Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile鈥揇NA Conjugates

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• 作者：Michael C. Wamberg ; Rafa艂 Wieczorek ; S酶ren Bo Brier ; Jan Willem de Vries ; Minseok Kwak ; Andreas Herrmann ; Pierre-Alain Monnard
• 刊名：Bioconjugate Chemistry
• 出版年：2014
• 出版时间：September 17, 2014
• 年：2014
• 卷：25
• 期：9
• 页码：1678-1688
• 全文大小：399K
• ISSN：1520-4812

文摘

The surface functionalization of fatty acid vesicles will allow their use as nanoreactors for complex chemistry. In this report, the tethering of several DNA conjugates to decanoic acid vesicles for molecular recognition and synthetic purposes was explored. Due to the highly dynamic nature of these structures, only one novel bola-amphiphile DNA conjugate could interact efficiently with or spontaneously pierce into the vesicle bilayers without jeopardizing their self-assembly or stability. This molecule was synthesized via a Cu(I)-catalyzed [3 + 2] azide鈥揳lkyne cycloaddition (click reaction), and consists of a single hydrocarbon chain of 20 carbons having on one end a triazole group linked to the 5鈥?phosphate of the nucleic acid and on the other side a hydroxyl-group. Its insertion was so effective that a fluorescent label on the DNA complementary to the conjugate could be used to visualize fatty acid structures.