Synthesis of an MIF-1 analogue containing enantiopure (S)-α- trifluoromethyl-proline and biological evaluation on nociception

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 122-129

  Jlalia, Ibtissem ^a   Lensen, Nathalie ^a   Chaume, Grégory ^a   Dzhambazova, Elena ^b   Astasidi, Liountmila ^b   Hadjiolova, Radka ^c   Bocheva, Adriana ^c   Brigaud, Thierry ^a  

^a Université Paris Seine   (France)

^b UNIVERSITY OF SOFIA   (Bulgaria)

^c MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

Acute pain; Analgesia; Fluorinated amino acids; Fluorinated peptides; MIF 1; Nociception

Indexed keywords

N(G) NITROARGININE METHYL ESTER; NALOXONE; PROLYLLEUCYLGLYCINAMIDE;

ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HOT PLATE TEST; IN VIVO STUDY; LIPOPHILICITY; MALE; NOCICEPTION; NONHUMAN; PAIN; PAIN THRESHOLD; PH; PRESSURE; RAT;

ACUTE PAIN; ANIMALS; DISEASE MODELS, ANIMAL; MALE; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MSH RELEASE-INHIBITING HORMONE; NARCOTIC ANTAGONISTS; NOCICEPTION; OLIGOPEPTIDES; RATS; RATS, WISTAR; RECEPTORS, OPIOID;

EID: 84872676171     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.041     Document Type: Article

References (67)

1. G.W. Reed, G.A. Olson, and R.D. Olson Neurosci. Biobehav. Rev. 18 1994 519 525
2. F. Cesselin Fundam. Clin. Pharmacol. 9 1995 409 433
3. W. Pan, and A.J. Kastin Peptides 28 2007 2411 2434
4. G.E. Drucker, R.F. Ritzmann, L.J. Wichlinski, K. Engh, J.H. Gordon, and J.Z. Fields Pharmacol. Biochem. Behav. 47 1994 141 145
5. C. Hara, and A.J. Kastin Pharmacol. Biochem. Behav. 24 1986 1785 1787
6. C. Hara, and A.J. Kastin Pharmacol. Biochem. Behav. 25 1986 757 761
7. R.K. Mishra, S. Chiu, P. Chiu, and C.P. Mishra Meth. Find. Exp. Clin. Pharmacol. 5 1983 203 233
8. M.I. Saleh, and R.M. Kostrzewa Peptides 10 1989 35 39
9. L.K. Srivastava, S.B. Bajwa, R.L. Johnson, and R.K. Mishra J. Neurochem. 50 1988 960 968
10. J.M. Castellano, J. Batrynchuk, K. Dolbeare, V. Verma, A. Mann, K.J. Skoblenick, R.L. Johnson, and R.K. Mishra Peptides 28 2007 2009 2015
11. A. Fisher, A. Mann, V. Verma, N. Thomas, R.K. Mishra, and R.L. Johnson J. Med. Chem. 49 2006 307 317 and references therein
12. A. Mann, V. Verma, K.J. Skoblenick, D. Basu, M.G.R. Beyaert, A. Fisher, N. Thomas, R.L. Johnson, and R.K. Mishra Eur. J. Pharmacol. 641 2010 96 101
13. T.C. Case, S.R. Snider, V.J. Hruby, and T. Rockway Life Sci. 36 1985 2531 2537
14. R.M. Kostrzewa, A.J. Kastin, and S.K. Sobrian Pharmacol. Biochem. Behav. 9 1978 375 378
15. R.K. Mishra, E.R. Marcotte, A. Chugh, C. Barlas, D. Whan, and R.L. Johnson Peptides 18 1997 1209 1215
16. M.C. Ott, R.K. Mishra, and R.L. Johnson Brain Res. 737 1996 287 291
17. J.R. Smith, and M. Morgan Gen. Pharmacol. 13 1982 203 207
18. R.H. Ehrensing, A.J. Kastin, P.F. Larsons, and G.A. Bishop Dis. Nerv. Syst. 38 1997 303 307
19. S. Sharma, P. Paladino, J. Gabriele, H. Saeedi, P. Henry, M. Chang, R.K. Mishra, and R.L. Johnson Peptides 24 2003 313 319
20. R.H. Ehrensing, A.J. Kastin, G.F. Wurzlow, G.F. Mitchell, and A.H. Mebane J. Affect. Disord. 31 1994 227 233
21. S. Rotzinger, D.A. Lovejoy, and L.A. Tan Peptides 31 2010 736 756
22. A. Bocheva, and E. Dzambazova-Maximova Meth. Find. Exp. Clin. Pharmacol. 26 2004 673 677
23. A.J. Kastin, R.D. Olson, R.H. Ehrensing, M.C. Berzas, A.V. Schally, and D.H. Coy Pharmacol. Biochem. Behav. 11 1979 721 723
24. R.H. Ehrensing, A.J. Kastin, and G.F. Michell Pharmacol. Biochem. Behav. 21 1984 975 978
25. P.W. Baures, A. Pradhan, W.H. Ojala, W.B. Gleason, R.K. Mishra, and R.L. Johnson Biorg. Med. Chem. Lett. 9 1999 2349 2352
26. E.M. Khalil, W.H. Ojala, A. Pradhan, V.D. Nair, W.B. Gleason, R.K. Mishra, and R.L. Johnson J. Med. Chem. 42 1999 628 637
27. M.C. Evans, A. Pradhan, S. Venkatraman, W.H. Ojala, W.B. Gleason, R.K. Mishra, and R.L. Johnson J. Med. Chem. 42 1999 1441 1447
28. E.M. Khalil, A. Pradhan, W.H. Ojala, W.B. Gleason, R.K. Mishra, and R.L. Johnson J. Med. Chem. 42 1999 2977 2987
29. K. Dolbeare, G.F. Pontoriero, S.K. Gupta, R.K. Mishra, and R.L. Johnson J. Med. Chem. 46 2003 727 733
30. A. Fisher, A. Mann, V. Verma, N. Thomas, R.K. Mishra, and R.L. Johnson J. Med. Chem. 49 2006 307 317
31. A.P. Vartak, K. Skoblenick, N. Thomas, R.K. Mishra, and R.L. Johnson J. Med. Chem. 50 2007 6725 6729
32. N. Lebouvier, C. Laroche, F. Huguenot, and T. Brigaud Tetrahedron Lett. 43 2002 2827 2830
33. F. Huguenot, and T. Brigaud J. Org. Chem. 71 2006 7075 7078
34. G. Chaume, M.-C. Van Severen, S. Marinkovic, and T. Brigaud Org. Lett. 8 2006 6123 6126
35. G. Chaume, M.-C. Van Severen, L. Ricard, and T. Brigaud J. Fluorine Chem. 129 2008 1104 1109
36. C. Caupène, G. Chaume, L. Ricard, and T. Brigaud Org. Lett. 11 2009 209 212
37. J. Simon, T.T. Nguyen, E. Chelain, N. Lensen, J. Pytkowicz, G. Chaume, and T. Brigaud Tetrahedron: Asymmetr. 22 2011 309 314
38. L. Moroder, C. Renner, J.J. Lopez, M. Mutter, and G. Tuchscherer C. Dugave, Cis-trans Isomerization in Biochemistry 2006 Wiley-VCH Weinheim 225 259
39. P. Karoyan, S. Sagan, O. Lequin, J. Quancard, S. Lavielle, and G. Chassaing Targets Heterocycl. Syst. 8 2004 216 273
40. B.C.J. van Esseveldt, P.W.H. Vervoort, F.L. van Delft, and F.P.J.T. Rutjes J. Org. Chem. 70 2005 1791 1795 and references therein
41. C.L. Jenkins, G. Lin, J. Duo, D. Rapolu, I.A. Guzei, R.T. Raines, and G.R. Krow J. Org. Chem. 69 2004 8565 8573 and references therein
42. J.R. Del Valle, and M. Goodman J. Org. Chem. 68 2003 3923 3931 and references therein
43. F. Bernardi, M. Garavelli, M. Scatizzi, C. Tomasini, V. Trigari, M. Crisma, F. Formaggio, C. Peggion, and C. Toniolo Chem. Eur. J. 8 2002 2516 2525
44. C. Tomasini, and M. Villa Tetrahedron Lett. 42 2001 5211 5214
45. P. Dumy, M. Keller, D.E. Ryan, B. Rohwedder, T. Wöhr, and M. Mutter J. Am. Chem. Soc. 119 1997 918 925
46. M. Keller, C. Sager, P. Dumy, M. Schutkowski, G.S. Fischer, and M. Mutter J. Am. Chem. Soc. 120 1998 2714 2720
47. G. Chaume, N. Lensen, C. Caupène, and T. Brigaud Eur. J. Org. Chem. 2009 5717 5724
48. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
49. M. Salwiczek, E.K. Nyakatura, U.I.M. Gerling, S. Ye, and B. Koksch Chem. Soc. Rev. 41 2012 2135 2171
50. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley-Blackwell New York
51. R. Smits, C.D. Cadicamo, K. Burger, and B. Koksch Chem. Soc. Rev. 37 2008 1727 1739 and references therein
52. T. Brigaud, G. Chaume, J. Pytkowicz, and F. Huguenot Chim. Oggi. 25 2007 8 10
53. B. Koksch, N. Sewald, H.-J. Hofmann, K. Burger, and H.-D. Jakubke J. Pept. Sci. 3 1997 157 167
54. C. Jaeckel, and B. Koksch Eur. J. Org. Chem. 2005 4483 4503
55. N.C. Yoder, and K. Kumar Chem. Soc. Rev. 31 2002 335 341
56. H. Meng, and K. Kumar J. Am. Chem. Soc. 129 2007 15615 15622
57. M. Molteni, C. Pesenti, M. Sani, A. Volonterio, and M. Zanda J. Fluorine Chem. 125 2004 1335 1743
58. M. Zanda New J. Chem. 28 2004 1401 1411
59. L. Merkel, and N. Budisa Org. Biomol. Chem. 10 2012 7241 7261
60. P.K. Mykhailiuk, S. Afonin, G.V. Palamarchuk, O.V. Shishkin, A.S. Ulrich, and I. Komarov Angew. Chem. Int. Ed. 47 2008 5765 5767
61. S.L. Grage, U.H.N. Duerr, S. Afonin, P.K. Mikhailiuk, I.V. Komarov, and A.S. Ulrich J. Magn. Reson. 191 2008 16 23
62. P.K. Mikhailiuk, S. Afonin, A.N. Chernega, E.B. Rusanov, M.O. Platonov, G.G. Dubinina, M. Berditsch, A.S. Ulrich, and I.V. Komarov Angew. Chem. Int. Ed. 45 2006 5659 5661
63. Y. Cury, G. Picolo, V.P. Gutierrez, and S.H. Ferreira Nitric Oxide 25 2011 243 254
64. T.R. Romero, L.C. Resende, and I.D. Duarte Nitric Oxide 25 2011 431 435
65. A. Bocheva, E. Dzambazova, B. Landzhov, and A. Bozhilova-Pastirova C. R. Acad. Bulg. Sci. 61 2008 535 542
66. E.P. Huang Curr. Biol. 7 1997 R141 R143
67. P. Vander Elst, M. Elseviers, E. De Cock, M. Van Marsenille, D. Tourwe, and G. Van Binst Int. J. Pept. Protein Res. 27 1986 633 642