New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands

被引：40

作者：

Aime, Silvio ^{[2
]}

Gianolio, Eliana ^{[2
]}

Arena, Francesca ^{[2
]}

Barge, Alessandro ^{[1
]}

Martina, Katia ^{[1
]}

Heropoulos, George ^{[3
]}

Cravotto, Giancarlo ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Sci & Tecnol Farm, I-10125 Turin, Italy

[2] Univ Turin, Dipartimento Chim IFM, I-10125 Turin, Italy

[3] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, Athens 11635, Greece

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 02期

关键词：

HUMAN SERUM-ALBUMIN; BETA-CYCLODEXTRIN; DERIVATIVES; BINDING; RELAXATION; COMPLEXES; CHEMISTRY; MOIETY; AGENTS; TOOL;

D O I：

10.1039/b812172a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bridged cyclodextrin dimers and trimers, in which respectively two and three hydrophobic cavities lie in close proximity, display much higher binding affinities and molecular selectivities than do parent cyclodextrins (CDs). By joining beta CD units with links inserted at different positions (2-2', 3-2', 6-2' or 6-2'-6 '') and interposing spacers of different lengths and shapes, multicavity structures can be synthesized that are precisely tailored to. t specific guest molecules. This enzyme-mimicking strategy can also be used to generate stable supramolecular adducts. A series of CD dimers and trimers was prepared in good yields by carrying out the critical synthetic steps under power ultrasound (US) or microwave (MW) irradiation. Starting from azide and acetylenic CD derivatives, we exploited an efficient MW-promoted Huisgen 1,3-dipolar cycloaddition in the presence of Cu(I) salts. The resulting bridged CD derivatives gave stable adducts with magnetic-resonance-imaging contrast agents (MRI CAs) containing gadolinium(III) chelates. These inclusion complexes were found to be 2 to 3 orders of magnitude more stable than those formed by beta CD and to be endowed with high relaxivity

引用

页码：370 / 379

页数：10

共 45 条

[1] Improved syntheses of bis(β-cyclodextrin) derivatives, new carriers for gadolinium complexes [J].