Preparation and characterization of polymeric host molecules, β-cyclodextrin linked chitosan derivatives having different linkers

Buranaboripan, Wanvisa; Lang, Weeranuch; Motomura, Erika; Sakairi, Nobuo

doi:10.1016/j.ijbiomac.2014.05.016

Cited by 21 publications

(9 citation statements)

References 30 publications

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“…Beside the use of quaternary ammonium chitosan, the choice of a 10-atom long spacer arm may have contributed to the increased DEX apparent solubility obtained with the conjugated product. Indeed, Buranaboripan et al 2014 [42] described two chitosan-bCD derivatives mainly differing in spacer length; in particular, a C0 and C4 (4-butylamido linking arm) spacers. Both derivatives were tested with 6-(p-toluidino)-2-napthalene-6-sulfonate (TNS) fluorescence probe and the studies were performed in acetate buffer to favor the aqueous solubility of the macromolecules.…”

Section: Discussionmentioning

confidence: 99%

A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone

Piras

Zambito

Burgalassi

et al. 2018

J Mater Sci: Mater Med

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The ocular bioavailability of lipophilic drugs, such as dexamethasone, depends on both drug water solubility and mucoadhesion/permeation. Cyclodextrins and chitosan are frequently employed to either improve drug solubility or prolong drug contact onto mucosae, respectively. Although the covalent conjugation of cyclodextrin and chitosan brings to mucoadhesive drug complexes, their water solubility is restricted to acidic pHs. This paper describes a straightforward grafting of methyl-β-cyclodextrin (MCD) on quaternary ammonium chitosan (QA-Ch60), mediated by hexamethylene diisocyanate. The resulting product is a water-soluble chitosan derivative, having a 10-atom long spacer between the quaternized chitosan and the cyclodextrin. The derivative is capable of complexing the model drug dexamethasone and stable complexes were also observed for the lyophilized products. Furthermore, the conjugate preserves the mucoadhesive properties typical of quaternized chitosan and its safety as solubilizing excipient for ophthalmic applications was preliminary assessed by in vitro cytotoxicity evaluations. Taken as a whole, the observed features appear promising for future processing of the developed product into 3D solid forms, such as controlled drug delivery systems, films or drug eluting medical devices.

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Section: Discussionmentioning

confidence: 99%

A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone

Piras

Zambito

Burgalassi

et al. 2018

J Mater Sci: Mater Med

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“…These two spectra are similar and they both show absorption peaks at around 3430 and 2868 cm −1 , which are ascribed to the stretching vibrations of hydrogen‐bonded O–H (overlapping N–H) and C–H (–CH 2 ), respectively. It was also found that the peak at 894 cm −1 appears in the spectra of CS and AD‐CS, which represents the bending β‐pyranyl vibration . However, the absorption peak at 2868 cm −1 increases in intensity compared with the decreased band intensity at around 3430 cm −1 after substitution of the adamantane group, which can contribute to the introduction of the methylene‐containing AD group and the partial conversion of –NH 2 to –NH due to the amidation reaction.…”

Section: Resultsmentioning

confidence: 96%

An injectable and self‐healing novel chitosan hydrogel with low adamantane substitution degree

Cheng

Yang

Qiao

et al. 2019

Polymer International

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Chitosan (CS) is a semi-natural polymer with supreme biological function, while the strong interchain hydrogen bonds cause poor water solubility and limit its broader use. To break the semi-rigid structure of CS, a kind of CS modified by adamantane (AD-CS) was successfully synthesized by amidation reaction with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride as catalyst. The chemical structure of AD-CS was characterized by Fourier transform infrared spectroscopy and 1 H NMR. The AD substitution degree of CS is around 2%, calculated by 1 H NMR. A soft and transparent hydrogel composed of hydrogen bonds was obtained directly by simply adding a certain amount of water under mild conditions. Rheological measurements were carried out to research the mechanism of hydrogel formation by measuring the influence of different additives and conditions on the AD-CS hydrogel. Reinforced hydrogels were prepared by freezing and thawing. The mechanical strength and self-healing property of reinforced and pristine hydrogels were assessed with an oscillatory rheometer. The modulus of the reinforced hydrogel was obviously enhanced without much loss of self-healing property. Other properties such as adhesion, injectability and temperature response were also studied. These injectable and self-healing hydrogels show potential value in medical care. Additionally, this is a new method to design CS hydrogels with their original interchain hydrogen bonds.

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“…The maximum absorbance variation (Δabs x TRI concentration) was observed at a TRI:CD ratio of 0.5, which is associated with the formation of soluble complexes with a 1:1 stoichiometry (Buranaboripan, Lang, Motomura, & Sakairi, 2014 Regarding solubility diagrams, the complexes with derivative CDs (RMβCD and HPβCD) were able to solubilize more drug than the βCD complexes (binary-binary and ternary-ternary comparisons) through the increment of solubility parameters, as can be observed in Table 2, and further in supplementary Table 3.…”

Section: Phase Solubility Studiesmentioning

confidence: 97%

Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone

Araújo

Zoppi

Barbosa

et al. 2016

Carbohydrate Polymers

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A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring "A" of the drug with H(3) and H(5) protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.

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Preparation and characterization of polymeric host molecules, β-cyclodextrin linked chitosan derivatives having different linkers

Cited by 21 publications

References 30 publications

A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone

A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone

An injectable and self‐healing novel chitosan hydrogel with low adamantane substitution degree

Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone

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