Unexpected effect of halogenation on the water solubility of small organic compounds
文献类型：期刊论文
| 作者 | Zhang, Jianfang1,2; Gulyas, Kinga Virag3; Li, Jintian2; Ma, Minfei2; Zhou, Liping2; Wu, Leyun2; Xiong, Ruisheng3; Erdelyi, Mate3; Zhu, Weiliang1,2 ; Xu, Zhijian1,2
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| 刊名 | Computers in biology and medicine
 |
| 出版日期 | 2024-04-01 |
| 卷号 | 172页码:108209 |
| DOI | 10.1016/j.compbiomed.2024.108209 |
| 文献子类 | Article |
| 英文摘要 | Halogenation is an indispensable method in the structural modification of lead compounds. It is known to increase lipophilicity and is hence used to improve membrane permeability and thus bioavailability. In this study, we compare the water solubility (logS) of organohalogen compounds and their non-halogenated parent compounds using the molecular matched pair (MMP) analysis method. Unexpectedly, 19.9% of the compounds increased their water solubility upon halogenation. Iodination was observed to have the greatest effect on solubility, followed by chlorination, bromination, and fluorination. Introducing amino, hydroxyl and carboxyl groups into organohalogens improves their aqueous solubilities, whereas introducing a trifluoromethyl group has the opposite effect. According to our quantum chemical calculations, the increased water solubility upon halogenation is, at least partially, attributed to an increased polarity and polarizability. These results improve our understanding of the influence of halogenation on bioactivity. |
| 语种 | 英语 |
| WOS记录号 | MEDLINE:38460313 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/317018]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Zhu, Weiliang; Xu, Zhijian |
| 作者单位 | 1.School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, 210046, China 2.State Key Laboratory of Drug Research; Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China 3.Department of Chemistry - BMC, Uppsala University, SE-751 23, Uppsala, Sweden |
| 推荐引用方式 GB/T 7714 | Zhang, Jianfang,Gulyas, Kinga Virag,Li, Jintian,et al. Unexpected effect of halogenation on the water solubility of small organic compounds[J]. Computers in biology and medicine,2024,172:108209. |
| APA | Zhang, Jianfang.,Gulyas, Kinga Virag.,Li, Jintian.,Ma, Minfei.,Zhou, Liping.,...&Xu, Zhijian.(2024).Unexpected effect of halogenation on the water solubility of small organic compounds.Computers in biology and medicine,172,108209. |
| MLA | Zhang, Jianfang,et al."Unexpected effect of halogenation on the water solubility of small organic compounds".Computers in biology and medicine 172(2024):108209. |
入库方式： OAI收割
来源：上海药物研究所
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