Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Oguchi, Tamio; Tozuka, Yuichi; Hanawa, Takehisa; Mizutani, Mayuko; Sasaki, Nahomi; Limmatvapirat, Sontaya; Yamamoto, Keiji

doi:10.1248/cpb.50.887

Cited by 19 publications

(9 citation statements)

References 21 publications

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“…Studies on the solid-state complexation of coground mixtures of cholic acid with either methyl p-hydroxybenzoate or ibuprofen demonstrated the formation of crystalline inclusion complexes during room temperature grinding and the formation of an amorphous phase under cryogenic conditions (25). The amorphous phase transformed to the crystalline complex after 1 h of heat treatment at 60-C.…”

Section: Discussionmentioning

confidence: 99%

Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase

et al. 2006

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Section: Discussionmentioning

confidence: 99%

Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase

et al. 2006

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“…In case of profens, the unique significance of supramolecular chirality phenomena for their bioactivity and separation can be illustrated by some evidences of their interaction with some bile acids. Thus, characteristic supramolecular inclusion behavior was reported by Oguchi et al [14] which considers solidstate complexation between cholic acid and ibuprofen with 2:1 stoichiometry. Interestingly, profens have been shown to be potent supra-*Address correspondence to this author at the Department of Pharmaco-Bromatology & Molecular Nutrition, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, PL-85-067 Bydgoszcz, Poland; Tel: +4852 3915; Fax: +4852 3817; E-mail: gbazylak@cm.umk.pl molecular stereoselective activators and inhibitors of the two distict sites of predominant isoform of the mammalian liver enzyme 3--hydrosteroid dehydrogenase which is involved in the metabolism of bile acids [15].…”

Section: Introductionmentioning

confidence: 75%

Supramolecular Chiro-Biomedical Assays and Enantioselective HPLC Analyses for Evaluation of Profens as Non-Steroidal Anti-Inflammatory Drugs, Potential Anticancer Agents and Common Xenobiotics

Ali¹,

Hussain²,

Saleem³

et al. 2008

CDDT

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The permanent world-wide increase in therapeutic administration of racemic profens as easy available non-prescribed analgesic drugs and a common first-choice anti-inflammatory agents was recently linked with renewed interest in their beneficial use, also as enantiopure formulations, to treat and/or prevent a variety of human malignancies including its four major types as colorectal, breast, lung, and prostate cancer. This underlies the continuous need of selecting perfectly suited chiral separation methods of profens capable to determine nanolevels of a distomer in presence of the eutomer in a variety of complex biological and environmental media. Thus, current improvements for direct enantiomeric separations of profens by well defined supramolecular-based chiral HPLC and recently developed monolithic, combinatorial, bimodal and polymeric chiral stationary phases employing a modern supramolecular chirality concepts has been outlined in this review. The use of diverse supramolecular approaches for chiral HPLC as an easy accessible tool enabling fast development of nanoscale enantioselective, high-throughput and gradient screening procedures for in situ monitoring of stereoselective ADME properties of profens in range of anticancer drug discovery technologies has been also addressed.

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“…The possible reason for DCA to selectively enclathrate (all-E) lycopene isomer is probably due to its acyclic and straight chain hydrocarbon structure with open ends. Oguchi et al, 2002, reported that DCA crystalline assembly channels are suitable for accommodating relatively large linear guest molecules through hydrogen bonding. The weak hydrogen bonds play an important role for various selective inclusion processes (Nakano et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

Lycopene (Z) – isomers enrichment and separation

Kessy

Zhang

2013

Int J of Food Sci Tech

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Summary (All‐E)‐ Lycopene undergoes geometrical isomerisation into (Z)‐lycopene isomers with thermal treatment. Influence of three isomerisation methods including ethyl acetate reflux, microwave‐assisted reflux and ultrasound/microwave‐assisted reflux, and isolation of (all‐E)‐lycopene from other carotenoids and (Z) lycopene isomers through selective inclusion by deoxycholic acid (3α, 12α dihydroxy‐5βcolan‐24‐oic‐acid, DCA) were investigated. The results showed that microwave and ultrasound/microwave‐assisted reflux were not significantly different at P < 0.05, but both were significantly different (P < 0.05) over refluxing in ethyl acetate, proportion of (Z)‐lycopene isomers reached 54% after refluxing for 5 h. Heterogeneous mixture of isomerised tomato oleoresin containing 54% (Z)‐lycopene isomers and 40% (all‐E)‐lycopene and deoxycholic acid in dichloromethane was incubated at 25 °C for 2 h. Then, the mixture was filtered and from the filtrate 96.6% (Z)‐isomers enriched lycopene was obtained. The processes can be used in the production of enriched (Z)‐lycopene isomers for food supplements and functional food industry as a natural bioactive ingredient.

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Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Cited by 19 publications

References 21 publications

Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase

Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase

Supramolecular Chiro-Biomedical Assays and Enantioselective HPLC Analyses for Evaluation of Profens as Non-Steroidal Anti-Inflammatory Drugs, Potential Anticancer Agents and Common Xenobiotics

Lycopene (Z) – isomers enrichment and separation

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