Improved syntheses of bis(beta-cyclodextrin) derivatives, new carriers for gadolinium complexes

Organic & Biomolecular Chemistry
S AimeGiancarlo Cravotto

Abstract

In the last decade a number of reports have been published on the synthesis and characterization of bridged cyclodextrin dimers (bis-CDs) connected with linkers of different lengths and structures. These dimers, having two hydrophobic cavities in close proximity, display much higher binding affinities and molecular selectivities than parent CDs, forming stable supramolecular adducts. We describe new synthetic protocols for the preparation of bis(beta-CDs) bearing 2-2', 3-3' and 6-6' bridges. Some of the critical steps were carried out either under high-intensity ultrasound (US) or microwave (MW) irradiation. Bis(beta-CDs) containing 6-6' ureido- and thioureido-bridges were prepared in high yields by a MW-promoted aza-Wittig reaction using polymer-bound triphenylphosphine, while those containing 2,2' and 3,3' bridges were prepared from mono-alkenyl beta-CDs by the cross-metathesis reaction (homodimerization) in the presence of 2(nd)-generation Grubbs catalyst under sonochemical conditions. By these improved protocols CD dimers could be obtained in gram amounts to prepare stable adducts of bis-CDs with contrast agents (CAs) containing gadolinium(iii) chelates. In the case of Gd(iii) chleate "G-1" the inclusion complexes were foun...Continue Reading

References

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Citations

Feb 11, 2014·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·E GianolioS Aime
Sep 30, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Jonathan MartinelliRamon Vilar
Dec 25, 2013·Beilstein Journal of Organic Chemistry·Diego CarnaroglioGiancarlo Cravotto
Mar 16, 2016·Beilstein Journal of Organic Chemistry·Giancarlo CravottoKatia Martina
Dec 26, 2008·Organic & Biomolecular Chemistry·Silvio AimeGiancarlo Cravotto
Dec 17, 2010·Beilstein Journal of Organic Chemistry·Ivan SnajdrMartin Kotora
Jun 15, 2011·Organic Letters·Aixia WangChang-Chun Ling
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Petr Kasal, Jindřich Jindřich

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