DNA condensation and cell transfection properties of guanidinium calixarenes: Dependence on macrocycle lipophilicity, size, and conformation
DNA condensation and cell transfection properties of guanidinium calixarenes: Dependence on macrocycle lipophilicity, size, and conformation
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DOI：
10.1021/ja0634425
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发表时间：
2006-11-15
影响因子：
15
通讯作者：
Ungaro, Rocco
中科院分区：
文献类型：
--
作者：
Sansone, Francesco;Dudic, Miroslav;Ungaro, Rocco
在上边缘用胍鎓基团和在下边缘用烷基链官能化的杯[n]芳烃结合DNA，使其缩合，并且在某些情况下，根据其结构和亲脂性促进细胞转染。原子力显微镜（AFM）研究表明，在DNA结合时，锥胍杯[4]芳烃的亲脂链的疏水缔合驱动分子内DNA缩合物的形成，其特征在于DNA环从致密的核中出现。此外，己基和辛基链赋予这些杯芳烃细胞转染能力。相反，较大的和构象上移动的杯[6]-和杯[8]芳烃甲氧基衍生物形成分子间聚集体，其特征在于由多个plectomene组成的“柳珊瑚样”结构。这些加合物，其中链间连接由静电相互作用主导，不能促进细胞转染。最后，1，3-交替构象的杯[4]芳烃表现出中间行为，因为它们缩合DNA，但该过程由电荷-电荷相互作用驱动。
Calix[n]arenes functionalized with guanidinium groups at the upper rim and alkyl chains at the lower rim bind to DNA, condense it, and in some cases, promote cell transfection depending on their structure and lipophilicity. Atomic force microscopy (AFM) studies indicate that upon DNA binding the hydrophobic association of the lipophilic chains of cone guanidinium calix[4] arenes drives the formation of intramolecular DNA condensates, characterized by DNA loops emerging from a dense core. Furthermore, hexyl and octyl chains confer to these calixarenes cell transfection capabilities. Conversely, larger and conformationally mobile calix[6]- and calix[8] arene methoxy derivatives form intermolecular aggregates characterized by "gorgonlike" structures composed of multiple plectomenes. These adducts, in which interstrand connections are dominated by electrostatic interactions, fail to promote cell transfection. Finally, calix[4] arenes in a 1,3-alternate conformation show an intermediate behavior because they condense DNA, but the process is driven by charge-charge interactions.