Analytical characterization of cyclodextrins: History, official methods and recommended new techniques

Szente, Lajos; Szemán, Julianna; Sohajda, Tamás

doi:10.1016/j.jpba.2016.05.009

Cited by 59 publications

(35 citation statements)

References 101 publications

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“…They are cyclic oligosaccharides (α-D-glucopyranose) obtained from starch shaped as truncated cones (Szente et al, 2016). Several interactions such as hydrogen bonds, van der Waals', electrostatic, charge-transfer and hydrophobic binding lead to host-guest type inclusion complexes and partly or complete encapsulation of a drug (Loftsson and Brewster, 1996) providing increased drug solubility, bioavailability or stability and decreasing unpleasant taste and smell (Szejtli and Szente, 2005).The β-CD and its derivatives, including hydroxypropyl-β-CD (HP-β-CD) and sulfobutyl ether-β-CD (SBE-β-CD) are the most commonly used CDs in pharmaceutical industry (Jambhekar and Breen, 2016) and were chosen for PZQ on the basis of previous studies (Becket et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Comparative in vitro and in vivo taste assessment of liquid praziquantel formulations

Münster

Mohamed-Ahmed

Immohr

et al. 2017

International Journal of Pharmaceutics

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The taste of pharmaceuticals strongly affects the compliance of patients. This study investigated the applicability of the electronic tongue and rodent brief-access taste aversion (BATA) model for the bitter compound praziquantel (PZQ) and taste masked liquid formulations for PZQ. In a comparative study maltodextrin (MD) Kleptose linecaps 17 was selected as an alternative taste masking agent to two cyclodextrins; hydroxypropyl-beta-cyclodextrin (HP-β-CD) and sulfobutyl ether-beta-cyclodextrin (SBE-β-CD). A phase solubility study showed the highest affinity and solubilization capabilities for SBE-β-CD over HP-β-CD and MD, suggesting the highest taste masking ability for SBE-β-CD. No reliable results were achieved for PZQ with the Insent electronic tongue. Thus this system was not used for further evaluation of solutions with MD and CDs to confirm the results of the solubility study. In contrast the BATA model demonstrated conclusive responses for the aversiveness of PZQ. The concentration of PZQ inhibiting 50% of water lick numbers (called IC value) was 0.06mg/ml. In contrast to the phase solubility study, the MD enabled an equal taste masking effect in vivo in comparison to both CDs. Moreover HP-β-CD showed superior taste masking capabilities for PZQ compared to SBE-β-CD as the SBE-β-CD itself was less acceptable for the rodents than HP-β-CD. In conclusion, the BATA model was identified as a more efficient taste assessment tool for the pure PZQ and liquid formulations in contrast to the electronic tongue and the phase solubility study.

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Section: Introductionmentioning

confidence: 99%

Comparative in vitro and in vivo taste assessment of liquid praziquantel formulations

Münster

Mohamed-Ahmed

Immohr

et al. 2017

International Journal of Pharmaceutics

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“…174,175 The external surface of the CD that offers protons (H1, H2, H4, H6) provides it a hydrophilic nature, whereas its cavity displays hydrophobic characteristics due to the presence of rings of C-H groups (H3 and H5) together with a ring of oxygen atoms forming glycosidic linkages. [176][177][178] Therefore, CDs are truncated cone-shaped molecules with a relatively hydrophobic cavity and an external hydrophilic surface that can form supramolecular structures (inclusion complexes, ICs) with various molecules, mainly small molecules. The interactions, such as van der Waals, hydrophobic, and hydrogen bonding, contribute to the driving forces of IC formation, which can modify the biological, physical, and chemical properties of guest molecules.…”

Section: Cyclodextrinsmentioning

confidence: 99%

Nanotechnology-based drug delivery systems for control of microbial biofilms: a review

Ramos¹,

Silva²,

Spósito³

et al. 2018

IJN

215

104

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Since the dawn of civilization, it has been understood that pathogenic microorganisms cause infectious conditions in humans, which at times, may prove fatal. Among the different virulent properties of microorganisms is their ability to form biofilms, which has been directly related to the development of chronic infections with increased disease severity. A problem in the elimination of such complex structures (biofilms) is resistance to the drugs that are currently used in clinical practice, and therefore, it becomes imperative to search for new compounds that have anti-biofilm activity. In this context, nanotechnology provides secure platforms for targeted delivery of drugs to treat numerous microbial infections that are caused by biofilms. Among the many applications of such nanotechnology-based drug delivery systems is their ability to enhance the bioactive potential of therapeutic agents. The present study reports the use of important nanoparticles, such as liposomes, microemulsions, cyclodextrins, solid lipid nanoparticles, polymeric nanoparticles, and metallic nanoparticles, in controlling microbial biofilms by targeted drug delivery. Such utilization of these nanosystems has led to a better understanding of their applications and their role in combating biofilms.

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“…The characteristic shape (truncated cone appearance, doughnut, toroidal-, or cylinder-like shape) is given by the rigid chair conformation of the chiral glucose units and the spatial arrangement of the various functional groups (Martin et al, 2018;Szente et al, 2016). As a consequence of CDs' conformation, all the secondary -OH groups (corresponding to the carbon atoms from 2nd and 3rd positions of the glucose units) are at one of the edges of the cavity (on the wider rim), while the primary -OH groups are on the opposite end of the cavity.…”

Section: Chemical Structure and Propertiesmentioning

confidence: 99%

Cyclodextrins – development and applications of these versatile oligosaccharides

2020

Biomater Tissue Eng Bull

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. Cyclodextrins (CDs) are cyclic oligossacharides which have been known and studied for almost 130 years. This review aims to highlight the most important findings registered over this time, the physicochemical properties, preparation methods and uses of cyclodextrins, with special focus on their recently discovered applications. Due to their unique conformation, cyclodextrins are able to encapsulate a wide range of chemical entities, impacting on their solubility, bioavailability, stability, and shelf-life. Their complex formation properties together with the production from natural sources opens the door for cyclodextrins to be used in numerous and varied industries. However, the most important consumer of these versatile sugars is represented by the biomedical domain, where cyclodextrins find uses in drug formulations, delivery systems, medical textiles, implantable devices, tissue engineering, and many other connex applications. Moreover, intense research is still performed for this compounds, to develop and extend their therapeutic potential and serve as promising alternatives for treatment of severe diseases.

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Analytical characterization of cyclodextrins: History, official methods and recommended new techniques

Cited by 59 publications

References 101 publications

Comparative in vitro and in vivo taste assessment of liquid praziquantel formulations

Comparative in vitro and in vivo taste assessment of liquid praziquantel formulations

Nanotechnology-based drug delivery systems for control of microbial biofilms: a review

Cyclodextrins – development and applications of these versatile oligosaccharides

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