A Comparative Study of Thiol-Terminated Surface Modification by Click Reactions: Thiol-yne Coupling versus Thiol-ene Michael Addition
A Comparative Study of Thiol-Terminated Surface Modification by Click Reactions: Thiol-yne Coupling versus Thiol-ene Michael Addition
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DOI：
10.1002/admi.201801343
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发表时间：
2018-12-01
影响因子：
5.4
通讯作者：
Hirtz, Michael
中科院分区：
文献类型：
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作者：
Dadfar, Seyed Mohammad Mahdi;Sekula-Neuner, Sylwia;Hirtz, Michael
两种快速，高效，无金属催化剂的共轭路线的共价连接的功能化合物的功能化表面的扫描探针光刻方法进行了比较。所研究的方法有硫醇-炔偶联法（TYC）和硫醇-烯迈克尔加成法（特马）。首先，使用（3-巯丙基）三甲氧基硅烷（MPTMS）对羟基封端的玻璃的表面进行硫醇化。然后，在不同的实验中，硫醇封端的表面被发现的微通道悬臂斑点与不同的荧光和非荧光油墨含有环炔（二苯并环辛炔（DBCO））或烯烃（马来酰亚胺）基团。用不同的荧光团的实验表明，这两种路线是成功的耦合功能部分的表面在短时间内和低温。比较生物素-DBCO和生物素-马来酰亚胺的蛋白质结合实验，揭示了通过特马途径固定的生物素的更高的表面密度。本研究的结果可应用于生物传感器的设计和制作，适用于蛋白质检测和其他生物医学/生物学应用。
Two quick and efficient, metal catalyst free conjugation routes for the covalent attachment of functional compounds to functionalized surfaces by scanning probe lithography methods are compared in the presented work. The studied methods are thiol-yne coupling (TYC) and thiol-ene Michael addition (TEMA). First, the surface of hydroxyl-terminated glass is thiolated using (3-mercaptopropyl)trimethoxysilane (MPTMS). Then, in the distinct experiments, the thiol-terminated surface is spotted by microchannel cantilever spotting with different fluorescent and nonfluorescent inks containing cycloalkyne (dibenzocyclooctyne (DBCO)) or alkene (maleimide) groups. Experiments with different fluorophores show that both routes are successful in coupling functional moieties to the surface in a short time and low temperature. Comparing the protein binding experiments for biotin-DBCO and biotin-maleimide reveals a higher surface density of immobilized biotin via the TEMA route. The results from this study are applicable in design and fabricating of biosensors, appropriate for protein detection and other biomedical/biological applications.