A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution

A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution

A co-crystal of rosiglitazone (Rsg) with berberine (Bbr), Rsg-Bbr, was prepared by the solvent evaporation method and characterized. The results showed that the electrostatic attraction existed between the nitrogen anion of rosiglitazone and the quaternary ammonium cation of berberine, and C-H···O h...

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Main Authors: Xiaoshu Guan, Lan Jiang, Linhong Cai, Li Zhang, Xiangnan Hu
Format: Article
Language:English
Published: MDPI AG 2020-09-01
Series:Molecules
Subjects:
co-crystal
rosiglitazone
berberine
electrostatic attraction
moisture adsorption
dissolution rate
Online Access:https://www.mdpi.com/1420-3049/25/18/4288
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spelling doaj-5eaeb6f2df8f461a95f82d0884fa30312020-11-25T02:31:34ZengMDPI AGMolecules1420-30492020-09-01254288428810.3390/molecules25184288A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and DissolutionXiaoshu Guan0Lan Jiang1Linhong Cai2Li Zhang3Xiangnan Hu4Department of Medicinal Chemistry, School of Pharmacy, Chongqing Medical University, Chongqing 400016, ChinaCollege of Environment and Resources, Chongqing Technology and Business University, Chongqing 400016, ChinaDepartment of Medicinal Chemistry, School of Pharmacy, Chongqing Medical University, Chongqing 400016, ChinaDepartment of Medicinal Chemistry, School of Pharmacy, Chongqing Medical University, Chongqing 400016, ChinaDepartment of Medicinal Chemistry, School of Pharmacy, Chongqing Medical University, Chongqing 400016, ChinaA co-crystal of rosiglitazone (Rsg) with berberine (Bbr), Rsg-Bbr, was prepared by the solvent evaporation method and characterized. The results showed that the electrostatic attraction existed between the nitrogen anion of rosiglitazone and the quaternary ammonium cation of berberine, and C-H···O hydrogen bonds were formed between Rsg and Bbr. In the crystal structure, rosiglitazone molecules stack into a supramolecular layer through π-π interactions while π-π interactions between berberine cations also result in a similar layer. The co-crystal presented a low moisture adsorption curve in the range of 0−95% relative humidity values at 25 °C. The improved dissolution rate of rosiglitazone in pH = 6.8 buffer solution could be achieved after forming co-crystal.https://www.mdpi.com/1420-3049/25/18/4288co-crystalrosiglitazoneberberineelectrostatic attractionmoisture adsorptiondissolution rate
collection DOAJ
language English
format Article
sources DOAJ
author Xiaoshu Guan
Lan Jiang
Linhong Cai
Li Zhang
Xiangnan Hu
spellingShingle Xiaoshu Guan
Lan Jiang
Linhong Cai
Li Zhang
Xiangnan Hu
A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
Molecules
co-crystal
rosiglitazone
berberine
electrostatic attraction
moisture adsorption
dissolution rate
author_facet Xiaoshu Guan
Lan Jiang
Linhong Cai
Li Zhang
Xiangnan Hu
author_sort Xiaoshu Guan
title A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
title_short A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
title_full A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
title_fullStr A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
title_full_unstemmed A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
title_sort new co-crystal of synthetic drug rosiglitazone with natural medicine berberine: preparation, crystal structures, and dissolution
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-09-01
description A co-crystal of rosiglitazone (Rsg) with berberine (Bbr), Rsg-Bbr, was prepared by the solvent evaporation method and characterized. The results showed that the electrostatic attraction existed between the nitrogen anion of rosiglitazone and the quaternary ammonium cation of berberine, and C-H···O hydrogen bonds were formed between Rsg and Bbr. In the crystal structure, rosiglitazone molecules stack into a supramolecular layer through π-π interactions while π-π interactions between berberine cations also result in a similar layer. The co-crystal presented a low moisture adsorption curve in the range of 0−95% relative humidity values at 25 °C. The improved dissolution rate of rosiglitazone in pH = 6.8 buffer solution could be achieved after forming co-crystal.
topic co-crystal
rosiglitazone
berberine
electrostatic attraction
moisture adsorption
dissolution rate
url https://www.mdpi.com/1420-3049/25/18/4288
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