A photochemical method for patterning the immobilization of ligands and cells to self-assembled monolayers

This work describes a chemically well defined method for patterning ligands to self-assembled monolayers (SAMs) of alkanethiolates on gold. This method begins with monolayers presenting a nitroveratryloxycarbonyl (NVOC)-protected hydroquinone which is photochemically irradiated to reveal a hydroquin...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 20(2004), 17 vom: 17. Aug., Seite 7223-31
1. Verfasser: Dillmore, W Shannon (VerfasserIn)
Weitere Verfasser: Yousaf, Muhammad N, Mrksich, Milan
Format: Aufsatz
Sprache:English
Veröffentlicht: 2004
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S. Benzoquinones Cyclopentanes Hydroquinones Ligands Membranes, Artificial Oligopeptides Sulfhydryl Compounds mehr... Polyethylene Glycols 3WJQ0SDW1A Gold 7440-57-5 arginyl-glycyl-aspartic acid 78VO7F77PN Fluorescein TPY09G7XIR
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245 1 2 |a A photochemical method for patterning the immobilization of ligands and cells to self-assembled monolayers 
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520 |a This work describes a chemically well defined method for patterning ligands to self-assembled monolayers (SAMs) of alkanethiolates on gold. This method begins with monolayers presenting a nitroveratryloxycarbonyl (NVOC)-protected hydroquinone which is photochemically irradiated to reveal a hydroquinone group. The resulting hydroquinone is then oxidized to the corresponding benzoquinone, providing a site for the Diels-Alder mediated immobilization of ligands. The rate constant for the photochemical deprotection is 0.032 s(-1) (with an intensity of approximately 100 mW/cm(2) between 355 and 375 nm), corresponding to a half-life of 21 s. The hydroquinone is oxidized to the benzoquinone using either electrochemical or chemical oxidation and then functionalized by reaction with a cyclopentadiene-tagged ligand. Two methods for patterning the immobilization of ligands are described. In the first, the substrate is illuminated through a mask to generate a pattern of hydroquinone groups, which are elaborated with ligands. In the second method, an optical microscope fit with a programmable translational stage is used to write patterns of deprotection which are then again elaborated with ligands. This technique is characterized by the use of well-defined chemical reactions to control the regions and densities of ligand immobilization and will be important for a range of applications that require patterned ligands for biospecific interactions 
650 4 |a Journal Article 
650 4 |a Research Support, N.I.H., Extramural 
650 4 |a Research Support, U.S. Gov't, Non-P.H.S. 
650 7 |a Benzoquinones  |2 NLM 
650 7 |a Cyclopentanes  |2 NLM 
650 7 |a Hydroquinones  |2 NLM 
650 7 |a Ligands  |2 NLM 
650 7 |a Membranes, Artificial  |2 NLM 
650 7 |a Oligopeptides  |2 NLM 
650 7 |a Sulfhydryl Compounds  |2 NLM 
650 7 |a Polyethylene Glycols  |2 NLM 
650 7 |a 3WJQ0SDW1A  |2 NLM 
650 7 |a Gold  |2 NLM 
650 7 |a 7440-57-5  |2 NLM 
650 7 |a arginyl-glycyl-aspartic acid  |2 NLM 
650 7 |a 78VO7F77PN  |2 NLM 
650 7 |a Fluorescein  |2 NLM 
650 7 |a TPY09G7XIR  |2 NLM 
700 1 |a Yousaf, Muhammad N  |e verfasserin  |4 aut 
700 1 |a Mrksich, Milan  |e verfasserin  |4 aut 
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