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Pharmaceutics
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Cyclodextrin-Based Drug Delivery System
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Cyclodextrin-Based Drug Delivery System

A special issue of Pharmaceutics (ISSN 1999-4923). This special issue belongs to the section "Drug Delivery and Controlled Release".

Deadline for manuscript submissions: closed (30 July 2020) | Viewed by 27707

Special Issue Editors

Dr. Ana Cristina Faria Ribeiro

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Guest Editor
Department of Chemistry, University of Coimbra, 3004 - 535 Coimbra, Portugal
Interests: transport properties; thermodynamic properties; electrolytes; polyelectrolytes; polymers; carbohydrates; drugs
Special Issues, Collections and Topics in MDPI journals
Dr. Ana Maria Telmo Dias Pereira Vicente Cabral

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Guest Editor
Faculty of Pharmacy, University of Coimbra, 3000-548 Coimbra, Portugal
Interests: pharmaceutical chemistry; organic synthesis; heterocycles; drugs; transport properties
Special Issues, Collections and Topics in MDPI journals
Emeritus Prof. Miguel Angel Esteso

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Guest Editor
1. Catholic University of Santa Teresa de Jesús de Ávila, 05005 Ávila, Spain
2. Department of Analytical Chemistry, Physical Chemistry and Chemical Engineering, University of Alcalá, 28805 Alcalá de Henares (Madrid), Spain
Interests: physical chemistry; (in)organic chemicals; drugs; wastewater treatment; food chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrin-based drug delivery systems have become important systems in fundamental and applied research due to their wide range of applications in pharmaceutical chemistry and human and veterinary medicine.

Cyclodextrins are among the most important carriers used in drug release systems for local anaesthetics and other pharmaceuticals. The basis for this popularity is the ability of these compounds to solubilize poorly soluble drugs, resulting in striking increases in their water solubilities and rates of diffusion.

However, despite the many reasons that justify the importance of these complex systems, our understanding of them has not yet been well-established. Moreover, the transport and thermodynamic behaviour of multicomponent chemical systems under physiological conditions are still poorly understood, even though this is a prerequisite for systems with safer and more effective anaesthetic formulations. Their characterization is, therefore, very important as it helps us to better understand their structure and the behavior of different drugs in aqueous solutions containing these macrocycles, supply scientific and technological communities with data on these important parameters in solution transport and thermodynamic processes, and to model them for practical applications.

Prof. Ana Cristina Faria Ribeiro
Prof. Ana Maria Telmo Dias Pereira Vicente Cabral
Emeritus Prof. Miguel Angel Esteso
Guest Editors

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Keywords

  • cyclodextrins
  • ionic and non-ionic drugs
  • transport properties
  • thermodynamic properties
  • salts.

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Published Papers (7 papers)

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Research

20 pages, 4958 KiB  
Article
Chitosan/Polycyclodextrin (CHT/PCD)-Based Sponges Delivering VEGF to Enhance Angiogenesis for Bone Regeneration
by Carla Palomino-Durand, Marco Lopez, Pierre Marchandise, Bernard Martel, Nicolas Blanchemain and Feng Chai
Pharmaceutics 2020, 12(9), 784; https://doi.org/10.3390/pharmaceutics12090784 - 19 Aug 2020
Cited by 11 | Viewed by 3562
Abstract
Vascularization is one of the main challenges in bone tissue engineering (BTE). In this study, vascular endothelial growth factor (VEGF), known for its angiogenic effect, was delivered by our developed sponge, derived from a polyelectrolyte complexes hydrogel between chitosan (CHT) and anionic cyclodextrin [...] Read more.
Vascularization is one of the main challenges in bone tissue engineering (BTE). In this study, vascular endothelial growth factor (VEGF), known for its angiogenic effect, was delivered by our developed sponge, derived from a polyelectrolyte complexes hydrogel between chitosan (CHT) and anionic cyclodextrin polymer (PCD). This sponge, as a scaffold for growth factor delivery, was formed by freeze-drying a homogeneous CHT/PCD hydrogel, and thereafter stabilized by a thermal treatment. Microstructure, water-uptake, biodegradation, mechanical properties, and cytocompatibility of sponges were assessed. VEGF-delivery following incubation in medium was then evaluated by monitoring the VEGF-release profile and its bioactivity. CHT/PCD sponge showed a porous (open porosity of 87.5%) interconnected microstructure with pores of different sizes (an average pore size of 153 μm), a slow biodegradation (12% till 21 days), a high water-uptake capacity (~600% in 2 h), an elastic property under compression (elastic modulus of compression 256 ± 4 kPa), and a good cytocompatibility in contact with osteoblast and endothelial cells. The kinetic release of VEGF was found to exert a pro-proliferation and a pro-migration effect on endothelial cells, which are two important processes during scaffold vascularization. Hence, CHT/PCD sponges were promising vehicles for the delivery of growth factors in BTE. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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18 pages, 5760 KiB  
Article
Development and Characterization of Orally Disintegrating Tablets Containing a Captopril-Cyclodextrin Complex
by Adina Magdalena Musuc, Valentina Anuta, Irina Atkinson, Vlad Tudor Popa, Iulian Sarbu, Constantin Mircioiu, Ghaleb Abdalameer Abdalrb, Mirela Adriana Mitu and Emma Adriana Ozon
Pharmaceutics 2020, 12(8), 744; https://doi.org/10.3390/pharmaceutics12080744 - 7 Aug 2020
Cited by 30 | Viewed by 3767
Abstract
Captopril is the first angiotensin I-converting enzyme inhibitor widely used for the treatment of hypertension. Based on the well-known benefits of cyclodextrin inclusion complexes, the present study investigated the ability of β-cyclodextrin to include captopril. Solid inclusion complexes of captopril with β–cyclodextrin in [...] Read more.
Captopril is the first angiotensin I-converting enzyme inhibitor widely used for the treatment of hypertension. Based on the well-known benefits of cyclodextrin inclusion complexes, the present study investigated the ability of β-cyclodextrin to include captopril. Solid inclusion complexes of captopril with β–cyclodextrin in a 1:2 molar ratio were prepared by using the paste method of complexation. For comparison purposes, a simple physical mixture with the same molar ratio was also prepared. Fourier-transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction and simultaneous thermal analysis were used to characterize the raw materials, physical mixture and solid inclusion complex. In order to provide the drug in a more accessible and patient-compliant form following masking its bitter taste, as well as ensuring the appropriate release kinetics, the investigated complex was formulated as orally disintegrating tablets. The study of captopril dissolution in both compendial and simulated saliva media suggested the Noyes Whitney model as the best mathematical model to describe the release phenomena. A clinical study on healthy volunteers also highlighted the taste improvement of the new formulation as compared to conventional tablets. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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18 pages, 2395 KiB  
Article
Transungual Delivery, Anti-Inflammatory Activity, and In Vivo Assessment of a Cyclodextrin Polypseudorotaxanes Nail Lacquer
by Francisco Fernández-Campos, Francesc Navarro, Adrian Corrales, Jordi Picas, Eloy Pena, Jordi González and Francisco J. Otero-Espinar
Pharmaceutics 2020, 12(8), 730; https://doi.org/10.3390/pharmaceutics12080730 - 4 Aug 2020
Cited by 9 | Viewed by 4804
Abstract
A new cyclodextrin polypseudorotaxanes nail lacquer (Regenail®) containing biotin, methyl sulphonyl methane (MSM), and dimethylsilanediol salicylate was developed and evaluated in vitro and in vivo. The product was developed to improve nail status and diminish signs of pathological nail alterations. A [...] Read more.
A new cyclodextrin polypseudorotaxanes nail lacquer (Regenail®) containing biotin, methyl sulphonyl methane (MSM), and dimethylsilanediol salicylate was developed and evaluated in vitro and in vivo. The product was developed to improve nail status and diminish signs of pathological nail alterations. A reference product (Betalfatrus®) was used for comparative purposes. An in vitro permeation experiment in hooves showed high MSM and biotin absorption. The content of sulfur and silicon in hooves was also found to be higher compared with the reference product. MSM was tested in human keratinocytes, exhibiting a good cytotoxicity profile and anti-inflammatory activity by the reduction in IL-8 and TNF-α under LPS stimuli. A clinical study was performed to check product safety and efficacy against nail brittleness and alterations such as Beau’s lines and onychorrhexis. A reduction in both alterations and in surface roughness without alteration of nail structure was observed, with a good level of patient acceptance and satisfaction. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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14 pages, 3115 KiB  
Article
Ophthalmic In Situ Gelling System Containing Lanosterol Nanoparticles Delays Collapse of Lens Structure in Shumiya Cataract Rats
by Noriaki Nagai, Kazuki Umachi, Hiroko Otake, Mikako Oka, Noriko Hiramatsu, Hiroshi Sasaki and Naoki Yamamoto
Pharmaceutics 2020, 12(7), 629; https://doi.org/10.3390/pharmaceutics12070629 - 4 Jul 2020
Cited by 11 | Viewed by 2846
Abstract
We attempted to prepare ophthalmic in situ gel formulations containing lanosterol (Lan) nanoparticles (LA-NPs/ISG) and investigated the characteristics, delivery pathway into the lens, and anti-cataract effects of LA-NPs/ISG using SCR-N (rats with slight lens structure collapse) and SCR-C (rats with a combination of [...] Read more.
We attempted to prepare ophthalmic in situ gel formulations containing lanosterol (Lan) nanoparticles (LA-NPs/ISG) and investigated the characteristics, delivery pathway into the lens, and anti-cataract effects of LA-NPs/ISG using SCR-N (rats with slight lens structure collapse) and SCR-C (rats with a combination of remarkable lens structure collapse and opacification). LA-NPs/ISG was prepared by bead milling of the dispersions containing 0.5% Lan powder, 5% 2-hydroxypropyl-β-cyclodextrin, 0.5% methylcellulose, 0.005% benzalkonium chloride, and 0.5% mannitol. The particle size distribution of Lan was 60–250 nm. The LA-NPs/ISG was gelled at 37 °C, and the LA-NPs/ISG was taken into the cornea by energy-dependent endocytosis and then released to the intraocular side. In addition, the Lan contents in the lenses of both SCR-N and SCR-C were increased by the repetitive instillation of LA-NPs/ISG (twice per day). The space and structure collapse in the lens of SCR-N with aging was attenuated by the instillation of LA-NPs/ISG. Moreover, the repetitive instillation of LA-NPs/ISG attenuated the changes in cataract-related factors (the enhancement of nitric oxide levels, calpain activity, lipid peroxidation levels, Ca2+ contents, and the decrease of Ca2+-ATPase activity) in the lenses of SCR-C, and the repetitive instillation of LA-NPs/ISG delayed the onset of opacification in the SCR-C. It is possible that the LA-NPs/ISG is useful in maintaining lens homeostasis. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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21 pages, 2796 KiB  
Article
Development and Evaluation of Matrices Composed of β-cyclodextrin and Biodegradable Polyesters in the Controlled Delivery of Pindolol
by Agnieszka Lis-Cieplak, Filip Charuk, Marcin Sobczak, Anna Zgadzaj, Agata Drobniewska, Łukasz Szeleszczuk and Ewa Oledzka
Pharmaceutics 2020, 12(6), 500; https://doi.org/10.3390/pharmaceutics12060500 - 30 May 2020
Cited by 11 | Viewed by 2958
Abstract
Polymer-drug conjugates are currently being more widely investigated for the treatment of hypertension. In view of the above, in the first stage of our work, we used nontoxic β-cyclodextrin (β-CD) as effective, simple, inexpensive, and safe for the human body initiator for the [...] Read more.
Polymer-drug conjugates are currently being more widely investigated for the treatment of hypertension. In view of the above, in the first stage of our work, we used nontoxic β-cyclodextrin (β-CD) as effective, simple, inexpensive, and safe for the human body initiator for the synthesis of biocompatible and biodegradable functionalized polymers suitable for the medical and pharmaceutical applications. The obtained polymeric products were synthesized through a ring-opening polymerization (ROP) of ε-caprolactone (CL), d,l-, and l,l-lactide (LA and LLA). The chemical structures of synthesized materials were elucidated based on 1H NMR and solid-state carbon-13 cross-polarization/magic angle spinning nuclear magnetic resonance (13C CP/MAS NMR) analysis, while the incorporation of β-CD molecule into the polymer chain was confirmed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Furthermore, molecular modeling has been applied to investigate the intrachain rigidities and chain architectures for several representative structures. The obtained and thoroughly characterized branched matrices were then used to generate the first β-cyclodextrin/biodegradable polymer/β-blocker conjugate through the successful conjugation of pindolol. The conjugates were fabricated by carbodiimide-mediated coupling reaction. The branched biodegradable materials released the drug in vitro in a sustained manner and without “burst release” and thus have the ability to treat different heart diseases. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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26 pages, 8251 KiB  
Article
Mucoadhesive Vaginal Discs based on Cyclodextrin and Surfactants for the Controlled Release of Antiretroviral Drugs to Prevent the Sexual Transmission of HIV
by Fernando Notario-Pérez, Araceli Martín-Illana, Raúl Cazorla-Luna, Roberto Ruiz-Caro, Aitana Tamayo, Juan Rubio and Veiga María-Dolores
Pharmaceutics 2020, 12(4), 321; https://doi.org/10.3390/pharmaceutics12040321 - 2 Apr 2020
Cited by 10 | Viewed by 3601
Abstract
The strategies for developing vaginal microbicides to protect women against human immunodeficiency virus (HIV) sexual transmission are constantly changing. Although the initial dosage forms required daily administration to offer effective protection, the trend then moved towards sustained-release dosage forms that require less frequency [...] Read more.
The strategies for developing vaginal microbicides to protect women against human immunodeficiency virus (HIV) sexual transmission are constantly changing. Although the initial dosage forms required daily administration to offer effective protection, the trend then moved towards sustained-release dosage forms that require less frequency of administration in order to improve women’s compliance with the treatment. Nevertheless, another possible strategy is to design on-demand products that can be used in a coitally-dependent manner and only need to be administered immediately before intercourse to offer protection. Vaginal discs based on freeze-dried hydroxypropylmethyl cellulose gels have been developed for this purpose, containing two surfactants, i.e., sodium dodecyl sulphate and polysorbate 60, alone or in combination with 2-hydroxypropyl-β-cyclodextrin, to achieve a formulation capable of incorporating both hydrophilic and lipophilic drugs. Several studies have been carried out to evaluate how the inclusion of these substances modifies the structure of gels (viscosity and consistency studies) and the porosimetry of the freeze-dried discs (scanning electron microscopy micrographs, mechanical properties, swelling behaviour). The drug release and mucoadhesive properties of the discs have also been evaluated with a view to their clinical application. The systems combining sodium dodecyl sulphate and 2-hydroxypropyl-β-cyclodextrin were found to be adequate for the vaginal administration of both Tenofovir and Dapivirine and also offer excellent mucoadhesion to vaginal tissue; these discs could therefore be an interesting option for a coitally-dependent administration to protect women against HIV transmission. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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15 pages, 8200 KiB  
Article
Comparative Evaluation of Solubility, Cytotoxicity and Photostability Studies of Resveratrol and Oxyresveratrol Loaded Nanosponges
by Nilesh Kumar Dhakar, Adrián Matencio, Fabrizio Caldera, Monica Argenziano, Roberta Cavalli, Chiara Dianzani, Marco Zanetti, José Manuel López-Nicolás and Francesco Trotta
Pharmaceutics 2019, 11(10), 545; https://doi.org/10.3390/pharmaceutics11100545 - 20 Oct 2019
Cited by 66 | Viewed by 5107
Abstract
Resveratrol and oxyresveratrol are natural polyphenolic stilbenes with several important pharmacological activities. However, low solubility and aqueous instability are the major limitations in their drug delivery applications. In the present work, we demonstrated the encapsulation of resveratrol and oxyresveratrol with nanosponge to improve [...] Read more.
Resveratrol and oxyresveratrol are natural polyphenolic stilbenes with several important pharmacological activities. However, low solubility and aqueous instability are the major limitations in their drug delivery applications. In the present work, we demonstrated the encapsulation of resveratrol and oxyresveratrol with nanosponge to improve solubility and stability. Several characterization techniques were used to confirm the encapsulation of both drug molecules within the nanosponges. The high encapsulation efficiency of resveratrol (77.73%) and oxyresveratrol (80.33%) was achieved within the nanosponges. Transmission electron microscopy suggested uniform spherical size particles of resveratrol and oxyresveratrol loaded nanosponges. Compared to free drugs, better protection against UV degradation was observed for resveratrol-loaded nanosponge (2-fold) and oxyresveratrol-loaded nanosponge (3-fold). Moreover, a higher solubilization of resveratrol- and oxyresveratrol-loaded nanosponges lead to a better antioxidant activity compared to drug molecules alone. Cytotoxicity studies against DU-145 prostate cancer cell lines further suggested improved activity of both resveratrol and oxyresveratrol-loaded nanosponges without any significant toxicity of blank nanosponges. Full article
(This article belongs to the Special Issue Cyclodextrin-Based Drug Delivery System)
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