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Synthesis and biological activity of endomorphin-2 analogs incorporating piperidine-2-, 3- or 4-carboxylic acids instead of proline in position 24391

Public Access

Published

Peer reviewed scientific article

DOI : http://dx.doi.org/10.1111/j.1747-0285.2008.00678.x [1]

Authors

Staniszewska,R. [2]; Fichna,J. [3]; Gach,K. [4]; Toth,G. [5]; J Poels [6]; J. Vanden Broeck [7]; A.E. Janecka [8]

Keywords

  1. 0 [9]
  2. acid [10]
  3. Acids [11]
  4. Activity [12]
  5. Aequorin [13]
  6. Amino Acid Substitution [14]
  7. Amino acids [15]
  8. an [16]
  9. Animals [17]
  10. antagonists & inhibitors [18]
  11. article [19]
  12. AS [20]
  13. brain [21]
  14. Brain Chemistry [22]
  15. Calcium [23]
  16. Carboxylic Acids [24]
  17. chemistry [25]
  18. Comparison [26]
  19. electronic [27]
  20. Functional [28]
  21. im [29]
  22. Inhibitory Concentration 50 [30]
  23. Institute [31]
  24. IS [32]
  25. journal [33]
  26. Laboratories [34]
  27. medical [35]
  28. Oligopeptides [36]
  29. Piperidines [37]
  30. Proline [38]
  31. rats [39]
  32. Receptor [40]
  33. receptors [41]
  34. Receptors,Opioid,mu [42]
  35. Research [43]
  36. Research Support [44]
  37. SB - IM [45]
  38. stability [46]
  39. Universities [47]
  40. university [48]

Abstract:

Novel endomorphin-2 (EM-2) analogs have been synthesized, incorporating unnatural amino acids with six-membered heterocyclic rings, such as piperidine-2-, 3- and 4-carboxylic acids (Pip, Nip and Inp, respectively) instead of Pro in position 2. [(R)-Nip(2)]EM-2 displayed an extremely high affinity for the mu-opioid receptor with IC(50) = 0.04 +/- 0.01 nM in comparison with IC(50) = 0.69 +/- 0.03 nM for EM-2. This analog was also very potent in the aequorin luminescence-based functional calcium assay and showed significantly enhanced stability in rat brain homogenate
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Source URL:https://sciensano.be/en/biblio/synthesis-and-biological-activity-endomorphin-2-analogs-incorporating-piperidine-2-3-or-4-carboxylic

Links
[1] http://dx.doi.org/10.1111/j.1747-0285.2008.00678.x [2] https://sciensano.be/en/biblio?f%5Bauthor%5D=22989&f%5Bsearch%5D=Staniszewska%2CR. [3] https://sciensano.be/en/biblio?f%5Bauthor%5D=22968&f%5Bsearch%5D=Fichna%2CJ. [4] https://sciensano.be/en/biblio?f%5Bauthor%5D=22974&f%5Bsearch%5D=Gach%2CK. [5] https://sciensano.be/en/biblio?f%5Bauthor%5D=26829&f%5Bsearch%5D=Toth%2CG. [6] https://sciensano.be/en/people/jeroen-poels/biblio [7] https://sciensano.be/en/biblio?f%5Bauthor%5D=21003&f%5Bsearch%5D=J.%20Vanden%20Broeck [8] https://sciensano.be/en/biblio?f%5Bauthor%5D=22980&f%5Bsearch%5D=A.E.%20Janecka [9] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2235&f%5Bsearch%5D=0 [10] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2022&f%5Bsearch%5D=acid [11] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2025&f%5Bsearch%5D=Acids [12] https://sciensano.be/en/biblio?f%5Bkeyword%5D=945&f%5Bsearch%5D=Activity [13] https://sciensano.be/en/biblio?f%5Bkeyword%5D=20847&f%5Bsearch%5D=Aequorin [14] https://sciensano.be/en/biblio?f%5Bkeyword%5D=23316&f%5Bsearch%5D=Amino%20Acid%20Substitution [15] https://sciensano.be/en/biblio?f%5Bkeyword%5D=3774&f%5Bsearch%5D=Amino%20acids [16] https://sciensano.be/en/biblio?f%5Bkeyword%5D=843&f%5Bsearch%5D=an [17] https://sciensano.be/en/biblio?f%5Bkeyword%5D=423&f%5Bsearch%5D=Animals [18] https://sciensano.be/en/biblio?f%5Bkeyword%5D=3474&f%5Bsearch%5D=antagonists%20%26%20inhibitors [19] https://sciensano.be/en/biblio?f%5Bkeyword%5D=618&f%5Bsearch%5D=article [20] https://sciensano.be/en/biblio?f%5Bkeyword%5D=846&f%5Bsearch%5D=AS [21] https://sciensano.be/en/biblio?f%5Bkeyword%5D=5400&f%5Bsearch%5D=brain [22] https://sciensano.be/en/biblio?f%5Bkeyword%5D=23664&f%5Bsearch%5D=Brain%20Chemistry [23] https://sciensano.be/en/biblio?f%5Bkeyword%5D=20058&f%5Bsearch%5D=Calcium [24] https://sciensano.be/en/biblio?f%5Bkeyword%5D=23667&f%5Bsearch%5D=Carboxylic%20Acids [25] https://sciensano.be/en/biblio?f%5Bkeyword%5D=4965&f%5Bsearch%5D=chemistry [26] https://sciensano.be/en/biblio?f%5Bkeyword%5D=1194&f%5Bsearch%5D=Comparison [27] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2169&f%5Bsearch%5D=electronic [28] https://sciensano.be/en/biblio?f%5Bkeyword%5D=3963&f%5Bsearch%5D=Functional [29] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2184&f%5Bsearch%5D=im [30] https://sciensano.be/en/biblio?f%5Bkeyword%5D=23670&f%5Bsearch%5D=Inhibitory%20Concentration%2050 [31] https://sciensano.be/en/biblio?f%5Bkeyword%5D=954&f%5Bsearch%5D=Institute [32] https://sciensano.be/en/biblio?f%5Bkeyword%5D=525&f%5Bsearch%5D=IS [33] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2190&f%5Bsearch%5D=journal [34] https://sciensano.be/en/biblio?f%5Bkeyword%5D=543&f%5Bsearch%5D=Laboratories [35] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2061&f%5Bsearch%5D=medical [36] https://sciensano.be/en/biblio?f%5Bkeyword%5D=3648&f%5Bsearch%5D=Oligopeptides [37] https://sciensano.be/en/biblio?f%5Bkeyword%5D=20958&f%5Bsearch%5D=Piperidines [38] https://sciensano.be/en/biblio?f%5Bkeyword%5D=23673&f%5Bsearch%5D=Proline [39] https://sciensano.be/en/biblio?f%5Bkeyword%5D=5418&f%5Bsearch%5D=rats [40] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2319&f%5Bsearch%5D=Receptor [41] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2322&f%5Bsearch%5D=receptors [42] https://sciensano.be/en/biblio?f%5Bkeyword%5D=20898&f%5Bsearch%5D=Receptors%2COpioid%2Cmu [43] https://sciensano.be/en/biblio?f%5Bkeyword%5D=606&f%5Bsearch%5D=Research [44] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2331&f%5Bsearch%5D=Research%20Support [45] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2214&f%5Bsearch%5D=SB%20-%20IM [46] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2562&f%5Bsearch%5D=stability [47] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2343&f%5Bsearch%5D=Universities [48] https://sciensano.be/en/biblio?f%5Bkeyword%5D=2346&f%5Bsearch%5D=university