Inclusion complexes of sulphanilamide drugs and β-cyclodextrin: a theoretical approach

Venkatesh, G.; Sivasankar, Thirugnanasambandam; Karthick, M.; Rajendiran, N.

doi:10.1007/s10847-012-0248-z

Cited by 33 publications

(11 citation statements)

References 34 publications

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“…DSC and thermogravimetric analysis are complementary techniques that have been used to characterize thermal properties of polymeric and other host–guest systems. , Changes in the enthalpy of dehydration of the host due to displacement of cavity water have been used to indicate formation of host–guest complexes . The DSC thermograms of the native β-CD hydrate, the 1:1, and 2:1 β-CD/PFBA ICs are depicted in Figure .…”

Section: Resultsmentioning

confidence: 99%

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorobutyric Acid

et al. 2014

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The structural characterization of solid- and solution-state inclusion complexes (ICs) of β-cyclodextrin (β-CD; host) with perfluorobutyric acid (PFBA; guest) is presented in this study. Complexes in the solid state were prepared at various host/guest mole ratios (i.e., 1:1 and 2:1) using a modified dissolution method. Thermal analyses and multinuclear 13C NMR methods employing direct polarization (DP) and cross-polarization (CP) techniques with magic angle spinning (MAS) and high-power 1H/19F decoupling were used to characterize the solid-state host–guest complexes. Unequivocal evidence of the formation of β-CD/PFBA inclusion compounds was provided using 19F → 13C CP/MAS NMR results. Powder X-ray diffraction reveals that PFBA forms a “cage-type” structure with β-CD, in which the guest adopts gauche and near-linear conformations in the 1:1 and 2:1 complexes, respectively, according to Fourier transform infrared spectroscopy results. Interpretation of the NMR splitting patterns of PFBA spectrum in solution reveals that PFBA undergoes fast rotation of the CF3 group on a 3-fold axis, while the remainder of the chain experiences a significant C–C bond rotation; hence, it is not locked in a particular rotamer configuration. The distribution of the rotational and axial motions in the β-CD/PFBA complexes in the solid state as revealed by NMR relaxation dynamic studies is a function of the host/guest mole ratios and is determined by the binding geometry of the guest.

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Section: Resultsmentioning

confidence: 99%

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorobutyric Acid

et al. 2014

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“…The calculated quantum chemical parameters [52][53][54] such as frontier molecular orbitals (HOMO and LUMO), HOMO-LUMO energy gap, dipole moment (µ) [55] and the percentage of variation of HOMO-LUMO gap |ΔE g | [56,57] can be useful for rationalizing the electronic properties of both γ-CD and the formed inclusion complex BaP/γ-CD. The computed values for these quantities are listed in Table 2.…”

Section: Electronic and Sensing Properties Of γ-Cd Towards Bapmentioning

confidence: 99%

Molecular DFT Investigation on the Inclusion Complexation of Benzo[a]pyrene with γ-Cyclodextrin

Mesri¹,

Belhocine²,

Messikh³

et al. 2021

MHC

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The complexation process between benzo[a]pyrene (BaP) and γ-cyclodextrin (γ-CD) was computationally studied using DFT methodology. Several initial configurations of the interaction of BaP with γ-CD were explored to determine the most stable inclusion complex. According to the calculated complexation energies, the BaP/γ-CD complex is found to be the most favorable energetically when the BaP guest is totally entrapped into γ-CD cavity. The inclusion process involving the encapsulation of two guests BaP in the cavity of γ-CD is also thermodynamically favored. Van der Waals interactions play a determinant role in stabilizing BaP/γ-CD and 2BaP/γ-CD complexes.

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“…In the last decade, CDs have been widely used to form inclusion complexes with various drugs for different purposes, the investigation of such interaction with unstudied drugs or existing ones is of great importance; this includes the subject of this work, namely triterpenes acid-based drugs [ 12 - 13 ] . Among the CDs, β-CD is the most commonly used, based on its low cost, availability, and complex-forming capacity.…”

Section: Introductionmentioning

confidence: 99%

Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study

et al. 2017

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Ursolic acid (UA) and oleanolic acid (OA) are insoluble drugs. The objective of this study was to encapsulate them into β-cyclodextrin (β-CD) and compare the solubility and intermolecular force of β-CD with the two isomeric triterpenic acids. The host-guest interaction was explored in liquid and solid state by ultraviolet-visible absorption,1 H NMR, phase solubility analysis, and differential scanning calorimetry, X-ray powder diffractometry, and molecular modeling studies. Both experimental and theoretical studies revealed that β-CD formed 1: 1 water soluble inclusion complexes and the complexation process was naturally favorable. In addition, the overall results suggested that ring E with a carboxyl group of the drug was encapsulated into the hydrophobic CD nanocavity. Therefore, a clear different inclusion behavior was observed, and UA exhibited better affinity to β-CD compared with OA in various media due to little steric interference, which was beneficial to form stable inclusion complex with β-CD and increase its water solubility effectively.

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Inclusion complexes of sulphanilamide drugs and β-cyclodextrin: a theoretical approach

Cited by 33 publications

References 34 publications

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorobutyric Acid

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorobutyric Acid

Molecular DFT Investigation on the Inclusion Complexation of Benzo[a]pyrene with γ-Cyclodextrin

Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study

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