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Nanomaterials
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Nanoconstructs Based on Cyclodextrins
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Nanoconstructs Based on Cyclodextrins

A special issue of Nanomaterials (ISSN 2079-4991).

Deadline for manuscript submissions: closed (31 January 2021) | Viewed by 31468

Special Issue Editor

Prof. Dr. Antonino Mazzaglia

E-Mail Website
Guest Editor
CNR-ISMN, c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences of the University of Messina, Viale F. Stagno D'Alcontres 31, I-98166 Messina, Italy
Interests: cyclodextrins; self-assembly; nanodelivery; phototherapeutics; hybrids nanobiomaterials; carbon nanomaterials; nanomedicine; regenerative medicine
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cyclodextrin nanoconstructs (CDnc) have recently aroused the interest of scientific community thanks to a plethora of potential applications. This issue will be focused on nanoconstructs based on native or modified CDs leading to novel polymeric, amphiphilic, metal, and hybrid backbones in material science. These nanoplatforms can have the ability to covalently conjugate active moieties and complex guests through supramolecular interactions or physical entrapment. In this scenario, four research themes are here envisaged:
i) CDnc for drug delivery and nanomedicine (including nanomaterials for pharmaceutics, theranostic, and scaffolds displaying nanodomains for regenerative medicine);
ii) CDnc in food manufacturing;
iii) CDnc in green chemistry and environmental sustainability (together with novel systems built in a nanoscale range for catalysis and conservation of cultural heritage);
iv) Toxicological studies and CDnc/cell interactions;
v) CDnc in renewable energy processes.

Articles will include synthesis of novel functionalized CDs and the formation of nanoassemblies with potential applications in i-v themes or novel and significant applications in i-v of known CDnc. Mini-reviews on the abovementioned research subjects and not recently documented (at least in the last five years) are also fully welcome.

Prof. Antonino Mazzaglia
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Nanomaterials is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • cyclodextrins
  • self-assembly
  • hydrogels
  • drug delivery
  • regenerative medicine
  • theranostic
  • nutraceutics
  • stimuli-responsive materials
  • green chemistry
  • cyclodextrin nanoconstructs/cell interactions

Published Papers (7 papers)

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Research

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17 pages, 5497 KiB  
Article
Therapeutic Efficacy and Biodistribution of Paclitaxel-Bound Amphiphilic Cyclodextrin Nanoparticles: Analyses in 3D Tumor Culture and Tumor-Bearing Animals In Vivo
by Gamze Varan, Cem Varan, Süleyman Can Öztürk, Juan M. Benito, Güneş Esendağlı and Erem Bilensoy
Nanomaterials 2021, 11(2), 515; https://doi.org/10.3390/nano11020515 - 18 Feb 2021
Cited by 11 | Viewed by 4136
Abstract
The uniqueness of paclitaxel’s antimitotic action mechanism has fueled research toward its application in more effective and safer cancer treatments. However, the low water solubility, recrystallization, and side effects hinder the clinical success of classic paclitaxel chemotherapy. The aim of this study was [...] Read more.
The uniqueness of paclitaxel’s antimitotic action mechanism has fueled research toward its application in more effective and safer cancer treatments. However, the low water solubility, recrystallization, and side effects hinder the clinical success of classic paclitaxel chemotherapy. The aim of this study was to evaluate the in vivo efficacy and biodistribution of paclitaxel encapsulated in injectable amphiphilic cyclodextrin nanoparticles of different surface charges. It was found that paclitaxel-loaded amphiphilic cyclodextrin nanoparticles showed an antitumoral effect earlier than the drug solution. Moreover, the blank nanoparticles reduced the tumor growth with a similar trend to the paclitaxel solution. At 24 h, the nanoparticles had not accumulated in the heart and lungs according to the biodistribution assessed by in vivo imaging. Therefore, our results indicated that the amphiphilic cyclodextrin nanoparticles are potentially devoid of cardiac toxicity, which limits the clinical use and commercialization of certain polymeric nanoparticles. In conclusion, the amphiphilic cyclodextrin nanoparticles with different surface charge increased the efficiency of paclitaxel in vitro and in vivo. Cyclodextrin nanoparticles could be a good candidate vehicle for intravenous paclitaxel delivery. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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19 pages, 3206 KiB  
Article
Cyclodextrin Cationic Polymer-Based Nanoassemblies to Manage Inflammation by Intra-Articular Delivery Strategies
by Annalaura Cordaro, Roberto Zagami, Milo Malanga, Jagadeesh Kumar Venkatesan, Carmen Alvarez-Lorenzo, Magali Cucchiarini, Anna Piperno and Antonino Mazzaglia
Nanomaterials 2020, 10(9), 1712; https://doi.org/10.3390/nano10091712 - 29 Aug 2020
Cited by 7 | Viewed by 3100
Abstract
Injectable nanobioplatforms capable of locally fighting the inflammation in osteoarticular diseases, by reducing the number of administrations and prolonging the therapeutic effect is highly challenging. β-Cyclodextrin cationic polymers are promising cartilage-penetrating candidates by intra-articular injection due to the high biocompatibility and ability to [...] Read more.
Injectable nanobioplatforms capable of locally fighting the inflammation in osteoarticular diseases, by reducing the number of administrations and prolonging the therapeutic effect is highly challenging. β-Cyclodextrin cationic polymers are promising cartilage-penetrating candidates by intra-articular injection due to the high biocompatibility and ability to entrap multiple therapeutic and diagnostic agents, thus monitoring and mitigating inflammation. In this study, nanoassemblies based on poly-β-amino-cyclodextrin (PolyCD) loaded with the non-steroidal anti-inflammatory drug diclofenac (DCF) and linked by supramolecular interactions with a fluorescent probe (adamantanyl-Rhodamine conjugate, Ada-Rhod) were developed to manage inflammation in osteoarticular diseases. PolyCD@Ada-Rhod/DCF supramolecular nanoassemblies were characterized by complementary spectroscopic techniques including UV-Vis, steady-state and time-resolved fluorescence, DLS and ζ-potential measurement. Stability and DCF release kinetics were investigated in medium mimicking the physiological conditions to ensure control over time and efficacy. Biological experiments evidenced the efficient cellular internalization of PolyCD@Ada-Rhod/DCF (within two hours) without significant cytotoxicity in primary human bone marrow-derived mesenchymal stromal cells (hMSCs). Finally, polyCD@Ada-Rhod/DCF significantly suppressed IL-1β production in hMSCs, revealing the anti-inflammatory properties of these nanoassemblies. With these premises, this study might open novel routes to exploit original CD-based nanobiomaterials for the treatment of osteoarticular diseases. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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20 pages, 4392 KiB  
Article
In Vitro and Ex Vivo Evaluation of Nepafenac-Based Cyclodextrin Microparticles for Treatment of Eye Inflammation
by Blanca Lorenzo-Veiga, Patricia Diaz-Rodriguez, Carmen Alvarez-Lorenzo, Thorsteinn Loftsson and Hakon Hrafn Sigurdsson
Nanomaterials 2020, 10(4), 709; https://doi.org/10.3390/nano10040709 - 09 Apr 2020
Cited by 27 | Viewed by 4543
Abstract
The aim of this study was to design and evaluate novel cyclodextrin (CD)-based aggregate formulations to efficiently deliver nepafenac topically to the eye structure, to treat inflammation and increase nepafenac levels in the posterior segment, thus attenuating the response of inflammatory mediators. The [...] Read more.
The aim of this study was to design and evaluate novel cyclodextrin (CD)-based aggregate formulations to efficiently deliver nepafenac topically to the eye structure, to treat inflammation and increase nepafenac levels in the posterior segment, thus attenuating the response of inflammatory mediators. The physicochemical properties of nine aggregate formulations containing nepafenac/γ-CD/hydroxypropyl-β (HPβ)-CD complexes as well as their rheological properties, mucoadhesion, ocular irritancy, corneal and scleral permeability, and anti-inflammatory activity were investigated in detail. The results were compared with a commercially available nepafenac suspension, Nevanac® 3 mg/mL. All formulations showed microparticles, neutral pH, and negative zeta potential (–6 to –27 mV). They were non-irritating and nontoxic and showed high permeation through bovine sclera. Formulations containing carboxymethyl cellulose (CMC) showed greater anti-inflammatory activity, even higher than the commercial formulation, Nevanac® 0.3%. The optimized formulations represent an opportunity for topical instillation of drugs to the posterior segment of the eye. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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15 pages, 1949 KiB  
Article
Polypseudorotaxanes of Pluronic® F127 with Combinations of α- and β-Cyclodextrins for Topical Formulation of Acyclovir
by Cristina Di Donato, Rosa Iacovino, Carla Isernia, Gaetano Malgieri, Angela Varela-Garcia, Angel Concheiro and Carmen Alvarez-Lorenzo
Nanomaterials 2020, 10(4), 613; https://doi.org/10.3390/nano10040613 - 27 Mar 2020
Cited by 20 | Viewed by 6029
Abstract
Acyclovir (ACV) is one of the most used antiviral drugs for the treatment of herpes simplex virus infections and other relevant mucosal infections caused by viruses. Nevertheless, the low water solubility of ACV limits both its bioavailability and antiviral performance. The combination of [...] Read more.
Acyclovir (ACV) is one of the most used antiviral drugs for the treatment of herpes simplex virus infections and other relevant mucosal infections caused by viruses. Nevertheless, the low water solubility of ACV limits both its bioavailability and antiviral performance. The combination of block copolymer micelles and cyclodextrins (CDs) may result in polypseudorotaxanes with tunable drug solubilizing and gelling properties. However, the simultaneous addition of various CDs has barely been investigated yet. The aim of this work was to design and characterize ternary combinations of Pluronic® F127 (PF127), αCD and βCD in terms of polypseudorotaxane formation, rheological behavior, and ACV solubilization ability and controlled release. The formation of polypseudorotaxanes between PF127 and the CDs was confirmed by FT-IR spectroscopy, X-ray diffraction, and NMR spectroscopy. The effects of αCD/βCD concentration range (0–7% w/w) on copolymer (6.5% w/w) gel features were evaluated at 20 and 37 °C by rheological studies, resulting in changes of the copolymer gelling properties. PF127 with αCD/βCD improved the solubilization of ACV, maintaining the biocompatibility (hen’s egg test on the chorio-allantoic membrane). In addition, the gels were able to sustain acyclovir delivery. The formulation prepared with similar proportions of αCD and βCD provided a slower and more constant release. The results obtained suggest that the combination of Pluronic with αCD/βCD mixtures can be a valuable approach to tune the rheological features and drug release profiles from these supramolecular gels. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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26 pages, 4432 KiB  
Article
Design of Engineered Cyclodextrin Derivatives for Spontaneous Coating of Highly Porous Metal-Organic Framework Nanoparticles in Aqueous Media
by Giovanna Cutrone, Xue Li, Juan M. Casas-Solvas, Mario Menendez-Miranda, Jingwen Qiu, Gábor Benkovics, Doru Constantin, Milo Malanga, Borja Moreira-Alvarez, José M. Costa-Fernandez, Luis García-Fuentes, Ruxandra Gref and Antonio Vargas-Berenguel
Nanomaterials 2019, 9(8), 1103; https://doi.org/10.3390/nano9081103 - 01 Aug 2019
Cited by 27 | Viewed by 4244
Abstract
Nanosized metal-organic frameworks (nanoMOFs) MIL-100(Fe) are highly porous and biodegradable materials that have emerged as promising drug nanocarriers. A challenging issue concerns their surface functionalization in order to evade the immune system and to provide molecular recognition ability, so that they can be [...] Read more.
Nanosized metal-organic frameworks (nanoMOFs) MIL-100(Fe) are highly porous and biodegradable materials that have emerged as promising drug nanocarriers. A challenging issue concerns their surface functionalization in order to evade the immune system and to provide molecular recognition ability, so that they can be used for specific targeting. A convenient method for their coating with tetraethylene glycol, polyethylene glycol, and mannose residues is reported herein. The method consists of the organic solvent-free self-assembly on the nanoMOFs of building blocks based on β-cyclodextrin facially derivatized with the referred functional moieties, and multiple phosphate groups to anchor to the nanoparticles’ surface. The coating of nanoMOFs with cyclodextrin phosphate without further functional groups led to a significant decrease of macrophage uptake, slightly improved by polyethylene glycol or mannose-containing cyclodextrin phosphate coating. More notably, nanoMOFs modified with tetraethylene glycol-containing cyclodextrin phosphate displayed the most efficient “stealth” effect. Mannose-coated nanoMOFs displayed a remarkably enhanced binding affinity towards a specific mannose receptor, such as Concanavalin A, due to the multivalent display of the monosaccharide, as well as reduced macrophage internalization. Coating with tetraethylente glycol of nanoMOFs after loading with doxorubicin is also described. Therefore, phosphorylated cyclodextrins offer a versatile platform to coat nanoMOFs in an organic solvent-free, one step manner, providing them with new biorecognition and/or “stealth” properties. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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20 pages, 10687 KiB  
Article
In vivo Efficacy and Safety Evaluation of Lactosyl-β-cyclodextrin as a Therapeutic Agent for Hepatomegaly in Niemann-Pick Type C Disease
by Yuki Maeda, Keiichi Motoyama, Rena Nishiyama, Taishi Higashi, Risako Onodera, Hideaki Nakamura, Toru Takeo, Naomi Nakagata, Yusei Yamada, Yoichi Ishitsuka, Yuki Kondo, Tetsumi Irie, Takumi Era and Hidetoshi Arima
Nanomaterials 2019, 9(5), 802; https://doi.org/10.3390/nano9050802 - 25 May 2019
Cited by 13 | Viewed by 4430
Abstract
Niemann-Pick type C disease (NPC) is a fatal, autosomal recessive disorder, which causes excessive accumulation of free cholesterol in endolysosomes, resulting in progressive hepatomegaly and neurodegeneration. Currently, 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) is used at a high dose for the treatment of NPC, risking lung toxicity [...] Read more.
Niemann-Pick type C disease (NPC) is a fatal, autosomal recessive disorder, which causes excessive accumulation of free cholesterol in endolysosomes, resulting in progressive hepatomegaly and neurodegeneration. Currently, 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) is used at a high dose for the treatment of NPC, risking lung toxicity and hearing loss during treatment. One method to reduce the required dose of HP-β-CyD for the treatment of hepatomegaly is to actively deliver β-cyclodextrin (β-CyD) to hepatocytes. Previously, we synthesized lactosyl-β-CyD (Lac-β-CyD) and demonstrated that it lowers cholesterol in NPC model liver cells. In the present study, we studied the efficacy and safety of Lac-β-CyD treatment of hepatomegaly in Npc1−/− mice. After subcutaneous administration, Lac-β-CyD accumulated in the liver and reduced hepatomegaly with greater efficacy than HP-β-CyD. In addition, subcutaneous administration of a very high dose of Lac-β-CyD was less toxic to the lungs than HP-β-CyD. Notably, the accumulation of intracellular free cholesterol in endolysosomes of NPC-like liver cells was significantly lower after administration of Lac-β-CyD than after treatment with HP-β-CyD. In conclusion, these results suggest that Lac-β-CyD is a candidate for the effective treatment of hepatomegaly in NPC. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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Review

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28 pages, 3044 KiB  
Review
Cyclodextrins as a Key Piece in Nanostructured Materials: Quantitation and Remediation of Pollutants
by Carolina Belenguer-Sapiña, Enric Pellicer-Castell, Adela R. Mauri-Aucejo, Ernesto Francisco Simó-Alfonso and Pedro Amorós
Nanomaterials 2021, 11(1), 7; https://doi.org/10.3390/nano11010007 - 23 Dec 2020
Cited by 15 | Viewed by 4059
Abstract
Separation and pre-concentration of trace pollutants from their matrix by reversible formation of inclusion complexes has turned into a widely studied field, especially for the benefits provided to different areas. Cyclodextrins are non-toxic oligosaccharides that are well known for their host–guest chemistry, low [...] Read more.
Separation and pre-concentration of trace pollutants from their matrix by reversible formation of inclusion complexes has turned into a widely studied field, especially for the benefits provided to different areas. Cyclodextrins are non-toxic oligosaccharides that are well known for their host–guest chemistry, low prices, and negligible environmental impact. Therefore, they have been widely used as chiral selectors and delivery systems in the pharmaceutical and food industry over time. However, their use for extraction purposes is hampered by their high solubility in water. This difficulty is being overcome with a variety of investigations in materials science. The setting-up of novel solid sorbents with improved properties thanks to the presence of cyclodextrins at their structure is still an open research area. Some properties they can offer, such as an increased selectivity or a good distribution along the surface of a solid support, which provides better accessibility for guest molecules, are characteristics of great interest. This systematic review reports the most significant uses of cyclodextrins for the adsorption of pollutants in different-origin samples based on the works reported in the literature in the last years. The study has been carried out indistinctly for quantitation and remediation purposes. Full article
(This article belongs to the Special Issue Nanoconstructs Based on Cyclodextrins)
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