Fluorescent monomers: "bricks" that make a molecularly imprinted polymer "bright"

详细信息    查看全文

• 作者：Wei Wan ; Sabine Wagner ; Knut Rurack
• 关键词：Chemical sensors ; Fluorescence ; Molecularly imprinted polymers ; Dyes ; Sol–gel
• 刊名：Analytical and Bioanalytical Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：408
• 期：7
• 页码：1753-1771
• 全文大小：5,025 KB
• 参考文献：1.Kaplan RM, Stone AA (2013) Bringing the laboratory and clinic to the community: mobile technologies for health promotion and disease prevention. Annu Rev Psychol 64:471–498CrossRef
  2.Chan M, Estève D, Escriba C, Campo E (2008) A review of smart homes—present state and future challenges. Comput Methods Prog Biomed 91:55–81CrossRef
  3.Whitmore A, Agarwal A, Xu LD (2015) The Internet of things—a survey of topics and trends. Inf Syst Front 17:261–272CrossRef
  4.Zerger A, Rossel RAV, Swain DL, Wark T, Handcock RN, Doerr VAJ, Bishop-Hurley GJ, Doerr ED, Gibbons PG, Lobsey C (2010) Environmental sensor networks for vegetation, animal and soil sciences. Int J Appl Earth Obs Geoinf 12:303–316CrossRef
  5.Bǎnicǎ FG (2012) Chemical sensors and biosensors: fundamentals and applications. Wiley, Chichester
  6.Sellergren B (ed) (2000) Molecularly imprinted polymers: man-made mimics of antibodies and their application in analytical chemistry. Elsevier, Oxford
  7.Henry OYF, Cullen DC, Piletsky SA (2005) Optical interrogation of molecularly imprinted polymers and development of MIP sensors: a review. Anal Bioanal Chem 382:947–956CrossRef
  8.Moreno-Bondi MC, Navarro-Villoslada F, Benito-Peña E, Urraca JL (2008) Molecularly imprinted polymers as selective recognition elements in optical sensing. Curr Anal Chem 4:316–340CrossRef
  9.Suryanarayanan V, Wu CT, Ho KC (2010) Molecularly imprinted electrochemical sensors. Electroanalysis 22:1795–1811CrossRef
  10.Wackerlig J, Lieberzeit PA (2015) Molecularly imprinted polymer nanoparticles in chemical sensing - synthesis, characterisation and application. Sensors Actuators B 207:144–157CrossRef
  11.Uludǎg Y, Piletsky SA, Turner AFP, Cooper MA (2007) Piezoelectric sensors based on molecular imprinted polymers for detection of low molecular mass analytes. FEBS J 274:5471–5480CrossRef
  12.Batra D, Shea KJ (2003) Novel trifunctional building blocks for fluorescent polymers. Org Lett 5:3895–3898CrossRef
  13.Wu Y, Liu Y, Gao X, Gao K, Xia H, Luo M, Wang X, Ye L, Shi Y, Lu B (2015) Monitoring bisphenol A and its biodegradation in water using a fluorescent molecularly imprinted chemosensor. Chemosphere 119:515–523CrossRef
  14.Marsh D (2009) Reaction fields in the environment of fluorescent probes: polarity profiles in membranes. Biophys J 96:2549–2558CrossRef
  15.Rykowska I, Wasiak W (2006) Properties, threats, and methods of analysis of bisphenol A and its derivatives. Acta Chromatogr 16:7–27
  16.Koike T, Watanabe T, Aoki S, Kimura E, Shiro M (1996) A novel biomimetic zinc(ii)−fluorophore, dansylamidoethyl−pendant macrocyclic tetraamine 1,4,7,10-tetraazacyclododecane (cyclen). J Am Chem Soc 118:12696–12703CrossRef
  17.Huang W (2005) Voltammetric determination of bisphenol a using a carbon paste electrode based on the enhancement effect of cetyltrimethylammonium bromide (CTAB). Bull Kor Chem Soc 26:1560–1564CrossRef
  18.Fontanesi C, Borsari M, Andreoli R, Benedetti L, Grandi G, Battistuzzi Gavioli G (1989) Electrochemical behaviour of N-tosylglycine and N-dansylglycine in several solvents. The role of the RSO2̶ groups on the physicochemical properties of glycine. Electrochim Acta 34:759–765CrossRef
  19.Liao Y, Wang W, Wang B (1999) Building fluorescent sensors by template polymerization: the preparation of a fluorescent sensor for l -tryptophan. Bioorg Chem 27:463–476CrossRef
  20.Gomez-Mendoza M, Marin ML, Miranda MA (2014) Two-channel dansyl/tryptophan emitters with a cholic acid bridge as reporters for local hydrophobicity within supramolecular systems based on bile salts. Org Biomol Chem 12:8499–8504CrossRef
  21.Sjöback R, Nygren J, Kubista M (1995) Absorption and fluorescence properties of fluorescein. Spectrochim Acta A 51:L7–L21CrossRef
  22.Nguyen TH, HardwickSA TS, Grattan KTV (2012) Intrinsic fluorescence-based optical fiber sensor for cocaine using a molecularly imprinted polymer as the recognition element. IEEE Sensors J 12:255–260CrossRef
  23.Gao L, Li X, Zhang Q, Dai J, Wei X, Song Z, Yan Y, Li C (2014) Molecularly imprinted polymer microspheres for optical measurement of ultra trace nonfluorescent cyhalothrin in honey. Food Chem 156:1–6CrossRef
  24.Guan X, Lai S, Su Z (2010) Facile preparation and potential application of water-soluble polymeric temperature/pH probes bearing fluorescein. J Appl Polym Sci 122:1968–1975CrossRef
  25.Lavignac N, Allender CJ, Brain KR (2004) 4-(3-Aminopropylene)-7-nitrobenzofurazan: a new polymerisable monomer for use in homogeneous molecularly imprinted sorbent fluoroassays. Tetrahedron Lett 45:3625–3627CrossRef
  26.Nguyen TH, Ansell RJ (2009) Fluorescent imprinted polymer sensors for chiral amines. Org Biomol Chem 7:1211–1220CrossRef
  27.Kubo H, Yoshioka N, Takeuchi T (2005) Fluorescent imprinted polymers prepared with 2-acrylamidoquinoline as a signaling monomer. Org Lett 7:359–362CrossRef
  28.Zhao J, Nie L, Zhang L, Jin Y, Peng Y, Du S, Jiang N (2013) Molecularly imprinted layer-coated silica nanoparticle sensors with guest-induced fluorescence enhancement: theoretical prediction and experimental observation. Anal Methods 5:3009–3015CrossRef
  29.Rathbone DL, Su D, Wang Y, Billington DC (2000) Molecular recognition by fluorescent imprinted polymers. Tetrahedron Lett 41:123–126CrossRef
  30.Rathbone DL, Bains A (2005) Tools for fluorescent molecularly imprinted polymers. Biosens Bioelectron 20:1438–1442CrossRef
  31.Zhou Y, Xu W, Tong A, Tong C (2006) Synthesis and spectral characterization of a novel fluorescent functional monomer 2,4-dimethyl-7-acrylamine-1,8-naphthyridine. Spectrosc Spectr Anal 26:496–498
  32.Turkewitsch P, Wandelt B, Darling GD, Powell WS (1998) Fluorescent functional recognition sites through molecular imprinting. A polymer-based fluorescent chemosensor for aqueous cAMP. Anal Chem 70:2025–2030CrossRef
  33.Ephardt H, Fromherz P (1989) Fluorescence and photoisomerization of an amphiphilic aminostilbazolium dye as controlled by the sensitivity of radiationless deactivation to polarity and viscosity. J Phys Chem 93:7717–7725CrossRef
  34.Wandelt B, Turkewitsch P, Wysocki S, Darling GD (2002) Fluorescent molecularly imprinted polymer studied by time-resolved fluorescence spectroscopy. Polymer 43:2777–2785CrossRef
  35.Wandelt B, Mielniczak A, Turkewitsch P, Wysocki S (2003) Steady-state and time-resolved fluorescence studies of fluorescent imprinted polymers. J Lumin 102–103:774–781CrossRef
  36.Wandelt B, Mielniczak A, Cywinski P (2004) Monitoring of cAMP-imprinted polymer by fluorescence spectroscopy. Biosens Bioelectron 20:1031–1039CrossRef
  37.Chen Z, Álvarez-Pérez M, Navarro-Villoslada F, Moreno-Bondi MC, Orellana G (2014) Fluorescent sensing of “quat” herbicides with a multifunctional pyrene-labeled monomer and molecular imprinting. Sensors Actuators B 191:137–142CrossRef
  38.Zhang H, Verboom W, Reinhoudt DN (2001) 9-(Guanidinomethyl)-10-vinylanthracene: a suitable fluorescent monomer for MIPs. Tetrahedron Lett 42:4413–4416CrossRef
  39.Güney O, Cebeci FÇ (2010) Molecularly imprinted fluorescent polymers as chemosensors for the detection of mercury ions in aqueous media. J Appl Polym Sci 117:2373–2379CrossRef
  40.Güney O, Yilmaz Y, Pekcan Ö (2002) Metal ion templated chemosensor for metal ions based on fluorescence quenching. Sensors Actuators B 85:86–89CrossRef
  41.Lopes Pinheiro SC, Descalzo AB, Raimundo IM Jr, Orellana G, Moreno-Bondi MC (2012) Fluorescent ion-imprinted polymers for selective Cu(II) optosensing. Anal Bioanal Chem 402:3253–3260CrossRef
  42.Manju S, Hari PR, Sreenivasan K (2010) Fluorescent molecularly imprinted polymer film binds glucose with a concomitant changes in fluorescence. Biosens Bioelectron 26:894–897CrossRef
  43.Lakowicz JR (ed) (1994) Probe design and chemical sensing, vol 4. Kluwer, New York
  44.Inoue Y, Kuwahara A, Ohmori K, Sunayama H, Ooya T, Takeuchi T (2013) Fluorescent molecularly imprinted polymer thin films for specific protein detection prepared with dansyl ethylenediamine-conjugated O-acryloyl l-hydroxyproline. Biosens Bioelectron 48:113–119CrossRef
  45.Wagner R, Wan W, Biyikal M, Benito-Peña E, Moreno-Bondi MC, Lazraq I, Rurack K, Sellergren B (2013) Synthesis, spectroscopic, and analyte-responsive behavior of a polymerizable naphthalimide-based carboxylate probe and molecularly imprinted polymers prepared thereof. J Org Chem 78:1377–1389CrossRef
  46.Wan W, Biyikal M, Wagner R, Sellergren B, Rurack K (2013) Fluorescent sensory microparticles that “light-up” consisting of a silica core and a molecularly imprinted polymer (MIP) shell. Angew Chem Int Ed 52:7023–7027CrossRef
  47.Piletska EV, Guerreiro AR, Romero-Guerra M, Chianella I, Turner APF, Piletsky SA (2008) Design of molecular imprinted polymers compatible with aqueous environment. Anal Chim Acta 607:54–60CrossRef
  48.Polyakov M (1931) Adsorption properties and structure of silica gel. Zh Fiz Khim 2:799–805
  49.Dickey F (1945) The preparation of specific adsorbents. Proc Natl Acad Sci U S A 35:227–229CrossRef
  50.Feng H, Wang N, Tran TT, Yuan L, Li J, Cai Q (2014) Surface molecular imprinting on dye–(NH2)–SiO2NPs for specific recognition and direct fluorescent quantification of perfluorooctanesulfonate. Sensors Actuators B 195:266–273CrossRef
  51.Leung MKP, Chow CF, Lam MHW (2001) A sol-gel derived molecular imprinted luminescent PET sensing material for 2,4-dichlorophenoxyacetic acid. J Mater Chem 11:2985–2991CrossRef
  52.Bissell RA, de Silva AP, Gunaratne HQN, Lynch PLM, Maguire GEM, McCoy CP, Sandanayake KRAS (1993) Fluorescent PET (photoinduced electron transfer) sensors. Top Curr Chem 168:223–264CrossRef
  53.Tan J, Wang HF, Yan XP (2009) A fluorescent sensor array based on ion imprinted mesoporous silica. Biosens Bioelectron 24:3316–3321CrossRef
  54.Deng Q, Wu J, Zhai X, Fang G, Wang S (2013) Highly selective fluorescent sensing of proteins based on a fluorescent molecularly imprinted nanosensor. Sensors 13:12994–13004CrossRef
  55.Suga Y, Sunayama H, Ooya T, Takeuchi T (2013) Molecularly imprinted polymers prepared using protein-conjugated cleavable monomers followed by site-specific post-imprinting introduction of fluorescent reporter molecules. Chem Commun 49:8450–8452CrossRef
  56.Sunayama H, Ooya T, Takeuchi T (2010) Fluorescent protein recognition polymer thin films capable of selective signal transduction of target binding events prepared by molecular imprinting with a post-imprinting treatment. Biosens Bioelectron 26:458–462CrossRef
  57.Sunayama H, Ooya T, Takeuchi T (2014) Fluorescent protein-imprinted polymers capable of signal transduction of specific binding events prepared by a site-directed two-step post-imprinting modification. Chem Commun 50:1347–1349CrossRef
  58.Carlson CA, Lloyd JA, Dean SL, Walker NR, Edmiston PL (2006) Sensor for fluorene based on the incorporation of an environmentally sensitive fluorophore proximal to a molecularly imprinted binding site. Anal Chem 78:3537–3542CrossRef
  59.Swager TM (1998) The molecular wire approach to sensory signal amplification. Acc Chem Res 31:201–207CrossRef
  60.McQuade DT, Pullen AE, Swager TM (2000) Conjugated polymer-based chemical sensors. Chem Rev 100:2537–2574CrossRef
  61.Li J, Kendig CE, Nesterov EE (2007) Chemosensory performance of molecularly imprinted fluorescent conjugated polymer materials. J Am Chem Soc 129:15911–15918CrossRef
  62.Yang JS, Swager TM (1998) Porous shape persistent fluorescent polymer films: an approach to TNT sensory materials. J Am Chem Soc 120:5321–5322CrossRef
  63.Awino JK, Zhao Y (2014) Molecularly imprinted nanoparticles as tailor-made sensors for small fluorescent molecules. Chem Commun 50:5752–5755CrossRef
  64.Poma A, Turner APF, Piletsky SA (2010) Advances in the manufacture of MIP nanoparticles. Trends Biotechnol 28:629–637CrossRef
  65.Gao D, Zhang Z, Wu M, Xie C, Guan G, Wang D (2007) A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles. J Am Chem Soc 129:7859–7866CrossRef
  66.Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRef
  67.Cywinski P, Sadowska M, Danel A, Buma WJ, Brouwer AM, Wandelt B (2007) Fluorescent, molecularly imprinted thin-layer films based on a common polymer. J Appl Polym Sci 105:229–235CrossRef
  68.Ton XA, Acha V, Bonomi P, Tse Sum Bui B, Haupt K (2015) A disposable evanescent wave fiber optic sensor coated with a molecularly imprinted polymer as a selective fluorescence probe. Biosens Bioelectron 64:359–366CrossRef
  69.Zhu S, Fischer T, Wan W, Descalzo AB, Rurack K (2011) Luminescence amplification strategies integrated with microparticle and nanoparticle platforms. Top Curr Chem 300:51–91CrossRef
  
• 作者单位：Wei Wan (1)
  Sabine Wagner (1)
  Knut Rurack (1)
  
  1. Chemical and Optical Sensing Division (1.9), BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489, Berlin, Germany
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Food Science
  Inorganic Chemistry
  Physical Chemistry
  Monitoring, Environmental Analysis and Environmental Ecotoxicology
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1618-2650

文摘

Molecularly imprinted polymers (MIPs) are potent and established recognition phases in separation and enrichment applications. Because of their robustness, versatility and format adaptability, they also constitute very promising sensing phases, especially when the active sensing element is directly integrated into the MIP. Fluorescent MIPs incorporating fluorescent monomers are perhaps the best developed and most successful approach here. This article reviews the state of the art in this field, discussing the pros and cons of the use of fluorescent dye and probe derivatives as such monomers, the different molecular interaction forces for template complexation, signalling modes and a variety of related approaches that have been realized over the years, including Förster resonance energy transfer processes, covalent imprinting, postmodification attachment of fluorescent units and conjugated polymers as MIPs; other measurement schemes and sensing chemistries that use MIPs and fluorescence interrogation to solve analytical problems (fluorescent competitive assays, fluorescent analytes, etc.) are not covered here. Throughout the article, photophysical processes are discussed to facilitate understanding of the effects that can occur when one is planning for a fluorescence response to happen in a constrained polymer matrix. The article concludes with a concise assessment of the suitability of the different formats for sensor realization.