NMR investigation of a novel excipient, α‐glucosylhesperidin, as a suitable solubilizing agent for poorly water‐soluble drugs

Zhang, Junying; Tozuka, Yuichi; Uchiyama, Hiromasa; Higashi, Kenjirou; Moribe, Kunikazu; Takeuchi, Hirofumi; Yamamoto, Keiji

doi:10.1002/jps.22606

Cited by 28 publications

(9 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Improving the dissolution profile of poorly water-soluble drugs significantly enhanced their bioavailability. We proposed that the presence of aggregated nanostructures of transglycosylated materials played an important role in the pronounced enhancement of the apparent solubility of the drugs by forming self-associated structures with a hydrophobic skeleton core Zhang et al, 2011Zhang et al, , 2014. Rutin (quercetin-3-rutinoside), a flavonol glycoside, is found in many plants, such as onion, broccoli and buckwheat (Calabro et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Enhanced solubility of quercetin by forming composite particles with transglycosylated materials

Fujimori

Kadota

Shimono

et al. 2015

Journal of Food Engineering

Self Cite

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Enhanced solubility of quercetin by forming composite particles with transglycosylated materials

Fujimori

Kadota

Shimono

et al. 2015

Journal of Food Engineering

Self Cite

View full text Add to dashboard Cite

“…The self-organization of surfactants and amphiphilic polymers into micelles has been widely researched using many analytical methods, including the measurement of surface tension, Fourier transform infrared spectroscopy, relaxation studies using 1 H nuclear magnetic resonance, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). [18][19][20][21][22] The ITC method has been used to characterize micellar-based systems because the detailed thermodynamic behavior of micellization could be determined by a single experiment, without the need of a probe. 22,23) The main objective of this study was to evaluate the micellization properties of Soluplus ® in water and its solubility enhancement effect on an amorphous solid dispersion (ASD) system.…”

mentioning

confidence: 99%

Evaluation of the Micellization Mechanism of an Amphipathic Graft Copolymer with Enhanced Solubility of Ipriflavone

et al. 2016

Self Cite

View full text Add to dashboard Cite

The main purpose of this study was to investigate the solubilization enhancement properties of an amphipathic graft copolymer, Soluplus ® , on test compounds. Micellization of Soluplus ® in solution was characterized by evaluating the changes in the surface activity, turbidity, and thermodynamic behavior. To assess the feasibility of Soluplus ® as a polymeric carrier of solid dispersions, freeze-dried samples of ipriflavone were prepared, and the physicochemical properties of the carrier plus ipriflavone were evaluated in terms of solubility, dissolution, and crystallinity. The surface tension of the solution decreased depending on the polymer concentration, and gradual turbidity increase was observed. Isothermal titration calorimetry was used to measure the thermal reaction accompanying the micellization of Soluplus ® and indicated that a colloidal micelle formation improved solubility. The prepared formulations, particularly at a ratio of ipriflavone : Soluplus ® 1 : 10 (w/w) exhibited a dramatically improved solubility of ipriflavone that was ca. 70-fold higher than that of untreated ipriflavone. The solubilization mechanism of Soluplus ® was partially elucidated and suggested that its strategic application could improve the solubility of hydrophobic compounds.Key words isothermal titration calorimetry; ipriflavone; amphipathic graft copolymer; solubility Among the available technologies, the solid dispersion technique is commonly used as one of the most promising strategies for the enhancement of the solubility, dissolution rate, and bioavailability of poorly water-soluble compounds. A solid dispersion system can be defined as a distribution of active pharmaceutical ingredients as molecular amorphous particles and/or in the microcrystalline state into a carrier matrix-like polymer.1) The physicochemical characteristics of polymeric carriers could dominate the pharmaceutical properties of a solid dispersion system. 2,3) Based on the characteristic properties of a polymeric carrier, a number of solid dispersion systems possessing various functional properties such as sustained release, pH-dependent release, self-emulsifying properties, and site-specific release have been developed. [4][5][6][7] In particular, amphiphilic polymers have been found to be beneficial for the enhancement of not only solubility but also of the oral bioavailability of poorly water-soluble compounds because they form micellar structures that contain the compound. 6,8) Soluplus ® , a graft copolymer consisting of polyvinyl caprolactam, polyvinyl acetate, and polyethyleneglycol, has been applied to the design of solid-dispersion formulations with poorly water-soluble substances to improve their solubility and bioavailability.9,10) The copolymer exhibits an amphipathic property attributed to its hydrophilic and hydrophobic residues, which could contribute to the formation of micelles in water. Unlike conventional polymers such as polyvinylpyrrolidone and hydroxypropyl methylcellulose, Soluplus ® is bifunctional and can act as both a polym...

show abstract

“…Nuclear overhauser effect spectroscopy (NOESY) is an excellent solution two‐dimensional NMR technique that utilizes the effect of nearby atoms (≤5 Å) undergoing spin‐lattice relaxation to probe the average distance between the interacting spins . NOESY has shown applications in probing the state of intermolecular interactions/distances among drug–polymer and medium during solubilization of poorly soluble APIs prepared as ASD with a novel excipient, α‐glucosylhesperidin . Also, the mechanism of generation and maintenance of supersaturation during dissolution of drug from mefenamic acid (MFA)/Eudragit EPO ASD was unravelled using NOESY difference technique .…”

Section: Molecular Interactions Of Solid Dispersions In Solution/dissmentioning

confidence: 99%

Structural and Dynamic Properties of Amorphous Solid Dispersions: The Role of Solid-State Nuclear Magnetic Resonance Spectroscopy and Relaxometry

Paudel

Geppi

Mooter

2014

Journal of Pharmaceutical Sciences

117

103

View full text Add to dashboard Cite

NMR investigation of a novel excipient, α‐glucosylhesperidin, as a suitable solubilizing agent for poorly water‐soluble drugs

Cited by 28 publications

References 41 publications

Enhanced solubility of quercetin by forming composite particles with transglycosylated materials

Enhanced solubility of quercetin by forming composite particles with transglycosylated materials

Evaluation of the Micellization Mechanism of an Amphipathic Graft Copolymer with Enhanced Solubility of Ipriflavone

Structural and Dynamic Properties of Amorphous Solid Dispersions: The Role of Solid-State Nuclear Magnetic Resonance Spectroscopy and Relaxometry

Contact Info

Product

Resources

About