Biomimetic synthetic receptors as molecular recognition elements

Recognition Receptors in Biosensors

Volumn , Issue , 2010, Pages 777-816

  Schneider, Hans Jörg ^a   Lim, Soojin ^b   Strongin, Robert M ^b  

^a SAARLAND UNIVERSITY   (Germany)

^b PORTLAND STATE UNIVERSITY   (United States)

Author keywords

Noncovalent interactions; Selectivity; Sensitivity; Sensors; Supramolecular complexes

Indexed keywords

EID: 84894435146     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4419-0919-0_20     Document Type: Chapter

References (200)

1. Abe H, Mawatari Y, Teraoka H, Fujimoto K, Inouye M (2004) Synthesis and molecular recognition of pyrenophanes with polycationic or amphiphilic functionalities: Artificial plate-shaped cavitand incorporating arenas and nucleotides in water. J Org Chem 69:495-504
2. Abraham MH, Enomoto K, Clarke ED, Sexton G (2002) Hydrogen bond basicity of the chlorogroup; hexachlorocyclohexanes as strong hydrogen bond bases. J Org Chem 67:4782-4786
3. Albrecht M (2007) Supramolecular chemistry-general principles and selected examples from anion recognition and metallosupramolecular chemistry. Naturwissenschaften 94:951-966
4. Alptürk O, Rusin O, Fakayode SO, Wang W, Escobedo JO, Warner IM, Crowe WE, Kŕal V, Pruet JM, Strongin RM (2006) Lanthanide complexes as fluorescent indicators for neutral sugars and cancer biomarkers. Proc Natl Acad Sci USA 103:9756-9760
5. Amendola V, Fabbrizzi L (2006) What anions do to N-H-containing receptors. Acc Chem Res 39:343-353
6. Anslyn EV (2007) Supramolecular analytical chemistry. J Org Chem 72:687-699
7. Aoyama Y, Tanaka Y, Toi H, Ogoshi H (1988) Polar host-guest interaction. binding of nonionic polar compounds with resorcinol-Aldehyde cyclooligomer as a lipophylic polar host. J Am Chem Soc 110:634-635
8. Aoyama Y, Tanaka Y, Sugahara S (1989) Molecular Recognition. 5. Molecular recognition of sugars via hydrogen-bonding interaction with a synthetic polyhydroxy macrocycle. J Am Chem Soc 111:5397-5404
9. Aoyama Y, Nagai Y, Otsuki J, Kobayashi K, Toi H (1992) Selective binding of sugar to b-cyclodextrin: A prototype for sugar-sugar interaction in water. Angew Chem Int Ed Engl 31:745-747
10. Arduini A, Demuru D, Pochini A, Secchi A (2005) Recognition of quaternary ammonium cations by calyx arene derivatives supported on gold nanoparticles. Chem Commun: 645-647
11. Arena G, Contino A, Gulino FG, Magri A, Sansone F, Sciotto D, Ungaro R (1999) Complexation of native L-Alpha-Aminoacids by water soluble calyx arenes. Tetrahedron Lett 40:1597-1600
12. Ariga K, Kunitake T (2005) Supramolecular chemistry: Fundamentals and applications. Springer, Berlin
13. Atwood JL, Steed JW (2004) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York
14. Badjic JD, Nelson A, Cantrill SJ, Turnbull WB, Stoddart JF (2005) Multivalency and cooperativity in supramolecular chemistry. Acc Chem Res 38:723-732
15. Bag B, Bharadwaj PK (2005) Fluorescence enhancement of a signaling system in the simultaneous presence of transition and alkali metal ions: A potential and logic gate. Chem Commun: 513-515.
16. Basabe-Desmonts L, Reinhoudt DN, Crego-Calama M (2007) Design of fluorescent materials for chemical sensing. Chem Soc Rev 36:993-1017
17. Baudoin O, Gonnet F, Teulade-Fichou MP, Vigneron JP, Tabet JC, Lehn JM (1999) Molecular recognition of nucleotide pairs by a cyclo-bis-intercaland-Type receptor molecule: A spectrophotometric and electrospray mass spectrometry study. Chem Eur J 5:2762-2771
18. Beer PD, Gale PA (2001) Anion recognition and sensing: The state of the art and future perspectives. Angew Chem Int Ed 40:486-516
19. Beer PD, Gale PA, Smith DK (1999) Supramolecular chemistry. Oxford Chemistry Primers Text No. 74, Oxford University Press
20. Best MD, Tobey SL, Anslyn EV (2003) Abiotic guanidinium containing receptors for anionic species. Coord Chem Rev 240:3-15
21. Bianchi A, Bowman-James K, García-España E (1997) The supramolecular chemistry of anions. Wiley-VCH, Weinheim
22. Biesaga M, Pyrzynska K, Trojanowicz M (2000) Porphyrins in analytical chemistry. Talanta 51:209-224
23. Bowman-James K (2005) Alfred Werner revisited: The coordination chemistry of anions. Acc Chem Res 38:671-678
24. Brooks SJ, Edwards PR, Gale PA, Light ME (2006) Carboxylate complexation by a family of easy-To-make ortho-phenylenediamine based bis-ureas: Studies in solution and the solid state. New J Chem 30:65-70
25. Buhleier E, Wehner W, Vögtle F (1978) Ligand structure and complexation,.22. 2, 6-bis(aminomethyl) pyridine as a complex ligand and new building block for crown ether synthesis. Liebigs Ann Chem 1978:537-544
26. Bush ME, Bouley ND, Urbach AR (2005) Charge-mediated recognition of N-Terminal tryptophan in aqueous solution by a synthetic host. J Am Chem Soc 127:14511-14517
27. Butterfield SM, Sweeney MM, Waters ML (2003) A designed beta-hairpin peptide for molecular recognition of ATP in water. J Am Chem Soc 125:9580-9581
28. Butterfield SA, Sweeney MM, Waters ML (2005) The recognition of nucleotides with model b-hairpin receptors: Investigation of critical contacts and nucleotide selectivity. J Org Chem 70:1105-1114
29. Cacciarini M, Azov VA, Seiler P, Kunzer H, Diederich F (2005) Selective steroid recognition by a partially bridged resorcin arene cavitand. Chem Comm: 5269-5271
30. Cao H, Heagy MD (2004) Fluorescent chemosensors for carbohydrates: A decade's worth of bright spies for saccharides in review. J Fluoresc 14:569-584
31. Chang KJ, Jeong KS, Moon D, Lah MS (2005) Indole-based macrocycles as a class of receptors for anions. Angew Chem Int Ed Engl 44:7926-7929
32. Choi K, Hamilton AD (2003) Rigid macrocyclic triamides as anion receptors: Anion-dependent binding stoichiometries and H-1 chemical shift changes. J Am Chem Soc 125:10241-10249
33. Clare JP, Ayling AJ, Joos JB, Sisson AL, Magro G, Perez-Payan MN, Lambert TN, Shukla R, Smith BD, Davis AP (2005) Substrate discrimination by cholapod anion receptors: Geometric effects and the "affinity-selectivity principle". J Am Chem Soc 127:10739-10746
34. Clark HA, Kopelman R, Tjalkens R, Philbert MA (1999) Optical nanosensors for chemical analysis inside single living cells. 2. Sensors for pH and calcium and the intracellular application of PEBBLE sensors. Anal Chem 71:4837-4843
35. Coterón JM, Hacket F, Schneider H-J (1996) Interactions of hydroxy compounds and sugars with anions. J Org Chem 61:1429-1435
36. Cragg P (2005) A practical guide to supramolecular chemistry. Wiley, New York
37. Czarnik AW (1994) Chemical communication in water using fluorescent chemosensors. Acc Chem Res 27:302-308
38. Das G, Hamilton AD (1997) Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors. Tetrahedron Lett 38:3675-3678
39. Davis AP, Wareham RS (1999) Carbohydrate recognition through noncovalent interactions: A challenge for biomimetic and supramolecular chemistry. Angew Chem Int Ed 38:2978-2996
40. De Namor AFD, Blackett PM, Cabaleiro MC, Al Rawi JMA (1994) Cyclodextrin-monosaccharide interactions in water. J Chem Soc Faraday Trans 90:845-847
41. De Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515-1566
42. Dejong MR, Engbersen JFJ, Huskens J, Reinhoudt DN (2000) Cyclodextrin dimers as receptor molecules for steroid sensors. Chem Eur J 6:4034-4040
43. Desvergne JP, Czarnik AW (1997) Chemosensors of ion and molecule recognition, NATO ASI Ser., Ser. C, vol 492. Kluwer, Dordrecht
44. Diaz-Garcia ME, Pina-Luis G, Rivero I (2006) Combinatorial solid-phase organic synthesis for developing materials with molecular recognition properties. Trends Anal Chem 25:112-121
45. Dietrich B, Guilhem J, Lehn JM, Pascard C, Sonveaux E (1984) Molecular recognition in anion coordination chemistry-structure, binding constants and receptor-substrate complementarity of a series of anion cryptates of a macrobicyclic receptor molecule. Helv Chim Acta 67:91-104
46. Dietrich B, Dilworth B, Lehn JM, Souchez JP, Cesario M, Guilhem J, Pascard C (1996) Anion cryptates: Synthesis, crystal structures, and complexation constants of fluoride and chloride inclusion complexes of polyammonium macrobicyclic ligands. Helv Chim Acta 79:569-587
47. Douteau-Guevel N, Perret F, Coleman AW, Morel JP, Morel-Desrosiers N (2002) Binding of dipeptides and tripeptides containing lysine or arginine by p-sulfonatocalixarenes in water: NMR and microcalorimetric studies. J Chem Soc Perkin Trans 2 3:524-532
48. Dukh M, S; aman D, Lang K, Pouzar V, C &; erný I, Drašar P, Kŕal V (2003) Steroid-porphyrin conjugate for saccharide sensing in protic media. Org Biomol Chem 1:3458-3463
49. Dunitz JD (1995) Win some, lose some-enthalpy-entropy compensation in weak intermolecular interactions. Chem Biol 2:709-712
50. Echavarren A, Galan A, de Mendoza J, Salmeron A, Lehn JM (1989) Chiral Recognition of aromatic carboxylate anions by an optically-Active abiotic receptor containing a rigid guanidinium binding subunit. J Am Chem Soc 111:4994-4995
51. Eliseev AV, Schneider HJ (1994) Molecular recognition of nucleotides, nucleosides, and sugars by aminocyclodextrins. J Am Chem Soc 116:6081-6088
52. Fabbrizzi L, Licchelli M, Pallavicini P, Sacchi D, Taglietti A (1996) Sensing of transition metals through fluorescence quenching or enhancement. A review. Analyst 121:1763-1768
53. Fabbrizzi L, Foti F, Taglietti A (2005) Metal-containing trifurcate receptor that recognizes and senses citrate in water. Org Lett 7:2603-2606
54. Fenniri H, Hosseini MW, Lehn J-M (1997) Molecular recognition of NADP(H) and ATP by macrocyclic polyamines bearing acrydine groups. Helv Chim Acta 80:786-803
55. Ferrand Y, Crump MP, Davis AP (2007) A synthetic lectin analog for biomimetic disaccharide recognition. Science 318:619-622
56. Forgacs E, Cserhati T (2004) Study of the interaction of some steroidal drugs with cyclodextrin derivatives. Analyt Lett 37:1897-1908
57. Fujimoto T, Shimizu C, Hayashida O, Aoyama Y (1998) Ternary complexation involving protein. molecular transport to saccharide-binding proteins using macrocyclic saccharide cluster as specific transporter. J Am Chem Soc 120:601-602
58. Gale PA, Sessler JL, Kral V, Lynch V (1996) Calix pyrroles: Old yet new anion-binding agents. J Am Chem Soc 118:5140-5141
59. Ghidini E, Ugozzoli F, Ungaro R, Harkema S, El-Fald AA, Reinhoudt DN (1990) Complexation of alkali-metal cations by conformationally rigid, stereoisomeric calix arene crown ethers: A quantitative-evaluation of preorganization. J Am Chem Soc 112:6979-6985
60. Goto H, Furusho Y, Yashima E (2007) Double helical oligoresorcinols specifically recognize oligosaccharides via heteroduplex formation through noncovalent interactions in water. J Am Chem Soc 129:9168-9174
61. Guo CX, Boullanger P, Liu T, Jiang L (2005) Size effect of polydiacetylene vesicles functionalized with glycolipids on their colorimetric detection ability. J Phys Chem B 109:18765-18771
62. Hacket F, Coterón JM, Schneider H-J, Kazachenko VP (1997) The complexation of glucose and other monosaccharides with cyclodextrins. Can J Chem 75:52-55
63. Hacket F, Simova S, Schneider H-J (2001) The complexation of peptides by aminocyclodextrins. J Phys Org Chem 14:159-170
64. Hamai S, Ikeda H, Ueno A (1998) H-1-NMR investigation of the binding of 2-methylnaphthalene to alpha-cyclodextrin in D2O solutions. J Incl Phenom Mol Recogn 31:265-273
65. Hamasaki K, Usui S, Ikeda H, Ikeda T, Ueno A (1997) Dansyl-modified cyclodextrins as fluorescent chemosensors for molecular recognition. Supramol Chem 8:125-135
66. Hamilton AD (1996) Supramolecular control of structure and reactivity: Perspectives in supramolecular chemistry. Wiley, New York
67. Hanshaw RG, Smith BD (2005) New reagents for phosphatidylserine recognition and detection of apoptosis. Bioorg Med Chem 13:5035-5042
68. Hartley JH, James TD, Ward CJ (2000) Synthetic receptors. Perkin Trans 1 19:3155-3184
69. Hayashi T, Aya T, Nonoguchi M, Mizutani T, Hisaeda Y, Kitagawi S, Ogoshi H (2002) Chiral recognition and chiral sensing using zinc porphyrin dimmers. Tetrahedron 58:2803-2811
70. Hayashida O, Nishayama K, Aoyama Y (1999) Preparation and host-guest interaction of novel macrocyclic sugar clusters having mono- and oligosaccharides. Tetrahedron Lett 40:3407-3410
71. Heinz U, Hergetschweiler K, Acklin P, Faller B, Lattmann R, Schnebli HP (1999) 4-[3, 5-Bis (2-hydroxyphenyl)-1, 2, 4-Triazol-1-yl]benzoic acid: A novel efficient and selective iron(III) complexing agent. Angew Chem Int Edi 38:2568-2570
72. Helgeson RC, Koga K, Timko JM, Cram DJ (1973) Complete optical resolution by differential complexation in solution between a chiral cyclic polyether and an alpha-Amino-Acid. J Am Chem Soc 95:3021-3033
73. Hirsch W, Muller T, Pizer R, Ricatto PJ (1995) Complexation of glucose by a- and b- cyclodextrins. Can J Chem 73:12-15
74. Hosseini MW, Blacker AJ, Lehn JM (1988) Multiple molecular recognition and catalysis -nucleotide binding and atp hydrolysis by a receptor molecule bearing an anion binding-site, an intercalator group, and a catalytic site. J Chem Soc Chem Commun 9:596-598
75. Houk KN, Leach AG, Kim SP, Zhang XY (2003) Binding affinities of host-guest, protein-ligand, and protein-Transition-state complexes. Angew Chem Int Ed Engl 42:4872-4897
76. Hunter CA (2004) Quantifying intermolecular interactions: Guidelines for the molecular recognition toolbox. Angew Chem Int Ed Engl 43:5310-5324
77. Ikeda H, Nakamura M, Ise N, Oguma N, Nakamura A, Ikeda T, Toda F, Ueno A (1996) Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins. J Am Chem Soc 118:10980-10988
78. Impellizzeri G, Pappalardo G, D'Alessandro F, Rizzarelli E, Savioano M, Iacovino R, Benedetti E, Pedone C (2000) Solid state and solution conformation of 6-{4-[N-Tert-butoxycarbonyl-N-(N0-ethyl)propanamide]imidazolyl}-6- deoxycyclomaltoheptaose: Evidence of self-inclusion of the Boc group within the beta-cyclodextrin cavity. Eur J Org Chem 6:1065-1076
79. Inoye M, Miyake T, Furusyo M, Nakazumi H (1995) Molecular recognition of b-ribofuranosides by synthetic polypyridine-macrocyclic receptors. J Am Chem Soc 117:12416-12425
80. Inoye M, Chiba J, Nakazumi H (1999) Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible lincage. J Org Chem 64:8170-8176
81. Inoye M, Takahashi K, Nakazumi H (1999) Remarkably strong, uncharged hydrogen-bonding interactions of polypyridine-macrocyclic receptors for deoxyribofuranosides. J Am Chem Soc 121:341-345
82. Ishi-i T, Mateos-Timoneda MA, Timmerman P, Crego-Calama M, Reinhoudt DN, Shinkai S (2003) Self-Assembled receptors that stereoselectively recognize a saccharide. Angew Chem Int Ed Engl 42:2300-2305
83. James TD (2007) Saccharide-selective boronic acid based photoinduced electron transfer (PET) fluorescent sensors. In creative chemical sensor systems. Top Curr Chem 277:107-152
84. James TD, Shinkai S (2002) Artificial receptors as chemosensors for carbohydrates. In Host-Guest Chemistry. Top Curr Chem 218:159-200
85. James TD, Shinkai S (2005) Fluorescent saccharide sensors. In: Geddes Chris D, Lakowicz Joseph R (eds) Advanced concepts in fluorescence sensing, part B. topics in fluorescence spectroscopy 10:41-67
86. James TD, Linnane P, Shinkai S (1996) Fluorescent saccharide receptors: A sweet solution to the design, assembly and evaluation of boronic acid derived PET sensors. Chem Commun 3: 281-288
87. James TD, Sandanayake KRAS, Shinkai S (1996) Angew Chem Int Ed 35:1911-1922
88. Kano K (1997) Mechanisms for chiral recognition by cyclodextrins. J Phys Org Chem 10:286-291
89. Katz E, Willner I (2004) Integrated nanoparticle-biomolecule hybrid systems: Synthesis, properties, and applications. Angew Chem Int Ed Engl 43:6042-6108
90. Kikkeri R, Traboulsi H, Humbert N, Gumienna-Kontecka E, Arad-Yellin R, Melman G, Elhabiri M, Albrecht-Gary AM, Shanzer A (2007) Toward iron sensors: Bioinspired tripods based on fluorescent phenol-oxazoline coordination sites. Inorg Chem 46:2485-2497
91. Kikuchi Y, Kato Y, Tanaka Y, Toi H, Aoyama Y (1991) Molecular recognition and stereoselectivity: Geometrical requirements for the multiple hydrogen-bonding interaction of diols with multidentate polyhydroxy macocycle. J Am Chem Soc 113:1349-1354
92. Kikuchi Y, Kobayashi K, Aoyama Y (1992) Complexation of chiral glycols, steroidal polyols, and sugars with a multibenzenoid, achiral host as studied by induced circular dichroism spectroscopy: Exciton chirality induction in resorcinol-Aldehyde cyclotetramer and its use as a supramolecular probe for the assignements of stereochemistry of chiral guests. J Am Chem Soc 114:1351-1358
93. Kikuchi Y, Tanaka Y, Sutarto S, Kobayashi K, Toi H, Aoyama Y (1992) Highly cooperative binding of alkyl glucopyranosydes to the resorcinol cyclic tetramer due to intracomplex guest-guest hydrogen bonding: Solvophobicity/ solvophilicity control by an alkyl group of the geometry, stoichiometry, stereoselectivity, and cooperativity. J Am Chem Soc 114: 10302-10306
94. Kim SK, Moon B-S, Park JH, Seo YI, Koh HS, Yoon YJ, Lee KD, Yoon J (2005) A fluorescent cavitand for the recognition of GTP. Tetrahedron Lett 46:6617-6620
95. Kobayashi K, Asakawa Y, Kikuchi Y, Toi H, Aoyama Y (1993) CH-p interactions as an important driving force of host-guest complexation in apolar organic media. binding of monools and acetylated compounds to resorcinol cyclic tetramer as studied by 1h nmr and circular dichroism spectroscopy. J Am Chem Soc 115:2648-2654
96. Koblenz TS, Wassenaar J, Reek JNH (2008) Reactivity within a confined self-Assembled nanospace. Chem Soc Rev 37:247-262
97. Kopelman R, Dourado S (1996) Is smaller better?-Scaling of characteristics with size of fiberoptic chemical and biochemical sensors. Proc SPIE- Intern Soc Opt Eng 2836:2-11
98. Kŕal V, Rusin O, Charv́atov́a J, Anzenbacher P Jr, Fogl J (2000) Porphyrin phosphonates: Novel anionic receptors for saccharide recognition. Tetrahedron Lett 41:10147-10151
99. Kŕal V, Rusin O, Schmidtchen FP (2001) Novel porphyrin-cryptand cyclic systems: Receptor for saccharide recognition in water. Org Lett 3:873-876
100. Kŕal V, Kŕalov́a J, Kapĺanek P, Bríza T, Mart́asek P (2006) Quo vadis porphyrin chemistry? Physiol Res 55(Suppl 2):S3-S26
101. Kŕalov́a J, Koivukorpi J, Kejík Z, Poučkov́a P, Sievänen E, Kolehmainen E, Kŕal V (2008) Porphyrin-bile acid conjugates: From saccharide recognition in the solution to the selective cancer cell fluorescence detection. Org Biomol Chem 6:1548-1552
102. Kruppa M, König B (2006) Reversible coordinative bonds in molecular recognition. Chem Rev 106:3520-3560
103. Kruppa M, Mandl C, Miltschitzky S, König B (2005) A luminescent receptor with affinity for N-Terminal histidine in peptides in aqueous solution. J Am Chem Soc 127:3362-3365
104. Kubik S, Goddard R (2002) Conformation and anion binding properties of cyclic hexapeptides containing L-4-hydroxyproline and 6-Aminopicolinic acid subunits. Proc Nat Acad Sci USA 99:5127-5132
105. Kubik S, Reyheller C, Stuwe S (2005) Recognition of anions by synthetic receptors in aqueous solution. J Incl Phenom 52:137-187
106. Kubo K, Sakurai T, Mori A (1999) Complexation and fluorescence behavior of 9, 10-bis[bis(betahydroxyethyl) aminomethyl]anthracene. Talanta 50:73-77
107. Kumar S, Schneider HJ (1989) The Complexation of Estrogens and Tetralins in the Cavities of Azoniacyclophanes. J Chem Soc Perkin Trans 2:245-250
108. Kurihara K, Ohto K, Tanaka Y, Aoyama Y, Kunitake T (1991) Molecular recognition of sugars by monolayers of resorcinol-dodecanal cyclotetramer. J Am Chem Soc 113:444-450
109. Lakowicz JR (1994) Probe design and chemical sensing. Plenum, New York
110. Lambert TN, Smith BD (2003) Synthetic receptors for phospholipid headgroups. Coord Chem Rev 240:129-141
111. Lehn JM (1995) Supramolecular chemistry: Concepts and perspectives. Wiley-VCH, Weinheim
112. Lehn JM, Atwood JL, Davies JED, MacNicol DD, MacNicol DD, Vögtle F (1996) Comprehensive supramolecular chemistry, vol 1-11. Pergamon. Elsevier, Oxford
113. Liu Y, Chen Y, Li B, Wada T, Inoue Y (2001) Cooperative multipoint recognition of organic dyes by bis(beta-cyclodextrin)s with 2, 20-bipyridine-4, 40-dicarboxy tethers. Chem Eur J 7: 2528-2535
114. Liu Y, Yang YW, Yang EC, Guan XD (2004) Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. J Org Chem 69:6590-6602
115. Lützen A (2007) Supramolekulare Chemie-Chemie jenseits desMoleküls. CHEMKON 14:123-130
116. Mahoney JM, Beatty AM, Smith BD (2001) Selective recognition of an alkali halide contact ionpair. J Am Chem Soc 123:5847-5848
117. Mammen M, Choi SK, Whitesides GM (1998) Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors. Angew Chem Int Ed Engl 37:2755-2794
118. Mandl CP, König B (2005) Luminescent crown ether amino acids: Selective binding to N-Terminal lysine in peptides. J Org Chem 70:670-674
119. Matsushita A, Kuwabara T, Nakamura A, Ikeda H, Ueno A (1997) Guest-induced colour changes and molecule-sensing abilities of p-nitrophenol-modified cyclodextrins. J Chem Soc Perkin Trans 2: 1705-1710.
120. Mazik M, Buthe AC (2008) Highly effective receptors showing di- vs. monosaccharide preference. Org Biomol Chem 6:1558-1568
121. Mazik M, Cavga H (2007) An acyclic aminonaphthyridine-based receptor for carbohydrate recognition: Binding studies in competitive solvents. Eur J Org Chem: 3633-3638
122. Mazik M, KuschelM(2008) Amide, amino, hydroxy and aminopyridine groups as building blocks for carbohydrate receptors. Eur J Org Chem: 1517-1526
123. Meyer EA, Castellano RK, Diederich F (2003) Interactions with aromatic rings in chemical and biological recognition. Edit Angew Chem-Int 42:1210-1250
124. Mizutani T, Wada K, Kitagawa S (2002) Hydrophobic environment of gable-Type bisporphyrin receptors in water promotes binding of amines and oligopeptides. Chemical Communications: 1626-1627
125. Moreno-Corral R, Lara KO (2008) Complexation studies of nucleotides by tetrandrine derivatives bearing anthraquinone and acridine groups. Supramol Chem 20:427-435
126. Mulder A, Huskens J, Reinhoudt DN (2004) Multivalency in supramolecular chemistry and nanofabrication. Org Biomol Chem 2:3409-3424
127. Müller G, Riede J, Schmidtchen FP (1988) Host-guest bonding of oxoanions to guanidinium anchor groups. Angew Chem Int Ed Engl 27:1516-1518
128. Narita M, Hamada F (2000) The synthesis of a fluorescent chemo-sensor system based on regioselectively dansyl-Tosyl-modified beta- and gamma-cyclodextrins. J Chem Soc Perkin Trans 2:823-832
129. Nassimbeni LR (2003) Physicochemical aspects of host-guest compounds. Acc Chem Res 36:631-637
130. O'Neil EJ, Smith BD (2006) Anion recognition using dimetallic coordination complexes. Coord Chem Rev 250:3068-3080
131. Ogoshi H, Mizutani T (1998) Multifunctional and chiral porphyrins: Model receptors for chiral recognition. Acc Chem Res 31:81-89
132. Oshovsky GV, Reinhoudt DN, Verboom W (2007) Supramolecular chemistry in water. Angew Chem Int Ed 46:2366-2393
133. Page D, Zanini D, Roy R (1996) Macromolecular recognition: Effect of multivalency in the inhibition of binding of yeast mannan to concanavalin A and pea lectins by mannosylated dendrimers. Bioorg Med Chem 4:1949-1961
134. Palde PB, Gareiss PC, Miller BL (2008) Selective Recognition of Alkyl Pyranosides in Protic and Aprotic Solvents. J Am Chem Soc 130:9566-9573
135. Paulini R, Müller K, Diederich F (2005) Orthogonal multipolar interactions in structural chemistry and biology. Edit Angew Chem-Int 44:1788-1805
136. Peczuh MW, Hamilton AD (2000) Peptide and protein recognition by designed molecules. Chem Rev 100:2479-2493
137. Penadés S, Fuhrhop J-H (eds) (2002) Host-guest chemistry : Mimetic approaches to study carbohydrate recognition (Top. Curr. Chem.; 218). Springer, Berlin, 241
138. Prodi L (2005) Luminescent chemosensors: From molecules to nanoparticles. New J Chem 29: 20-31
139. Prodi L, Bolletta F, Montalti M, Zaccheroni N (2000) Luminescent chemosensors for transition metal ions. Coord Chem Rev 205:59-83
140. Rao JH, Lahiri J, Isaacs L, Weis RM, Whitesides GM (1998) A trivalent system from vancomycin center dot D-Ala-D-Ala with higher affinity than avidin center dot biotin. Science 280: 708-711
141. Rao JH, Lahiri J, Isaacs L, Weis RM, Whitesides GM (2000) Design, synthesis, and characterization of a high-Affinity trivalent system derived from vancomycin and L-Lys-D-Ala-D-Ala. J Am Chem Soc 122:2698-2710
142. Ray D, Bharadwaj PK (2008) A coumarin-derived fluorescence probe selective for magnesium. Inorg Chem 47:2252-2254
143. Raymond KN (1994) Recognition and Transport of Natural and Synthetic Siderophores by Microbes. Pure & Appl Chem 66:773-781
144. Reilly SD, Khalsa GRK, Ford DK, Brainard JR, Hay BP, Smith PH (1995) Octaazacryptand Complexation of the Fluoride-Ion. Inorg Chem 34:569-575
145. Rekharsky MV, Yamamura H, Kawai M, Inoue Y (2003) Complexation and chiral recognition thermodynamics of gamma-cyclodextrin with N-Acetyl- and N-carbobenzyloxy-dipeptides possessing two aromatic rings. J Org Chem 68:5228-5235
146. Rekharsky MV, Mori T, Yang C, Ko YH, Selvapalam N, Kim H, Sobransingh D, Kaifer AE, Liu SM, Isaacs L, Chen W, Moghaddam S, Gilson MK, Kim KM, Inoue Y (2007) A synthetic hostguest system achieves avidin-biotin affinity by overcoming enthalpy-entropy compensation. Proc Natl Acad Sci USA 104:20737-20742
147. Rekharsky MV, Yamamura H, Ko YH, Selvapalam N, Kim K, Inoue Y (2008) Sequence recognition and self-sorting of a dipeptide by cucurbit uril and cucurbit uril. Chem Commun 2236-2238
148. Rettig W, Strehmel B, Schrader S, Seifert H (1999) Applied fluorescence in chemistry, biology, and medicine. Springer, Berlin, p 179
149. Rurack K (2001) Flipping the light switch 'ON'-The design of sensor molecules that show cationinduced fluorescence enhancement with heavy and transition metal ions. Spectrochim Acta A Mol Biomol Spectrosc 57:2161-2195
150. Rusin O, Kŕal V (2001) 1, 10-Binaphthyl substituted calixresorcinols-methyl red complexes: Receptors for saccharide sensing. Tetrahedron Lett. 42:4235-4238
151. Rusin O, Lang K, Kŕal V (2002) 1, 10-Binaphthyl-Substituted Macrocycles as Receptor for Saccharide Recognition. Chem Eur J 8:655-663
152. Salvatierra D, Sanchez-Ruiz X, Garduno R, Cervello E, Jaime C, Vergili A, Sanchez-Ferrando F (2000) Enantiodifferentiation by complexation with beta-cyclodextrin: Experimental (NMR) and theoretical (MD, FEP) studies. Tetrahedron 56:3035-3041
153. Schalley C (2007) Analytical methods in supramolecular chemistry. Wiley-VCH, Weinheim
154. Schmidtchen FP (2005) Artificial host molecules for the sensing of anions. Topics in Current Chemistry: Anion Sensing. 255:1-29
155. Schmidtchen FP, Berger M (1997) Artificial organic host molecules for anions. Chem Rev 97:1609-1646
156. Schmuck C, Wennemers H (2004) Highlights in bioorganic chemistry: Methods and applications. Wiley-VCH, Weinheim
157. Schneider H-J (1991) Mechanisms of molecular recognition: Investigations of organic host guest complexes. Angew Chem Int Ed 30:1417-1436
158. Schneider H-J (1994) Linear free-energy relationships and pairwise interactions in supramolecular chemistry. Chem Soc Rev 22:227-234
159. Schneider H-J (2009) Binding mechanisms in supramolecular complexes. Angen Chem Int Ed Engl 48:3294-3977
160. Schneider H-J, Kato K (2007) Direct translation of chiral recognition into mechanical motion. Angew Chem Int Ed Engl 46:2694-2696
161. Schneider H-J, Sirish M (2000) Highly efficient complexations of a porphyrin dimer with remarkably small differences between nucleosides and nucleotides/the predominance of stacking interactions for nucleic acid components. J Am Chem Soc 122:5881-5882
162. Schneider H-J, Yatsimirsky A (2000) Principles and methods in supramolecular chemistry. Wiley, Chichester
163. Schneider H-J, Yatsimirsky A (2008) Selectivity in supramolecular host-guest complexes. Chem Soc Rev 263-277
164. Schneider SE, O'Neil SN, Anslyn EV (2000) Coupling rational design with libraries leads to the production of an ATP selective chemosensor. J Am Chem Soc 122:542-543
165. Schneider H-J, Tianjun L, Lomadze N (2004) Sensitivity increase in molecular recognition by decrease of the sensing particle size and by increase of the receptor binding site-A case with chemomechanical polymers. Chem Commun: 2436-2437.
166. Schrader T, Hamilton M (2005) Functional synthetic receptors. Wiley-VCH, Weinheim 428 pp
167. Schrader T, Koch S (2007) Artificial protein sensors. Mol BioSyst 3:241-248
168. Schug KA, Lindner W (2005) Noncovalent binding between guanidinium and anionic groups: Focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on] ate and sulf[on]ate residues. Chem Rev 105:67-113
169. Sears P, Wong C-H (1999) Carbohydrate mimetics: A new strategy for tackling the problem of carbohydrate-mediated biological recognition. Angew Chem Int Ed 38:2300-2324
170. Shahgaldian P, Pieles U (2006) Cyclodextrin derivatives as chiral supramolecular receptors for enantioselective sensing. Sensors 6:593-615
171. Shanzer A, Libman J, Lytton SD, Glickstein H, Cabantchik ZI (1991) Reversed siderophores act as antimalarial agents. Proc Natl Acad Sci USA 88:6585-6589
172. Shi Y, Schneider H-J (1999) Interactions between aminocalixarenes and nucleosides or nucleic acids. J Chem Soc Perkin Trans 2:1797-1803
173. Shinkai S, Robertson A (2001) The design of molecular artificial sugar sensing systems. In: New trends in fluorescence spectroscopy. Springer Series on Fluorescence 1:173-185
174. Sirish M, Schneider H-J (1999) Porphyrin derivatives as water-soluble receptors for peptides. Chem Commun: 907-908
175. Sirish M, Chertkov VA, Schneider H-J (2002) Porphyrin-based peptide receptors: Syntheses and NMR analysis. J Chem Eur J 8:1181-1188
176. Steed JW, Atwood JL (2000) Supramolecular Chemistry. Wiley, Chichester
177. Steed JW, Turner DR, Wallace KJ (2007) Core concepts in supramolecular chemistry and nanochemistry. Wiley, Chichester
178. Striegler S (2003) Carbohydrate recognition in cross-linked sugar-Templated poly(acrylates). Macromolecules 36:1310-1317
179. Striegler S (2003) Selective carbohydrate recognition by synthetic receptors in aqueous solution. Curr Org Chem 7:81-102
180. Striegler S, Dittel M(2003) A sugar discriminating binuclear copper(II) complex. J Am Chem Soc 125:11518-11524
181. Striegler S, Dittel M(2005) A sugar's choice: Coordination to a mononuclear or a dinuclear copper (II) complex? Inorg Chemistry 44:2728-2733
182. Sugimoto N, Miyoshi D, Zou J (2000) Development of small peptides recognizing a monosaccharide by combinatorial chemistry. Chem Commun 2295-2296
183. Tanaka Y, Khare C, Yonezawa M, Aoyama Y (1990) Highly stereoselective glycosidation of ribose solubilized in apolar organic media via host-guest complexation. Tetrahedron Lett 43:6193-6196
184. Uccello-Barretta G, Balzano F, Cuzzola A, Menicagli R, Salvadori P (2000) NMR detection of the conformational distortion induced in cyclodextrins by introduction of alkyl or aromatic substituents. Eur J Org Chem 3:449-453
185. Usui S, Tanabe T, Ikeda H, Ueno A (1998) The structure of mono-(3-Amino-3-deoxy)-Alphacyclodextrin in aqueous solution-Molecular dynamics and NMR studies. J Mol Struct 442:161-168
186. Vacca A, Nativi C, Cacciarini M, Pergoli R, Roelens S (2004) A new tripodal receptor for molecular recognition of monosaccharides. A paradigm for assessing glycoside binding affinities and selectivities by H-1 NMR spectroscopy. J Am Chem Soc 126:16456-16465
187. Vögtle F (1993) Supramolecular chemistry: An introduction. Wiley
188. Vögtle, F (ed) (1995) Comprehensive supramolecular chemistry. vol 2. Pergamon
189. Wallimann P, Marti T, Furer A, Diederich F (1997) Steroids in molecular recognition. Chem Rev 97:1567-1608
190. Wang Y, Ikeda T, Ikeda H, Ueno A, Toda F (1994) Dansyl-b-cyclodextrins as fluorescent sensors responsive to organic compounds. Bull Chem Soc Jpn 67:1598-1607
191. Wang W, Gao X, Wang B (2002) Boronic acid-based sensors. Curr Org Chem 6:1285-1317
192. Wehner M, Janssen D, Schäfer G, Schrader, T (2006) Sequence-selective peptide recognition with designed modules. Eur J Org Chem: 138-153
193. Werner F, Schneider HJ (2000) Complexation of anions including nucleotide anions by openchain host compounds with amide, urea, and aryl functions. Helv Chim Acta 83:465-478
194. Williams DH, Stephens E, O'Brien DP, Zhou M (2004) Understanding noncovalent interactions: Ligand binding energy and catalytic efficiency from ligand-induced reductions in motion within receptors and enzymes. Angew Chem Int Ed 43:6596-6616
195. Wiskur SL, Ait-Haddou H, Lavigne JJ, Anslyn EV (2001) Teaching old indicators new tricks. Acc Chem Res 34:963-972
196. Xu H, Xu XH, Dabestani R, Brown GM, Fan L, Patton S, Ji HF (2002) Supramolecular fluorescent probes for the detection of mixed alkali metal ions that mimic the function of integrated logic gates. J Chem Soc Perkin Trans 2:636-643
197. Yan J, Fang H, Wang B (2005) Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design. Med Res Rev 25:490-520
198. Zadmard R, Schrader T (2006) DNA recognition with large calixarene dimers. Angew Chem Int Ed 45:2703-2706
199. Zielenkiewicz W, Marcinowicz A, Cherenok S, Kalchenko VI, Poznanski J (2006) Phosphorylated calixarenes as receptors of L-Amino acids and dipeptides: Calorimetric determination of Gibbs energy, enthalpy and entropy of complexation. Supramol Chem 18:167-176
200. Žinić M, Vigneron J-P, Lehn J-M (1995) Binding of nucleotides in water by phenanthridinium bis (intercland) receptor molecules. Chem Commun: 1073-1075