Design and Synthesis of a 18-Cyclodextrin Oligomer: A New Platform with Potential Application as a Dendrimeric Multicarrier

被引：17

作者：

Barge, Alessandro ^{[1
]}

Caporaso, Marina ^{[1
]}

Cravotto, Giancarlo ^{[1
]}

Martina, Katia ^{[1
]}

Tosco, Paolo ^{[1
]}

Aime, Silvio ^{[2
,3
,4
]}

Carrera, Carla ^{[2
,3
,4
]}

Gianolio, Eliana ^{[2
,3
,4
]}

Pariani, Giorgio ^{[2
,3
,4
]}

Corpillo, Davide ^{[5
]}

机构：

[1] Univ Turin, Dept Drug Sci & Technol, I-10125 Turin, Italy

[2] Univ Turin, Dept Chem IFM, I-10126 Turin, Italy

[3] Univ Turin, Mol Imaging Ctr, I-10126 Turin, Italy

[4] Univ Turin, Preclin Imaging Ctr, I-10126 Turin, Italy

[5] Bioind Pk Silvano Fumero SpA, ABLE Biosci, I-10010 Colleretto Giacosa, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 36期

关键词：

click chemistry; cyclodextrin oligomers; Gd-based contrast agents; imaging agents; microwave chemistry; MRI CONTRAST AGENTS; BETA-CYCLODEXTRIN; TARGETED NANOPARTICLES; SUPRAMOLECULAR ADDUCTS; GAMMA-CYCLODEXTRIN; DELIVERY; CYCLOADDITION; ULTRASOUND; COMPLEXES; SYSTEM;

D O I：

10.1002/chem.201301215

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the synthesis and characterization of a water-soluble, star-shaped macromolecular platform consisting of eight -cyclodextrin (-CD) units anchored to the narrower rim of a -CD core through bis(triazolyl)alkyl spacers. The efficient synthetic protocol is based on the microwave (MW)-promoted Cu-catalyzed 1,3-dipolar cycloaddition of CD monoazides to CD monoacetylenes. The ligand-hosting capability of the construct has been assessed by relaxometric titration and nuclear magnetic relaxation dispersion (NMRD) profiling, which showed it to be good, and this was supported by molecular dynamics simulations. To demonstrate the feasibility of obtaining supramolecular structures with high hosting ability, we designed a dimeric platform, formed by joining two nonamers through the -CD cores through a bis(lithocholic acid) linker. With a view to the potential biological applications, cytotoxicity and extent of binding to human serum albumin were assessed. The properties of this dendrimeric multicarrier make it suitable for pharmaceutical and diagnostic purposes, ranging from targeted drug delivery to molecular imaging.

引用

页码：12086 / 12092

页数：7

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