A selective biomimetic tweezer for noradrenaline

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12086-12087

  Molt, O ^a   Rubeling D ^a   Schrader, T ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; ADRENALIN; BETA ADRENERGIC RECEPTOR; CATECHOL; DOPAMINE; ETHANOLAMINE; GLYCINE; METHANOL; NORADRENALIN; PHENETHYLAMINE; PROPRANOLOL; TRYPTOPHAN DERIVATIVE; TRYPTOPHAN METHYL ESTER; TYROSINE METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; BIOMIMETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; DEVICE; DRUG SELECTIVITY; ELECTROCHEMICAL ANALYSIS; NORADRENALIN RELEASE; NUCLEAR MAGNETIC RESONANCE; SENSOR; TITRIMETRY;

ALKYNES; BIOMIMETIC MATERIALS; BIPHENYL COMPOUNDS; KINETICS; NOREPINEPHRINE; PHENAZINES; PHOSPHONIC ACIDS; RECEPTORS, ADRENERGIC, BETA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 10744231349     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035212l     Document Type: Article

References (21)

1. (a) Ligett, S. B. Pharmacology 2000, 61, 167-173.
2. (b) Bock, M. G.; Patane, M. A. Annu. Rep. Med. Chem. 2000, 35, 221-230.
3. For an overview, see: Schrader, T.; Herm, M.; Molt, O. Chem. Eur. J. 2002, 8, 1485-1499.
4. (a) Zimmerman, S. C. Top. Curr. Chem. 1993, 165, 71-102.
5. (b) Brown, S. P.; Schaller, T.; Seelbach, U. P.; Koziol, F.; Ochsenfeld, C.; Klärner, F.-G.; Spiess, H. W. Angew. Chem., Int. Ed. 2001, 40, 717-720.
6. (c) Krebs, F. C.; Jorgensen, M. J. Org. Chem. 2001, 66, 6169-6173.
7. For complexation through charged hydrogen bonds, see: Echavarren, A.; Galan, A.; Lehn, J.-M.; de Mendoza, J. J. Am. Chem. Soc. 1989, 111, 4994-4995; Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746; Berger, M.; Schmidtchen, F. P. J. Am. Chem Soc. 1999, 121, 9986-9993. For catechol binding with cleft-type hosts, see: Sijbesma, R. P.; Nolte, R. J. Top. Curr. Chem. 1995, 175, 25-26.
8. For complexation through charged hydrogen bonds, see: Echavarren, A.; Galan, A.; Lehn, J.-M.; de Mendoza, J. J. Am. Chem. Soc. 1989, 111, 4994-4995; Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746; Berger, M.; Schmidtchen, F. P. J. Am. Chem Soc. 1999, 121, 9986-9993. For catechol binding with cleft-type hosts, see: Sijbesma, R. P.; Nolte, R. J. Top. Curr. Chem. 1995, 175, 25-26.
9. For complexation through charged hydrogen bonds, see: Echavarren, A.; Galan, A.; Lehn, J.-M.; de Mendoza, J. J. Am. Chem. Soc. 1989, 111, 4994-4995; Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746; Berger, M.; Schmidtchen, F. P. J. Am. Chem Soc. 1999, 121, 9986-9993. For catechol binding with cleft-type hosts, see: Sijbesma, R. P.; Nolte, R. J. Top. Curr. Chem. 1995, 175, 25-26.
10. For complexation through charged hydrogen bonds, see: Echavarren, A.; Galan, A.; Lehn, J.-M.; de Mendoza, J. J. Am. Chem. Soc. 1989, 111, 4994-4995; Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746; Berger, M.; Schmidtchen, F. P. J. Am. Chem Soc. 1999, 121, 9986-9993. For catechol binding with cleft-type hosts, see: Sijbesma, R. P.; Nolte, R. J. Top. Curr. Chem. 1995, 175, 25-26.
11. All synthetic details are found in the Supporting Information.
12. Safarowsky, O.; Nieger, M.; Fröhlich, R.; Vögtle, F. Angew. Chem., Int. Ed. 2000, 39, 1616-1618; Zimmerman, S. Bioorg. Med. Chem. 1996, 4, 1107.
13. Safarowsky, O.; Nieger, M.; Fröhlich, R.; Vögtle, F. Angew. Chem., Int. Ed. 2000, 39, 1616-1618; Zimmerman, S. Bioorg. Med. Chem. 1996, 4, 1107.
14. Wilcox, C. S. In Frontiers in Supramolecular Chemistry; Schneider, H. J., Ed.; Verlag Chemie: Weinheim, 1991; p 123.
15. -1 by dilution titration.
16. No molecular ion peaks were found for host dimers or higher aggregates.
17. MacroModel 7.0, Schrödinger Inc., Force-Field: Amber*, Monte Carlo simulations in water: 3000 steps.
18. Due to the low methanol solubility of 1, the NMR titrations had to be carried out at millimolar concentration, and the amount of added host did often not surpass 2 equiv. At these conditions, however, the complexation-induced shifts remained rather small, and only in the case of noradrenaline was 80% saturation reached. In all other cases, saturation did not exceed 50%, owing to their weak affinity towards 1. To secure the high Ka value found for noradrenaline, we repeated the respective binding experiment and obtained similar association constants from two independent proton signals.
19. For a recent review, see: Ariga, K.; Kunitake, T. Acc. Chem. Res. 1998, 31, 371-378.
20. Kolusheva, S.; Shahal, T.; Jelinek, R. J. Am. Chem. Soc. 2000, 122, 776-780.
21. Lahav, M.; Kharitonov, A. B.; Willner, I. Chem. Eur. J. 2001, 7, 3992-3997.