大豆苷元离子对化合物形成的实验与理论研究:溶解度、氢键、稳定性

IF 3.4 4区 医学 Q2 PHARMACOLOGY & PHARMACY
Zhaoyang Zhang, Sheng Wang, Qianlei Wang, Qian Ye, Wenjuan Wang
{"title":"大豆苷元离子对化合物形成的实验与理论研究:溶解度、氢键、稳定性","authors":"Zhaoyang Zhang,&nbsp;Sheng Wang,&nbsp;Qianlei Wang,&nbsp;Qian Ye,&nbsp;Wenjuan Wang","doi":"10.1208/s12249-025-03049-z","DOIUrl":null,"url":null,"abstract":"<div><p>Ion pairs represent a robust molecular force arising from the union of oppositely charged ions, held together by Coulomb attraction. Daidzein (Dai), categorized as a BCS IV drug, faces limitations in clinical application due to its relatively low solubility. To enhance the drug’s solubility, a Dai ion pair was prepared, and the mechanism underlying ion-pair formation was investigated. A comprehensive approach, combining experimental techniques and theoretical calculations, such as scanning electron microscopy, powder X-ray diffraction, differential scanning calorimetry, Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, X-ray Photoelectron Spectroscopy, and computational simulation was employed to explore the ion-pair formation mechanism. The findings indicate a significant improvement in Dai solubility through the preparation of Arg and Lys ion-pair compounds. The results revealed that the Dai–Lys ion pair exhibited more short hydrogen bonds and fewer long hydrogen bonds than did the Dai–Arg ion pair, strengthening the intermolecular interactions and improving crystal structure stability. This study effectively enhanced the solubility of Dai and offers valuable insights into the mechanisms underlying ion pair formation in ionizable drugs.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":6925,"journal":{"name":"AAPS PharmSciTech","volume":"26 2","pages":""},"PeriodicalIF":3.4000,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Experimental and Theoretical Investigation of the Formation of Daidzein Ion-pair Compounds: Solubility, Hydrogen Bonds, Stability\",\"authors\":\"Zhaoyang Zhang,&nbsp;Sheng Wang,&nbsp;Qianlei Wang,&nbsp;Qian Ye,&nbsp;Wenjuan Wang\",\"doi\":\"10.1208/s12249-025-03049-z\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Ion pairs represent a robust molecular force arising from the union of oppositely charged ions, held together by Coulomb attraction. Daidzein (Dai), categorized as a BCS IV drug, faces limitations in clinical application due to its relatively low solubility. To enhance the drug’s solubility, a Dai ion pair was prepared, and the mechanism underlying ion-pair formation was investigated. A comprehensive approach, combining experimental techniques and theoretical calculations, such as scanning electron microscopy, powder X-ray diffraction, differential scanning calorimetry, Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, X-ray Photoelectron Spectroscopy, and computational simulation was employed to explore the ion-pair formation mechanism. The findings indicate a significant improvement in Dai solubility through the preparation of Arg and Lys ion-pair compounds. The results revealed that the Dai–Lys ion pair exhibited more short hydrogen bonds and fewer long hydrogen bonds than did the Dai–Arg ion pair, strengthening the intermolecular interactions and improving crystal structure stability. This study effectively enhanced the solubility of Dai and offers valuable insights into the mechanisms underlying ion pair formation in ionizable drugs.</p><h3>Graphical Abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":6925,\"journal\":{\"name\":\"AAPS PharmSciTech\",\"volume\":\"26 2\",\"pages\":\"\"},\"PeriodicalIF\":3.4000,\"publicationDate\":\"2025-02-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"AAPS PharmSciTech\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://link.springer.com/article/10.1208/s12249-025-03049-z\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"PHARMACOLOGY & PHARMACY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"AAPS PharmSciTech","FirstCategoryId":"3","ListUrlMain":"https://link.springer.com/article/10.1208/s12249-025-03049-z","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"PHARMACOLOGY & PHARMACY","Score":null,"Total":0}
引用次数: 0

摘要

离子对代表了一种强大的分子力,由带相反电荷的离子结合而产生,通过库仑引力保持在一起。大豆苷元(Daidzein, Dai)属于BCS IV类药物,由于其溶解度相对较低,在临床应用中受到限制。为了提高药物的溶解度,制备了Dai离子对,并对离子对形成的机制进行了研究。采用扫描电镜、粉末x射线衍射、差示扫描量热法、傅里叶变换红外光谱、质子核磁共振光谱、x射线光电子能谱、计算模拟等实验技术与理论计算相结合的综合方法探讨离子对形成机理。研究结果表明,通过制备Arg和Lys离子对化合物,可以显著改善Dai的溶解度。结果表明,Dai-Lys离子对比Dai-Arg离子对具有更多的短氢键和更少的长氢键,增强了分子间的相互作用,提高了晶体结构的稳定性。该研究有效地增强了Dai的溶解度,并为电离药物中离子对形成的机制提供了有价值的见解。图形抽象
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Experimental and Theoretical Investigation of the Formation of Daidzein Ion-pair Compounds: Solubility, Hydrogen Bonds, Stability

Ion pairs represent a robust molecular force arising from the union of oppositely charged ions, held together by Coulomb attraction. Daidzein (Dai), categorized as a BCS IV drug, faces limitations in clinical application due to its relatively low solubility. To enhance the drug’s solubility, a Dai ion pair was prepared, and the mechanism underlying ion-pair formation was investigated. A comprehensive approach, combining experimental techniques and theoretical calculations, such as scanning electron microscopy, powder X-ray diffraction, differential scanning calorimetry, Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, X-ray Photoelectron Spectroscopy, and computational simulation was employed to explore the ion-pair formation mechanism. The findings indicate a significant improvement in Dai solubility through the preparation of Arg and Lys ion-pair compounds. The results revealed that the Dai–Lys ion pair exhibited more short hydrogen bonds and fewer long hydrogen bonds than did the Dai–Arg ion pair, strengthening the intermolecular interactions and improving crystal structure stability. This study effectively enhanced the solubility of Dai and offers valuable insights into the mechanisms underlying ion pair formation in ionizable drugs.

Graphical Abstract

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
AAPS PharmSciTech
AAPS PharmSciTech 医学-药学
CiteScore
6.80
自引率
3.00%
发文量
264
审稿时长
2.4 months
期刊介绍: AAPS PharmSciTech is a peer-reviewed, online-only journal committed to serving those pharmaceutical scientists and engineers interested in the research, development, and evaluation of pharmaceutical dosage forms and delivery systems, including drugs derived from biotechnology and the manufacturing science pertaining to the commercialization of such dosage forms. Because of its electronic nature, AAPS PharmSciTech aspires to utilize evolving electronic technology to enable faster and diverse mechanisms of information delivery to its readership. Submission of uninvited expert reviews and research articles are welcomed.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信