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• W4386863841 abstract "ABSTRACTObjective To synthesis a novel “Pharmaceutical Cocrystal” of berberine (BBR) with coformer 3-methylcinnamic acid (3MCA) for increasing its solubility and intestinal absorption property.Significance BBR-HCl has poor liposolubility, difficulty in penetrating the cell membrane and absorption in the gastrointestinal tract, low bioavailability, and its clinical application is limited. A new cocrystal is formed by the interaction between 3-MCA and BBR through molecular interaction, which improves the physicochemical properties, intestinal absorption property, and hygroscopicity.Methods The solvent evaporation method was used to synthesize BCR-3MCA cocrystal. The physicochemical properties of the crystals were confirmed by different spectral techniques i.e., by X-ray diffraction (PXRD, SXRD), Thermogravimetry and Differential Thermal Analysis (DSC, TGA), and Scanning electron microscopy (SEM). Hygroscopicity of the cocrystal was evaluated by Dynamic water vapor sorption (DVS). The intestinal absorption property was evaluated by the Ussing Chamber system.Results BBR and 3MCA can be directly self-assembled into uniform co-crystal by hydrogen bonds and π -π stacking interactions. Compared with BBR-HCl, the solubility of BBR-3MCA cocrystal in polar solvents of water, methanol, ethanol, and isopropanol increased by 13.9, 1.5, 4.7, and 15.8 times respectively. The apparent absorption and the absorption rate constants were increased by 7.7, and 5.6 times respectively. Surprisingly, BBR-3MCA co-crystal almost had no hygroscopicity.Conclusions The absolute molecular structure of the co-crystal was further confirmed by single crystal X-ray diffraction. The hydrogen bonds drove the formation of X-like one-dimensional unit. Compared to the BBR-HCl, BBR-3MCA cocrystal displayed superior dissolution and solubility performance, improve physical-chemical properties and significantly improve intestinal absorption.Keywords: berberine3-methylcinnamic acidco-crystalsingle crystal structureusing chamber systemsolubilityDisclaimerAs a service to authors and researchers we are providing this version of an accepted manuscript (AM). Copyediting, typesetting, and review of the resulting proofs will be undertaken on this manuscript before final publication of the Version of Record (VoR). During production and pre-press, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal relate to these versions also. AcknowledgmentsThe authors would like to thank Zhang CX from Shiyanjia Lab (www.shiyanjia.com) for the SXRD analysis.Conflict of InterestThe authors declare no conflict of interest.Data-Availability-StatementThe authors confirm that the crystallographic data supporting the findings of this study are openly available in CCDC at https://www.ccdc.cam.ac.uk/structures/, reference number [2178594].other data are available within the article and its supplementary materials.Table 1. Crystallographic characteristics and the X-ray data collection and structure refinement parameters for BBR-3MCADownload CSVDisplay TableTable 2. Hydrogen Bonding Distances and Angles of BBR–3MCADownload CSVDisplay TableTable3. The solubility of BBR-HCl and BBR-3MCA (mg/mL) at 37 °C in different solventsDownload CSVDisplay TableTable. 4 The absorption rate constant and apparent of permeability coefficient in rat jejunal segment of BBR-HCl and BBR-3MCADownload CSVDisplay TableFigure 1. Chemical structure of Berberine (BBR) and 3-Methylcinnamic acid (3-MCA).Display full sizeFigure 2. FT-IR diagrams of 3MCA (a), 3MCA and BBR Mix (b), BBR (c), BBR-3MCA Cocrystal (d).Display full sizeFigure 3. The 1H-NMR and 13C-NMR spectra of BBR, 3MCA, BBR–3MCA Cocrystal, BBR and 3MCA physical mixture.Display full sizeFigure 4. Powder X-ray diffractograms of 3MCA, 3MCA and BBR Mix, BBR, BBR-3MCA.Display full sizeFigure 5. The ORTEP molecular structures of complexes (a) to (c) shown as 30% thermal ellipsoid probabilities of BBR–3MCA cocrystal, (a) thermal ellipsoid drawing including atomic labelling scheme, (b) key intermolecular interactions (hydrogen bonds are teal colored), (c) molecular packing.Display full sizeFigure 6. Thermal properties of 3MCA, BBR-HCl, BBR-3MCA Cocrystal, (a) TGA and (b) DSC.Display full sizeFigure 7. SEM images of BBR-3MCA Co-Crystal (a) single crystal picture 500μm, (b) single crystal picture 200μm, (c) single crystal picture 20μm.Display full sizeFigure 8. DVS isotherms(a)and Dissolution profile(b) of BBR-HCl and BBR-3MCA cocrystalDisplay full size" @default.
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• W4386863841 date "2023-09-19" @default.
• W4386863841 modified "2023-10-11" @default.
• W4386863841 title "Novel Co-Crystal of 3-Methylcinnamic Acid with Berberine(1:1): Synthesis, Characterization, and Intestinal Absorption Property" @default.
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• W4386863841 doi "https://doi.org/10.1080/03639045.2023.2259460" @default.
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