Citation: Dezhi Yang, Hongjuan Wang, Qiwen Liu, Penghui Yuan, Ting Chen, Li Zhang, Shiying Yang, Zhengzheng Zhou, Yang Lu, Guanhua Du. Structural landscape on a series of rhein: Berberine cocrystal salt solvates: The formation, dissolution elucidation from experimental and theoretical investigations[J]. Chinese Chemical Letters, ;2022, 33(6): 3207-3211. doi: 10.1016/j.cclet.2021.10.012 shu

Structural landscape on a series of rhein: Berberine cocrystal salt solvates: The formation, dissolution elucidation from experimental and theoretical investigations

Dezhi Yang ^{a, 1} ,
Hongjuan Wang ^{a, 1} ,
Qiwen Liu ^a ,
Penghui Yuan ^a ,
Ting Chen ^a ,
Li Zhang ^a ,
Shiying Yang ^a ,
Zhengzheng Zhou ^{b, *,} ,
Yang Lu ^{a, *,} ,
Guanhua Du ^{c, *,}

a.
Beijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Department of Hygiene Inspection and Quarantine Science, School of Public Health, Southern Medical University (Guangdong Provincial Key Laboratory of Tropical Disease Research, NMPA Key Laboratory for Safety Evaluation of Cosmetics), Guangzhou 510515, China
c.
Beijing City Key Laboratory of Drug Target and Screening Research, National Center for Pharmaceutical Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

zhouzz418@smu.edu.cn

luy@imm.ac.cn

dugh@imm.ac.cn

Received Date: 7 September 2021
Revised Date: 28 September 2021
Accepted Date: 8 October 2021
Available Online: 14 October 2021

Figures(4)

The specific crystalline form of a compound remarkably affects its physicochemical properties. Therefore, a detailed analysis of the structural features and intermolecular interactions of a multi-component crystal is feasible to understand the relationships among the structure, physicochemical properties and the formation mechanism. In the present study, three novel cocrystal salt solvates of rhein and berberine were reported for the first time. Various solid characterizations and theoretical computations based on density functional theory (DFT) were carried out to demonstrate the intermolecular interactions. The theoretical computation shows that the strongest interaction existed between berberine cation and rhein anion, and the electrostatic interaction play a dominant role. However, no salt bond was observed between them. Further intrinsic dissolution rate analysis in water shows that the monohydrate exhibits 17 times enhancement in comparison with rhein. The rhein and berberine combined in ionic state in cocrystal salt is the main reason for the solubility improvement. This paper suggests that the interactions between the different components can be visualized and qualitatively and quantitatively analyzed by theoretical computation, which is helpful to understand the relationship between stereochemical structure and physicochemical properties of multi-component complex.
- Cocrystal,
- Rhein,
- Berberine,
- Theoretical computation,
- Energy decomposition analysis,
- Solubility
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