Inclusion Complexes of Nateglinide with HP–β–CD and L-Arginine for Solubility and Dissolution Enhancement: Preparation, Characterization, and Molecular Docking Study

Suvarna, Vasanti; Kajwe, Apeksha; Murahari, Manikanta; Pujar, Gurubasavaraj V.; Inturi, Bharathkumar; Sherje, Atul P.

doi:10.1007/s12247-017-9275-z

Cited by 33 publications

(20 citation statements)

References 40 publications

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“…Complexes with a stability constant value between 100 and 1000 mol L −1 have biological application. Values lesser than 100 mol L −1 give unstable drug–CD complexes, and values higher than 1000 mol L −1 adversely affect drug absorption [ 27 ]. The significant enhancement in the stability constant and complexation efficiency were achieved with the addition of TPGS as a ternary substance.…”

Section: Resultsmentioning

confidence: 99%

Formulation and Evaluation of Supramolecular Food-Grade Piperine HP β CD and TPGS Complex: Dissolution, Physicochemical Characterization, Molecular Docking, In Vitro Antioxidant Activity, and Antimicrobial Assessment

et al. 2020

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The purpose of the present study was to improve the aqueous solubility, dissolution, and antioxidant activity of the water-insoluble drug piperine (PIP). The study was performed by preparing PIP binary inclusion complex (PIP BIC) and piperine ternary inclusion complex (PIP TIC) by different methods. The effect of a hydrophilic auxiliary substance (TPGS) was assessed with addition to PIP and hydroxypropyl beta cyclodextrin (HP β CD) complex. The phase solubility study was performed to evaluate the complexation efficiency and stability constant. The aqueous solubility, dissolution, physicochemical assessment, antioxidant activity, antimicrobial activity, and molecular docking were further evaluated to check the effect of the complexation of PIP. The stability constant (Ks) value was found to be 238 and 461 M−1 for the binary and ternary inclusion complex. The dissolution study results showed a marked enhancement of release in comparison to pure drug. XRD and SEM studies revealed the presence of more agglomerated and amorphous structures of PIP, which confirmed the formation of complexes. The results of DPPH radical scavenging and antimicrobial activity showed a significant (p < 0.05) enhancement in scavenging activity for PIP TIC (microwave irradiation (MI)). The docking studies have revealed that the binding affinity of TPGS at the PIP-HP β CD complex was −5.2 kcal/mol.

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Section: Resultsmentioning

confidence: 99%

Formulation and Evaluation of Supramolecular Food-Grade Piperine HP β CD and TPGS Complex: Dissolution, Physicochemical Characterization, Molecular Docking, In Vitro Antioxidant Activity, and Antimicrobial Assessment

et al. 2020

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“…In fact, several theoretical and experimental studies have validated that tetraalkylammonium cations and amino acids are able to form van der waals interactions or strong hydrogen bonds with CDs . In the “α‐CD/AAILs/enantiomers” ternary system, enantiomers tended to occupy the hydrophobic cavity of α‐CD; however, the formed inclusion complex was not stable because of the unsuitable cavity size.…”

Section: Resultsmentioning

confidence: 99%

Enhanced enantioselectivity of native α‐cyclodextrins by the synergy of chiral ionic liquids in capillary electrophoresis

Zhang

Xue

et al. 2018

J of Separation Science

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In the cyclodextrins family, the native α‐cyclodextrin has almost been abandoned in capillary electrophoresis chiral separation due to its much weaker enantioselectivity compared with β‐cyclodextrin and their derivatives. In this work, several amino acid chiral ionic liquids were selected to establish synergistic enantioseparation systems with native α‐cyclodextrin. Enhanced enantioselectivities were observed in the chiral ionic liquids/α‐cyclodextrin synergistic systems compared with single α‐cyclodextrin system. A series of comparison experiments were performed to demonstrate the superiority of the synergistic systems. Primary parameters affecting the enantioseparation were systematically optimized, including the type and concentration of chiral ionic liquids, α‐cyclodextrin concentration, buffer pH, and applied voltage. Best separations of the model enantiomers were obtained in a 20 mM Tris/H3PO4 buffer at pH 2.5 containing 3% (m/v) α‐cyclodextrin and 30 mM tetramethylammonium‐l‐arginine. The results show that the α‐cyclodextrin is also worth our attention when selecting chiral selectors for capillary electrophoresis enantioseparation of specific racemic compound.

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“…glyburide-HPβCDarginine 1:1:0.5 co-grinding ternary complex showed higher solubility in both aqueous media and buffer pH 7.5 ternary complex exhibits significant improvement in the dissolution profile compared with the pure drug in unbuffered aqueous media [20] repaglinide-HPβCDarginine 1:1:1 coevaporation kneading coevaporate complex showed maximum increase in solubility of drug (475-fold) ternary complexes showed enhanced dissolution rate [21] nateglinide-HPβCDarginine 1:1:1 kneading coevaporation spray-drying ternary complexes showed higher solubility in both aqueous media and buffer pH 1.2 ternary complexes showed better performance (DE5 = 22) compared with the drug alone (DE5 = 6.6) [22] cefixime-βCD-arginine cefixime-HPβCDarginine spray-drying ternary complex showed better drug solubility ternary complex with HPβCD exhibit better performance (DE2 = 25) compared with the drug alone (DE2 = 0.75) [23] rifampicin-βCD-arginine 1:1:1 freeze-drying ternary complex showed an increase in the drug solubility ternary complex showed an increase in the dissolved percentage of the drug (53% versus 25% for drug alone) higher antibiofilm activity with respect to pure rifampicin [24] Pharmaceutics 2021, 13, 1099…”

Section: Amino Acids As Auxiliary Agentsmentioning

confidence: 99%

“…Arginine was the best candidate for forming ternary complexes with both drugs. The authors found the following values for stability constant and complexation efficiency: repaglinide–HPβCD, 333 M −1 and 0.025; repaglinide–HPβCD–arginine, 4407 M −1 and 0.340; nateglinide–HPβCD, 382 M −1 and 0.435; nateglinide–HPβCD–arginine, 464 M −1 and 0.526 [ 21 , 22 ].…”

Section: Amino Acids As Auxiliary Agentsmentioning

confidence: 99%

Cyclodextrin Multicomponent Complexes: Pharmaceutical Applications

et al. 2021

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Cyclodextrins (CDs) are naturally available water-soluble cyclic oligosaccharides widely used as carriers in the pharmaceutical industry for their ability to modulate several properties of drugs through the formation of drug–CD complexes. The addition of an auxiliary substance when forming multicomponent complexes is an adequate strategy to enhance complexation efficiency and to facilitate the therapeutic applicability of different drugs. This review discusses multicomponent complexation using amino acids; organic acids and bases; and water-soluble polymers as auxiliary excipients. Special attention is given to improved properties by including information on the solubility, dissolution, permeation, stability and bioavailability of several relevant drugs. In addition, the use of multicomponent CD complexes to enhance therapeutic drug effects is summarized.

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Inclusion Complexes of Nateglinide with HP–β–CD and L-Arginine for Solubility and Dissolution Enhancement: Preparation, Characterization, and Molecular Docking Study

Cited by 33 publications

References 40 publications

Formulation and Evaluation of Supramolecular Food-Grade Piperine HP β CD and TPGS Complex: Dissolution, Physicochemical Characterization, Molecular Docking, In Vitro Antioxidant Activity, and Antimicrobial Assessment

Formulation and Evaluation of Supramolecular Food-Grade Piperine HP β CD and TPGS Complex: Dissolution, Physicochemical Characterization, Molecular Docking, In Vitro Antioxidant Activity, and Antimicrobial Assessment

Enhanced enantioselectivity of native α‐cyclodextrins by the synergy of chiral ionic liquids in capillary electrophoresis

Cyclodextrin Multicomponent Complexes: Pharmaceutical Applications

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