Host-guest Inclusion Complexes between Mitiglinide and the Naturally Occurring Cyclodextrins α, β, and γ: A Theoretical Approach

Azzam, Khaldun M. Al; Muhammad, Erma Fatiha

doi:10.15171/apb.2015.040

Cited by 14 publications

(7 citation statements)

References 11 publications

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“… 12 Cyclodextrins are able to modify the pharmacological properties of the encapsulated active substances such as solubility, bioavailability, chemical stability, dispersibility, and toxicity; thus, by the preparation of inclusion complexes with cyclodextrin molecules it can be possible to enhance or improve such properties of the active compounds. 13 − 16 …”

Section: Introductionmentioning

confidence: 99%

“…The most widely accepted host for complex formation is β-CD due to its suitable cavity diameter and low production cost. , β-Cyclodextrin consists of seven α- d -glucopyranose units joined by α-1,4-linkages . Cyclodextrins are able to modify the pharmacological properties of the encapsulated active substances such as solubility, bioavailability, chemical stability, dispersibility, and toxicity; thus, by the preparation of inclusion complexes with cyclodextrin molecules it can be possible to enhance or improve such properties of the active compounds. − …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of an Inclusion Complex of dl-Aminoglutethimide with β-Cyclodextrin and Its Innovative Application in a Biological System: Computational and Experimental Investigations

et al. 2022

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Our present study intended to investigate the encapsulation of DL-AGT within the lipophilic cavity of a β-CD molecule. The consequential inclusion system was characterized by UV–visible spectroscopy and 1 H NMR, PXRD, SEM, and FT-IR studies. Molecular docking was performed for the inclusion complex to discover the most proper orientation, and it was seen that the drug DL-AGT fits into the cavity of β-CD in a 1:1 ratio, which was also confirmed from the Job plot. Furthermore, a comparison was done on the basis of cell viability between the drug and its inclusion complex.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of an Inclusion Complex of dl-Aminoglutethimide with β-Cyclodextrin and Its Innovative Application in a Biological System: Computational and Experimental Investigations

et al. 2022

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“…Moreover, their results revealed that the formation of more stable MIT/ γ-CD complex compared to MIT/β-CD or MIT/α-CD complexes is mostly due to diversity in intermolecular hydrogen bonding. [68] …”

Section: Methodsmentioning

confidence: 99%

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

Abdolmaleki

Ghasemi

2017

Chem Biol Drug Des

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Cyclodextrin (CD) is a subset of the macrocyclic structural class, which is an important class of small organic agents that are useful functional excipients. They have wide range application possibilities in different fields of sciences such as material preparation, medicine, analytical chemistry, and separation processes. They are used widely in pharmaceutical formulations and drug delivery for increasing the water solubility of low soluble drugs and drug candidates. Due to the ring structure, they behave differently than smaller molecules and may be capable of hitting new classes of targets. A macrocyclic molecule presents varied functionality and stereochemical complexity in a pre-organized conformation of the ring structure. This can result in high selectivity and affinity for protein targets while conserving enough bioavailability to arrive at intracellular locations. Regardless of these valuable features, and the verified success of several marketed macrocycle drugs isolated from natural compounds, this class has been little explored in drug development. This study describes some of the key features of the CDs therapeutic discovery. Also, the application of computational chemistry approaches such as QSAR/QSPR, molecular docking, and molecular/quantum mechanics for modeling of CD-drug system is reviewed briefly. K E Y W O R D Sbioavailability, computational, cyclodextrin, drug design, drug discovery, macrocyclic, therapeutic

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“…Molecular Modeling. Molecular modeling study was performed as previously reported [19,28,29] by using the semiempirical PM3 method of Hyperchem Professional software (version 8.0). The initial structures of neutral LAP and -CD were constructed with the help of Hyperchem 8.0 and optimized with PM3.…”

Section: Phase-solubilitymentioning

confidence: 99%

Physicochemical Characterization and Cyclodextrin Complexation of the Anticancer Drug Lapatinib

Tóth

Jánoska

Völgyi

et al. 2017

Journal of Chemistry

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Lapatinib (LAP), the tyrosine kinase inhibitor drug with moderate bioavailability, was characterized in terms of physicochemical properties: acid-base characteristics, lipophilicity, and solubility. The highly lipophilic nature of the drug and its extremely low water solubility (S0=0.82 nM) limit the development of a parenteral formulation. In order to enhance solubility and bioavailability, inclusion complex formation with cyclodextrins (CDs) is a promising method of choice. Therefore, LAP-CD interactions were also studied by a multianalytical approach. The stability constants of LAP with native cyclodextrins, determined by UV spectroscopy, identified the seven-membered β-CD as the most suitable host. Continuous variation method (Job’s plot) by 1H NMR showed a 1 : 1 stoichiometry for the complexes. The geometry of the complex was elucidated by 2D ROESY NMR measurements and molecular modeling, indicating that the partial molecular encapsulation includes the fluorophenyl ring of LAP. Phase-solubility studies with four CDs, β-CD, (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD), randomly methylated-β- (RAMEB-) cyclodextrin, and sulfobutylether-β-cyclodextrin (SBE-β-CD), show an AL type diagram and highly increased solubility via CD complexation. The results are especially promising with SBE-β-CD, exerting more than 600-fold gain in solubility. The equilibrium and structural information presented herein can offer the molecular basis for an improved drug formulation with enhanced bioavailability.

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Host-guest Inclusion Complexes between Mitiglinide and the Naturally Occurring Cyclodextrins α, β, and γ: A Theoretical Approach

Cited by 14 publications

References 11 publications

Synthesis and Characterization of an Inclusion Complex of dl-Aminoglutethimide with β-Cyclodextrin and Its Innovative Application in a Biological System: Computational and Experimental Investigations

Synthesis and Characterization of an Inclusion Complex of dl-Aminoglutethimide with β-Cyclodextrin and Its Innovative Application in a Biological System: Computational and Experimental Investigations

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

Physicochemical Characterization and Cyclodextrin Complexation of the Anticancer Drug Lapatinib

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