Yohimbine dimers exhibiting binding selectivities for human α(2a)- versus α(2b)-adrenergic receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 7, 2000, Pages 627-630

  Zheng, Weiping ^a,b   Lei, Longping ^c   Lalchandani, Shilpa ^e   Sun, Guoping ^a,d   Feller, Dennis R ^e   Miller, Duane D ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

^c BRIGHAM AND WOMEN S HOSPITAL   (United States)

^d NATIONAL EYE INSTITUTE   (United States)

^e NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 2A ADRENERGIC RECEPTOR; ALPHA 2B ADRENERGIC RECEPTOR; DIMER; YOHIMBINE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CHO CELL; DRUG DESIGN; DRUG RECEPTOR BINDING; NONHUMAN; PARTIAL DRUG SYNTHESIS;

ADRENERGIC ALPHA-ANTAGONISTS; ANIMALS; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; DIMERIZATION; HUMANS; RECEPTORS, ADRENERGIC, ALPHA-2; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION; YOHIMBINE;

ANIMALIA; CRICETINAE; CRICETULUS GRISEUS;

EID: 0034599595     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00068-8     Document Type: Article

References (43)

1. Starke, K. Rev. Physiol. Biochem. Pharmacol. 1981, 88, 199.
2. For reviews, see (a) Bylund, D. B. FASEB J. 1992, 6, 832; (b) Bylund, D. B.; Eikenberg, D. C.; Hieble, J. P.; Langer, S. Z.; Lefkowitz, R. J.; Minneman, K. P.; Molinoff, P. B.; Ruffolo Jr., R. R.; Trendelenburg, U. Pharmacol. Rev. 1994, 46, 121; (c) Hieble, J. P.; Bondinell, W. E.; Ruffolo Jr., R. R. J. Med. Chem. 1995, 38, 3415; (d) Hieble, J. P.; Ruffolo Jr., R. R. Prog. Drug Res. 1996, 47, 81.
3. For reviews, see (a) Bylund, D. B. FASEB J. 1992, 6, 832; (b) Bylund, D. B.; Eikenberg, D. C.; Hieble, J. P.; Langer, S. Z.; Lefkowitz, R. J.; Minneman, K. P.; Molinoff, P. B.; Ruffolo Jr., R. R.; Trendelenburg, U. Pharmacol. Rev. 1994, 46, 121; (c) Hieble, J. P.; Bondinell, W. E.; Ruffolo Jr., R. R. J. Med. Chem. 1995, 38, 3415; (d) Hieble, J. P.; Ruffolo Jr., R. R. Prog. Drug Res. 1996, 47, 81.
4. For reviews, see (a) Bylund, D. B. FASEB J. 1992, 6, 832; (b) Bylund, D. B.; Eikenberg, D. C.; Hieble, J. P.; Langer, S. Z.; Lefkowitz, R. J.; Minneman, K. P.; Molinoff, P. B.; Ruffolo Jr., R. R.; Trendelenburg, U. Pharmacol. Rev. 1994, 46, 121; (c) Hieble, J. P.; Bondinell, W. E.; Ruffolo Jr., R. R. J. Med. Chem. 1995, 38, 3415; (d) Hieble, J. P.; Ruffolo Jr., R. R. Prog. Drug Res. 1996, 47, 81.
5. For reviews, see (a) Bylund, D. B. FASEB J. 1992, 6, 832; (b) Bylund, D. B.; Eikenberg, D. C.; Hieble, J. P.; Langer, S. Z.; Lefkowitz, R. J.; Minneman, K. P.; Molinoff, P. B.; Ruffolo Jr., R. R.; Trendelenburg, U. Pharmacol. Rev. 1994, 46, 121; (c) Hieble, J. P.; Bondinell, W. E.; Ruffolo Jr., R. R. J. Med. Chem. 1995, 38, 3415; (d) Hieble, J. P.; Ruffolo Jr., R. R. Prog. Drug Res. 1996, 47, 81.
6. (a) Harrison, J. K.; Pearson, W. R.; Lynch, K. R. TiPS 1991, 12, 62;
7. (b) Aantaa, R.; Marjamaki, A.; Scheinin, M. Ann. Med. 1995, 27, 439.
8. Link, R. E.; Stevens, M. S.; Kulatunga, M.; Scheinin, M.; Barsh, G. S.; Kobilka, B. K. Mol. Pharmacol. 1995, 48, 48;
9. (b) Link, R. E.; Desai, K.; Hein, L.; Stevens, M. E.; Chruscinski, A.; Bernstein, D.; Barsh, G. S.; Kobilka, B. K. Science, 1996, 273, 803;
10. (c) MacMillan, L. B.; Hein, L.; Smith, M. S.; Piascik, M. T.; Limbird, L. E. Ibid 1996, 273, 801;
11. (d) MacMillan, L. B.; Lakhlani, P.; Lovinger, D.; Limbird, L. E. Recent Prog. Horm. Res. 1998, 53, 25.
12. For reviews, see (a) Ruffolo, R. R. Jr.; Bondinell, W.; Hieble, J. P. J. Med. Chem. 1995, 38, 3681; (b) Clark, R. D.; Michel, A. D.; Whiting, R. L. Prog. Med. Chem. 1986, 23, 1.
13. For reviews, see (a) Ruffolo, R. R. Jr.; Bondinell, W.; Hieble, J. P. J. Med. Chem. 1995, 38, 3681; (b) Clark, R. D.; Michel, A. D.; Whiting, R. L. Prog. Med. Chem. 1986, 23, 1.
14. (a) Yound, P.; Berge, J.; Chapman, H.; Cawthorne, M. A. Eur. J. Pharmacol. 1989, 168, 381;
15. (b) Devedjian, J.-C.; Esclapez, F.; Denis-Pouxviel, C.; Paris, H. Ibid 1994, 252, 43;
16. (c) Meana, J. J.; Callado, L. F.; Pazos, A.; Grijalba, B.; Garcia-Sevilla, J. A. Ibid 1996, 372, 385;
17. (d) Beeley, L. J.; Berge, J. M.; Chapman, H.; Hieble, P.; Kelly, J.; Naselsky, D. P.; Rockell, C. M.; Young, P. W. Bioorg. Med. Chem. 1995, 3, 1693;
18. (e) Michel, A. D.; Loury, D. N.; Whiting, R. L. Br. J. Pharmacol. 1990, 99, 560;
19. (f) Uhlen, S.; Porter, A. C.; Neubig, R. R. J. Pharmacol. Exp. Ther. 1994, 277, 1558;
20. (g) Blaxall, H. S.; Murphy, T. J.; Baker, J. C.; Ray, C.; Bylund, D. B. Ibid 1991, 259, 323;
21. (h) Bylund, D. B.; Blaxall, H. S.; Iverson, L. J.; Caron, M. G.; Lefkowitz, R. J.; Lomasney, J. W. Mol. Pharmacol. 1992, 42, 1;
22. (i) Okumura, K.; Koike, K.; Asai, H.; Takayanagi, I. Gen. Pharmacol. 1988, 19, 463.
23. (a) Portoghese, P. S.; Larson, D. L.; Yim, C. B.; Sayre, L. M.; Ronsisvalle, G.; Lipkowski, A. W.; Takemori, A. E.; Rice, K. C.; Tam, S. W. J. Med. Chem. 1985, 28, 1140;
24. (b) Erez, M.; Takemori, A. E.; Portoghese, P. S. Ibid. 1982, 25, 847;
25. (c) Portoghese, P. S. Ibid 1992, 35, 1927;
26. (d) Portoghese, P. S. TiPS 1989, 10, 230;
27. (e) Shimohigashi, Y.; Costa, T.; Chen, H.-C.; Rodbard, D. Nature 1982, 297, 333;
28. (f) LeBoulluec, K. L.; Mattson, R. J.; Mahle, C. D.; McGovern, R. T.; Nowak, H. P.; Gentile, A. J. Bioorg. Med. Chem. Lett. 1995, 5, 123;
29. (g) Cwirla, S. E.; Balasubramanian, P.; Duffin, D. J.; Wagstrom, C. R.; Gates, C. M.; Singer, S. C.; Davis, A. M.; Tansik, R. L.; Mattheakis, L. C.; Boytos, C. M.; Schatz, P. J.; Baccanari, D.; Wrighton, N. C.; Barrett, R. W.; Dower, W. J. Science 1997, 276, 1696.
30. Goldberg, M. R.; Robertson, D. Pharmacol. Rev. 1983, 35, 143.
31. (a) Domino, S. E.; Repaske, M. G.; Bonner, C. A.; Kennedy, M. E.; Wilson, A. L.; Brandon, S.; Limbird, L. E. Methods Enzymol. 1992, 275, 181;
32. (b) Wilson, A. L.; Seibert, K.; Brandon, S.; Cragoe, E. J. Jr.; Limbird, L. E. Mol. Pharmacol. 1991, 39, 481.
33. 13C NMR) and elemental analysis;
34. 10c the stereo centers that are susceptible to epimerization during the coupling reaction and the subsequent reaction work up are those at C16 and Cl7. However, the integrity of their stereochemistry was conserved as confirmed by decoupling NMR studies; (Only rings D and E are shown for clarity),
35. (c) Morrison, G. A. Fortschr. Chem. Organ. Naturstoffe 1967, 25, 269.
36. Uhlen, S.; Axelrod, D.; Keefer, J. R.; Limberg, L. E.; Neubig, R. R. Pharmacol. Commun. 1995, 6, 155.
37. (a) Maggio, R.; Vogel, Z.; Wess, J. Proc. Natl. Acad. Sci. USA 1993, 90, 3103;
38. (b) Maggio, R.; Barbier, P.; Fornai, F.; Corsini, G. U. J. Biol. Chem. 1996, 277, 31055.
39. Swiss Protein Databank. 1998, Accession Number: p08913 and p18089.
40. Guyer, C. A.; Horstman, D. A.; Wilson, A. L.; Clark, J. D.; Cragoe Jr., E. J.; Limbird, L. E. J. Biol. Chem. 1990, 265, 17307.
41. (a) Zeng, D.; Harrison, J. K.; D'Angelo, D. D.; Barber, C. M.; Tucker, A. L.; Lu, Z.; Lynch, K. R. Proc. Natl. Acad. Sci. USA 1990, 87, 3102;
42. (b) Lanier, S. M.; Homey, C. J.; Patenauda, C.; Graham, R. M. J. Biol. Chem. 1988, 263, 14491.
43. Cheng, Y.; Prusoff, W. H. Biochem. Pharmacol. 1973, 22, 3099.