Biofunctionalization on alkylated silicon substrate surfaces via "click" chemistry.
Biofunctionalization on alkylated silicon substrate surfaces via "click" chemistry.
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通过“点击”化学对烷基化硅底物表面进行生物功能化。
DOI：
10.1021/ja1025497
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发表时间：
2010-11-24
影响因子：
15
通讯作者：
Cai, Chengzhi
中科院分区：
文献类型：
--
作者：
Qin, Guoting;Santos, Catherine;Zhang, Wen;Li, Yan;Kumar, Amit;Erasquin, Uriel J.;Liu, Kai;Muradov, Pavel;Trautner, Barbara Wells;Cai, Chengzhi
硅衬底的生物功能化对于硅基生物传感器和器件的发展具有重要意义。与氧化硅中间层上的常规有机硅氧烷膜相比，通过Si-C键直接结合到非氧化硅衬底的有机单层提高了检测灵敏度和抗水解裂解的稳定性。报道了这样的单分子膜，其呈现高密度的末端炔基，用于通过铜催化的叠氮化物-炔1，3-偶极环加成（CuAAC，“点击”反应）进行生物缀合。然而，在这些单层平台上的CuAAC反应的产率低。此外，蛋白质在所得表面上的非特异性吸附仍然是许多潜在生物应用的主要障碍。在此，我们报告了一种新型的“点击”单分子膜生长的选择性，光活化的表面氢化硅烷化的α，ω-烯炔，其中的炔基末端的保护与三甲基锗（TMG）基团，在氢封端的硅衬底。膜上的TMG基团在Cu（I）存在下在水溶液中容易地去除。值得注意的是，脱锗和随后的CuAAC与各种叠氮化物的反应可以以良好的产率组合成单一步骤。因此，将具有叠氮基标签的寡聚（乙二醇）（OEG）附接至TMG-炔表面，导致OEG封端的表面，其将蛋白质（纤维蛋白原）的非特异性吸附降低> 98%。CuAAC反应可以以微阵列形式进行，以在蛋白质抗性OEG背景上产生具有不同密度的甘露糖和生物素阵列。我们还证明了单层平台可以用甘露糖官能化，用于高度特异性地将活靶标（表达菌毛的大肠杆菌）捕获到硅基底上。
Biofunctionalization of silicon substrates is important to the development of silicon-based biosensors and devices. Compared to conventional organosiloxane films on silicon oxide intermediate layers, organic monolayers directly bound to the non-oxidized silicon substrates via Si-C bonds enhance the sensitivity of detection and the stability against hydrolytic cleavage. Such monolayers presenting a high density of terminal alkynyl groups for bioconjugation via copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC, a “click” reaction) were reported. However, yields of the CuAAC reactions on these monolayer platforms were low. Also, the non-specific adsorption of proteins on the resultant surfaces remained a major obstacle for many potential biological applications. Herein, we report a new type of “clickable” monolayers grown by selective, photo-activated surface hydrosilylation of α,ω-alkenynes, where the alkynyl terminal is protected with a trimethylgermanyl (TMG) group, on hydrogen-terminated silicon substrates. The TMG groups on the film are readily removed in aqueous solutions in the presence of Cu(I). Significantly, the degermanylation and the subsequent CuAAC reaction with various azides could be combined into a single step in good yields. Thus, oligo(ethylene glycol) (OEG) with an azido-tag was attached to the TMG-alkyne surfaces, leading to OEG-terminated surfaces that reduced the non-specific adsorption of protein (fibrinogen) by >98%. The CuAAC reaction could be performed in microarray format to generate arrays of mannose and biotin with varied densities on the protein-resistant OEG background. We also demonstrated that the monolayer platform could be functionalized with mannose for highly specific capturing of living targets (Escherichia coli expressing fimbriae) onto the silicon substrates.
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影响因子：
3.9
作者：
Cicero, RL;Linford, MR;Chidsey, CED
通讯作者：
Chidsey, CED
影响因子：
6.1
作者：
Ainslie KM;Desai TA
通讯作者：
Desai TA
影响因子：
15
作者：
Cao, Peigen;Xu, Ke;Heath, James R.
通讯作者：
Heath, James R.
影响因子：
15
作者：
Bryan, MC;Fazio, F;Wong, CH
通讯作者：
Wong, CH
影响因子：
4.4
作者：
Alfredsson, Y;Brena, B;Siegbahn, H
通讯作者：
Siegbahn, H