Maleimide-Functionalized Self-Assembled Monolayers for the Preparation of Peptide and Carbohydrate Biochips

Houseman, Benjamin T.; Gawalt, Ellen S.; Mrksich, Milan

doi:10.1021/la0262304

Cited by 388 publications

(408 citation statements)

References 59 publications

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“…In these examples a monolayer presenting a maleimide group at low density against a background of oligo(ethylene glycol) groups is treated with a thiol-tagged ligand. 43 The maleimide group selectively reacts with the thiol functionality of the ligand and the glycol groups are effective at preventing unwanted protein adsorption in subsequent assays. Characterization of the monolayer with mass spectrometry shows clear peaks corresponding to the maleimide-terminated alkanethiolate prior to the reaction and of the immobilized adducts following reaction.…”

Section: Immobilization Of Ligandsmentioning

confidence: 99%

Mass Spectrometry of Self-Assembled Monolayers: A New Tool for Molecular Surface Science

2008

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Most reactions can be performed in solution and on a surface. Yet the challenges faced in applying known reactions or in developing entirely new reactions for modifying surfaces remain formidable. The products of many reactions performed in solution can be characterized in minutes and even products having complex structures can be characterized in hours. When performed on surfaces, even the most basic reactions require a substantial effort-requiring several weeks-to characterize the yields and structures of the products. This contrast stems from the lack of convenient analytical tools that provide rapid information on the structures of molecules attached to a surface. This review describes recent work that has established mass spectrometry as a powerful method for developing and characterizing a broad range of chemical reactions of molecules attached to self-assembled monolayers of alkanethiolates on gold. The SAMDI-TOF mass spectrometry technique will enable a next generation of applications of molecularly defined surfaces to problems in chemistry and biology. Keywordsbiochip; interfacial reactions; label-free; self-assembled monolayer; SAMDI-TOF mass spectrometryThe scientific and engineering disciplines have developed sophisticated toolboxes for making matter-including examples from organic chemistry to create small molecules with virtually unlimited complexity, molecular biology to prepare macromolecules with a precise arrangement of amino acids and a defined tertiary structure, and lithographic methods to fashion inorganic and metallic materials into integrated circuits and devices. Each of these approaches is based on distinct methods for assembling matter and each relies on analytical methods that can characterize the structures that they generate. In the bottom-up approaches common to synthetic chemistry, a range of methods including NMR and x-ray diffraction are used to delineate the connectivity of atoms within molecules. The biopolymers created using enzyme-mediated conversions are characterized using electrophoretic methods and high resolution mass spectrometry, while integrated circuits are characterized with electron microscopy, scanning probe tools, and sensitive spectroscopies. The tools remain fundamental to each of these areas, enabling further advances in the preparation of their respective targets.The pursuit of structures with at least one dimension sized between 1-100 nm-which underlies the nanoscience and technology discipline that has grown over the past decade-is likewise dependent on analytical methods, and in several cases has been hampered by a lack of methods having appropriate performance. 1 For example, it remains difficult to characterize the products resulting from treatment of proteins or carbon nanotubes with organic reagents 2 and it is still difficult to characterize the dynamic structures of lipid rafts in bilayer membranes. 3 This review deals with the analogous challenge of characterizing the molecular structures of Published as: ACS Nano. 2008 January ; 2(1): 7-18...

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Section: Immobilization Of Ligandsmentioning

confidence: 99%

Mass Spectrometry of Self-Assembled Monolayers: A New Tool for Molecular Surface Science

2008

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“…[20] Briefly, titanium (40 ) and gold (220 ) were evaporated onto glass coverslips using an electron beam evaporator (Thermionics) at a rate of 0.2-0.4 nm s À1 with a pressure of 1.0 10 À6 Torr. Monolayers were formed by immersing these substrates into an ethanolic solution containing a mixture of a symmetric tri(ethylene glycol)-terminated disulfide (EG 3 ) and an asymmetric disulfide with tri(ethylene glycol) and maleimide head groups for 12-16 h at room temperature .…”

Section: Methodsmentioning

confidence: 99%

An Inhibitor of a Cell Adhesion Receptor Stimulates Cell Migration

2010

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The integrins are a family of heterodimeric receptors that play a universal role in mediating the adhesion of cells to the extracellular matrix. As such, the differential interactions of the receptors at the front and back ends of the cell are important in regulating the migration of cells. [1] Approximately one-half of the integrins recognize the canonical RGD motif found in fibronectin, and a significant body of work has shown that model substrates presenting the RGD peptide support the adhesion and migration of cells. [2] Inhibitors of the integrin receptor have been explored as reagents that may block cell migration and recent work has advanced a class of soluble RGD peptides as possible therapeutics that display anti-metastatic activity. [3][4][5] But the molecular mechanisms by which these compounds block migration have not been elucidated and have recently been contradicted by work that demonstrates that the soluble antagonists can also promote the migration of tumor cells. [6][7][8] Herein, we use a well-defined model system to assess the influence of soluble inhibitors on cell migration and we show that the integrin antagonists are able to promote the migration of cells.The RGD-mimetic compounds cilengitide and S36578 were developed as integrin antagonists and are now in early phase clinical trials for cancer therapy. [9,10] These compounds, at micromolar concentrations, were shown to block cell migration, but recent work reported that lower concentrations of these drugs can actually enhance the growth of tumors in vivo by promoting migration and VEGF-mediated angiogenesis. [7] Other recent work has investigated the analogy between tumor angiogenesis and wound healing [3,11] with the finding that the fibronectin-derived Pro-His-SerArg-Asn (PHSRN) peptide can stimulate migration of human kerotinocytes and fibroblasts and accelerate wound healing in obese diabetic mice. [8] Our group [12,13] and others [14] have suggested that PHSRN antagonizes RGD binding, and therefore may accelerate migration by inhibiting the integrinmediated adhesion. Additionally, it has been reported that addition of insulin-like growth factor binding protein (IGFBP-1) which contains the RGD sequence in the cell culture medium increases the migration of CHO cells twofold compared to cells treated with Trp-Gly-Asp (WGD). [6] The literature contains several additional contradictory reports as to the effect of soluble RGD-containing proteins on adhesion and migration. [5,15] Mechanistic studies of the roles of ligand-receptor interactions in cell migration are challenging because it is difficult to control which interactions operate between cell and matrix. This limitation is particularly relevant to in vivo experiments, where a broad range of signals and matrix constituents are present and not always defined. [16] Even in the laboratory, it can be difficult to reproducibly present matrix ligands to a cell in order to obtain reproducible matrix formulations. [5] To address these limitations, we use selfassembled monolayers that presen...

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“…2c) (17). Tri(ethylene glycol) groups also present on the monolayer are intended to reduce nonspecific adsorption of protein and increase the likelihood that the valerate groups remain accessible to the cell-surface cutinase.…”

Section: And Materials and Methods)mentioning

confidence: 99%

“…Maleimideterminated and oligoethylene glycol-terminated alkanethiolates were synthesized as described in ref. 17. All intermediates gave satisfactory 1 H NMR spectra.…”

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confidence: 87%

Engineering a biospecific communication pathway between cells and electrodes

Collier

Mrksich

2006

Proc. Natl. Acad. Sci. U.S.A.

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Methods for transducing the cellular activities of mammalian cells into measurable electronic signals are important in many biotechnical applications, including biosensors, cell arrays, and other cell-based devices. This manuscript describes an approach for functionally integrating cellular activities and electrical processes in an underlying substrate. The cells are engineered with a cellsurface chimeric receptor that presents the nonmammalian enzyme cutinase. Action of this cell-surface cutinase on enzyme substrate self-assembled monolayers switches a nonelectroactive hydroxyphenyl ester to an electroactive hydroquinone, providing an electrical activity that can be identified with cyclic voltammetry. In this way, cell-surface enzymatic activity is transduced into electronic signals. The development of strategies to directly interface the activities of cells with materials will be important to enabling a broad class of hybrid microsystems that combine living and nonliving components.biomaterial ͉ extracellular matrix ͉ signal transduction T he development of strategies for controlling the interface between a cell and a material is important in a wide range of settings, including the enablement of cell-based sensing technologies, the growth of tissue-engineered products for medicine, and the preparation of substrates for studies of cell adhesion. For example, cell-based sensors are now important for screening compounds in drug discovery programs (1, 2) and are being developed as diagnostic tools to identify biowarfare agents in environmental samples (3). In both cases, cells are integrated into a microsystem to provide sensing functions that cannot be achieved with the common molecular strategies. The development of schemes for integrating the functions of the cell and the material particularly for the electronic materials that are used in microfabrication will further advance the goal of using living cells as components in hybrid microsystems. In this paper we report a strategy in which both cells and the electrode surfaces are engineered to specifically and directly interact with each other by way of a receptor-ligand interaction to produce electronic signals. This example is a significant alternative to current indirect methods for transducing cellular activities into electronic signals based on the electrical activity of excitable cells (4-6) or the use of bioluminescent (7,8) or fluorescent (9-11) reporter proteins in that the technique we describe here constitutes a direct communication pathway from cell to electrode. Thus, the need for bulky optical instrumentation is eliminated, and the number of potentially noise-enhancing signal transduction steps is minimized. Here we demonstrate an approach that combines a biological modification of the cell surface and a chemical modification of an electrode surface to install a unique molecular transduction pathway that can convert a specific cellular activity into an electrical signal.Our strategy relies on engineering the surface of a cell with a chimeric protein...

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Maleimide-Functionalized Self-Assembled Monolayers for the Preparation of Peptide and Carbohydrate Biochips

Cited by 388 publications

References 59 publications

Mass Spectrometry of Self-Assembled Monolayers: A New Tool for Molecular Surface Science

Mass Spectrometry of Self-Assembled Monolayers: A New Tool for Molecular Surface Science

An Inhibitor of a Cell Adhesion Receptor Stimulates Cell Migration

Engineering a biospecific communication pathway between cells and electrodes

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