Toward Plasmonic Biosensors Functionalized by a Photoinduced Surface Reaction

We present a method for efficient coupling of amine nucleophilic molecules of choice to a nanostructured gold surface via photoinduced surface chemistry. The method is based on photoactive self-assembled monolayers and can be used to functionalize localized surface plasmon resonance (LSPR) based biosensors with biorecognition motifs while reducing nonspecific binding via introduction of hydrophilic units. The photoactive linker molecule, 5-bromo-7-nitroindoline, couples nucleophilic molecules such as biotin ethylenediamine to a surface when exposed to UV-light. The specific, noncovalent recognition between biotin and streptavidin is used for demonstration of a simple biorecognition assay based on the LSPR sensing principle. By doing so, one can envision that the binding of any streptavidin fusion protein, being attached to specific spots at the gold surface, is monitored by an LSPR peak shift. Since the surface functionalization is based on a photoinduced reaction, this method can be used to functionalize...

[1]  C. Reese,et al.  A photo-induced rearrangement involving aryl participation , 1962 .

[2]  D. A. Ben-Efraim,et al.  Light-sensitive amides. The photosolvolysis of substituted 1-acyl-7-nitroindolines , 1976 .

[3]  J. Kaplan,et al.  Rapid photolytic release of adenosine 5'-triphosphate from a protected analogue: utilization by the Na:K pump of human red blood cell ghosts. , 1978, Biochemistry.

[4]  R. Givens,et al.  Photochemistry of phosphate esters : an efficient method for the generation of electrophiles , 1984 .

[5]  G. Whitesides,et al.  Adsorption of proteins onto surfaces containing end-attached oligo(ethylene oxide): a model system using self-assembled monolayers , 1993 .

[6]  S. P. Fodor,et al.  Light-generated oligonucleotide arrays for rapid DNA sequence analysis. , 1994, Proceedings of the National Academy of Sciences of the United States of America.

[7]  M. Sugimoto,et al.  Acyloxycoumarinylmethyl-caged cAMP, the photolabile and membrane-permeable derivative of cAMP that effectively stimulates pigment-dispersion response of melanophores. , 1996, Biochemical and biophysical research communications.

[8]  G. Mcgall,et al.  Light-directed synthesis of high-density oligonucleotide arrays using semiconductor photoresists. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[9]  Ling Peng,et al.  Synthesis and Characterization of Photolabile Choline Precursors as Reversible Inhibitors of Cholinesterases: Release of Choline in the Microsecond Time Range , 1996 .

[10]  J. Corrie,et al.  Synthesis and properties of carbamoyl derivatives of photolabile benzoins , 1997 .

[11]  R. Givens,et al.  New Photoactivated Protecting Groups. 7.p-Hydroxyphenacyl: A Phototrigger for Excitatory Amino Acids and Peptides1 , 1997 .

[12]  George M. Whitesides,et al.  Molecular Conformation in Oligo(ethylene glycol)-Terminated Self-Assembled Monolayers on Gold and Silver Surfaces Determines Their Ability To Resist Protein Adsorption , 1998 .

[13]  E M Callaway,et al.  Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[14]  E. Krause,et al.  Deactivation Behavior and Excited-State Properties of (Coumarin-4-yl)methyl Derivatives. 1. Photocleavage of (7-Methoxycoumarin-4-yl)methyl-Caged Acids with Fluorescence Enhancement , 1999 .

[15]  M. Sussman,et al.  Maskless fabrication of light-directed oligonucleotide microarrays using a digital micromirror array , 1999, Nature Biotechnology.

[16]  C. Bochet.  Wavelength-selective cleavage of photolabile protecting groups , 2000 .

[17]  M. Pirrung,et al.  3'-nitrophenylpropyloxycarbonyl (NPPOC) protecting groups for high-fidelity automated 5' --> 3' photochemical DNA synthesis. , 2001, Organic letters.

[18]  S. Frings,et al.  Highly Efficient and Ultrafast Phototriggers for cAMP and cGMP by Using Long-Wavelength UV/Vis-Activation , 2001 .

[19]  S. Watanabe,et al.  Reductive ring opening of o-nitrobenzylidene acetals of monosaccharides: synthesis and photolysis of some photolabile sugars. , 2001, Organic letters.

[20]  K. Nicolaou,et al.  A New Photolabile Linker for the Photoactivation of Carboxyl Groups , 2001 .

[21]  I. Chaiken,et al.  Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds. A model study. , 2002, Organic letters.

[22]  V. Hagen,et al.  Deactivation behavior and excited-state properties of (coumarin-4-yl)methyl derivatives. 2. Photocleavage of selected (coumarin-4-yl)methyl-caged adenosine cyclic 3',5'-monophosphates with fluorescence enhancement. , 2002, The Journal of organic chemistry.

[23]  J. Corrie,et al.  Mechanisms of photorelease of carboxylic acids from 1-acyl-7-nitroindolines in solutions of varying water content , 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[24]  J. Corrie,et al.  Photolytic cleavage of 1-(2-nitrophenyl)ethyl ethers involves two parallel pathways and product release is rate-limited by decomposition of a common hemiacetal intermediate. , 2003, Journal of the American Chemical Society.

[25]  C. Schultz,et al.  Synthesis of caged myo-inositol 1,3,4,5-tetrakisphosphate , 2003 .

[26]  K. Jacobson,et al.  Preparation and light-directed activation of caged proteins. , 2003, Methods in enzymology.

[27]  T. M. Dore,et al.  Bhc-diol as a photolabile protecting group for aldehydes and ketones. , 2003, Organic letters.

[28]  H. Kettenmann,et al.  DMACM‐Caged Adenosine Nucleotides: Ultrafast Phototriggers for ATP, ADP, and AMP Activated by Long‐Wavelength Irradiation , 2003, Chembiochem : a European journal of chemical biology.

[29]  J. Corrie,et al.  Flash photolytic release of alcohols from photolabile carbamates or carbonates is rate-limited by decarboxylation of the photoproduct , 2005, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[30]  Pierre-Michel Adam,et al.  Role of localized surface plasmons in surface-enhanced Raman scattering of shape-controlled metallic particles in regular arrays , 2005 .

[31]  Mingde Zhu,et al.  Kinetic analysis of a high-affinity antibody/antigen interaction performed by multiple Biacore users. , 2006, Analytical biochemistry.

[32]  Tatsuro Endo,et al.  Multiple label-free detection of antigen-antibody reaction using localized surface plasmon resonance-based core-shell structured nanoparticle layer nanochip. , 2006, Analytical chemistry.

[33]  H. Fredriksson,et al.  Hole–Mask Colloidal Lithography , 2007 .

[34]  T Neumann,et al.  SPR-based fragment screening: advantages and applications. , 2007, Current topics in medicinal chemistry.

[35]  H. Misawa,et al.  Nanoparticle plasmon-assisted two-photon polymerization induced by incoherent excitation source. , 2008, Journal of the American Chemical Society.

[36]  Yasuhiko Yoshida,et al.  Arraying heterotypic single cells on photoactivatable cell-culturing substrates. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[37]  Jeffrey N. Anker,et al.  Biosensing with plasmonic nanosensors. , 2008, Nature materials.

[38]  J. Camarero.  Recent developments in the site‐specific immobilization of proteins onto solid supports , 2008, Biopolymers.

[39]  Romain Quidant,et al.  Plasmon near-field coupling in metal dimers as a step toward single-molecule sensing. , 2009, ACS nano.

[40]  Mikael Käll,et al.  Refractometric sensing using propagating versus localized surface plasmons: a direct comparison. , 2009, Nano letters.

[41]  Mikael Käll,et al.  High-resolution microspectroscopy of plasmonic nanostructures for miniaturized biosensing. , 2009, Analytical chemistry.

[42]  J. Micklefield,et al.  Selective covalent protein immobilization: strategies and applications. , 2009, Chemical reviews.

[43]  J. Lakowicz,et al.  Plasmon-enhanced fluorescence from single fluorophores end-linked to gold nanorods. , 2010, Journal of the American Chemical Society.

[44]  M. T. Neves-Petersen,et al.  Arraying prostate specific antigen PSA and Fab anti‐PSA using light‐assisted molecular immobilization technology , 2010, Protein science : a publication of the Protein Society.

[45]  Seth M Cohen,et al.  Photochemical activation of a metal-organic framework to reveal functionality. , 2010, Angewandte Chemie.

[46]  K. Schaumburg,et al.  Optically induced linking of protein and nanoparticles to gold surfaces. , 2010, Bioconjugate chemistry.

[47]  Igor Zorić,et al.  Indirect nanoplasmonic sensing: ultrasensitive experimental platform for nanomaterials science and optical nanocalorimetry. , 2010, Nano letters.

[48]  Verónica San Miguel,et al.  Wavelength-selective caged surfaces: how many functional levels are possible? , 2011, Journal of the American Chemical Society.

[49]  Mikael Käll,et al.  Plasmon-enhanced colorimetric ELISA with single molecule sensitivity. , 2011, Nano letters.

[50]  S. Mercier,et al.  Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group , 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[51]  P. Pallavicini,et al.  Optical method for predicting the composition of self-assembled monolayers of mixed thiols on surfaces coated with silver nanoparticles. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[52]  M. Orrit,et al.  Optical detection of single non-absorbing molecules using the surface plasmon resonance of a gold nanorod. , 2012, Nature nanotechnology.