the (S)-form is biologically active and primarily responsible for the antiinflammatory activity of the drug Nevertheless, it has been shown that in aqueous media, CDs can form different kinds of both inclusion and noninclusion complexes besides giving rise to micellar-type Table 2 Stability constant K C and CE obtained for all the investigated inclusion complexes aggregates able to solubilize drugs.…”

Section: Resultsmentioning

confidence: 97%

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

et al. 2011

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The effects of chiral discrimination in inclusion complexes formed by native β-cyclodextrin and its substituted form (namely methyl-β-cyclodextrin) with racemate or pure enantiomers of the non-steroidal antiinflammatory drug ibuprofen have been investigated in water. Stability constants and complexation efficiency have been determined for these host-guest systems with a 1:1 molar ratio from phase solubility profiles, showing that in aqueous solution, methylated cyclodextrin is a better complex agent than native cyclodextrin, with more enhanced effects for the (R)-enantiomer. These results have been validated using NMR technique. In particular, 1 H NMR spectra in D 2 O show a splitting of the signals for the methyl group and the aromatic protons close to the asymmetric centre of the racemate ibuprofen included in cyclodextrin cavity.

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Section: Resultsmentioning

confidence: 97%

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

et al. 2011

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“…Several new types of research found the binding free energy between ibuprofen and β-CD was stronger than a complex of HP-β-CD and ibuprofen. [77,78] However, Mura get the HP-β-CD-solubilizing effectiveness for ibuprofen was more powerful than β-CD in aqueous solution. [78] Núñez-Agüero applied MM-GBSA method for enthalpy calculation of ibuprofen/β-CD complex.…”

Section: Quantum Mechanicsmentioning

confidence: 99%

“…[77,78] However, Mura get the HP-β-CD-solubilizing effectiveness for ibuprofen was more powerful than β-CD in aqueous solution. [78] Núñez-Agüero applied MM-GBSA method for enthalpy calculation of ibuprofen/β-CD complex. [79] Djemil et al [57] used different QM methods (e.g.…”

Section: Quantum Mechanicsmentioning

confidence: 99%

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

Abdolmaleki

Ghasemi

2017

Chem Biol Drug Des

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Cyclodextrin (CD) is a subset of the macrocyclic structural class, which is an important class of small organic agents that are useful functional excipients. They have wide range application possibilities in different fields of sciences such as material preparation, medicine, analytical chemistry, and separation processes. They are used widely in pharmaceutical formulations and drug delivery for increasing the water solubility of low soluble drugs and drug candidates. Due to the ring structure, they behave differently than smaller molecules and may be capable of hitting new classes of targets. A macrocyclic molecule presents varied functionality and stereochemical complexity in a pre-organized conformation of the ring structure. This can result in high selectivity and affinity for protein targets while conserving enough bioavailability to arrive at intracellular locations. Regardless of these valuable features, and the verified success of several marketed macrocycle drugs isolated from natural compounds, this class has been little explored in drug development. This study describes some of the key features of the CDs therapeutic discovery. Also, the application of computational chemistry approaches such as QSAR/QSPR, molecular docking, and molecular/quantum mechanics for modeling of CD-drug system is reviewed briefly. K E Y W O R D Sbioavailability, computational, cyclodextrin, drug design, drug discovery, macrocyclic, therapeutic

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“…Chemical shift differences may also occur when specific interactions are taking place between a drug and the amorphous matrix it is formulated in, and these interactions can be localized to certain moieties of the molecules involved, given that the resonances can be assigned properly. Examples of using solid-state NMR to study drug-matrix interactions can be found in [24,[33][34][35][36].…”

Section: Mobility and Dynamicsmentioning

confidence: 99%

Solid‐state NMR Spectroscopy

Lubach

Munson

2006

Polymorphism

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Comparative Study of the Inclusion Properties of ß-Cyclodextrins for Ketoprofen And Ibuprofen in Solution and in The Solid State

Cited by 18 publications

References 4 publications

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

Solid‐state NMR Spectroscopy

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