Calix[4]arene sulfonate hosts selectively modified on the upper rim: a study of nicotine binding strength and geometry

被引：5

作者：

Warmerdam, Zoey ^{[1
]}

Kamba, Bianca E. ^{[2
]}

Shaurya, Alok ^{[1
]}

Sun, XuXin ^{[1
]}

Maguire, Mary K. ^{[1
]}

Hof, Fraser ^{[1
]}

机构：

[1] Univ Victoria, Dept Chem, 3800 Finnerty Rd, Victoria, BC V8W 3V6, Canada

[2] Univ Duisburg Essen, Dept Struct & Med Biochem, Essen, Germany

来源：

SUPRAMOLECULAR CHEMISTRY | 2021年 / 33卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Calixarenes; macrocycles; host-guest chemistry; NMR; drug; nicotine;

D O I：

10.1080/10610278.2021.1873991

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present the synthesis and structure-activity relationships of sulfonatocalix[4]arene hosts bearing novel substitutions. The calix[4]arenes are modified on the upper rim at either one or two of the phenolic units, where the dual modifications are introduced regioselectively on neighbouring or opposing phenols. The calix[4]arenes are mono- or di-functionalised with nitro or formyl groups, with the remaining upper-rim sites in all cases occupied by sulphonates. Equilibrium association constants were determined between each host and the guests nicotine, nornicotine, and cotinine. Indicator displacement-based binding studies show that nicotine binds most strongly to the different members of the library followed by nornicotine, whereas cotinine displays weak to no binding. NMR titrations were carried out with nicotine and show different host-guest interaction geometries for the formyl-calix[4]arenes versus the nitro-calix[4]arenes.

引用

页码：88 / 96

页数：9

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