Molecular Imprinting PDF
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325 Topics in Current Chemistry Editorial Board: K.N. Houk C.A. Hunter M.J. Krische J.-M. Lehn l l l S.V. Ley M. Olivucci J. Thiem M. Venturi P. Vogel l l l l C.-H. Wong H. Wong H. Yamamoto l l Topics in Current Chemistry Recently Published and Forthcoming Volumes MolecularImprinting NovelSamplingApproachesinHigher VolumeEditor:KarstenHaupt DimensionalNMR Vol.325,2012 VolumeEditors:MartinBilleter, VladislavOrekhov Activity-BasedProteinProfiling Vol.316,2012 VolumeEditor:StephanA.Sieber Vol.324,2012 AdvancedX-RayCrystallography VolumeEditor:KariRissanen Vol.315,2012 BeautyinChemistry VolumeEditor:LuigiFabbrizzi Pyrethroids:FromChrysanthemumtoModern Vol.323,2012 IndustrialInsecticide VolumeEditors:NoritadaMatsuo,TatsuyaMori ConstitutionalDynamicChemistry Vol.314,2012 VolumeEditor:MihailBarboiu UnimolecularandSupramolecular Vol.322,2012 ElectronicsII VolumeEditor:RobertM.Metzger EPRSpectroscopy Vol.313,2012 VolumeEditors:MalteDrescher, GunnarJeschke UnimolecularandSupramolecular Vol.321,2012 ElectronicsI VolumeEditor:RobertM.Metzger RadicalsinSynthesisIII Vol.312,2012 VolumeEditors:MarkusR.Heinrich, Bismuth-MediatedOrganicReactions AndreasGansa¨uer VolumeEditor:ThierryOllevier Vol.320,2012 Vol.311,2012 ChemistryofNanocontainers Peptide-BasedMaterials VolumeEditor:TimothyDeming VolumeEditors:MarkusAlbrecht, Vol.310,2012 F.EkkehardtHahn Vol.319,2012 AlkaloidSynthesis VolumeEditor:Hans-JoachimKno¨lker LiquidCrystals:MaterialsDesignand Vol.309,2012 Self-Assembly VolumeEditor:CarstenTschierske FluorousChemistry Vol.318,2012 VolumeEditor:Istva´nT.Horva´th Vol.308,2012 Fragment-BasedDrugDiscoveryandX-Ray Crystallography MultiscaleMolecularMethodsinApplied VolumeEditors:ThomasG.Davies, Chemistry MarkoHyvo¨nen VolumeEditors:BarbaraKirchner, Vol.317,2012 JadranVrabec Vol.307,2012 Molecular Imprinting Volume Editor: Karsten Haupt With Contributions by C. Ayela (cid:1) M.E. Benito-Pen˜a (cid:1) A. Biffis (cid:1) M. Bompart (cid:1) D. Carboni (cid:1) P.J. Cywinski (cid:1) G. Dvorakova (cid:1) A. Falcimaigne-Cordin (cid:1) K. Flavin (cid:1) K. Haupt (cid:1) G. Horvai (cid:1) W. Kutner (cid:1) A.V. Linares (cid:1) G.J. Mohr (cid:1) M.C. Moreno-Bondi (cid:1) A.J. Moro (cid:1) G. Orellana (cid:1) M. Resmini (cid:1) S. Suriyanarayanan (cid:1) B. Tse Sum Bui (cid:1) B. To´th (cid:1) J.L. Urraca Editor Prof.KarstenHaupt Compie`gneUniversityofTechnology UMRCNRS6022 Compie`gne France ISSN0340-1022 e-ISSN1436-5049 ISBN978-3-642-28420-5 e-ISBN978-3-642-28421-2 DOI10.1007/978-3-642-28421-2 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2012932901 #Springer-VerlagBerlinHeidelberg2012 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. 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Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editor Prof.KarstenHaupt Compie`gneUniversityofTechnology UMRCNRS6022 Compie`gne France Editorial Board Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley UniversityofCalifornia UniversityChemicalLaboratory DepartmentofChemistryandBiochemistry LensfieldRoad 405HilgardAvenue CambridgeCB21EW LosAngeles,CA90024-1589,USA GreatBritain [email protected] [email protected] Prof.Dr.ChristopherA.Hunter Prof.Dr.MassimoOlivucci DepartmentofChemistry Universita`diSiena UniversityofSheffield DipartimentodiChimica SheffieldS37HF,UnitedKingdom ViaADeGasperi2 c.hunter@sheffield.ac.uk 53100Siena,Italy [email protected] Prof.MichaelJ.Krische Prof.Dr.JoachimThiem UniversityofTexasatAustin Institutfu¨rOrganischeChemie Chemistry&Biochemistry Department Universita¨tHamburg 1UniversityStationA5300 Martin-Luther-King-Platz6 AustinTX,78712-0165,USA 20146Hamburg,Germany [email protected] [email protected] Prof.Dr.Jean-MarieLehn Prof.Dr.MargheritaVenturi ISIS DipartimentodiChimica 8,alle´eGaspardMonge Universita`diBologna BP70028 viaSelmi2 67083StrasbourgCedex,France 40126Bologna,Italy [email protected] [email protected] vi EditorialBoard Prof.Dr.PierreVogel Prof.Dr.HenryWong LaboratoryofGlycochemistry TheChineseUniversityofHongKong andAsymmetricSynthesis UniversityScienceCentre EPFL–Ecolepolytechniquefe´derale DepartmentofChemistry deLausanne Shatin,NewTerritories EPFLSBISICLGSA [email protected] BCH5307(Bat.BCH) 1015Lausanne,Switzerland Prof.Dr.HisashiYamamoto pierre.vogel@epfl.ch ArthurHollyComptonDistinguished Prof.Dr.Chi-HueyWong Professor DepartmentofChemistry Professor of Chemistry, Scripps Research TheUniversityofChicago Institute 5735SouthEllisAvenue PresidentofAcademiaSinica Chicago,IL60637 AcademiaSinica 773-702-5059 128AcademiaRoad USA Section2,Nankang [email protected] Taipei115 Taiwan [email protected] Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer’s eBook package Chemistry andMaterialsScience.Ifalibrarydoesnotoptforthewholepackagethebookseries may be bought on a subscription basis. 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InreferencesTopicsinCurrentChemistryisabbreviatedTop CurrChemandis citedasajournal. ImpactFactor2010:2.067;Section“Chemistry,Multidisciplinary”:Rank44of144 Preface Likeakeyinalock,antibodiesfitperfectlywiththeirtargetantigensandareableto recognise and bind them with high affinity and selectivity. They have, therefore, found numerousapplications inmedicine, bothfor diagnosticsandtreatment, and in biotechnology. For example, enzyme-linked immunosorbent assays are widely usedtodetectandquantifysmallandlargetargetsviaaspecificbiologicalrecog- nition mechanism. On the other hand, antibodies are also used to treat certain infections and other diseases, and have saved many lives. More recently, new cancer therapies have been developed based on antibodies. However, antibodies arenotalwaysperfectfortheseapplicationsbecausetheyareunstableoutoftheir native environment, may be degraded by proteases, and tend to be difficult to integrate into standard industrial fabrication processes. In addition, an antibody fortheparticulartargetofinterest,inparticularforsmallmolecules,cansometimes bedifficulttoobtain.Ithasthereforebeenalong-termdreamofresearcherstobe able to obtain such structures synthetically – creating tailor-made receptors for agivenmoleculartarget.Onesurprisinglysimplewayofachievingthisisthrough themolecularimprintingofsyntheticpolymers. Molecularimprintingisaprocesswhereinteractingandcross-linkingmonomers are arranged around a molecular template, followed by polymerisation to form a cast-likeshell.Thetemplateisusuallythetargetmoleculetoberecognisedbythe syntheticantibody,oraderivativethereof.Initially,themonomersformacomplex withthetemplatethroughcovalentornon-covalentinteractions.Afterpolymerisa- tionandremovalofthetemplate,bindingsitesareexposedthatarecomplementary tothe target molecule insize, shape, and position offunctional groups, which are heldinplacebythecross-linkedpolymermatrix.Inessence,amolecularmemoryis imprintedinthepolymer,whichisnowcapableofselectivelyrebindingthetarget. Thus, molecularly imprinted polymers (MIPs) possess two of the most important featuresofbiological antibodies –the abilitytorecogniseandbind specific target molecules. When these MIPs were first described in the 1970s and early 1980s by Wulff [1] and Mosbach [2], they were merely used as specific separation materials, for ix x Preface example,forthechromatographicseparationofenantiomers.Itwasnotuntil1993 and Mosbach’s seminal paper in Nature [3] that the great potential of MIPs as synthetic antibody mimics was recognised. This resulted in a nearly exponential increase in the number of publications in the area, with several hundreds per annum over the recent years. There are a number of potential application areas that have been identified for MIPs, all based on their capability to specifically recognise molecular targets: affinity separation, chemical sensors and assays, directed synthesis and enzyme-like catalysis, and biomedical applications like drugdelivery.Todate,themainapplicationareaisanalyticalchemistry,andduring the past decade, the only commercially available MIPs have been solid-phase extraction matrices for sample preparation and analyte pre-concentration, mainly for biomedical and food analyses. These are commercialised by the Swedish company Biotage and by the French PolyIntell. However, apart from separation, other promising commercial applications of MIPs are sensors and assay systems. Indeed,MIP-coatedwipesforthedetectionofexplosivesaremorerecentproducts commercialisedbytheUScompanyRaptor. AnexcitingrecenttrendgoestowardstheuseofMIPsformedicaltreatment,in particular for drug delivery. One example is the use of MIPs in contact lenses for drug delivery to the eye. In fact, there is a considerable need for more efficient delivery of ocular therapeutics. This can be achieved by using the molecular selectivity and affinity of an MIP to extend and control the residence time of drugs on the eye surface and thereby limiting drug loss by lacrimation, drainage, andnon-productiveabsorption[4].Ontheotherhand,itisalsoconceivabletouse MIPsfortheremovalofunwantedmoleculesfromourbody.Whiletherehavebeen no reports in the literature on real applications with living organisms, there are afewexamplesontheremovaloftoxicsubstances,forexamplebilirubinandmetal ions, from biological fluids using extracorporeal devices [5], and the Israeli–US company Semorex lists an MIP for phosphate removal from the gastrointestinal systemasoneoftheirproducts. In a similar direction, that is, using MIPs directly as drugs, goes the work by Cutivet et al. [6], who have developed water-compatible MIP microgels that strongly and selectively inhibit the protease trypsin, enzyme inhibitors being potential drug candidates. The inhibitory power of these MIPs was three orders ofmagnitudehigherthanthatofsmall-moleculeinhibitorslikebenzamidine.Very recently, Shea and colleagues [7] have made an exciting new contribution to the MIP field. They created molecular imprints for the cytotoxic peptide melittin, the main component of bee venom, in the surface of polymer nanoparticles, obtaining,asaresult,anartificialantibodythatcouldbeusedfortheinvivocapture and neutralisation of melittin in mice. The authors for the first time demonstrated the possibility of in vivo application of the imprinted nanoparticles in mice. Normally, when mice are injected into the blood stream with a certain dose of melittin, they die within less than an hour due to the cytolytic activity of this peptide. However, when the MIP nanoparticles were injected shortly after the peptide,thesurvivaltimeandrateofthemiceincreasedconsiderably.
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