Cyclodextrin/surfactant inclusion complexes: An integrated view of their thermodynamic and structural properties

Araújo, Larissa dos Santos Silva; Lazzara, Giuseppe; Chiappisi, Leonardo

doi:10.1016/j.cis.2021.102375

Cited by 41 publications

(37 citation statements)

References 119 publications

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“…Generally, the drug loading capacity of cyclodextrin complexes is calculated by the mass ratio of drugs in the complex to the whole complex (Kfoury et al., 2017 ; Lima et al., 2019 ). In addition, most of the cyclodextrins derivatives have a wide molar mass distribution due to different degrees and positions of substituents (dos Santos Silva Araújo et al., 2021 ). Therefore, the solubilization capacity of CDs was evaluated by comparing the Frax solubility in the CDs of equal mass percentage concentration (see section 3.1), rather than molar concentration.…”

Section: Resultsmentioning

confidence: 99%

Rational formulation engineering of fraxinellone utilizing 6-O-α-D-maltosyl-β-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy

Feng

Yang

et al. 2021

Drug Delivery

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Although Fraxinellone (Frax) isolated from Dictamnus albus L. possessed excellent anti-hepatic fibrosis activity, oral administration of Frax suffered from the inefficient therapeutic outcome in vivo due to negligible oral absorption. At present, the oral formulation of Frax is rarely exploited. For rational formulation design, we evaluated preabsorption risks of Frax and found that Frax was rather stable while poorly dissolved in the gastrointestinal tract (78.88 μg/mL), which predominantly limited its oral absorption. Further solubility test revealed the outstanding capacity of cyclodextrin derivatives (CDs) to solubilize Frax (6.8–12.8 mg/mL). This led us to study the inclusion complexes of Frax with a series of CDs and holistically explore their drug delivery performance. Characterization techniques involving 1 H-NMR, FT-IR, DSC, PXRD, and molecular docking confirmed the most stable binding interactions when Frax complexed with 6-O-α-D-maltosyl-β-cyclodextrin (G 2 -β-CD-Frax). Notably, G 2 -β-CD-Frax exhibited the highest solubilizing capacity, fast dissolution rate, and superior Caco-2 cell internalization with no obvious toxicity. Pharmacokinetic studies demonstrated markedly higher oral bioavailability of G 2 -β-CD-Frax (5.8-fold that of free drug) than other Frax-CDs. Further, long-term administration of G 2 -β-CD-Frax (5 mg/kg) efficiently inhibited CCl 4 -induced hepatic fibrosis in the mouse without inducing any toxicity. Our results will inspire the continued advancement of optimal oral Frax formulations for anti-fibrotic therapy.

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Section: Resultsmentioning

confidence: 99%

Rational formulation engineering of fraxinellone utilizing 6-O-α-D-maltosyl-β-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy

Feng

Yang

et al. 2021

Drug Delivery

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“…CDs are a class of cyclic oligosaccharides. α-CD, β-CD and γ-CD are well known, consisting of 6, 7 and 8 α-(1-4)D-glucopyranoside ( Bruns 2019 , Dos Santos Silva Araújo et al. 2021 ).…”

Section: Discussionmentioning

confidence: 99%

“…Surfactants are typical guest compounds of CDs. DS − forms a CD–DS − compound with a hydrophobic tail stuck in the hole of CD ( Dos Santos Silva Araújo et al. 2021 ).…”

Section: Discussionmentioning

confidence: 99%

Letter to the Editor: Speedy Plant Genotyping by SDS-Tolerant Cyclodextrin-PCR

Nakanishi

Kawashima

Naganawa

et al. 2022

Plant and Cell Physiology

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“…The most varied compounds are those that can establish supramolecular interactions either through the hydrophobic effect or through, e.g., hydrogen bonds. To give some examples we can mention surfactants ( Valente and Söderman, 2014 ; dos Santos Silva Araújo et al, 2021 ), drugs ( Uekama et al, 1998 ; Rajbanshi et al, 2018 ; Saokham et al, 2018 ; Tian et al, 2020 ), organic pollutants ( Cova T. F. G. G. et al, 2018 ; Filho et al, 2018 ; Liu Q. et al, 2020 ), dyes ( Bezerra et al, 2020 ), and metal ions ( Buvári and Barcza, 1989 ; Ribeiro et al, 2006 ; Prochowicz et al, 2017 ). The versatility of these oligosaccharides makes their application highly attractive in distinct fields such as pharmaceutical (the main one among them all) ( Loftsson and Brewster, 1996 ; Loftsson and Duchene, 2007 ), food technology ( Matencio et al, 2020c ; Gonzalez Pereira et al, 2021 ), textile ( Bezerra et al, 2020 ), wastewater treatment ( Sikder et al, 2019 ; Chodankar et al, 2021 ; Cova et al, 2021 ), detergency ( Schlüter et al, 2020 ) and paper ( Aguado et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin-Based Nanosponges: Overview and Opportunities

et al. 2022

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Nanosponges are solid cross-linked polymeric nano-sized porous structures. This broad concept involves, among others, metal organic frameworks and hydrogels. The focus of this manuscript is on cyclodextrin-based nanosponges. Cyclodextrins are cyclic oligomers of glucose derived from starch. The combined external hydrophilicity with the internal hydrophobic surface constitute a unique “microenvironment”, that confers cyclodextrins the peculiar ability to form inclusion host‒guest complexes with many hydrophobic substances. These complexes may impart beneficial modifications of the properties of guest molecules such as solubility enhancement and stabilization of labile guests. These properties complemented with the possibility of using different crosslinkers and high polymeric surface, make these sponges highly suitable for a large range of applications. Despite that, in the last 2 decades, cyclodextrin-based nanosponges have been developed for pharmaceutical and biomedical applications, taking advantage of the nontoxicity of cyclodextrins towards humans. This paper provides a critical and timely compilation of the contributions involving cyclodextrins nanosponges for those areas, but also paves the way for other important applications, including water and soil remediation and catalysis.

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Cyclodextrin/surfactant inclusion complexes: An integrated view of their thermodynamic and structural properties

Cited by 41 publications

References 119 publications

Rational formulation engineering of fraxinellone utilizing 6-O-α-D-maltosyl-β-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy

Rational formulation engineering of fraxinellone utilizing 6-O-α-D-maltosyl-β-cyclodextrin for enhanced oral bioavailability and hepatic fibrosis therapy

Letter to the Editor: Speedy Plant Genotyping by SDS-Tolerant Cyclodextrin-PCR

Cyclodextrin-Based Nanosponges: Overview and Opportunities

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