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International Journal of Molecular Sciences
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22 August 2007

Developments in Molecular Recognition and Sensing at Interfaces

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Supermolecules Group, National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044, Japan
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Int. J. Mol. Sci.2007, 8(8), 864-883;https://doi.org/10.3390/i8080864
This article belongs to the Section Molecular Recognition
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Abstract

In biological systems, molecular recognition events occur mostly within interfacial environments such as at membrane surfaces, enzyme reaction sites, or at the interior of the DNA double helix. Investigation of molecular recognition at model interfaces provides great insights into biological phenomena. Molecular recognition at interfaces not only has relevance to biological systems but is also important for modern applications such as high sensitivity sensors. Selective binding of guest molecules in solution to host molecules located at solid surfaces is crucial for electronic or photonic detection of analyte substances. In response to these demands, molecular recognition at interfaces has been investigated extensively during the past two decades using Langmuir monolayers, self-assembled monolayers, and lipid assemblies as recognition media. In this review, advances of molecular recognition at interfaces are briefly summarized.

1. Introduction

Molecular recognition is one of the most important chemical events in biological systems and has been mimicked in supramolecular chemistry as, for example, artificial enzymes [–]. Most of the supramolecular systems for molecular recognition are composed of molecularly dispersed states in homogeneous solutions. However, this is quite apart from the situation seen in biological systems. Molecular recognition in living systems occurs mostly at interfacial environments such as membrane surfaces, enzyme reaction sites, or at the interior of the DNA double helix.
Why have biological systems adopted interfacial environments for molecular recognition? A part of the answer was provided by pioneering work by Kunitake and co-workers [] who compared binding efficiency between guanidinium and phosphate in three different environments (Figure 1). Binding constants of adenosine monophosphate (AMP) to guanidinium functionality in aqueous aggregates such as micelle or bilayer vesicles were evaluated at 102–104 M−1. These values are significantly larger than those between molecularly-dispersed guanidinium and phosphate in water (1.4 M−1) []. Surprisingly, a large enhancement in binding constant was reported for binding of AMP to guanidinium groups when embedded at a water surface []. These results clearly indicate that molecular recognition can be achieved much more efficiently at an appropriate interface.
Figure 1. Typical binding constants between phosphate and guanidinium for various aqueous media interfaces: (a) in aqueous solution; (b) on the surface of micelles and bilayers; (c) at the air-water interface. Reprinted with permission from [] ©1996, American Chemical Society.
In order to further understand these findings, Sakurai and co-workers considered theoretical aspects of molecular recognition at the air–water interface using a quantum chemical approach including reaction field calculations combined with AM1 molecular orbital methods [–]. Guanidinium host and phosphate guest were placed in various positions at a model interface consisting of a lipid layer (low dielectric, ɛ = 2) and water phase (high dielectric, ɛ = 80). The calculated binding energies depended significantly on the position of the binding site relative to the two-phase boundary. A large binding constant was obtained when the binding site was located in the lipid phase, while positioning the guanidinium deep in the water phase resulted in a very small binding energy. Even when the hydrogen bonding site was positioned in the water phase, the site is affected electronically by the low dielectric lipid layer, which strengthens intermolecular hydrogen bonding and electrostatic interactions. As a result, the binding constant increases significantly at the border between lipid and aqueous phases. These quantum chemical calculations suggested advantageous aspects of interfacial environments for efficient molecular recognition of substances in aqueous media.
Molecular recognition at interfaces not only has relevance to biological systems but also is important for modern applications such as high sensitivity sensors. Selective binding of guest molecules in solution to host molecules located at a solid surface is crucial for electronic and photonic detection of target substances. In response to these demands, molecular recognition at interfaces has been researched extensively during the past two decades using Langmuir monolayers, self-assembled monolayers, and lipid assemblies as recognition media. In this review, advances of molecular recognition at interfaces are briefly summarized.

3. Molecular Recognition at Other Interfaces

Apart from the air-water interface, various interfacial environments provide media useful for molecular recognition and its related functions. In particular, self-assembled monolayers (SAM) are often used for sensor applications because the SAM structures facilitate contact with artificial devices such as electrodes and field effect transistors, as has been reviewed by Reinhoudt and co-workers []. Okahata and co-workers developed a siloxane-linked monolayer attached to a porous glass surface for permeation control [–]. They applied the same structure onto a tin dioxide electrode, where insertion of alkylalcohol into the alkylsiloxane monolayer could be electrochemically detected []. Geiger and co-workers reported use of an enhanced surface second harmonic generation (SHG) signal for detection of the toxic metal pollutant chromium(VI) at custom-made amino acid functionalized fused quartz/water interfaces []. Chromate adsorption isotherms recorded at pH 7 were suggestive of an intramolecular chelation mechanism that would be important when four or more hydrogen-bonding moieties were displayed toward the incoming chromate. Credo et al. reported a method to manipulate conductance using molecular recognition at a SAM surface []. As illustrated in Figure 7, a binder molecule, diacyl 2,6-diaminopyridine decanethiolate (DAP, Figure 7A) was inserted into a background monolayer of decanethiolate on Au(111) using replacement lithography. Electroactive functionalization of the monolayer was then achieved through binding of the complementary ferrocene-terminated uracil to the binder molecule. Ferrocene function can be replaced by dodecyl uracil for erasing conductance. Current-voltage properties of the patterned region were monitored by using an STM tip. Noncovalent self-assembly provides a potential method to install and subsequently remove electroactive functionality in molecular electronics systems. Kitano and Taira used SAM structures of cyclodextrin derivatives for detection of bisphenol-type substances. They examined complexation of various kinds of bisphenols by a SAM of thiolated α-cyclodextrin on a gold electrode by cyclic voltammetry using hydroquinone as a probe []. On the basis of the inhibitory effect of bisphenols on the inclusion of hydroquinone by the surface-confined cyclodextrin, the association constants of bisphenols with the immobilized α-cyclodextrin were estimated. Use of β-cyclodextrin [] and hexasodium calix[]arene hexasulfonic acid [] as host structures were also reported by the same research group. Willner and co-workers demonstrated photochemical imprinting of molecular recognition sites for phenoxynaphthacene quinone in SAM assembled on Au surfaces []. The primary step of their approach includes the assembly of the trans-phenoxynaphthacenequinone monolayer, followed by the rigidification of the monolayer with long chain alkanethiols generating a densely packed quinone monolayer. The second process involves the photoisomerization of the monolayer to the ana-quinone state, followed by the nucleophilic displacement of the quinone with butylamine. The binding of phenoxynaphthacenequinone to the imprinted recognition sites reveals selectivity, and structurally related substrates did not associate with the imprinted sites.
Figure 7. Functionalization and erasing at the surface of self-assembled monolayer. Reprinted with permission from [] ©2002, American Chemical Society.
Combining recognition events with appropriate analytical methods can yield sensor devices suitable for biological applications. Zeng, Wang, and co-workers demonstrated that an unlabeled carbohydrate mass sensor in combination with lectin-bacterial O-antigen recognition can be used for detection of high molecular weight bacterial targets with remarkably high sensitivity and enhanced specificity []. A functional mannose self-assembled monolayer in combination with lectin concanavalin A (Con A) was used as the molecular recognition element for detection of Escherichia coli W1485 using QCM as a transducer. Whitesides and co-workers reported the synthesis of bifunctional polyacrylamides containing pendant vancomycin and fluorescein groups, and the use of these polymers to direct antibodies against fluorescein to SAM presenting D-alanine-D-alanine groups []. Liu and Amiridis studied the interaction of avidin with biotin on functionalized quartz surfaces terminated with 3-aminopropyltrimethoxysilane, 2,2′-(ethylenedioxy)bis(ethylenediamine), and fourth generation amine-terminated polyamidoamine dendrimers, using the FTIR-RAS technique []. Advincula and co-workers reported nanomolar detection and specific recognition of pinacolyl methylphosphonate, a hydrolysis product and an analog of a relatively persistent class of toxic nerve agents []. In this system a modified polyamidoamine carbazole/Cu2+ dendrimer, which is electrochemically cross-linked on a self-assembled monolayer (SAM) modified Au substrate, acted as an active sensing element for trapping the nerve agent analogs.
Other unique approaches using SAM structures have been reported. Bunker, Stoddart, and co-workers developed supramolecular machines using SAM structures in which molecular configurations can be reversibly programmed using electrochemical stimuli []. The proposed machines addressed the chemistry of substrate surfaces for integrated microfluidic systems. Interactions between the tethered tetracationic cyclophane host cyclobis(paraquat-p-phenylene) and dissolved π-electron-rich guest molecules, such as tetrathiafulvalene, were reversibly switched by oxidative electrochemistry. As reviewed by Rotello and co-workers [], SAM structures can be prepared on size-controlled nanoparticles, providing scaffolds for sensing target molecules. Sanchez-Cortes and co-workers reported the use of 25,27-diethyl-dithiocarbamic-26,28-dihydroxy-p-tert-butylcalix[]arene in the functionalization of Ag nanoparticles for pyrene detection by surface-enhanced Raman scattering (SERS) [].
Immiscible liquids produce a dynamic interface such as the water-oil interface that have been also used as media for specific molecular recognition. Kitamura and co-workers investigated molecular recognition mediated by hydrogen-bonding interactions at a water-CCl4 interface by means of time-resolved total internal reflection (TIR) fluorescence spectroscopy []. In the presence of N,N-dioctadecyl-[ ,,]triazine-2,4,6-triamine (DTT) in the CCl4 phase, the fluorescence decay profiles of riboflavin in aqueous phase were significantly modified, as compared with those observed in the absence of DTT, with the relevant amplitude varying with the concentration of DTT. Watarai and co-workers reported a molecular recognition system of the interfacial aggregation of monocationic palladium(II)-2-(5-bromo-2-pyridylazo)-5-diethylaminophenol complex with neutral diazine or purine bases at the toluene-water system []. The formation of interfacial aggregates of these complexes was investigated by centrifugal liquid membrane (CLM)/UV-Vis spectroscopy, CLM/resonance Raman spectroscopy and optical microscopy. The palladium(II)-2-(5-bromo-2-pyridylazo)-5-diethylaminophenol complex formed interfacial aggregates preferentially with purine bases (adenine and guanine). Alkali metal ion recognition with [2-hydroxy-5-(4-nitrophenylazo)phenyl]-methyl-15-crown-5 at the heptane-water interface was investigated by Teramae and co-workers, using in situ second harmonic generation (SHG) spectroscopy []. It was revealed experimentally that the Na+ and K+ complexes were flatter while the Li+ complex exhibited a lift-up orientation at the heptane-water interface.
Because of its relevance to biological systems, molecular recognition at the surface of aqueous lipid bilayers has also been investigated [–]. Sasaki et al. reported lead ion recognition by a crown ether functionalized lipid membrane []. The receptor-lipid with the crown ether at the head group and a pyrene fluorescent tag on the hydrophobic tail was synthesized and incorporated into bilayers of distearylphosphatidylcholine. The functionalized bilayer exhibited selective affinity for lead ions in aqueous buffered solution (pH 7.4) and a fluorescence response that was linear over the concentration range 10−7 to 10−4 M metal ions. Recognition and binding of lead ions at the membrane surface resulted in a rapid and prominent reorganization of the receptor-lipids in the membrane that was measurable at both the macro- and nanoscales. Removal of the lead ions, through the addition of EDTA, resulted in recovery of the original fluorescence and the reaggregation of structures in the membrane. Darcy, Ravoo, and co-workers synthesized amphiphilic cyclodextrins through 6-S-alkylation of the primary side and introduction of a poly(ethylene glycol) chain to the secondary side of α-, β-, and γ-cyclodextrins, which formed nonionic bilayer vesicles in aqueous solution []. Molecular recognition of a hydrophobic anion (adamantane carboxylate) by the formed cyclodextrin vesicles was investigated by using capillary electrophoresis. The increase in electrophoretic mobility occurred when the hydrophobic anions bind to the nonionic cyclodextrin vesicles. Jelinek and co-workers proposed a molecular system in which interactions between antibodies and peptide epitopes displayed at a biomimetic membrane interface can be detected through induction of visible, rapid color transitions []. The colorimetric assembly consists of a phospholipid/polydiacetylene matrix anchoring a hydrophobic peptide displaying the epitope at its N-terminus. The colorimetric transitions observed in the assembly, corresponding to perturbation of the polydiacetylene framework, are induced only upon recognition of the displayed epitope by its specific antibody present in the aqueous solution. This system could be utilized for studying antigen-antibody interactions and peptide-protein recognition, epitope mapping, and rapid screening of biological and chemical libraries.
Examples at other interfaces with and without matrices are briefly summarized below. Bohrer et al. fabricated chemiresistive gas sensors by deposition of 50 nm thick films of cobalt phthalocyanine and metal-free phthalocyanine on interdigitated gold electrodes via organic molecular beam epitaxy []. Belfort and co-workers prepared two-dimensional surface molecular imprinting method using water-in-oil emulsion photo-polymerization on a microporous polypropylene substrate that was used to separate the bronchodilator, theophylline, from the mild stimulant, caffeine, both of similar chemical structure []. Kim et al. proposed a method for fabrication of patterned hydrogel microwells functionalized at their bases with antibodies to promote specific immobilization of lymphocytes []. Ma and co-workers reported an efficient silica coating process to prepare silica-coated gold nanorods []. The subsequent covalent bioconjugation of amino-functionalized gold nanorod films with goat anti-human-immunoglobulin G (anti-h-IgG) was successfully employed for the colorimetric detection of h-IgG in a model reaction based on the specific binding affinity between the proteins. Govorov, Kotov, and co-workers prepared molecular spring assemblies of CdTe nanowires and Au nanoparticles [], where the distance between the exciton and the plasmon can be reversibly varied. These systems were made protein-sensitive by incorporating antibodies in the molecular springs. Modulation of exciton–plasmon interactions could serve as a wavelength-based biodetection tool.

4. Future Perspectives

Interfacial media provide a variety of possibilities for molecular recognition. At the air-water interface complicated binding sites can be constructed through self-assembly of rather simple molecular modules, where it is possible to generate well-defined recognition sites such as biomolecular receptors. Recently, Ariga et al. reported unusual shifts in dissociation constants of amino acid residues at the air-water interface that were accompanied by enzyme-like catalytic activities []. Thus, the air-water interface will be more important for developments in biomimetic chemistry in the future. On the other hand, solid surfaces should be useful for molecular sensor device preparation, for instance, in the preparation of sensing-site arrays which will be important for highly integrated molecular devices. Recent developments in control of molecular arrangements on two-dimensional solid surfaces [–] should result in sensor arrays with ultrahigh spatial resolution. In addition, high-surface materials currently under development, such as mesoporous materials [,], should provide supports useful for efficient molecular recognition. A combination of advanced surface technologies and material chemistry with well-established molecular recognition sciences is crucial to the future development of this field.

Acknowledgements

The research described in this review was partially supported by Grant-in-Aid for Scientific Research on Priority Areas “Chemistry of Coordination Space” and a Grant-in-Aid for Science Research in a Priority Area “Super-Hierarchical Structures” from Ministry of Education, Science, Sports, and Culture, Japan, and Grants-in-Aid for Scientific Research (B) from Japan Society for the Promotion of Science.

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