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Pharmaceutics
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Cyclodextrins in Drug Delivery
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Cyclodextrins in Drug Delivery

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 September 2021) | Viewed by 33087

Special Issue Editors

Prof. Dr. Paola Mura

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Guest Editor
Department of Chemistry, University of Florence, via Schiff 6, Sesto Fiorentino, 50019 Florence, Italy
Interests: cyclodextrins complexes; dissolution; nanocarriers as drug delivery systems; drug-in cyclodextrin-in nanocarrier; transmucosal delivery
Special Issues, Collections and Topics in MDPI journals
Dr. Marzia Cirri

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Guest Editor
Department of Chemistry, University of Florence, via Schiff 6, Sesto Fiorentino, 50019 Florence, Italy
Interests: cyclodextrins; drug delivery systems; drug-in-cyclodextrin-in-nanolipid carriers; oral administration; pediatric formulations; topical delivery
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrins are one of the most versatile tools in pharmaceutical technology, due to their unique structural conformation. They are cyclic oligosaccharides consisting of (α-1,4-)-linked α-D-glucopyranose units with a hydrophilic outer surface and a hydrophobic central cavity, able to form non-covalent inclusion complexes with a wide range of molecules, including a variety of drugs. They are also able to form a variety of supramolecular structures (self-assembling systems, poly(pseudo)rotaxanes, cross-linked networks). Moreover, natural cyclodextrins can be opportunely derivatized and/or functionalized to further extend and enhance their possible applications.

Cyclodextrins play a very important role in formulation by improving drug solubility and/or dissolution, permeability, and physical and chemical stability, thus enhancing their bioavailability. Other applications include odor and taste masking, prevention of incompatibility, and control of drug release.

Moreover, their combined use with various nanocarriers can be an interesting approach to simultaneously increase the performance of both as drug carriers.

Due to their multifunctional properties, cyclodextrins can be exploited in the development of almost every kind of drug delivery system, aimed for oral, transdermal, parenteral, ocular, nasal, or rectal administration.

Authors are kindly invite to submit original papers, communications and reviews regarding potential applications of cyclodextrins in drug delivery, to be published in this Special Issue of Pharmaceutics.

Prof. Dr. Paola Mura
Prof. Dr. Marzia Cirri
Guest Editors

Manuscript Submission Information

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Keywords

  • cyclodextrins
  • drug delivery
  • inclusion complexes
  • supramolecular structures
  • drug-in cyclodextrin-in nanocarrier
  • solubility
  • stability
  • bioavailability

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Related Special Issue

Published Papers (9 papers)

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Research

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16 pages, 3961 KiB  
Article
Native Cyclodextrins as Complexation Agents for Pterostilbene: Complex Preparation and Characterization in Solution and in the Solid State
by Laura Catenacci, Alexios I. Vicatos, Milena Sorrenti, Maria Cristina Bonferoni and Mino R. Caira
Pharmaceutics 2022, 14(1), 8; https://doi.org/10.3390/pharmaceutics14010008 - 21 Dec 2021
Cited by 10 | Viewed by 2969
Abstract
Pterostilbene (3,5-dimethoxy-4′-hydroxystilbene, PTB) is a natural dietary stilbene, occurring primarily in blueberries and Pterocarpus marsupium heartwood. The interest in this compound is related to its different biological and pharmacological properties, such as its antioxidant, anti-inflammatory, and anticarcinogenic activities and its capacity to reduce [...] Read more.
Pterostilbene (3,5-dimethoxy-4′-hydroxystilbene, PTB) is a natural dietary stilbene, occurring primarily in blueberries and Pterocarpus marsupium heartwood. The interest in this compound is related to its different biological and pharmacological properties, such as its antioxidant, anti-inflammatory, and anticarcinogenic activities and its capacity to reduce and regulate cholesterol and blood sugar levels. Nevertheless, its use in therapy is hindered by its low aqueous solubility; to overcome this limitation we studied the feasibility of the use of cyclodextrins (CDs) as solubility-enhancing agents. CDs are natural macrocyclic oligomers composed of α-d-glucose units linked by α-1,4 glycosidic bonds to form torus-shaped molecules, responsible for inclusion complex formation with organic molecules. In particular, the aim of this study was to evaluate the feasibility of complexation between PTB and native CDs using various preparative methods. The isolated solid products were characterized using differential scanning calorimetry (DSC), simultaneous thermogravimetric/DSC analysis (TGA/DSC), Fourier transform infrared (FT-IR) spectroscopy, and X-ray diffraction (XRD) on powder and single crystals. The results indicated little or no evidence of the affinity of PTB to complex with α-CD using the kneading method. However, with β-CD and γ-CD thermal analysis revealed an interaction which was also corroborated by FT-IR and 1H-NMR spectroscopy. With β-CD, a hydrated complex of PTB was isolated and its characterization by single-crystal XRD revealed, for the first time, the mode of inclusion of the PTB molecule in the cavity of a CD. To complement the solid-state data, liquid-phase studies were carried out to establish the effect of CDs on the aqueous solubility of PTB and to determine the complex stoichiometries and the association constants for complex formation. Phase-solubility studies showed AL-type profiles for α- and β-CD and a BS profile for γ-CD, with K1:1 values of 1144, 4950, and 133 M−1 for α-CD·PTB, β-CD·PTB, and γ-CD·PTB, respectively. The stoichiometry of CD·PTB complexes, determined by Job’s method, revealed for each system a 1:1 molar ratio. The dissolution rate of PTB was approximately doubled just by employing simple physical mixtures, but the best performance was achieved by products obtained via kneading and co-precipitation, which effected the complete dissolution of PTB in 40 and 20 min for β-CD and γ-CD, respectively. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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19 pages, 4072 KiB  
Article
Combined Use of Cyclodextrins and Amino Acids for the Development of Cefixime Oral Solutions for Pediatric Use
by Marzia Cirri, Natascia Mennini, Giulia Nerli, Jessica Rubia, Enrico Casalone, Fabrizio Melani, Francesca Maestrelli and Paola Mura
Pharmaceutics 2021, 13(11), 1923; https://doi.org/10.3390/pharmaceutics13111923 - 13 Nov 2021
Cited by 9 | Viewed by 2945
Abstract
Cefixime (CEF) is a cephalosporin included in the WHO Model List of Essential Medicines for Children. Liquid formulations are considered the best choice for pediatric use, due to their great ease of administration and dose-adaptability. Owing to its very low aqueous solubility and [...] Read more.
Cefixime (CEF) is a cephalosporin included in the WHO Model List of Essential Medicines for Children. Liquid formulations are considered the best choice for pediatric use, due to their great ease of administration and dose-adaptability. Owing to its very low aqueous solubility and poor stability, CEF is only available as a powder for oral suspensions, which can lead to reduced compliance by children, due to its unpleasant texture and taste, and possible non-homogeneous dosage. The aim of this work was to develop an oral pediatric CEF solution endowed with good palatability, exploiting the solubilizing and taste-masking properties of cyclodextrins (CDs), joined to the use of amino acids as an auxiliary third component. Solubility studies indicated sulfobutylether-β-cyclodextrin (SBEβCD) and Histidine (His) as the most effective CD and amino acid, respectively, even though no synergistic effect on drug solubility improvement by their combined use was found. Molecular Dynamic and 1H-NMR studies provided insight into the interactions of binary CEF:His and ternary CEF:His:SBEβCD systems used to prepare CEF solutions, which resulted stable and maintained unchanged antimicrobial activity during the two-weeks-use in therapy. The ternary solution was superior in terms of more tolerable pH (5.6 vs. 4.7) and better palatability, being resulted completely odorless by a panel test. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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12 pages, 4192 KiB  
Article
Polysaccharide Cryogels Containing β-Cyclodextrin for the Delivery of Cannabidiol
by Denitsa Momekova, Yavor Danov, Georgi Momekov, Ervin Ivanov and Petar Petrov
Pharmaceutics 2021, 13(11), 1774; https://doi.org/10.3390/pharmaceutics13111774 - 23 Oct 2021
Cited by 15 | Viewed by 2992
Abstract
Cannabidiol (CBD) has attracted increasing interest due to its therapeutic potential for treating numerous diseases. However, CBD is very lipophilic and has very unfavorable pharmacokinetics and low bioavailability. Efforts are focused on developing drug delivery systems for enhanced solubilization and therapeutic activity of [...] Read more.
Cannabidiol (CBD) has attracted increasing interest due to its therapeutic potential for treating numerous diseases. However, CBD is very lipophilic and has very unfavorable pharmacokinetics and low bioavailability. Efforts are focused on developing drug delivery systems for enhanced solubilization and therapeutic activity of CBD. Here, we report the preparation of original super-macroporous cryogels from 2-hydroxyethyl cellulose (HEC) and β-cyclodextrin (β-CD) designed for the topical delivery of CBD. The cryogels were synthesized by photochemical crosslinking in a frozen aqueous system, purified, and then loaded with CBD. The effect of HEC/β-CD mass ratio (100:0; 50:50; 40:60 and 20:80) in the reaction mixture on the reaction efficiency, physico-mechanical properties of cryogels, drug release profile, and antineoplastic potential were evaluated in detail. The cryogels showed a bi-phasic release behavior: initial burst release in the first 3 hours followed by slower drug release which can be beneficial in the treatment of cutaneous neoplastic diseases. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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13 pages, 4103 KiB  
Article
Modulation of Temoporfin Distribution in Blood by β-Cyclodextrin Nanoshuttles
by Ilya Yakavets, Igor Yankovsky, Tatyana Zorina, Mikhail Belevtsev, Lina Bezdetnaya and Vladimir Zorin
Pharmaceutics 2021, 13(7), 1054; https://doi.org/10.3390/pharmaceutics13071054 - 9 Jul 2021
Cited by 1 | Viewed by 2352
Abstract
Photodynamic therapy represents a more targeted and less invasive alternative cancer treatment to traditional modalities. Temoporfin, as with many photosensitizers, is given by injection into a vein, and its subsequent fate is largely determined by the binding to plasma proteins and interaction with [...] Read more.
Photodynamic therapy represents a more targeted and less invasive alternative cancer treatment to traditional modalities. Temoporfin, as with many photosensitizers, is given by injection into a vein, and its subsequent fate is largely determined by the binding to plasma proteins and interaction with endothelial and blood cells. Thus, it is essential to be able to control and to alter the biodistribution of temoporfin in blood. In the present study, we evaluated the effect of co-administration of temoporfin with randomly methylated β-CD (Me-β-CD) on the distribution of temoporfin in the main subpopulations of blood cells of healthy donors using absorbance spectrophotometry and flow cytometry. We showed that cell-bound temoporfin fraction in blood strongly depends on the concentration of Me-β-CD. In fact, the accumulation of temoporfin in white blood cells was more sensitive than that in red blood cells, due to the higher volume of membranous organelles in white blood cells. Finally, we demonstrated that Me-β-CD significantly increases cellular uptake of temoporfin cancer human Burkitt′s lymphoma Raji cells. The presence of Me-β-CD resulted in a spotted pattern of temoporfin distribution in the plasma membrane compartment. Our results clearly demonstrated that β-CDs derivatives provide new options to modulate temoporfin biodistribution in blood. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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17 pages, 2804 KiB  
Article
Improvement of Butamben Anesthetic Efficacy by the Development of Deformable Liposomes Bearing the Drug as Cyclodextrin Complex
by Paola Mura, Francesca Maestrelli, Marzia Cirri, Giulia Nerli, Lorenzo Di Cesare Mannelli, Carla Ghelardini and Natascia Mennini
Pharmaceutics 2021, 13(6), 872; https://doi.org/10.3390/pharmaceutics13060872 - 12 Jun 2021
Cited by 11 | Viewed by 2597
Abstract
This work was aimed at enhancing butamben (BTB) anesthetic efficacy by the “drug-in cyclodextrin (CD)-in deformable liposomes” strategy. In the study, phase-solubility studies with natural (α-, β-, γ-) and derivative (hydroxypropyl-α-and β-, sulfobutylether-β, methyl-β) CDs evidenced the highest BTB affinity for βCD and [...] Read more.
This work was aimed at enhancing butamben (BTB) anesthetic efficacy by the “drug-in cyclodextrin (CD)-in deformable liposomes” strategy. In the study, phase-solubility studies with natural (α-, β-, γ-) and derivative (hydroxypropyl-α-and β-, sulfobutylether-β, methyl-β) CDs evidenced the highest BTB affinity for βCD and its derivatives and indicated methyl-βCD (RAMEB) as the best carrier. Drug-RAMEB complexes were prepared by different techniques and were characterized for solid-state and dissolution properties. The best BTB–RAMEB product was chosen for entrapment in the aqueous core of deformable liposomes containing stearylamine, either alone or with sodium cholate, as edge activators. Double-loaded (DL) liposomes, bearing the lipophilic drug (0.5% w/v) in the bilayer and its hydrophilic RAMEB complex (0.5% w/v) in the aqueous core, were compared to single-loaded (SL) liposomes bearing 1% w/v plain drug in the bilayer. All vesicles showed homogeneous dimensions (i.e., below 300 nm), high deformability, and excellent entrapment efficiency. DL-liposomes were more effective than SL ones in limiting drug leakage (<5% vs. >10% after a 3 months storage at 4 °C). In vivo experiments in rabbits proved that all liposomal formulations significantly (p < 0.05) increased the intensity and duration of drug anesthetic action compared to its hydroalcoholic solution; however, DL liposomes were significantly (p < 0.05) more effective than SL ones in prolonging BTB anesthetic effect, owing to the presence of the drug-RAMEB complex in the vesicle core, acting as a reservoir. DL liposomes containing both edge activators were found to have the best performance. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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21 pages, 5278 KiB  
Article
Functionalization of Gold Nanostars with Cationic β-Cyclodextrin-Based Polymer for Drug Co-Loading and SERS Monitoring
by Orlando Donoso-González, Lucas Lodeiro, Álvaro E. Aliaga, Miguel A. Laguna-Bercero, Soledad Bollo, Marcelo J. Kogan, Nicolás Yutronic and Rodrigo Sierpe
Pharmaceutics 2021, 13(2), 261; https://doi.org/10.3390/pharmaceutics13020261 - 15 Feb 2021
Cited by 23 | Viewed by 3678
Abstract
Gold nanostars (AuNSs) exhibit modulated plasmon resonance and have a high SERS enhancement factor. However, their low colloidal stability limits their biomedical application as a nanomaterial. Cationic β-cyclodextrin-based polymer (CCD/P) has low cytotoxicity, can load and transport drugs more efficiently than the corresponding [...] Read more.
Gold nanostars (AuNSs) exhibit modulated plasmon resonance and have a high SERS enhancement factor. However, their low colloidal stability limits their biomedical application as a nanomaterial. Cationic β-cyclodextrin-based polymer (CCD/P) has low cytotoxicity, can load and transport drugs more efficiently than the corresponding monomeric form, and has an appropriate cationic group to stabilize gold nanoparticles. In this work, we functionalized AuNSs with CCD/P to load phenylethylamine (PhEA) and piperine (PIP) and evaluated SERS-based applications of the products. PhEA and PIP were included in the polymer and used to functionalize AuNSs, forming a new AuNS-CCD/P-PhEA-PIP nanosystem. The system was characterized by UV–VIS, IR, and NMR spectroscopy, TGA, SPR, DLS, zeta potential analysis, FE-SEM, and TEM. Additionally, Raman optical activity, SERS analysis and complementary theoretical studies were used for characterization. Minor adjustments increased the colloidal stability of AuNSs. The loading capacity of the CCD/P with PhEA-PIP was 95 ± 7%. The physicochemical parameters of the AuNS-CCD/P-PhEA-PIP system, such as size and Z potential, are suitable for potential biomedical applications Raman and SERS studies were used to monitor PhEA and PIP loading and their preferential orientation upon interaction with the surface of AuNSs. This unique nanomaterial could be used for simultaneous drug loading and SERS-based detection. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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Review

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36 pages, 3296 KiB  
Review
Cyclodextrin-Modified Nanomaterials for Drug Delivery: Classification and Advances in Controlled Release and Bioavailability
by Daniel Andrés Real, Karen Bolaños, Josefina Priotti, Nicolás Yutronic, Marcelo J. Kogan, Rodrigo Sierpe and Orlando Donoso-González
Pharmaceutics 2021, 13(12), 2131; https://doi.org/10.3390/pharmaceutics13122131 - 10 Dec 2021
Cited by 58 | Viewed by 6401
Abstract
In drug delivery, one widely used way of overcoming the biopharmaceutical problems present in several active pharmaceutical ingredients, such as poor aqueous solubility, early instability, and low bioavailability, is the formation of inclusion compounds with cyclodextrins (CD). In recent years, the use of [...] Read more.
In drug delivery, one widely used way of overcoming the biopharmaceutical problems present in several active pharmaceutical ingredients, such as poor aqueous solubility, early instability, and low bioavailability, is the formation of inclusion compounds with cyclodextrins (CD). In recent years, the use of CD derivatives in combination with nanomaterials has shown to be a promising strategy for formulating new, optimized systems. The goals of this review are to give in-depth knowledge and critical appraisal of the main CD-modified or CD-based nanomaterials for drug delivery, such as lipid-based nanocarriers, natural and synthetic polymeric nanocarriers, nanosponges, graphene derivatives, mesoporous silica nanoparticles, plasmonic and magnetic nanoparticles, quantum dots and other miscellaneous systems such as nanovalves, metal-organic frameworks, Janus nanoparticles, and nanofibers. Special attention is given to nanosystems that achieve controlled drug release and increase their bioavailability during in vivo studies. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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26 pages, 3019 KiB  
Review
Cyclodextrin Multicomponent Complexes: Pharmaceutical Applications
by Virginia Aiassa, Claudia Garnero, Marcela R. Longhi and Ariana Zoppi
Pharmaceutics 2021, 13(7), 1099; https://doi.org/10.3390/pharmaceutics13071099 - 20 Jul 2021
Cited by 53 | Viewed by 5094
Abstract
Cyclodextrins (CDs) are naturally available water-soluble cyclic oligosaccharides widely used as carriers in the pharmaceutical industry for their ability to modulate several properties of drugs through the formation of drug–CD complexes. The addition of an auxiliary substance when forming multicomponent complexes is an [...] Read more.
Cyclodextrins (CDs) are naturally available water-soluble cyclic oligosaccharides widely used as carriers in the pharmaceutical industry for their ability to modulate several properties of drugs through the formation of drug–CD complexes. The addition of an auxiliary substance when forming multicomponent complexes is an adequate strategy to enhance complexation efficiency and to facilitate the therapeutic applicability of different drugs. This review discusses multicomponent complexation using amino acids; organic acids and bases; and water-soluble polymers as auxiliary excipients. Special attention is given to improved properties by including information on the solubility, dissolution, permeation, stability and bioavailability of several relevant drugs. In addition, the use of multicomponent CD complexes to enhance therapeutic drug effects is summarized. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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16 pages, 2668 KiB  
Review
Cyclodextrin-Based Supramolecular Complexes of Osteoinductive Agents for Dental Tissue Regeneration
by Masahiko Terauchi, Atsushi Tamura, Yoshinori Arisaka, Hiroki Masuda, Tetsuya Yoda and Nobuhiko Yui
Pharmaceutics 2021, 13(2), 136; https://doi.org/10.3390/pharmaceutics13020136 - 21 Jan 2021
Cited by 12 | Viewed by 2579
Abstract
Oral tissue regeneration has received growing attention for improving the quality of life of patients. Regeneration of oral tissues such as alveolar bone and widely defected bone has been extensively investigated, including regenerative treatment of oral tissues using therapeutic cells and growth factors. [...] Read more.
Oral tissue regeneration has received growing attention for improving the quality of life of patients. Regeneration of oral tissues such as alveolar bone and widely defected bone has been extensively investigated, including regenerative treatment of oral tissues using therapeutic cells and growth factors. Additionally, small-molecule drugs that promote bone formation have been identified and tested as new regenerative treatment. However, treatments need to progress to realize successful regeneration of oral functions. In this review, we describe recent progress in development of regenerative treatment of oral tissues. In particular, we focus on cyclodextrin (CD)-based pharmaceutics and polyelectrolyte complexation of growth factors to enhance their solubility, stability, and bioactivity. CDs can encapsulate hydrophobic small-molecule drugs into their cavities, resulting in inclusion complexes. The inclusion complexation of osteoinductive small-molecule drugs improves solubility of the drugs in aqueous solutions and increases in vitro osteogenic differentiation efficiency. Additionally, various anionic polymers such as heparin and its mimetic polymers have been developed to improve stability and bioactivity of growth factors. These polymers protect growth factors from deactivation and degradation by complex formation through electrostatic interaction, leading to potentiation of bone formation ability. These approaches using an inclusion complex and polyelectrolyte complexes have great potential in the regeneration of oral tissues. Full article
(This article belongs to the Special Issue Cyclodextrins in Drug Delivery)
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