Physicochemical Characterization and Cytotoxic Activity Evaluation of Hydroxymethylferrocene:β-Cyclodextrin Inclusion Complex

Iacovino, Rosa; Caso, Jolanda Valentina; Rapuano, Filomena; Russo, Alessio; Isidori, Marina; Lavorgna, Margherita; Malgieri, Gaetano; Isernia, Carla

doi:10.3390/molecules17056056

Cited by 29 publications

(25 citation statements)

References 41 publications

(40 reference statements)

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“…These results suggest that the inclusion complex was formed between β-CD and HPPA. The K b can be obtained from absorbance data using the modified Benesi-Hildebrand [25,26] Equation (1):…”

Section: Resultsmentioning

confidence: 99%

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β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation

Iacovino

Rapuano

Caso

et al. 2013

IJMS

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The aptitude of cyclodextrins (CDs) to form host-guest complexes has prompted an increase in the development of new drug formulations. In this study, the inclusion complexes of pipemidic acid (HPPA), a therapeutic agent for urinary tract infections, with native β-CD were prepared in solid state by kneading method and confirmed by FT-IR and 1H NMR. The inclusion complex formation was also characterized in aqueous solution at different pH via UV-Vis titration and phase solubility studies obtaining the stability constant. The 1:1 stoichiometry was established by a Job plot and the inclusion mechanism was clarified using docking experiments. Finally, the antibacterial activity of HPPA and its inclusion complex was tested on P. aeruginosa, E. coli and S. aureus to determine the respective EC50s and EC90s. The results showed that the antibacterial activity of HPPA:β-CD against E. coli and S. aureus is higher than that of HPPA. Furthermore, HPPA and HPPA:β-CD, tested on human hepatoblastoma HepG2 and MCF-7 cell lines by MTT assay, exhibited, for the first time, antitumor activities, and the complex revealed a higher activity than that of HPPA. The use of β-CD allows an increase in the aqueous solubility of the drug, its bioavailability and then its bioactivity.

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“…These results suggest that the inclusion complex was formed between β-CD and HPPA. The K b can be obtained from absorbance data using the modified Benesi-Hildebrand [25,26] Equation (1):…”

Section: Resultsmentioning

confidence: 99%

“…Measurements of pH were performed using a calibrated CRISON pH-meter Basic 20. To conveniently calculate the K b , we needed to rearrange the Benesi-Hildebrand equation [25] into a straight line form [26] shown in the Equation (1).…”

Section: Methodsmentioning

confidence: 99%

β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation

Iacovino

Rapuano

Caso

et al. 2013

IJMS

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“…It has been reported previously that DX forms a 1:1 inclusion complex with HPBCD and its binding constant has been determined by several authors ranging between 2000 and 2500 M −1 (42,43). Stability constant values ranging between 100 and 1000 M −1 are considered ideal (44). Smaller values indicates weak interactions between the cyclodextrin and the drug while values higher than 1000 M -1 suggest that incomplete release of the drug from the inclusion complex will take place (44).…”

Section: Loading and Releasementioning

confidence: 99%

“…Stability constant values ranging between 100 and 1000 M −1 are considered ideal (44). Smaller values indicates weak interactions between the cyclodextrin and the drug while values higher than 1000 M -1 suggest that incomplete release of the drug from the inclusion complex will take place (44). The complex formed between HPBCD and DX fulfill all this requirements.…”

Section: Loading and Releasementioning

confidence: 99%

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

et al. 2019

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Hydrogels have been extensively investigated as a platform for drug delivery. However, their use for the delivery of hydrophobic drugs has been limited by their incompatibility with hydrophobic drug molecules. The chemical modification of the structure of the hydrogels to include hydrophobic moieties has been proven to be a good alternative to increase the stability and solubility of hydrophobic drugs in the polymer matrix of the hydrogel. The inclusion of hydroxypropyl-β-cyclodextrins (HPBCD) and Tween ® 85 (T85) within hydrogel matrices has the potential to improve hydrophobic drug loading and release. HPBCD have the ability to host hydrophobic drug molecules in their cone-like structure, forming inclusion complexes through host-guest interactions. On the other hand, T85 is an amphiphilic molecule and, consequently, has the potential to increase hydrophilic drug loading within the hydrogels. In the present work, a new type of hydrogel made from poly(methyl vinyl ether-co-maleic acid) (GAN) and poly(ethylene glycol) (PEG) containing T85 and HPBCD was synthesized for hydrophobic drug release. Hydrogels were based on GAN crosslinked (PEG) and HPBCD and/or T85 via an esterification reaction in the solid state (solvent free). The synthesised hydrogels were characterised using Fourier transform infrared (FTIR) spectroscopy, swelling studies and contact angle measurements. The hydrogels showed swellings ranging from 140 to 180%. The inclusion of T85 in the hydrogels improved the wettability of the materials. On the other hand, the inclusion of HPBCD within the hydrogels decreased the wettability as the contact angle between the hydrogels and water increased with the HPBCD content. Finally, the materials were loaded with an ophthalmic drug, dexamethasone (DX). HPBC-containing hydrogels showed a higher DX uptake and, consequently, they showed a higher capacity of DX release. On the other hand, T85 containing hydrogels did not show any improvement over the hydrogels containing only GAN and PEG. The hydrogels were able to provide sustained DX release over periods of 6 hours.

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“…The outstanding structure of b-CD allows other guest molecules to insert themselves into a hole without a covalent bond [21] to form an inclusion complex. [22][23] The inclusion complex can change the guest properties [24][25][26] such as thermal characteristics, solubility [27] or chemical stability. b-CD is used in agricultural, [28] textile, [29] food and cosmetics industries due to its hostguest properties.…”

Section: Introductionmentioning

confidence: 99%

Study on Triclosan/Cyclodextrin Inclusion Complex for Natural Rubber Antibacterial Agent

Srithongkham

Sokhuma

Udomkusonsri

et al. 2015

Macromolecular Symposia

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Summary: This research aims to prepare antibacterial rubber from a natural rubber (NR) composite. Calcium sulfate dihydrate (CaSO 4 Á 2H 2 O, CS), or gypsum, has been used as a non-reinforced filler for NR due to its low cost, abundant availability and non-toxicity. However, the dihydrate form cannot disperse well in the natural rubber matrix. In this study, the CS was converted to calcium sulfate anhydrite (AII) form by heat treatment. An antibacterial agent imparted antibacterial properties to the natural rubber composite. b-cyclodextrin /Triclosan inclusion complex (b-CD/TR IC) was prepared in this research and applied as antibacterial agent for natural rubber composite. The b-CD/TR IC prevents loss of the antibacterial agent during rubber processing. The natural rubber-filled calcium sulfate anhydrite composite (NR-AII) mixed with b-CD/TR IC clearly showed antibacterial activity against E. coli at b-CD/TR IC content of 6 phr and S. aureus at b-CD/TR IC content of 3 phr.

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Physicochemical Characterization and Cytotoxic Activity Evaluation of Hydroxymethylferrocene:β-Cyclodextrin Inclusion Complex

Cited by 29 publications

References 41 publications

β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation

β-Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Pipemidic Acid: Characterization and Bioactivity Evaluation

Poly(methyl vinyl ether-co-maleic acid) Hydrogels Containing Cyclodextrins and Tween 85 for Potential Application as Hydrophobic Drug Delivery Systems

Study on Triclosan/Cyclodextrin Inclusion Complex for Natural Rubber Antibacterial Agent

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