The Power of Assemblies at Interfaces: Nanosensor Platforms Based on Synthetic Receptor Membranes

Synthetic sensing materials (artificial receptors) are some of the most attractive components of chemical/biosensors because of their long-term stability and low cost of production. However, the strategy for the practical design of these materials toward specific molecular recognition in water is not established yet. For the construction of artificial material-based chemical/biosensors, the bottom-up assembly of these materials is one of the effective methods. This is because the driving forces of molecular recognition on the receptors could be enhanced by the integration of such kinds of materials at the ‘interfaces’, such as the boundary portion between the liquid and solid phases. Additionally, the molecular assembly of such self-assembled monolayers (SAMs) can easily be installed in transducer devices. Thus, we believe that nanosensor platforms that consist of synthetic receptor membranes on the transducer surfaces can be applied to powerful tools for high-throughput analyses of the required targets. In this review, we briefly summarize a comprehensive overview that includes the preparation techniques for molecular assemblies, the characterization methods of the interfaces, and a few examples of receptor assembly-based chemical/biosensing platforms on each transduction mechanism.

[1]  Yun Hee Jang,et al.  Molecular dynamics simulation of amphiphilic bistable [2]rotaxane langmuir monolayers at the air/water interface. , 2005, Journal of the American Chemical Society.

[2]  C. Malitesta,et al.  QCM sensors for aqueous phenols based on active layers constituted by tetrapyrrolic macrocycle Langmuir films , 2009 .

[3]  A. Afzal,et al.  Advanced vapor recognition materials for selective and fast responsive surface acoustic wave sensors: a review. , 2013, Analytica chimica acta.

[4]  Hans-Jürgen Butt,et al.  Physics and Chemistry of Interfaces , 2003 .

[5]  Su-Moon Park,et al.  Electrochemical impedance spectroscopy. , 2010, Annual review of analytical chemistry.

[6]  Shizuo Tokito,et al.  Antibody- and Label-Free Phosphoprotein Sensor Device Based on an Organic Transistor. , 2016, Analytical chemistry.

[7]  A. van den Berg,et al.  A simple approach to sensor discovery and fabrication on self-assembled monolayers on glass. , 2004, Journal of the American Chemical Society.

[8]  T. Meade,et al.  Electrochemistry of redox-active self-assembled monolayers. , 2010, Coordination chemistry reviews.

[9]  Hsueh-Chia Chang,et al.  Surface acoustic wave devices for chemical sensing and microfluidics: A review and perspective. , 2017, Analytical methods : advancing methods and applications.

[10]  Katsuhiko Ariga,et al.  Molecular Recognition of Nucleotides by the Guanidinium Unit at the Surface of Aqueous Micelles and Bilayers. A Comparison of Microscopic and Macroscopic Interfaces , 1996 .

[11]  A. Majumdar,et al.  Inverse rectification in donor-acceptor molecular heterojunctions. , 2011, ACS nano.

[12]  R. Martínez‐Máñez,et al.  Signalling Mechanisms in Anion‐Responsive Push‐Pull Chromophores: The Hydrogen‐Bonding, Deprotonation and Anion‐Exchange Chemistry of Functionalized Azo Dyes , 2007 .

[13]  Shaoyi Jiang,et al.  Hierarchical zwitterionic modification of a SERS substrate enables real-time drug monitoring in blood plasma , 2016, Nature Communications.

[14]  Hongxia Chen,et al.  Potassium ion sensing using a self-assembled calix[4]crown monolayer by surface plasmon resonance , 2008 .

[15]  K. Raghavachari,et al.  Anion Binding in Solution: Beyond the Electrostatic Regime , 2017 .

[16]  S. Marre,et al.  Combining microfluidics and FT-IR spectroscopy: towards spatially resolved information on chemical processes , 2016 .

[17]  V. Ahsen,et al.  Self-assembly of phthalocyanines on quartz crystal microbalances for QCM liquid sensing applications , 2014 .

[18]  R. Kurita,et al.  Sequential Assessment of Multiple Epigenetic Modifications of Cytosine in Whole Genomic DNA by Surface Plasmon Resonance. , 2019, Analytical chemistry.

[19]  G. Brocks,et al.  Work functions of self-assembled monolayers on metal surfaces by first-principles calculations , 2006, cond-mat/0606663.

[20]  Wei-En Hsu,et al.  Review-field-effect transistor biosensing: Devices and clinical applications , 2018 .

[21]  F. Dickert,et al.  Cavities generated by self-organised monolayers as sensitive coatings for surface acoustic wave resonators , 2007, Analytical and bioanalytical chemistry.

[22]  Darryl Y. Sasaki,et al.  Specific, Multiple-Point Binding of ATP and AMP to a Guanidinium-Functionalized Monolayer , 1991 .

[23]  E. Anslyn Supramolecular analytical chemistry. , 2007, The Journal of organic chemistry.

[24]  A. Painelli,et al.  Optical Spectra of Push−Pull Chromophores in Solution: A Simple Model , 2000 .

[25]  Y. Ichikawa,et al.  Systematic Investigation of Molecular Recognition Ability in FET-based Chemical Sensors Functionalized with a Mixed Self-Assembled Monolayer System. , 2020, ACS applied materials & interfaces.

[26]  D. Beebe,et al.  The present and future role of microfluidics in biomedical research , 2014, Nature.

[27]  Hasuck Kim,et al.  Electrogenerated chemiluminescent anion sensing: selective recognition and sensing of pyrophosphate. , 2010, Analytical chemistry.

[28]  J. Bonacin,et al.  The use of modified electrodes by hybrid systems gold nanoparticles/Mn-porphyrin in electrochemical detection of cysteine , 2014 .

[29]  Toshiya Sakata,et al.  Simultaneous biosensing with quartz crystal microbalance with a dissipation coupled-gate semiconductor device. , 2013, Analytical chemistry.

[30]  G. Schreckenbach,et al.  Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding. , 2018, Journal of the American Chemical Society.

[31]  Samuel Marre,et al.  Microfluidic approaches for accessing thermophysical properties of fluid systems , 2019, Reaction Chemistry & Engineering.

[32]  Yan Zhou,et al.  Interfacial Structures and Properties of Organic Materials for Biosensors: An Overview , 2012, Sensors.

[33]  Tsuyoshi Minami,et al.  Sensing of carboxylate drugs in urine by a supramolecular sensor array. , 2013, Journal of the American Chemical Society.

[34]  Q. Cheng,et al.  Surface Plasmon Resonance: Material and Interface Design for Universal Accessibility. , 2018, Analytical chemistry.

[35]  Liping Ding,et al.  Chemically assembled monolayers of fluorophores as chemical sensing materials. , 2010, Chemical Society reviews.

[36]  R. Kurita,et al.  An alkylating immobilization linker for immunochemical epigenetic assessment. , 2017, Chemical communications.

[37]  T. Minami,et al.  Electric Detection of Phosphate Anions in Water by an Extended-gate-type Organic Field-effect Transistor Functionalized with a Zinc(II)–Dipicolylamine Derivative , 2016 .

[38]  Liping Ding,et al.  The Institute of Chemistry of Great Britain and Ireland. Journal and Proceedings. Part VI: 1941 , 1941 .

[39]  Michel Calame,et al.  Selective sodium sensing with gold-coated silicon nanowire field-effect transistors in a differential setup. , 2013, ACS nano.

[40]  Vincenzo Amendola,et al.  Surface plasmon resonance in gold nanoparticles: a review , 2017, Journal of physics. Condensed matter : an Institute of Physics journal.

[41]  C. Fan,et al.  DNA nanostructure-based universal microarray platform for high-efficiency multiplex bioanalysis in biofluids. , 2014, ACS applied materials & interfaces.

[42]  H. Pettersson,et al.  Dye-sensitized solar cells. , 2010, Chemical Reviews.

[43]  T. Minamiki,et al.  Potentiometric detection of biogenic amines utilizing affinity on a 4-mercaptobenzoic acid monolayer , 2019, Analytical Methods.

[45]  Bernard P. Puc,et al.  An integrated semiconductor device enabling non-optical genome sequencing , 2011, Nature.

[46]  Katsuhiko Ariga,et al.  25th Anniversary Article: What Can Be Done with the Langmuir‐Blodgett Method? Recent Developments and its Critical Role in Materials Science , 2013, Advanced materials.

[47]  Joon Won Park,et al.  Spatially nanoscale-controlled functional surfaces toward efficient bioactive platforms. , 2015, Journal of materials chemistry. B.

[48]  K. Tanizawa,et al.  Differential measurement with a microfluidic device for the highly selective continuous measurement of histamine released from rat basophilic leukemia cells (RBL-2H3). , 2002, Lab on a chip.

[49]  Lei You,et al.  Recent Advances in Supramolecular Analytical Chemistry Using Optical Sensing. , 2015, Chemical reviews.

[50]  Jean-Marie Lehn,et al.  Supramolecular Chemistry: Concepts And Perspectives , 2014 .

[51]  J. Kwak,et al.  Dendron-modified polystyrene microtiter plate: surface characterization with picoforce AFM and influence of spacing between immobilized amyloid beta proteins. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[52]  T. Minami,et al.  An anion sensor based on an organic field effect transistor. , 2015, Chemical communications.

[53]  L. Chau,et al.  Functional Biointerfaces Based on Mixed Zwitterionic Self-Assembled Monolayers for Biosensing Applications. , 2018, Langmuir : the ACS journal of surfaces and colloids.

[54]  S. Choi Synthetic Multivalent Molecules: Concepts and Biomedical Applications , 2004 .

[55]  J. Kwak,et al.  "Seeing and counting" individual antigens captured on a microarrayed spot with force-based atomic force microscopy. , 2010, Analytical chemistry.

[56]  Dongpeng Yan,et al.  Recent developments in stimuli-responsive luminescent films , 2019, Journal of Materials Chemistry C.

[57]  Yukari Sato,et al.  One-step detection of galectins on hybrid monolayer surface with protruding lactoside. , 2010, Analytical chemistry.

[58]  Rashid Bashir,et al.  Label-free electrical detection of pyrophosphate generated from DNA polymerase reactions on field-effect devices. , 2012, The Analyst.

[59]  Minoru Sakurai,et al.  Theoretical Study of Intermolecular Interaction at the Lipid−Water Interface. 1. Quantum Chemical Analysis Using a Reaction Field Theory , 1997 .

[60]  P. Paul,et al.  Structures of carbohydrate-boronic acid complexes determined by NMR and molecular modelling in aqueous alkaline media. , 2004, Organic & biomolecular chemistry.

[61]  E. W. Meijer,et al.  About Supramolecular Assemblies of π-Conjugated Systems , 2005 .

[62]  Kai Liu,et al.  Uncertainties in contact angle goniometry. , 2019, Soft matter.

[63]  H. Sugimura,et al.  Imaging micropatterned organosilane self‐assembled monolayers on silicon by means of scanning electron microscopy and Kelvin probe force microscopy , 2003 .

[64]  Xiaqing Wu,et al.  Molecular imprinting: perspectives and applications. , 2016, Chemical Society reviews.

[65]  M. Grätzel Dye-sensitized solar cells , 2003 .

[66]  J. Heberle,et al.  Surface-enhanced infrared absorption spectroscopy (SEIRAS) to probe monolayers of membrane proteins. , 2013, Biochimica et biophysica acta.

[67]  Roberto Paolesse,et al.  The light modulation of the interaction of l-cysteine with porphyrins coated ZnO nanorods , 2015 .

[68]  R. Kurita,et al.  Immobilization of DNA on Biosensing Devices with Nitrogen Mustard–Modified Linkers , 2019, Current protocols in nucleic acid chemistry.

[69]  Sundus Erbas-Cakmak,et al.  Artificial Molecular Machines , 2015, Chemical reviews.

[70]  Fabio Biscarini,et al.  Self-assembled monolayers in organic electronics. , 2017, Chemical Society reviews.

[71]  Gang-yu Liu,et al.  Preparation and Characterization of Solid-Supported Lipid Bilayers Formed by Langmuir-Blodgett Deposition: A Tutorial. , 2018, Langmuir : the ACS journal of surfaces and colloids.

[72]  H. Allen,et al.  Interfacial Supramolecular Structures of Amphiphilic Receptors Drive Aqueous Phosphate Recognition. , 2019, Journal of the American Chemical Society.

[73]  T. Aida,et al.  Guanidinium-based "molecular glues" for modulation of biomolecular functions. , 2017, Chemical Society reviews.

[74]  J. Bonacin,et al.  Preferential coordination of ruthenium complex as an electroactive self-assembled monolayer on gold substrate and its application in sensing of dopamine , 2019, Inorganic Chemistry Communications.

[75]  G. Whitesides,et al.  Self-assembled monolayers of thiolates on metals as a form of nanotechnology. , 2005, Chemical reviews.

[76]  A. C. Jamison,et al.  4-Mercaptophenylboronic acid SAMs on gold: comparison with SAMs derived from thiophenol, 4-mercaptophenol, and 4-mercaptobenzoic acid. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[77]  Oguz H. Elibol,et al.  Surface Immobilizable Chelator for Label-free Electrical Detection of Pyrophosphatew Chemcomm , 2022 .

[78]  Anand Gole,et al.  Surface-enhanced Raman spectroscopy of self-assembled monolayers: sandwich architecture and nanoparticle shape dependence. , 2005, Analytical chemistry.

[79]  Y. Okahata,et al.  A versatile planar QCM-based sensor design for nonlabeling biomolecule detection. , 2002, Analytical chemistry.

[80]  Katsuhiko Ariga,et al.  Theoretical Study of Intermolecular Interaction at the Lipid−Water Interface. 2. Analysis Based on the Poisson−Boltzmann Equation , 1997 .

[81]  Riku Kubota,et al.  Chemical Sensing Platforms Based on Organic Thin-Film Transistors Functionalized with Artificial Receptors. , 2019, ACS sensors.

[82]  Piet Bergveld,et al.  Thirty years of ISFETOLOGY ☆: What happened in the past 30 years and what may happen in the next 30 years , 2003 .

[83]  M. Canepa,et al.  Spectroscopic ellipsometry of self assembled monolayers: interface effects. The case of phenyl selenide SAMs on gold. , 2013, Physical chemistry chemical physics : PCCP.

[84]  Jon R. Askim,et al.  The Optoelectronic Nose: Colorimetric and Fluorometric Sensor Arrays. , 2018, Chemical reviews.

[85]  Qunfeng Yao,et al.  AuNPs Amplified Surface Acoustic Wave Sensor for Quantification of Exosomes. , 2020, ACS sensors.

[86]  E. Nakamura,et al.  Molecular and supramolecular control of the work function of an inorganic electrode with self-assembled monolayer of umbrella-shaped fullerene derivatives. , 2011, Journal of the American Chemical Society.

[87]  Donghyun Lee,et al.  Electrochemical detection of dopamine using periodic cylindrical gold nanoelectrode arrays , 2018, Scientific Reports.

[88]  Jiwei Cui,et al.  Innovation in Layer-by-Layer Assembly. , 2016, Chemical reviews.

[89]  R. Ras,et al.  Surface-wetting characterization using contact-angle measurements , 2018, Nature Protocols.

[90]  C. Chothia,et al.  The atomic structure of protein-protein recognition sites. , 1999, Journal of molecular biology.

[91]  Manuel A. Palacios,et al.  Supramolecular chemistry approach to the design of a high-resolution sensor array for multianion detection in water. , 2007, Journal of the American Chemical Society.

[92]  Kenjiro Fukuda,et al.  Printed Organic Transistors with Uniform Electrical Performance and Their Application to Amplifiers in Biosensors , 2015 .

[93]  B. Gibb,et al.  Molecular containers assembled through the hydrophobic effect. , 2015, Chemical Society reviews.

[94]  Caroline M. Whelan,et al.  HREELS, XPS, and Electrochemical Study of Benzenethiol Adsorption on Au(111) , 1999 .

[95]  Y. Hoshino,et al.  Engineering the binding kinetics of synthetic polymer nanoparticles for siRNA delivery. , 2019, Biomacromolecules.

[96]  Akinori Kawai,et al.  Optical detection of anions using N-(4-(4-nitrophenylazo)phenyl)-N′-propyl thiourea bound silica film , 2013 .

[97]  Amy L. Graham,et al.  Interface Dipoles Arising from Self-Assembled Monolayers on Gold: UV−Photoemission Studies of Alkanethiols and Partially Fluorinated Alkanethiols , 2003 .

[98]  Carles Cané,et al.  Discrimination of volatile compounds through an electronic nose based on ZnO SAW sensors , 2007 .

[99]  A. Ulman,et al.  Formation and Structure of Self-Assembled Monolayers. , 1996, Chemical reviews.

[100]  J. Moran‐Mirabal,et al.  Fluorescent labeling and characterization of cellulose nanocrystals with varying charge contents. , 2013, Biomacromolecules.

[101]  I. Hamachi,et al.  Protein recognition using synthetic small-molecular binders toward optical protein sensing in vitro and in live cells. , 2015, Chemical Society reviews.

[102]  Kenjiro Fukuda,et al.  An extended-gate type organic field effect transistor functionalised by phenylboronic acid for saccharide detection in water. , 2014, Chemical communications.