Inclusion complexes of β-cyclodextrin and polymorphs of mebendazole: Physicochemical characterization

Saidman, Elbio; Chattah, Ana K.; Aragón, Leslie; Sancho, Matias Israel; Camí, Gerardo Enrique; Garnero, Claudia; Longhi, Marcela R.

doi:10.1016/j.ejps.2018.11.012

Cited by 16 publications

(8 citation statements)

References 39 publications

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“…The smallest geometric distance (less than 4 Å) between ICaf atoms contributes to stabilization in the β-CD cavity since the potential for intermolecular interaction declines with the increase in the distance between the particles [ 22 ]. The result of the molecular coupling corroborates the FT-IR spectra, confirming the involvement of intermolecular hydrogen bonds [ 32 ]. Additionally, molecular docking confirmed that inclusion complexes in a 1:1 stoichiometry ratio are most stable.…”

Section: Resultssupporting

confidence: 61%

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

et al. 2020

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Isopentyl caffeate (ICaf) is a bioactive ester widely distributed in nature. Our patented work has shown promising results of this molecule against Leishmania. However, ICaf shows poor solubility, which limits its usage in clinical settings. In this work, we have proposed the development of an inclusion complex of ICaf in β-cyclodextrin (β-CD), with the aim to improve the drug solubility, and thus, its bioavailability. The inclusion complex (ICaf:β-CD) was developed applying three distinct methods, i.e., physical mixture (PM), kneading (KN) or co-evaporation (CO) in different molar proportions (0.25:1, 1:1 and 2:1). Characterization of the complexes was carried out by thermal analysis, Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and molecular docking. The ICaf:β-CD complex in a molar ratio of 1:1 obtained by CO showed the best complexation and, therefore, was selected for further analysis. Solubility assay showed a marked improvement in the ICaf:β-CD (CO, 1:1) solubility profile when compared to the pure ICaf compound. Cell proliferation assay using ICaf:β-CD complex showed an IC50 of 3.8 and 2.7 µg/mL against L. amazonesis and L. chagasi promastigotes, respectively. These results demonstrate the great potential of the inclusion complex to improve the treatment options for visceral and cutaneous leishmaniases.

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Section: Resultssupporting

confidence: 61%

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

et al. 2020

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“…Form A was found to be therapeutically ineffective, while form C was reported as the most effective. Polymorph B is toxic due to its high aqueous solubility [20]. However, the relevance between different polymorphs and therapeutic anticancer activity is still not fully investigated.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of the geometric and electronic characterization of carbendazim-based drug (Nocodazole)

Khattab

2020

Heliyon

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Scarcity in studies defining the precise three-dimensional structure of approved drugs has led to an abandoning of their use for other therapeutic indications. In this manuscript, we solely focus on studying computationally the anticancer drug "Nocodazole" as a model compound for anthelmintic drugs -due to structural similarity-proven to exert anticancer activity such as Mebendazole and Albendazole. Computations on Nocodazole structures deposited in the Protein Data Bank (PDB) revealed possible existence of at least 6 conformers of Nocodazole. By combining the reported experimental UV-Vis data with our calculations, two conformers were assigned as the predominant structures of Nocodazole. In addition, td-DFT calculations revealed that the conformational flexibility of Nocodazole results in significant changes in atomic and molecular charge densities. The results have ramifications in identification of possible conformers of carbendazim-based drugs for repurposing in oncology through giving deep insights in understanding the spatial and electronic changes upon drug binding to anticancer targets.

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“…The strength of other H-bonds is also considerably high, suggesting that these interactions increase inclusion complex stability. [47] Figure 6: Molecular graph of the furaneol:βCD inclusion complex generated with a wavefunction calculated at B3LYP/6-311G(2d,2p) level of theory. Color references: Red = oxygen, green = carbon and white = hydrogen YP/6-311G(2d,2p) level of theory.…”

Section: Molecular Modeling Of the Fur-βcd Inclusion Complexmentioning

confidence: 99%

Riboflavin sensitized photodegradation of Furaneol in a β-cyclodextrin complex

Gambetta

Reynoso

Natera

et al. 2021

Journal of Photochemistry and Photobiology A: Chemistry

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Inclusion complexes of β-cyclodextrin and polymorphs of mebendazole: Physicochemical characterization

Cited by 16 publications

References 39 publications

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

Theoretical study of the geometric and electronic characterization of carbendazim-based drug (Nocodazole)

Riboflavin sensitized photodegradation of Furaneol in a β-cyclodextrin complex

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