Methyl-Beta-Cyclodextrins: The Role of Number and Types of Substituents in Solubilizing Power

Fenyvesi, Éva; Szemán, Julianna; Csabai, Katalin; Szente, Lajos

doi:10.1002/jps.23917

Cited by 43 publications

(18 citation statements)

References 32 publications

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“…The DS has a great influence on the physicochemical properties of CDs and their ability to form complexes. For instance, randomly-methylated βCD (RMβCD) has the highest solubility in water when the degree of substitution is about 14, that is, when two-thirds of the OH-groups have been replaced by methoxy groups [ 36 ]. Increasing the DS above 14 decreases the RMβCD solubility.…”

Section: Physiochemical Properties Of Cyclodextrinsmentioning

confidence: 99%

Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes

et al. 2018

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Cyclodextrins (CDs), a group of oligosaccharides formed by glucose units bound together in a ring, show a promising ability to form complexes with drug molecules and improve their physicochemical properties without molecular modifications. The stoichiometry of drug/CD complexes is most frequently 1:1. However, natural CDs have a tendency to self-assemble and form aggregates in aqueous media. CD aggregation can limit their solubility. Through derivative formation, it is possible to enhance their solubility and complexation capacity, but this depends on the type of substituent and degree of substitution. Formation of water-soluble drug/CD complexes can increase drug permeation through biological membranes. To maximize drug permeation the amount of added CD into pharmaceutical preparation has to be optimized. However, solubility of CDs, especially that of natural CDs, is affected by the complex formation. The presence of pharmaceutical excipients, such as water-soluble polymers, preservatives, and surfactants, can influence the solubilizing abilities of CDs, but this depends on the excipients’ physicochemical properties. The competitive CD complexation of drugs and excipients has to be considered during formulation studies.

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Section: Physiochemical Properties Of Cyclodextrinsmentioning

confidence: 99%

Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes

et al. 2018

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“…These results showed that RAMEB is the best solubilizer among the studied CDs. The solubility enhancement of this CD towards many compounds has been reported in the literature [20–22]. However, HP-β-CD is the only β-CD derivative cited in the FDA’s list of Inactive Pharmaceutical Ingredients among the studied derivatives, therefore, further studies will focus on this CD.…”

Section: Resultsmentioning

confidence: 88%

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

Azzi¹,

Danjou

Landy

et al. 2017

Beilstein J. Org. Chem.

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Nerolidol (Ner), a major component of many plant essential oils, is known for its various biological properties. However, the low solubility of Ner in water and its susceptibility to degradation limit its application. The aim of our study was to improve the solubility and photostability of Ner through its encapsulation in different cyclodextrins (CDs). The formation constants of cis-, trans-Ner and their commercial mixture with various CDs (α-CD, β-CD, γ-CD, HP-β-CD, RAMEB, CRYSMEB and SBE-β-CD) were determined by phase solubility studies and confirmed by the spectral displacement UV-visible method. The solubility of cabreuva essential oil (EO) rich in trans-Ner was also evaluated by total organic carbon (TOC) analysis. The encapsulation efficiency (EE %) of Ner in HP-β-CD solid complexes was assessed by HPLC. The structural characterization of CD/trans-Ner inclusion complex was then conducted by NMR spectroscopy followed by molecular modelling studies. The effect of encapsulation on the Ner photostability was also carried out over time under UVB irradiation. AL-type phase-solubility diagrams were obtained, suggesting the formation of 1:1 CD/Ner inclusion complexes. The solubility of Ner was enhanced by approximately 70-fold in the presence of 10 mM HP-β-CD. Moreover, high EE % values were obtained for 5:1 and 10:1 HP-β-CD:Ner molar ratios. NMR and molecular modelling studies revealed the most stable structure for trans-Ner inside the CD cavity with the OH group oriented towards the wider rim of the CD. Finally, CD encapsulation of Ner as pure compound or as main component of the cabreuva EO, protected it from degradation. This effect was more pronounced as the concentration of CD increased. These findings suggested that CDs are promising encapsulating carriers for Ner by enhancing its solubility and stability and thereby its application in food industry.

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“…In the case of the methylated bCD derivatives, maximum curve was obtained for the solubility of polyunsaturated fatty acids, furosemide, amiodarone, and cholesterol with a maximum around DS~14. 55 In the case of sulfobutylether bCD, the picture is almost as complicated as in the case of HPBCD. 56 The 12 compounds studied by capillary electrophoresis could be classified into 4 groups concerning the complex association constant versus DS: minimum and maximum curve as well as ascending and descending curves were obtained depending on the structure of the model drug.…”

Section: Effect Of Ds On Solubilizing Propertiesmentioning

confidence: 99%

“Back to the Future”: A New Look at Hydroxypropyl Beta-Cyclodextrins

Malanga

Szemán

Fenyvesi

et al. 2016

Journal of Pharmaceutical Sciences

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Since the discovery about 30 years ago (2-hydroxypropyl) beta-cyclodextrin, a highly soluble derivative of beta-cyclodextrin, has become an approved excipient of drug formulations included both in the United States and European Pharmacopoeias. It is recommended to use as solubilizer and stabilizer for oral and parenteral formulations. Recently, its pharmacological activity has been recognized in various diseases. The increasing applications require a closer look to the structure-activity relationship. As (2-hydroxypropyl) beta-cyclodextrin (HPBCD) is always a mixture of isomers with various degrees and pattern of hydroxypropylation, no wonder that the products of different manufacturers are often different. Several HPBCDs were compared applying a battery of analytical tools including thin layer chromatography, high performance liquid chromatography (HPLC), HPLC-mass spectrometry (MS), and matrix-assisted laser desorption MS. We studied how the average degree of substitution affects the aggregation behavior, the toxicity, and the solubilizing effect on poorly soluble drugs. We found that the products with low average degree of substitution are more prone to aggregation. The samples studied are nontoxic to Caco-2 cells and have low hemolytic activity. The solubility enhancement of poorly soluble drugs decreases or increases with increasing degree of substitution or shows a maximum curve depending on the properties of the guest.

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Methyl-Beta-Cyclodextrins: The Role of Number and Types of Substituents in Solubilizing Power

Cited by 43 publications

References 32 publications

Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes

Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

“Back to the Future”: A New Look at Hydroxypropyl Beta-Cyclodextrins

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