Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd-Even Alternation in Physicochemical Properties

Lili Wang; Shuyu Liu; Jia Mei Chen; Yan Xiang Wang; Changquan Calvin Sun

doi:10.1021/acs.molpharmaceut.0c01250

Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd-Even Alternation in Physicochemical Properties

Lili Wang, Shuyu Liu, Jia Mei Chen, Yan Xiang Wang, Changquan Calvin Sun

Pharmaceutics

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

In this study, various structurally similar aliphatic dicarboxylic acids, namely, succinic acid, glutaric acid, adipic acid, and pimelic acid, were employed as coformers to obtain phase pure cocrystals with berberine chloride (BCl) by a slow solvent evaporation method. The structures of the four novel salt-cocrystals of BCl were determined by single crystal X-ray diffraction analysis and their solid-state properties were characterized. Compared with BCl·2H2O, all the cocrystals showed a higher melting point, improved powder dissolution and intrinsic dissolution rate (IDR), and lower hygroscopicity. It is noteworthy that the melting points and IDRs of these cocrystals exhibit an odd-even alternation with the carbon chain length of the acids.

Original language	English (US)
Pages (from-to)	1758-1767
Number of pages	10
Journal	Molecular pharmaceutics
Volume	18
Issue number	4
DOIs	https://doi.org/10.1021/acs.molpharmaceut.0c01250
State	Published - Apr 5 2021

Bibliographical note

Funding Information:
This study was financially supported by the Postgraduate Research and Innovation Project of Shanghai University of Engineering Science (20KY0410) and the CAMS Initiative for Innovative Medicine (2016-I2M-1-011).

Publisher Copyright:
© 2021 American Chemical Society.

Keywords

aliphatic dicarboxylic acids
berberine chloride
intrinsic dissolution rate
melting point
odd-even alternation
salt-cocrystals

PubMed: MeSH publication types

Journal Article
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title = "Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd-Even Alternation in Physicochemical Properties",

abstract = "In this study, various structurally similar aliphatic dicarboxylic acids, namely, succinic acid, glutaric acid, adipic acid, and pimelic acid, were employed as coformers to obtain phase pure cocrystals with berberine chloride (BCl) by a slow solvent evaporation method. The structures of the four novel salt-cocrystals of BCl were determined by single crystal X-ray diffraction analysis and their solid-state properties were characterized. Compared with BCl·2H2O, all the cocrystals showed a higher melting point, improved powder dissolution and intrinsic dissolution rate (IDR), and lower hygroscopicity. It is noteworthy that the melting points and IDRs of these cocrystals exhibit an odd-even alternation with the carbon chain length of the acids.",

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note = "Funding Information: This study was financially supported by the Postgraduate Research and Innovation Project of Shanghai University of Engineering Science (20KY0410) and the CAMS Initiative for Innovative Medicine (2016-I2M-1-011). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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AU - Wang, Lili

AU - Liu, Shuyu

AU - Chen, Jia Mei

AU - Wang, Yan Xiang

AU - Sun, Changquan Calvin

N1 - Funding Information: This study was financially supported by the Postgraduate Research and Innovation Project of Shanghai University of Engineering Science (20KY0410) and the CAMS Initiative for Innovative Medicine (2016-I2M-1-011). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/4/5

Y1 - 2021/4/5

N2 - In this study, various structurally similar aliphatic dicarboxylic acids, namely, succinic acid, glutaric acid, adipic acid, and pimelic acid, were employed as coformers to obtain phase pure cocrystals with berberine chloride (BCl) by a slow solvent evaporation method. The structures of the four novel salt-cocrystals of BCl were determined by single crystal X-ray diffraction analysis and their solid-state properties were characterized. Compared with BCl·2H2O, all the cocrystals showed a higher melting point, improved powder dissolution and intrinsic dissolution rate (IDR), and lower hygroscopicity. It is noteworthy that the melting points and IDRs of these cocrystals exhibit an odd-even alternation with the carbon chain length of the acids.

AB - In this study, various structurally similar aliphatic dicarboxylic acids, namely, succinic acid, glutaric acid, adipic acid, and pimelic acid, were employed as coformers to obtain phase pure cocrystals with berberine chloride (BCl) by a slow solvent evaporation method. The structures of the four novel salt-cocrystals of BCl were determined by single crystal X-ray diffraction analysis and their solid-state properties were characterized. Compared with BCl·2H2O, all the cocrystals showed a higher melting point, improved powder dissolution and intrinsic dissolution rate (IDR), and lower hygroscopicity. It is noteworthy that the melting points and IDRs of these cocrystals exhibit an odd-even alternation with the carbon chain length of the acids.

KW - aliphatic dicarboxylic acids

KW - berberine chloride

KW - intrinsic dissolution rate

KW - melting point

KW - odd-even alternation

KW - salt-cocrystals

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Novel Salt-Cocrystals of Berberine Hydrochloride with Aliphatic Dicarboxylic Acids: Odd-Even Alternation in Physicochemical Properties

Abstract

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