Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal

doi:10.1007/s13659-020-00256-y

Natural Products and Bioprospecting ›› 2020, Vol. 10 ›› Issue (4): 261-267.DOI: 10.1007/s13659-020-00256-y

• ORIGINAL ARTICLES • Previous Articles Next Articles

Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal

Ningbo Gong¹, Hongmei Yu¹, Ying Wang¹, Cheng Xing¹, Kun Hu¹, Guanhua Du², Yang Lu¹

1 Beijing Key Laboratory of Polymorphic Drugs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;
2 Beijing City Key Laboratory of Drug Target Identification and Drug Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Received:2020-04-25 Revised:2020-06-17 Online:2020-08-19 Published:2020-08-24
Contact: Guanhua Du, Yang Lu
Supported by:
We thank the financial support by National Key research and development Program of China (Grant No. 2016YFC1000900), CAMS Innovation Found for Medical Sciences (Grant No. 2017-I2M-1-010), Construction and application of technology integration system for efficient identification of natural/effective active small molecules (Grant No. 2018ZX09711001-001) and National Science and Technology Major Project of China (Grant No. 2018ZX09711001-010).

Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal

Ningbo Gong¹, Hongmei Yu¹, Ying Wang¹, Cheng Xing¹, Kun Hu¹, Guanhua Du², Yang Lu¹

1 Beijing Key Laboratory of Polymorphic Drugs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;
2 Beijing City Key Laboratory of Drug Target Identification and Drug Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

通讯作者: Guanhua Du, Yang Lu
基金资助:
We thank the financial support by National Key research and development Program of China (Grant No. 2016YFC1000900), CAMS Innovation Found for Medical Sciences (Grant No. 2017-I2M-1-010), Construction and application of technology integration system for efficient identification of natural/effective active small molecules (Grant No. 2018ZX09711001-001) and National Science and Technology Major Project of China (Grant No. 2018ZX09711001-010).

Abstract

Abstract: A cocrystal of diosgenin with piperazine in 2:1 stoichiometry was successfully synthesized. The solid form was prepared by liquid assisted grinding, slurry and crystallization methods. The cocrystal was characterized by powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, and structure determined by single crystal X-ray diffraction, the hydrogen bonds formed into fish bone structure along the[010] direction and all the molecules packed into 3D layer structure along a axis. After formation of cocrystal, the solubility of diosgenin was improved, and the solubility value in 0.2% SDS solution was approximately 1.5 times as large as that of the parent material.

Key words: Diosgenin, Piperazine, Cocrystal, Characterization, Solubility

摘要： A cocrystal of diosgenin with piperazine in 2:1 stoichiometry was successfully synthesized. The solid form was prepared by liquid assisted grinding, slurry and crystallization methods. The cocrystal was characterized by powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, Fourier transform infrared spectroscopy, and structure determined by single crystal X-ray diffraction, the hydrogen bonds formed into fish bone structure along the[010] direction and all the molecules packed into 3D layer structure along a axis. After formation of cocrystal, the solubility of diosgenin was improved, and the solubility value in 0.2% SDS solution was approximately 1.5 times as large as that of the parent material.

关键词: Diosgenin, Piperazine, Cocrystal, Characterization, Solubility

Ningbo Gong, Hongmei Yu, Ying Wang, Cheng Xing, Kun Hu, Guanhua Du, Yang Lu. Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal[J]. Natural Products and Bioprospecting, 2020, 10(4): 261-267.

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Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal

Crystal Structures, Stability, and Solubility Evaluation of a 2: 1 Diosgenin-Piperazine Cocrystal

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