Selective binding of methotrexate to monomeric, dimeric and polymeric cyclodextrins

Kritskiy, Iliya; Kumeev, R. S.; Volkova, Тatyana V.; Shipilov, D. A.; Kutyasheva, N. V.; Грачев, М. К.; Терехова, И. В.

doi:10.1039/c8nj02632g

Cited by 21 publications

(15 citation statements)

References 38 publications

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“…Polymeric CD consists of native CD linked with one (dimeric) or more (polymeric) spacers. These structures allow improved drug-binding abilities [14]. The truncated cone shape of CD with an internal hydrophobic cavity and external hydrophilic surface [15] makes the formation of inclusion complexes with hydrophobic compounds possible, such as curcumin [4,6], budesonide [16], prilocaine [17], etc., increasing their water solubility and bioavailability.…”

Section: Introductionmentioning

confidence: 99%

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Novel Findings about Double-Loaded Curcumin-in-HPβcyclodextrin-in Liposomes: Effects on the Lipid Bilayer and Drug Release

et al. 2018

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In this study, the encapsulation of curcumin (Cur) in “drug-in-cyclodextrin-in-liposomes (DCL)” by following the double-loading technique (DL) was proposed, giving rise to DCL–DL. The aim was to analyze the effect of cyclodextrin (CD) on the physicochemical, stability, and drug-release properties of liposomes. After selecting didodecyldimethylammonium bromide (DDAB) as the cationic lipid, DCL–DL was formulated by adding 2-hydroxypropyl-α/β/γ-CD (HPβCD)–Cur complexes into the aqueous phase. A competitive effect of cholesterol (Cho) for the CD cavity was found, so cholesteryl hemisuccinate (Chems) was used. The optimal composition of the DCL–DL bilayer was obtained by applying Taguchi methodology and regression analysis. Vesicles showed a lower drug encapsulation efficiency compared to conventional liposomes (CL) and CL containing HPβCD in the aqueous phase. However, the presence of HPβCD significantly increased vesicle deformability and Cur antioxidant activity over time. In addition, drug release profiles showed a sustained release after an initial burst effect, fitting to the Korsmeyer-Peppas kinetic model. Moreover, a direct correlation between the area under the curve (AUC) of dissolution profiles and flexibility of liposomes was obtained. It can be concluded that these “drug-in-cyclodextrin-in-deformable” liposomes in the presence of HPβCD may be a promising carrier for increasing the entrapment efficiency and stability of Cur without compromising the integrity of the liposome bilayer.

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Section: Introductionmentioning

confidence: 99%

“…Besides, CD can also improve thermal and physical stability and reduce drug toxicity [15]. Despite these advantages, in some cases, the amount of CD that is required to dissolve the drug is high, and can trigger toxic effects [14].…”

Section: Introductionmentioning

confidence: 99%

Novel Findings about Double-Loaded Curcumin-in-HPβcyclodextrin-in Liposomes: Effects on the Lipid Bilayer and Drug Release

et al. 2018

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“…Therefore, developing intelligent systems for drug delivery is essential. One strategy is to encapsulate the MTX within a matrix, such as CD, to form IC with the objective to increase the drug solubility and avoid interaction with the folate receptors in non-tumor cells [14,15,16]. Ensuring the release of MTX in the tumor will allow for a considerably high selectivity of action.…”

Section: Introductionmentioning

confidence: 99%

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

et al. 2018

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The inclusion compound (IC) of cyclodextrin (CD) containing the antitumor drug Methotrexate (MTX) as a guest molecule was obtained to increase the solubility of MTX and decrease its inherent toxic effects in nonspecific cells. The IC was conjugated with gold nanoparticles (AuNPs), obtained by a chemical method, creating a ternary intelligent delivery system for MTX molecules, based on the plasmonic properties of the AuNPs. Irradiation of the ternary system, with a laser wavelength tunable with the corresponding surface plasmon of AuNPs, causes local energy dissipation, producing the controlled release of the guest from CD cavities. Finally, cell viability was evaluated using MTS assays for β-CD/MTX and AuNPs + β-CD/MTX samples, with and without irradiation, against HeLa tumor cells. The irradiated sample of the ternary system AuNPs + β-CD/MTX produced a diminution in cell viability attributed to the photothermal release of MTX.

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“…Such knowledge would be useful to optimize the processes of obtaining CD complexes of betulin derivatives with the aim of their microencapsulation. CE is well suited for this purpose [12][13][14][15][16]. One of the widely used CE modes is ms ACE [3-5, 7, 8, 17-27]: apparent binding constants are calculated from dependencies of electrophoretic mobility of the compounds under study on ligand concentration in BGE.…”

Section: Abbreviationsmentioning

confidence: 99%

Electrophoretic mobility of ester betulin derivatives and their complexation with γ‐cyclodextrin studied by capillary electrophoresis in aqueous solutions at different pH values

2021

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In this article, capillary electrophoresis was used to measure the effective electrophoretic mobility of ester betulin derivatives as a pH function and to study their complexation with γ-cyclodextrin (γ-CD). The electrophoretic mobility of betulin 3,28-diphthalate (DPhB) and 3,28-disuccinate (DScB) changed unusually with decreasing pH: instead of decreasing, it first increased and then decreased. This fact as well as the turbidity of sample solutions at pH from 2.5 to 6, broadening of electrophoretic peaks and a decrease in the surface tension of the solutions indicates that these betulin derivatives, being amphiphilic compounds and weak acids, exist as micelles in aqueous solutions at pH 6 and below. The inclusion complexation of betulin derivatives with γ-CD at pH 9.18 and 4.5 was studied by mobility shift affinity capillary electrophoresis. At pH 9.18, the apparent binding (stability) constant logarithms for 1:1 γ-CD complexes of DPhB, betulin 3,28-disulfate (DSB) and DScB with 95% confidence interval limits were equal to 7. 44 ± 0.02, 7.09 (7.01-7.19), and 6.97 (6.87-7.08) at 25°C, respectively. At pH 4.5, the binding constant for the DSB complex was slightly lower, while the micelle formation did not allow determining the exact values of the constants for the DPhB and DScB complexes.

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Selective binding of methotrexate to monomeric, dimeric and polymeric cyclodextrins

Abstract: Selective binding of methotrexate to monomeric, dimeric and polymeric cyclodextrins characterized by formation of more stable complexes with dimeric β-cyclodextrin.

Cited by 21 publications

References 38 publications

Novel Findings about Double-Loaded Curcumin-in-HPβcyclodextrin-in Liposomes: Effects on the Lipid Bilayer and Drug Release

Novel Findings about Double-Loaded Curcumin-in-HPβcyclodextrin-in Liposomes: Effects on the Lipid Bilayer and Drug Release

Photothermally Controlled Methotrexate Release System Using β-Cyclodextrin and Gold Nanoparticles

Electrophoretic mobility of ester betulin derivatives and their complexation with γ‐cyclodextrin studied by capillary electrophoresis in aqueous solutions at different pH values

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