Synthesis of all-trans anandamide: A substrate for fatty acid amide hydrolase with dual effects on rabbit platelet activation

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8359-8365

  Ferreri, Carla ^a   Anagnostopoulos, Dimitris ^b   Lykakis, Ioannis N ^a   Chatgilialoglu, Chryssostomos ^a   Siafaka Kapadai, Athanassia ^b  

^a CNR   (Italy)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Amino hydrolase; Rabbit platelet aggregation; Trans arachidonic acid; Trans lipids

Indexed keywords

ANANDAMIDE; ARACHIDONIC ACID; FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; LACTATE DEHYDROGENASE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; IC 50; NONHUMAN; RABBIT; REACTION ANALYSIS; THROMBOCYTE AGGREGATION INHIBITION; TRANS ISOMER;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACID; ARACHIDONIC ACIDS; CALCIUM CHANNEL BLOCKERS; ENDOCANNABINOIDS; ETHANOLAMINE; LIPID METABOLISM; PLATELET ACTIVATION; POLYUNSATURATED ALKAMIDES; RABBITS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

ORYCTOLAGUS CUNICULUS;

EID: 51449115236     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.054     Document Type: Article

References (48)

1. Cravatt B.F., Prospero-Garcia O., Siuzdak G., Gilula N.B., Henriksen S.J., Boger D.L., and Lerner R.A. Science 268 (1995) 1506-1509
2. Huang S.M., Bisogno T., Petros T.J., Chang S.Y., Zavitsanos P.A., Zipkin R.E., Sivakumar R., Coop A., Maeda D.Y., De P.L., Burstein S., Di M., and Walker J.M. J. Biol. Chem. 276 (2001) 42639-42644
3. Saghatelian A., and Cravatt B.F. Life Sci. 77 (2005) 1759-1766
4. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., and Mechoulam R. Science 258 (1992) 1946-1949
5. Felder C.C., Briley E.M., Axelrod J., Simpson J.T., Mackie K., and Devane W. Proc. Natl. Acad. Sci. U. S. A. 90 (1993) 7656-7660
6. Wilson R.I., and Nicoll R.A. Nature 410 (2001) 588-592
7. Marsicano G., Goodenough S., Monory K., Hermann H., Eder M., Cannich A., Azad S.C., Cascio M.G., Gutierrez S.O., van der S.M., Lopez-Rodriguez M.L., Casanova E., Schutz G., Zieglgansberger W., Di M., Behl V.C., and Lutz B. Science 302 (2003) 84-88
8. Randall M.D., Harris D., Kendall D.A., and Ralevic V. Pharmacol. Ther. 95 (2002) 191-202
9. Varga K., Wagner J.A., Bridgen D.T., and Kunos G. FASEB J. 12 (1998) 1035-1044
10. Maccarrone M., Del P.D., and Finazzi-Agrò A. Thromb. Haemost. 88 (2002) 165-166
11. Maccarrone M., Bari M., Principe D.D., and Finazzi-Agro A. Thromb. Haemost. 89 (2003) 340-347
12. Fasia L., Karava V., and Siafaka-Kapadai A. Eur. J. Biochem. 270 (2003) 3498-3506
13. Braud S., Bon C., Touqui L., and Mounier C. FEBS Lett. 471 (2000) 12-16
14. McKinney M.K., and Cravatt B.F. Annu. Rev. Biochem. 74 (2005) 411-432
15. Bari M., Battista N., Fezza F., Gasperi V., and Maccarrone M. Mini. Rev. Med. Chem. 6 (2006) 257-268
16. Razdan R.K., and Mahadevan A. Chem. Phys. Lipids 121 (2002) 21-33
17. In: Vance D.E., and Vance J.E. (Eds). Lipoproteins and Membranes (2002), Elsevier, Amsterdam
18. Chatgilialoglu C., and Ferreri C. In: Dugave C. (Ed). Fatty Acids and Phospholipids (2006), Wiley-VCH, Wienheim 92-112
19. Berdeaux O., Chardigny J.M., Sébédio J.L., Mairot T., Poullain D., Vatèle J.M., and Noël J.P. J. Lipid Res. 37 (1996) 2244-2250
20. Ferreri C., Kratzsch S., Brede O., Marciniak B., and Chatgilialoglu C. Free Radical Biol. Med. 38 (2005) 1180-1187
21. Ferreri C., Faraone-Mennella M.R., Formisano C., Landi L., and Chatgilialoglu C. Free Radical Biol. Med. 33 (2002) 1516-1526
22. Anagnostopoulos D., Chatgilialoglu C., Ferreri C., Samadi A., and Siafaka-Kapadai A. Bioorg. Med. Chem. Lett. 15 (2005) 2766-2770
23. Ferreri C., Sassatelli F., Samadi A., Landi L., and Chatgilialoglu C. J. Am. Chem. Soc. 126 (2004) 1063-1072
24. Ferreri C., Costantino C., Perrotta L., Landi L., Mulazzani Q.G., and Chatgilialoglu C. J. Am. Chem. Soc. 123 (2001) 4459-4468
25. Williams C.M., and Mander L.N. Tetrahedron 57 (2001) 425-447
26. Seltzmann H.H., Fleming D.N., Thomas B.F., Gillan A.F., McCalliom D.S., Pertwee R.G., Compton D.R., and Martin B.R. J. Med. Chem. 40 (1997) 3626-3634
27. Bender M.L. Chem. Rev. 60 (1960) 53-113
28. Rudrum M. Eur. J. Med. Res. 1 (1995) 115-117
29. Truitt A., McNeill G., and Vanderhoek J.Y. Biochim. Biophys. Acta 1438 (1999) 239-246
30. Torres-Duarte A.P., and Vanderhoek J.Y. Biochim. Biophys. Acta 1640 (2003) 69-76
31. Larque E., Zamora S., and Gil A. Early Hum. Dev. 65 (2001) S31-S41
32. Zghibeh C.M., Raj G., Poff C.D., Falck J.R., and Balazy M. Anal. Biochem. 332 (2004) 137-144
33. Zambonin L., Ferreri C., Cabrini L., Prata C., Chatgilialoglu C., and Landi L. Free Radical Biol. Med. 40 (2006) 1549-1556
34. Simopoulos A.P. Am. J. Clin. Nutr. 70 (1999) 560S-569S
35. Thijssen M.A., and Mensink R.P. Handb. Exp. Pharmacol. 170 (2005) 165-194
36. Koltai M., and Braquet P.G. Agents Actions Suppl. 37 (1992) 333-339
37. Siafaka-Kapadai A., Hanahan D.J., and Javors M.A. J. Lipid Mediat. Cell Signal. 15 (1997) 215-232
38. McCollum L., Howlett A.C., and Mukhopdhyah S. J. Pharmacol. Exp. Ther. 321 (2007) 930-937
39. Randall M.D. Br. J. Pharm. 152 (2007) 671-675
40. Watanabe K., Matsunaga T., Nakamura S., Kimura T., Ho I.K., Yoshimura H., and Yamamoto I. Biol. Pharm. Bull. 22 (1999) 366-370
41. Piomelli D., Tarzia G., Duranti A., Tontini A., Mor M., Compton T.R., Dasse O., Monaghan E.P., Parrott J.A., and Putman D. CNS Drug Rev. 12 (2006) 21-38
42. Fegley D., Gaetani S., Duranti A., Tontini A., Mor M., Tarzia G., and Piomelli D. J. Pharmacol. Exp. Ther. 313 (2005) 352-358
43. Weber A., Ni J., Ling K.H., Acheampong A., Tang-Liu D.D., Burk R., Cravatt B.F., and Woodward D. J. Lipid Res. 45 (2004) 757-776
44. Yu M., Ives D., and Ramesha C.S. J. Biol. Chem. 272 (1997) 21181-21186
45. Karava V., Zafiriou P.M., Fasia L., Anagnostopoulos D., Boutou E., Vorgias C.E., Maccarrone M., and Siafaka-Kapadai A. Biochimie 87 (2005) 967-974
46. McPartland J.M., Matias I., Di M., and Glass M. Gene 370 (2006) :64-74
47. Siafaka-Kapadai A., and Hanahan D. Biochim. Biophys. Acta 1166 (1993) 217-221
48. Lowry O.W., Rosenbrough N.J., Farr A.L., and Randall R.J. J. Biol. Chem. 193 (1951) 265-275