文献类型：期刊文献

英文题名：Preparation, characterization, and crystal structures of novel sophocarpine salts with improvements on stability and solubility

作者：Wang, Yuan[1];Qian, Yi-Hui[1];Hong, Ming-Huang[1];Zhu, Bin[1];Ren, Guo-Bin[1,2];Qi, Ming -Hui[1]

机构：[1]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Met, Engn Res Ctr Pharmaceut Proc Chem, Lab Pharmaceut Crystal Engn & Technol,Minist Educ, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2023

卷号：1279

外文期刊名：JOURNAL OF MOLECULAR STRUCTURE

收录：;EI(收录号：20230413442593);WOS:【SCI-EXPANDED(收录号:WOS:000923767700001)】；

基金：This work was supported by National Natural Science Founda- tion of China (No. 22078094) and Shanghai Frontiers Science Cen- ter of Optogenetic Techniques for Cell Metabolism (Shanghai Mu- nicipal Education Commission) .

语种：英文

外文关键词：Crystal engineering; Crystal structure; Stability; Thermal properties; Sophocarpine

摘要：Crystal engineering has proved to be an effective and reliable approach to tailor the physicochemical properties of active pharmaceutical ingredients. In this work, three novel sophocarpine salts were pre-pared and reported, named sophocarpine-hesperetin (SC-HES), sophocarpine-L-(-) malic acid monohy-drate (SC-LMA MH), and sophocarpine-p-hydroxybenzoic acid monohydrate (SC-PHBA MH). The crystal structures of the salts were confirmed by infrared spectroscopy and single crystal X-ray diffraction. SC-HES exhibited a laminated molecular stacking structure, SC-LMA MH formed a wavy layered structure, while sophocarpine molecules filled in the voids of the reticular structure to form the 3D structure of the SC-PHBA MH. Thermal analysis shows that after salification, the melting point of the compound in-creased from 78 degrees C to over 120 degrees C, overcoming its low melting point. Lattice energy and Hirshfeld surface analysis indicated that lower lattice energy provides better thermal stability of the crystal and intermolec-ular hydrogen bonds (O-H middotmiddotmiddotO and N -> H middotmiddotmiddotO) play a key role in the construction of the crystal structures. In addition, the water solubility and hygroscopicity of the three salts were characterized and discussed, with SC-HES exhibiting satisfying physical stabilities and hygroscopicity, and SC-LMA MH achieving 6.7 times solubility than the free base, which provides viable options for solid dosage form development of the drug.(c) 2023 Elsevier B.V. All rights reserved.