Abstract
This chapter summarizes recent studies employing colorimetric vesicle-based systems for biomolecular sensing. Vesicular aggregates exhibit an important advantage as a biological sensing platform in that they mimic the cell membrane—the site of molecular docking, ligand–receptor binding, and other important processes that can be exploited as a means of signal generation. Particularly attractive for sensing applications is the use of colour changes visible to the naked eye or detected spectroscopically as the signal transduction mechanism.
Vesicle assemblies comprising polydiacetylene (PDA)—a chromatic polymer that undergoes blue–red transformations in response to varied biological analytes and processes—are the primary focus of this chapter. We discuss the features of PDA that make it a promising constituent in biosensing platforms, in particular its self-assembly properties, the rigid framework allowing incorporation of varied lipid constituents, and the chromatic transformations induced by reactions with biological analytes. Recent studies depicting distinct vesicle assemblies are summarized. Vesicles comprising chemically modified PDA, in which receptor units are attached to the polymer-surface head groups, have been employed for detection of chemical and biological toxins, viruses, and bacteria. Mixed vesicles in which lipid bilayer domains are incorporated within the PDA matrix have also been extensively used as colorimetric biomimetic membrane platforms for studying diverse membrane processes and cell-surface phenomena. The PDA-embedded lipid bilayers further facilitate anchoring of varied molecular markers and recognition modules.
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References
Linthicum DS, Patel J, Cairns N (2001) Antibody-based fluorescence polarization assay to screen combinatorial libraries for sweet taste compounds. Comb Chem High Throughput Screen 4:431–438
Ito Y et al. (2002) Escherichia coli and its application in a mediated amperometric glucose sensor. Biosens Bioelectron 17:993–998
Sargent A, Sadik OA (1999) Monitoring antibody–antigen reactions at conducting polymer-based immunosensors using impedance spectroscopy. Electrochim Acta 44:4667–4675
Eteshola E, Leckband D (2001) Development and characterization of an ELISA assay in PDMS microfluidic channels. Sens Actuators B Chem 72:129–133
Goddard NJ et al. (2002) Internally referenced resonant mirror devices for dispersion compensation in chemical sensing and biosensing applications. Sens Actuators A Phys 100:1–9
Ward CJ, Patel P, James T (2002) Molecular color sensors for monosaccharides. Org Lett 4:477–479
Poenar DP, Frencha PJ, Wolffenbuttela RF (1997) Colour sensors based on active interference filters using silicon-compatible materials. Sens Actuators A Phys 62:513–523
Bariain C et al. (2001) Behavioral experimental studies of a novel vapochromic material towards development of optical fiber organic compounds sensor. Sens Actuators B Chem 76:25–31
Kyunghoa K et al. (1997) Active optical thin-film waveguide sensor for ion sensing. Anal Chim Acta 343:199–208
Gambari R (2001) Biospecific interaction analysis: a tool for drug discovery and development. Am J Pharmacogenomics 1:119–135
Anglina R (1996) Colorimetric toxicity test. Biotechnol Adv 14:331
Poenar DP, Siu TM, Kiang TO (2002) Colour sensor for (bio)chemical/biological discrimination and detection. Mater Sci Semicond Process 5:17–22
Lenarczuk T, Glab S, Koncki R (2001) Application of Prussian blue-based optical sensor in pharmaceutical analysis. J Pharm Biomed Anal 26:163–169
Hisamoto H et al. (1998) Two-color fluorescent lithium ion sensor. Anal Chim Acta 373:271–289
Ignatov SG, Ferguson JA, Walt DR (2001) Highlight: recent trends in the application of evanescent wave biosensors. Biosens Bioelectron 16:109–113
Costa-Fernandez JM, Pereiro R, Sanz-Medel A (2006) The use of luminescent quantum dots for optical sensing. Trends Anal Chem 25(3):207–218
Sankaranarayanan S et al. (2000) The use of pHluorins for optical measurements of presynaptic activity. Biophys J 79:2199–2208
Olson KD, Deval P, Spudich JL (1992) Absorption and photochemistry of sensory rhodopsin. I: pH effects. Photochem Photobiol 56:1181–1187
Cheng Z, Aspinwall CA (2006) Nanometre-sized molecular oxygen sensors prepared from polymer-stabilized phospholipid vesicles. Analyst 131(2):236–243
Lee KS et al. (1999) Disposable liposome immunosensor for theophylline combining an immunochromatographic membrane and a thick-film electrode. Anal Chim Acta 380:17–26
Carbonell RG et al. (1997) Immunodiagnostic assay using liposomes carrying labels thereof on outer liposome surface. Biotechnol Adv 15:181
Hianik T et al. (1999) Immunosensors based on supported lipid membranes, protein films and liposomes modified by antibodies. Sens Actuators B Chem 57:201–212
Cooper MA et al. (2000) A vesicle capture sensor chip for kinetic analysis of interactions with membrane-bound receptors. Anal Biochem 277:196–205
Yang Y et al. (2000) A glucose sensor with improved haemocompatibilty. Biosens Bioelectron 15:221–227
Woodbury CPJ, Venton DL (1999) Methods of screening combinatorial libraries using immobilized or restrained receptors. J Chromatogr B Biomed Sci Appl 725:113–137
Toko K (2000) Taste sensor. Sens Actuators B Chem 64:205–215
Leatherbarrow RJ, Edwards PR (1999) Analysis of molecular recognition using optical biosensors. Curr Opin Chem Biol 3:544–547
Li SK, D'Emanuele A (2001) On-off transport through a thermoresponsive hydrogel composite membrane. J Control Release 75:55–67
Gonzalez-Manas JM, Kaschny P, Goni FM (1994) Use of merocyanine 540 as an optical probe in the study of membrane–surfactant interactions. J Phys Chem 98(41):10650–10654
Roberts MA, Durst RA (1995) Investigation of liposome-based immunomigration sensors for the detection of polychlorinated biphenyls. Anal Chem 67(3):482–491
Reeves SG, Durst RA (1995) Novel optical measurements approach for the quantitation of liposome immunomigration assays. Anal Lett 28(13):2347–2362
Okada S et al. (1998) Color and chromism of polydiacetylene vesicles. Acc Chem Res 31:229–239
Tanaka H et al. (1989) Thermochromic phase transitions of a polydiacetylene, poly(ETCD), studied by high-resolution solid-state C13 NMR. Macromolecules 22:1208–1215
Okada S, Charych DH (1997) Thermochromic transitions of synthetic lipid–polymer membranes. Berkeley Sci J 1:48–50
Lio A et al. (1997) Molecular imaging of thermochromic carbohydrate-modified polydiacetylene thin films. Langmuir 13:6524–6532
Lio A et al. (1996) Atomic force microscope study of chromatic transitions in polydiacetylene films. J Vac Sci Technol 14:1481–1484
Wenzel M, Atkinson GH (1989) Chromatic properties of polydiacetylene films. J Am Chem Soc 111:4123–4127
Berman A, Charych DH (1999) Oriented nucleation of inorganic salts on polymeric long chain acid monolayers. J Cryst Growth 198/199:796–801
Ringsdorf H, Schlarb B, Venzmer J (1988) Molecular architecture and function of polymeric oriented systems: models for the study of organization, surface recognition, and dynamics of biomembranes. Angew Chem Int Ed Engl 27:113–158
Jonas U et al. (1999) Reversible color switching and unusual solution polymerization of hydrazide-modified diacetylene lipids. J Am Chem Soc 121:4580–4588
Ahn DJ et al. (2003) Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli. J Am Chem Soc 125(30):8976–8977
Kolusheva S, Shahal T, Jelinek R (2000) Peptide–membrane interactions studied by a new phospholipid/polydiacetylene colorimetric vesicle assay. Biochemistry 39:15851–15859
Jelinek R, Kolusheva S (2001) Polymerized lipid vesicles as colorimetric biosensors for biotechnological applications. Biotechnol Adv 19:109–118
Jelinek R et al. (1998) Interfacial catalysis by phospholipases at conjugated lipid vesicles: colorimetric detection and NMR spectroscopy. Chem Biol 5:619–629
Okada SY, Jelinek R, Charych DH (1999) Induced color change of conjugated polymeric vesicles by interfacial catalysis of phospholipase A2. Angew Chem Int Ed 38:655–659
Wilson TE et al. (1994) Enzymic modification and X-ray photoelectron spectroscopy analysis of a functionalized polydiacetylene thin film. Langmuir 10:1512–1516
Charych D, Nagy JO (1996) Artificial cell membranes for diagnostics and therapeutics. Chemtech 26:24–28
Kolusheva S, Wachtel E, Jelinek R (2003) Biomimetic lipid/polymer colorimetric membranes: molecular and cooperative properties. J Lipid Res 44:65–71
Song J, Cisar JS, Bertozzi CR (2004) Functional self-assembling bolaamphiphilic polydiacetylenes as colorimetric sensor scaffolds. J Am Chem Soc 126(27):8459–8465
Sarkar A et al. (2005) Colorimetric biosensors based on polydiacetylene (PDA) and polyamidoamine (PAMAM) dendrimers. Polymer News 30(12):370–377
Peng H et al. (2005) Polydiacetylene/silica nanocomposites with tunable mesostructure and thermochromatism from diacetylenic assembling molecules. J Am Chem Soc 127(37):12782–12783
Charych DH et al. (1993) Specific interactions of influenza virus with organized assemblies of polydiacetylenes. Biomol Mater 292:153–161
Spevak W, Nagy JO, Charych D (1995) Molecular assemblies of functionalized polydiaceylenes. Adv Mater 7(1):85–89
Reichert A et al. (1995) Polydiacetylene liposomes functionalized with sialic acid bind and colorimetrically detect influenza virus. J Am Chem Soc 117:829–830
Pan JJ, Charych DH (1997) Molecular recognition and colorimetric detection of cholera toxin by polymerized liposomes. Langmuir 13:1365–1367
Litvin AL et al. (1995) Langmuir films of amino acid-modified diacetylenes as organic templates for biomimetic mineralization. Proc Soc Photo Opt Instrum Eng 2441:54–60
Litvin AL et al. (1995) Liquid crystalline texture in glycine-modified diacetylene Langmuir monolayers at room temperature. J Phys Chem 99:492–495
Jung YK, Park HG, Kim JM (2006) Polydiacetylene (PDA)-based colorimetric detection of biotin–streptavidin interactions. Biosens Bioelectron 21(8):1536–1544
Cheng Q, Stevens RC (1997) Coupling of an induced fit enzyme to polydiacetylene thin films: colorimetric detection of glucose. Adv Mater 9:481
Yamanaka SA et al. (1997) Solid-phase immobilization of optically responsive liposomes in sol–gel materials for chemical and biological sensing. Langmuir 13:5049–5053
Charych DH et al. (1994) Direct colorimetric detection of virus by a polymerized bilayer assembly. Biomol Mater Design 330:295–308
Wang C, Ma Z (2005) Colorimetric detection of oligonucleotides using a polydiacetylene vesicle sensor. Anal Bioanal Chem 382(7):1708–1710
Wang C, Ma Z, Su Z (2006) Facile method to detect oligonucleotides with functionalized polydiacetylene vesicles. Sens Actuators B Chem B113(1):510–515
Rangin M, Basu A (2004) Lipopolysaccharide identification with functionalized polydiacetylene liposome sensors. J Am Chem Soc 126(16):5038–5039
Kim JM et al. (2003) Immobilized polydiacetylene vesicles on solid substrates for use as chemosensors. Adv Mater 15(13):1118–1121
Su YI (2005) Assembly of polydiacetylene vesicles on solid substrates. J Colloid Interface Sci 292(1):271–276
Baek M-G, Stevens RC, Charych DH (2000) Design and synthesis of novel glycopolythiophene assemblies for colorimetric detection of influenza virus and E. coli. Bioconjug Chem 11:777–788
Spevak W et al. (1993) Polymerized liposomes containing C-glycosides of sialic acid: potent inhibitors of influenza virus in vitro infectivity. J Am Chem Soc 115:1146–1147
Pan JJ, Charych DH (1997) Molecular recognition and optical detection of biological pathogens at biomimetic membrane interfaces. Proc Soc Photo Opt Instrum Eng 3040:211–217
Song J et al. (2002) Smart materials for biosensing devices: cell-mimicking supramolecular assemblies and colorimetric detection of pathogenic agents. Biomed Microdevices 4(3):213–221
Ma G, Cheng Q (2005) Vesicular polydiacetylene sensor for colorimetric signaling of bacterial pore-forming toxin. Langmuir 21(14):6123–6126
Ma G, Cheng Q (2006) Manipulating FRET with polymeric vesicles: development of a mix-and-detect type fluorescence sensor for bacterial toxin. Langmuir 22(16):6743–6745
Kolusheva S, Boyer L, Jelinek R (2000) A colorimetric assay for rapid screening of antimicrobial peptides. Nat Biotechnol 18:225–227
Shai Y (1999) Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by α-helical antimicrobial and cell non-selective membrane-lytic peptides. Biochim Biophys Acta 1462:55–70
Charych DH, Spevak W, Nagy JO, Bednarski MD (1993) Mater Res Soc Symp Proc 292:153–161
Rozner S, Kolusheva S, Cohen Z, Dowhan W, Eichler J, Jelinek R (2003) Detection and analysis of membrane interactions by a biomimetic colorimetric lipid/polydiacetylene assay. Anal Biochem 319(1):96–104
Katz M, Tsubery H, Kolusheva S, Shames A, Fridkin M, Jelinek R (2003) Lipid binding and membrane penetration of polymyxin B derivatives studied in a biomimetic vesicle system. Biochem J 375(2):405–413
Halevy R et al. (2003) Membrane binding and permeation by indolicidin analogs studied by a biomimetic lipid/polydiacetylene vesicle assay. Peptides 24:1753–1761
Satchell DP et al. (2003) Quantitative interactions between cryptdin-4 amino terminal variants and membranes. Peptides 24:1795–1805
Tanabe H et al. (2004) Structure-activity determinants in paneth cell ±-defensins: loss-of-function in mouse cryptdin-4 by charge-reversal at arginine residue positions. J Biol Chem 279:11976–11983
Sheynis T et al. (2003) Bilayer localization of membrane-active peptides studied in bio-mimetic vesicles by visible and fluorescence spectroscopies. Eur J Biochem 270:4478–4487
Porat Y et al. (2003) The human islet amyloid polypeptide forms transient membrane-active protofilaments. Biochemistry 42:10971–10977
Su Y, Sinko PJ (2006) Drug delivery across the blood–brain barrier: why is it difficult? How to measure and improve it? Expert Opin Drug Deliv 3(3):419–435
Liu X, C Chen (2005) Strategies to optimize brain penetration in drug discovery. Curr Opin Drug Discov Devel 8(4):505–512
Cucullo L et al. (2005) Drug delivery and in vitro models of the blood–brain barrier. Curr Opin Drug Discov Devel 8(1):89–99
Katz M et al. (2006) Rapid colorimetric screening of drug interaction and penetration through lipid barriers. Pharm Res 23(3):580–587
Silbert L et al. (2006) Rapid chromatic detection of bacteria using a new biomimetic polymer sensor. Appl Environ Microbiol 72(11):7339–7344
Rangin M, Basu A (2004) Lipopolysaccharide Identification with functionalized polydiacetylene liposome sensors. J Am Chem Soc 126:5038–5039
Ma Z, Li J, Jiang L (2000) Influence of the spacer length of glycolipid receptors in polydiacetylene vesicles on the colorimetric detection of Escherichia coli. Langmuir 16:7801–7804
Ma Z et al. (1998) Colorimetric detection of Escherichia coli by polydiacetylene vesicles functionalized with glycolipid. J Am Chem Soc 120:12678–12679
Gophna U et al. (2002) Role of fibronectin in curli-mediated internalization. FEMS Microbiol Lett 212:55–58
Gophna UB et al. (2001) Curli fibers mediate internalization of Escherichia coli by eukaryotic cells. Infect Immun 69:2659–2665
Gill I, Ballesteros A (2003) Immunoglobulin–polydiacetylene sol–gel nanocomposites as solid-state chromatic biosensors. Angew Chem Int Ed 42(28):3264–3267
Kolusheva S, Shahal T, Jelinek R (2000) Cation-selective color sensors composed of ionophore-phospholipid-polydiacetylene mixed vesicles. J Am Chem Soc 122(5):776–780
Pressman BC (1976) Annu Rev Biochem 45:501
Reed PW (1979) Methods Enzymol 55:435
Kolusheva S et al. (2001) Rapid colorimetric detection of antibody-epitope recognition at a bio-mimetic membrane interface. J Am Chem Soc 123:417–422
Killian JA et al. (1996) Biochemistry 35:1037–1045
Zhang YP et al. (1995) Biochemistry 34:2362–2371
Gerondakis S, Bishop JM (1986) Mol Cell Biol 6:3677–3684
Chiang CM, Roeder RG (1993) Pept Res 6:62–64
Wilson IA et al. (1984) Cell 37:767–778
Kolusheva S et al. (2005) Selective detection of catecholamines by synthetic receptors embedded in chromatic polydiacetylene vesicles. J Am Chem Soc 127:10000–10001
Molt O, Rübeling D, Schrader T (2003) J Am Chem Soc 15:12086–12087
Schrader T, Zadmard R (2004) J Am Chem Soc 126:7752–7753
Kolusheva S et al. (2006) Color fingerprinting of proteins by calixarenes embedded in lipid/polydiacetylene vesicles. J Am Chem Soc 128(41):13592–13598
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Jelinek, R., Kolusheva, S. (2007). Biomolecular Sensing with Colorimetric Vesicles. In: Schrader, T. (eds) Creative Chemical Sensor Systems. Topics in Current Chemistry, vol 277. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_112
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DOI: https://doi.org/10.1007/128_2007_112
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