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Supramolecular Devices from Cyclodextrin: Synthesis and Pharmacological Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (19 December 2014) | Viewed by 37993

Special Issue Editor

Special Issue Information

Dear Colleagues,

In the field of research into nanomedicines and in the synthesis of devices of molecular size, various types of cyclodextrins have been intensively studied from a pharmacological point of view. Research has been focused on the transport of useful substances and of medicines, which, because of their insolubility in the bloodstream, limit the possibilities of medical treatment in the organism. From the formation of inclusion complexes to the formation of nanoparticles linked with natural or synthetic polymers, cyclodextrins have been successful because of their versatility to transport substances of small size or as part of supramolecular systems in the detection, isolation and elimination of toxins, heavy elements and molecules that, because of their physical-chemical characteristics, are difficult to handle in an aqueous environment.

Experimental data in the field of the synthesis of modified cyclodextrin and its application in the treatment of behavioral diseases, mood disorders or simply drug delivery, are part of this Special Issue, which is open to all researchers who are considering publishing their experimental results and contributing to the understanding of new applications in the fields of medicine, ecology and chemistry.

Dr. Eduardo Sobarzo-Sánchez
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules 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 1800 CHF (Swiss Francs).

Keywords

  • cyclodextrin
  • inclusion complex
  • drug delivery
  • nanomedicine

Published Papers (4 papers)

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Research

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2680 KiB  
Article
In Vitro and in Vivo Evaluation of Novel Cross-Linked Saccharide Based Polymers as Bile Acid Sequestrants
by Francisco Javier Lopez-Jaramillo, Maria Dolores Giron-Gonzalez, Rafael Salto-Gonzalez, Fernando Hernandez-Mateo and Francisco Santoyo-Gonzalez
Molecules 2015, 20(3), 3716-3729; https://doi.org/10.3390/molecules20033716 - 24 Feb 2015
Cited by 11 | Viewed by 6564
Abstract
Bile acid sequestrants (BAS) represent a therapeutic approach for the management of hypercholesterolemia that relies on the cationic polymeric nature of BAS to selectively bind negatively charged bile acids. We hypothesized that the cross-linking of β-cyclodextrin (β-CD) and saccharides such as starch or [...] Read more.
Bile acid sequestrants (BAS) represent a therapeutic approach for the management of hypercholesterolemia that relies on the cationic polymeric nature of BAS to selectively bind negatively charged bile acids. We hypothesized that the cross-linking of β-cyclodextrin (β-CD) and saccharides such as starch or dextrin with divinyl sulfone (DVS) yields homo- and hetero-polymeric materials with the ability to trap sterols. Our hypothesis was put to test by synthesizing a library of 22 polymers that were screened to evaluate their capability to sequester both cholesterol (CHOL) and cholic and deoxycholic acids (CA and DCA). Three polymers synthesized in high yield were identified as promising. Two were neutral hetero-polymers of β-CD and starch or dextrin and the third was a weakly cationic homo-polymer of starch, highlighting the importance of the cavity effect. They were tested in hypercholesterolemic male Wistar rats and their ability to regulate hypercholesterolemia was similar to that for the reference BAS cholestyramine, but with two additional advantages: (i) they normalized the TG level and (ii) they did not increase the creatinine level. Neither hepatotoxicity nor kidney injury was detected, further supporting them as therapeutical candidates to manage hypercholesterolemia. Full article
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3192 KiB  
Article
Divinyl Sulfone Cross-Linked Cyclodextrin-Based Polymeric Materials: Synthesis and Applications as Sorbents and Encapsulating Agents
by Julia Morales-Sanfrutos, Francisco Javier Lopez-Jaramillo, Mahmoud A. A. Elremaily, Fernando Hernández-Mateo and Francisco Santoyo-Gonzalez
Molecules 2015, 20(3), 3565-3581; https://doi.org/10.3390/molecules20033565 - 19 Feb 2015
Cited by 37 | Viewed by 12347
Abstract
The aim of this study was to evaluate the crosslinking abilities of divinyl sulfone (DVS) for the preparation of novel water-insoluble cyclodextrin-based polymers (CDPs) capable of forming inclusion complexes with different guest molecules. Reaction of DVS with native α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and/or [...] Read more.
The aim of this study was to evaluate the crosslinking abilities of divinyl sulfone (DVS) for the preparation of novel water-insoluble cyclodextrin-based polymers (CDPs) capable of forming inclusion complexes with different guest molecules. Reaction of DVS with native α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and/or starch generates a variety of homo- and hetero-CDPs with different degrees of crosslinking as a function of the reactants’ stoichiometric ratio. The novel materials were characterized by powder X-ray diffraction, electron microscopy and for their sorption of phenol and 4-nitrophenol. They were further evaluated as sorbents with phenolic pollutants (bisphenol A and β-naphthol) and bioactive compounds (the hormone progesterone and curcumin). Data obtained from the inclusion experiments show that the degree of cross-linking has a minor influence on the yield of inclusion complex formation and highlight the important role of the CDs, supporting a sorption process based on the formation of inclusion complexes. In general, the inclusion processes are better described by a Freundlich isotherm although an important number of them can also be fitted to the Langmuir isotherm with R2 ≥ 0.9, suggesting a sorption onto a monolayer of homogeneous sites. Full article
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851 KiB  
Article
The Synergistic Biologic Activity of Oleanolic and Ursolic Acids in Complex with Hydroxypropyl-γ-Cyclodextrin
by Codruţa Soica, Camelia Oprean, Florin Borcan, Corina Danciu, Cristina Trandafirescu, Dorina Coricovac, Zorin Crăiniceanu, Cristina Adriana Dehelean and Melania Munteanu
Molecules 2014, 19(4), 4924-4940; https://doi.org/10.3390/molecules19044924 - 17 Apr 2014
Cited by 88 | Viewed by 9216
Abstract
Oleanolic and ursolic acids are natural triterpenic compounds with pentacyclic cholesterol-like structures which gives them very low water solubility, a significant disadvantage in terms of bioavailability. We previously reported the synthesis of inclusion complexes between these acids and cyclodextrins, as well as their [...] Read more.
Oleanolic and ursolic acids are natural triterpenic compounds with pentacyclic cholesterol-like structures which gives them very low water solubility, a significant disadvantage in terms of bioavailability. We previously reported the synthesis of inclusion complexes between these acids and cyclodextrins, as well as their in vivo evaluation on chemically induced skin cancer experimental models. In this study the synergistic activity of the acid mixture included inside hydroxypropyl-gamma-cyclodextrin (HPGCD) was monitored using in vitro tests and in vivo skin cancer models. The coefficient of drug interaction (CDI) was used to characterize the interactions as synergism, additivity or antagonism. Our results revealed an increased antitumor activity for the mixture of the two triterpenic acids, both single and in complex with cyclodextrin, thus proving their complementary biologic activities. Full article
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Review

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1802 KiB  
Review
Inclusion and Functionalization of Polymers with Cyclodextrins: Current Applications and Future Prospects
by Christian Folch-Cano, Mehrdad Yazdani-Pedram and Claudio Olea-Azar
Molecules 2014, 19(9), 14066-14079; https://doi.org/10.3390/molecules190914066 - 09 Sep 2014
Cited by 98 | Viewed by 9369
Abstract
The numerous hydroxyl groups available in cyclodextrins are active sites that can form different types of linkages. They can be crosslinked with one another, or they can be derivatized to produce monomers that can form linear or branched networks. Moreover, they can form [...] Read more.
The numerous hydroxyl groups available in cyclodextrins are active sites that can form different types of linkages. They can be crosslinked with one another, or they can be derivatized to produce monomers that can form linear or branched networks. Moreover, they can form inclusion complexes with polymers and different substrates, modifying their physicochemical properties. This review shows the different applications using polymers with cyclodextrins, either by forming inclusion complexes, ternary complexes, networks, or molecularly imprinted polymers (MIPs). On one hand, the use of cyclodextrins enhances the properties of each polymer, and on the other the use of polymers decreases the amount of cyclodextrins required in different formulations. Both cyclodextrins and polymers contribute synergistically in several applications such as pharmacological, nutritional, environmental, and other industrial fields. The use of polymers based on cyclodextrins is a low cost easy to use potential tool with great future prospects. Full article
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