DNA Condensation and Cell Transfection Properties of Guanidinium Calixarenes: Dependence on Macrocycle Lipophilicity, Size, and Conformation

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• 作者：Francesco Sansone ; Miroslav Dudi//pubs.acs.org/images/entities/ccaron.gif" border="0"> ; Gaetano Donofrio ; Claudio Rivetti ; Laura Baldini ; Alessandro Casnati ; Sara Cellai ; Rocco Ungaro
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：November 15, 2006
• 年：2006
• 卷：128
• 期：45
• 页码：14528 - 14536
• 全文大小：606K
• 年卷期：v.128,no.45(November 15, 2006)
• ISSN：1520-5126

文摘

Calix[n]arenes functionalized with guanidinium groups at the upper rim and alkyl chains at thelower rim bind to DNA, condense it, and in some cases, promote cell transfection depending on their structureand lipophilicity. Atomic force microscopy (AFM) studies indicate that upon DNA binding the hydrophobicassociation of the lipophilic chains of cone guanidinium calix[4]arenes drives the formation of intramolecularDNA condensates, characterized by DNA loops emerging from a dense core. Furthermore, hexyl and octylchains confer to these calixarenes cell transfection capabilities. Conversely, larger and conformationallymobile calix[6]- and calix[8]arene methoxy derivatives form intermolecular aggregates characterized by"gorgonlike" structures composed of multiple plectomenes. These adducts, in which interstrand connectionsare dominated by electrostatic interactions, fail to promote cell transfection. Finally, calix[4]arenes in a1,3-alternate conformation show an intermediate behavior because they condense DNA, but the processis driven by charge-charge interactions.