Highly Sensitive Recognition of Substrates of Adrenergic Receptors at the Air/Water Interface

Angewandte Chemie - International Edition

Volumn 42, Issue 44, 2003, Pages 5509-5513

  Molt, Oliver ^a   Schrader, Thomas ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

blockers; Adrenergic receptors; Interfaces; Langmuir Blodgett films; Molecular recognition; Monolayers

Indexed keywords

LANGMUIR BLODGETT FILMS; LIPIDS; MONOLAYERS; SELF ASSEMBLY;

ADRENERGIC RECEPTORS;

HORMONES;

ADRENERGIC RECEPTOR; METHANOL; WATER;

AIR; ARTICLE; BINDING AFFINITY; CALCULATION; LINEAR REGRESSION ANALYSIS; NUCLEAR MAGNETIC RESONANCE; PROTEIN BINDING; QUANTITATIVE ANALYSIS; STANDARDIZATION; STOICHIOMETRY; TITRIMETRY;

AIR; MAGNETIC RESONANCE SPECTROSCOPY; RECEPTORS, ADRENERGIC; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTRATE SPECIFICITY; WATER;

EID: 0345708149     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352186     Document Type: Article

References (49)

1. a) T. P. Iismaa, T. J. Biden, J. Shine, G Protein-Coupled Receptors, Springer, Heidelberg, 1995;
2. b) Special Issue: G-Protein-Coupled Receptors, ChemBioChem 2002, 3, 913-1034.
3. a) D. A. Doyle, J. Morais Cabral, R. A. Pfuetzner, A. Kuo, J. M. Gulbis, S. L. Cohen, B. T. Chait, R. MacKinnon, Science 1998, 280, 69;
4. b) K. Palczewski, T. Kumasaka, T. Hori, C. A. Behnke, H. Motoshima, B. A. Fox, I. Le Trong, D. C. Teller, T. Okada, R. O. Stenkamp, M. Yamamoto, M. Miyano, Science 2000, 289, 739;
5. c) R. E. Stenkamp, S. Filipek, C. A. G. G. Driessen, D. C. Teller, K. Palczewski, Biochim. Biophys. Acta 2002, 1565, 168.
6. Approximatively 50% of all commercially available drugs interact with GPCRs: a) D. T. Chalmers, D. P. Behan, Nat. Rev. Drug Discovery 2002, 1, 599;
7. b) T. Klabunde, G. Hessler, ChemBioChem 2002, 3, 928.
8. H. Brockman, Curr. Opin. Struct. Biol. 1999, 9, 438.
9. M. Lahav, A. N. Shipway, I. Willner, J. Chem. Soc. Perkin Trans. 2 1999, 1925.
10. a) S. M. Strawbridge, S. J. Green, J. H. R. Tucker, Chem. Commun. 2000, 2393;
11. b) S. M. Strawbridge, S. J. Green, J. H. R. Tucker, Phys. Chem. Chem. Phys. 2000, 2, 2393.
12. L. Lamarque, P. Navarro, C. Miranda, V. J. Arán, C. Ochoa, F. Escarti, E. García-España, J. Latorre, S. V. Luis, J. F. Miravet, J. Am. Chem. Soc. 2001, 123, 10560.
13. C. Mannironi, A. Di Nardo, P. Fruscoloni, G. P. Tocchini-Valentini, Biochemistry 1997, 36, 9726.
14. a) D. R. Shankaran, M.-S. Won, Y.-B. Shim, Anal. Sci. 2001, 17, 9;
15. b) M. Del Pilar Taboada Sotomayor, A. A. Tanaka, L. T. Kubota, Anal. Chim. Acta 2002, 455, 215.
16. a) S. Trumpp-Kallmeyer, J. Hoflack, A. Bruinfels, M. Hibert, J. Med. Chem. 1992, 35, 3448;
17. b) K. Wieland, H. M. Zuurmond, C. Krasel, A. P. Ijzerman, M. J. Lohse, Proc. Natl. Acad. Sci. USA 1996, 93, 9276.
18. a) T. Schrader, Angew. Chem. 1996,108, 2816; Angew. Chem. Int. Ed. Engl. 1996, 35, 2649;
19. a) T. Schrader, Angew. Chem. 1996,108, 2816; Angew. Chem. Int. Ed. Engl. 1996, 35, 2649;
20. b) T. Schrader, J. Org. Chem. 1998, 63, 264;
21. c) T. Schrader, M. Herm, Chem. Eur. J. 2000, 6, 47.
22. The last generation of advanced biomimetic adrenaline hosts suffered from multiple benzylic connections with their high torsional entropy: a) T. Schrader, M. Herm, O. Molt, Angew. Chem. 2001, 113, 3244; Angew. Chem. Int. Ed. 2001, 40, 3148;
23. The last generation of advanced biomimetic adrenaline hosts suffered from multiple benzylic connections with their high torsional entropy: a) T. Schrader, M. Herm, O. Molt, Angew. Chem. 2001, 113, 3244; Angew. Chem. Int. Ed. 2001, 40, 3148;
24. b) T. Schrader, M. Herm, O. Molt, Chem. Eur. J. 2002, 8, 1485.
25. a) T. Kawase, Y. Seirai, H. R. Darabi, M. Oda, Y. Sarakai, K. Tashiro, Angew. Chem. 2003, 115, 1659; Angew. Chem. Int. Ed. 2003, 42, 1621;
26. a) T. Kawase, Y. Seirai, H. R. Darabi, M. Oda, Y. Sarakai, K. Tashiro, Angew. Chem. 2003, 115, 1659; Angew. Chem. Int. Ed. 2003, 42, 1621;
27. b) M. M. Haley, J. J. Pak, S. C. Brand, Top. Curr. Chem. 1999, 201, 82.
28. Monte Carlo simulations: MacroModel 7.0, Schrödinger Inc. 2000, Force field Amber*, water, 3000 steps; subsequent molecular dynamics simulations: 300 K, 10 ps.
29. S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627.
30. A. Ostrowicki, E. Koepp, F. Vögtle, Top. Curr. Chem. 1992, 161, 37.
31. a) R. Karaman, A. Goldblum, E. Breuer, H. Leader, J. Chem. Soc. Perkin Trans. 1 1989, 765;
32. b) E. Breuer, M. Safadi, M. Chorev, D. Gibson, J. Org. Chem. 1990, 55, 6147.
33. Protonation of the lithium salt leads to sharp NMR signals in methanol and a complete loss of the splitting of the diastereotopic methylene protons.
34. Dilution titration to determine self-association constants: C. S. Wilcox, Frontiers in Supramolecular Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr), VCH, Weinheim, 1991.
35. L. Fielding, Tetrahedron 2000, 56, 6151.
36. M. T. Blanda, J. H. Homer, M. Newcomb, J. Org. Chem. 1989, 54, 4626.
37. For experimental details see Supporting Information.
38. a) M. Higuchi, T. Koga, K. Taguchi, T. Kinoshita, Langmuir 2002, 18, 813;
39. b) D. Y. Sasaki, T. A. Waggoner, J. A. Last, T. M. Alam, Langmuir 2002, 18, 3714;
40. c) J. Lahiri, G. D. Fate, S. B. Ungashe, J. T. Groves, J. Am. Chem. Soc. 1996, 118, 2347.
41. J. Meunier, Colloids Surf. A 2000, 171, 33.
42. a) C. Lavoie, J.-F. Mercier, A. Salahpour, D. Umapathy, A. Breit, L.-R. Villeneuve, W.-Z. Zhu, R.-P. Xiao, E. G. Lakatta, M. Bouvier, T. E. Hebert, J. Biol. Chem. 2002, 277, 35402;
43. b) J. Xu, M. Paquet, A. G. Lau, J. D. Wood, C. A. Ross, R. A. Hall, J. Biol. Chem. 2001, 276, 41310.
44. -6M.[5-9]
45. K. Ariga, T. Kunitake, Acc. Chem. Res. 1998, 31, 371.
46. Solvatochromic red shifts with unpolar solvents originate from the stabilization of their more polarizable LUMO: C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, 2003, pp. 340-341.
47. A CT band does not develop, as judged from the colorless monolayer. However, a sandwich arrangement would be conceivable for the guest's catechol ring within the host aggregates.
48. A simple lipid-modified bisphosphonate embedded in the stearic acid monolayer did not produce any changes in the π-A diagram even at high guest concentrations in the aqueous subphase.
49. S. Kolusheva, T. Shahal, R. Jelinek, J. Am. Chem. Soc. 2000, 122, 776.