Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Banik, Abhijit; Gogoi, Paramartha; Saikia, Monali Dutta

doi:10.1007/s10847-011-0014-7

Cited by 18 publications

(11 citation statements)

References 53 publications

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“…The modified ␤-CD using 8-hydroxy quinoline possibly changed the ␤-CD cavity space and reduced the hydrogen bonding ef- fect of ␤-CD. This result was in agreement with the previous report [38]. MAA-MIP-A was synthesized by CDS (as supporting matrix) and MAA-MIP-B was synthesized by TsCDS (as supporting matrix).…”

Section: Binding Affinity Of Mipssupporting

confidence: 93%

“…S2B‐a, b). The typical features of β‐CD and GOTMS were presented by the peaks around 2928.93 and 2866.45 cm −1 , representing CH 2 and CH 3 stretching vibrations, respectively . As CDS was synthesized by β‐CD reaction with GOTMS and silica gel (Supporting Information Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Because the cavity of ␤-CD and template prometryne was relatively hydrophobic compared to water, the hydrophobic effect was increased with the water applied in the solvent. More template molecules have been driven into the cavities of MIPs [38,39]. The higher level of MAA-MIP-C adsorption for prometryne was observed at methanol/water (20:80, v/v) ( Fig.…”

Section: Influence Of Methanol and Water Ratio On Adsorptionmentioning

confidence: 99%

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Development of a molecularly imprinted polymer for prometryne clean-up in the environment

Miao

Geng

et al. 2013

J. Sep. Science

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Molecularly imprinted polymers (MIPs) are prepared on the surface of modified silica gel using prometryne as a template, methacrylic acid as the functional monomer, ethylene glycol dimethacrylate as a crosslinker, and 2,2-azobisisobutyronitrile as an initiator. The structure of the MIPs was characterized using SEM and FTIR spectroscopy. The selectivity of the MIPs for the template molecule prometryne was proven by adsorption experiments. Highly selective SPE cartridges of MIP particles were developed and an optimized prometryne procedure was developed for the enrichment and clean-up of prometryne residues in water, soil, and wheat samples. The concentrations of prometryne in the samples were analyzed by HPLC. The average recoveries of prometryne spiked for water at 0.05∼0.8 mg/L were 101.47-106.65% and the RSD was 2.63-4.71%. The average recoveries of prometryne spiked for soil at 0.05∼0.8 mg/L were 87.34-94.91% with the RSD being 2.77-8.41%. The average recoveries of prometryne spiked for wheat plant at 0.2∼2.0 mg/kg were 91.04-97.76% with the RSD being 6.53-10.69%. The method developed here can be regenerated and repeatedly used more than two dozen times.

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Section: Binding Affinity Of Mipssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Influence Of Methanol and Water Ratio On Adsorptionmentioning

confidence: 99%

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Development of a molecularly imprinted polymer for prometryne clean-up in the environment

Miao

Geng

et al. 2013

J. Sep. Science

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“…Apart from parent CDs its alkylated derivatives, e.g. 2-hydroxy propyl-β-CD (HP-β-CD) (Fig 1c), have also attracted growing interest due to their improved complexation efficiency, greater water solubility and less toxicity [3]. Inclusion complex formation with CDs is an approach to improve the aqueous solubility via molecular encapsulation of the drug within the cavity of the more soluble CD molecule [2,21].…”

Section: Scanning Electron Microscopy (Sem) and Thickness Measurementsmentioning

confidence: 99%

Electrospun Thermoplastic Polyurethane Mats Containing Naproxen– Cyclodextrin Inclusion Complex

Akduman

Özgüney

Kumbasar

2014

Autex Research Journal

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Incorporation of cyclodextrins (CDs) into electrospun nanofibrous materials can be considered as potential candidates for functional medical textile applications. Naproxen (NAP) is a type of non-steroidal anti-inflammatory drug commonly administered for the treatment of pain, inflammation and fever. Drug-inclusion complex formation with CDs is an approach to improve the aqueous solubility via molecular encapsulation of the drug within the cavity of the more soluble CD molecule. In this study, NAP or different NAP-CD inclusion complexes loaded nanofibres were successfully produced through electrospinning and characterised. The inclusion complex loaded mats exhibited significantly faster release profiles than NAP-loaded thermoplastic polyurethane (TPU) mats. Overall, NAP-inclusion complex loaded TPU electrospun nanofibres could be used as drug delivery systems for acute pain treatments since they possess a highly porous structure that can release the drug immediately.

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“…So far, many experimental methods were used to investigate the inclusion interaction of HP‐β‐CD and its guest, such as ultraviolet–visible (UV–vis), Fourier transform infrared (FTIR), fluorescence, circular dichroism, calorimetry, and nuclear magnetic resonance (NMR). [ 12–14 ] Most of the published papers mainly reported the inclusion interaction between CD and one guest molecule using various characterization methods. [ 15,16 ] However, the relationship between the separation factors of a large number of chiral drugs when enantioseparated in enantioselective liquid–liquid extraction and their inclusion constants with CD is rarely discussed.…”

Section: Introductionmentioning

confidence: 99%

Spectral study on inclusion interaction and enantiorecognition of 2‐aryl carboxylic acids with hydroxypropyl‐β‐cyclodextrin

Jin

Sun

et al. 2020

Chirality

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The inclusion interaction between hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) and 21 2‐aryl carboxylic acids was investigated by UV (ultraviolet) spectrophotometer. The inclusion constant of each 2‐aryl carboxylic acids with HP‐β‐CD was determined by Benesi–Hildebrand's equation. According to our previous work, it was found that a high inclusion constant for inclusion complex formed by a racemate and cyclodextrin was always observed with the fact that a high enantioseparation factor was achieved for the racemate in enantioseparation by liquid–liquid chromatography, which suggested that high binding combination between racemate and cyclodextrin is very important for a successful enantioseparation in enantioselective liquid–liquid extraction. Among all the studied subjects, mandelic acid enantiomer, 2,3‐diphenylpropionic acid enantiomer, and naproxen enantiomer were selected for the further study. The inclusion constants of enantiomers of these three subjects were determined by UV spectra, which indicated that a necessary difference in inclusion constants between enantiomer and cyclodextrin was also essential. It was found in UV spectra that the absorbance of the analytes with the addition of cyclodextrin would increase or decrease, which was determined by the type of electron excitation. The conformation changes of small molecules can lead to the changes of chromophore valence electron clouds distribution, causing the HOMO‐LUMO energy difference decreased. Thus, a red shift of the wavelength of the maximum absorption was produced indicating that the possibility of the molecular interaction of enantiomers with HP‐β‐CD exists.

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Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: experimental and molecular modeling studies

Cited by 18 publications

References 53 publications

Development of a molecularly imprinted polymer for prometryne clean-up in the environment

Development of a molecularly imprinted polymer for prometryne clean-up in the environment

Electrospun Thermoplastic Polyurethane Mats Containing Naproxen– Cyclodextrin Inclusion Complex

Spectral study on inclusion interaction and enantiorecognition of 2‐aryl carboxylic acids with hydroxypropyl‐β‐cyclodextrin

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