Pharmaceutical cocrystals of naringenin with improved dissolution performanceElectronic supplementary information (ESI) available: 1H NMR spectra of cocrystals, powder XRD patterns of racemic NAR, NARBTN form A after heating, and cocrystals after dissolution experiments. CCDC 1820077 and 1820098. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ce00341f

Pharmaceutical cocrystals of naringenin with improved dissolution performanceElectronic... Naringenin (NAR), a natural flavanone compound, has received increasing attention in recent years due to its diverse pharmacological activities. However, this bioflavonoid shows poor solubility and therefore is difficult to absorb on oral ingestion. To improve the solubility of NAR, co-crystallization trials were performed, and four NAR cocrystals were obtained for the first time. All products were comprehensively characterized by a range of analytical methods, including single crystal and powder X-ray diffraction (XRD), liquid and solid state nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), and differential scanning calorimetry (DSC). The dissolution studies revealed that all the four cocrystals, namely, NARisonicotinamide (NARINM), NARpicolinic acid (NARPCA), and two modifications of NARbetaine (NARBTN), exhibit improved apparent solubilities and intrinsic dissolution rates (IDRs) relative to the parent NAR. Two NARBTN forms are monotropically related. Additionally, BTN was used for the first time to form cocrystals with flavonoid compounds, which may provide crystallographic inspiration for the cocrystal design and screening of these kinds of bioactive molecules. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png CrystEngComm Royal Society of Chemistry

Pharmaceutical cocrystals of naringenin with improved dissolution performanceElectronic supplementary information (ESI) available: 1H NMR spectra of cocrystals, powder XRD patterns of racemic NAR, NARBTN form A after heating, and cocrystals after dissolution experiments. CCDC 1820077 and 1820098. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ce00341f

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Publisher
The Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
1466-8033
D.O.I.
10.1039/c8ce00341f
Publisher site
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Abstract

Naringenin (NAR), a natural flavanone compound, has received increasing attention in recent years due to its diverse pharmacological activities. However, this bioflavonoid shows poor solubility and therefore is difficult to absorb on oral ingestion. To improve the solubility of NAR, co-crystallization trials were performed, and four NAR cocrystals were obtained for the first time. All products were comprehensively characterized by a range of analytical methods, including single crystal and powder X-ray diffraction (XRD), liquid and solid state nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), and differential scanning calorimetry (DSC). The dissolution studies revealed that all the four cocrystals, namely, NARisonicotinamide (NARINM), NARpicolinic acid (NARPCA), and two modifications of NARbetaine (NARBTN), exhibit improved apparent solubilities and intrinsic dissolution rates (IDRs) relative to the parent NAR. Two NARBTN forms are monotropically related. Additionally, BTN was used for the first time to form cocrystals with flavonoid compounds, which may provide crystallographic inspiration for the cocrystal design and screening of these kinds of bioactive molecules.

Journal

CrystEngCommRoyal Society of Chemistry

Published: May 11, 2018

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