Skip to main content

Recent Advances in the Chemistry and Biology of Stable Synthetic Lipoxin Analogues

  • Chapter
  • First Online:
Heteroaromatic Lipoxin A4 Analogues

Part of the book series: Springer Theses ((Springer Theses))

  • 296 Accesses

Abstract

The Lipoxin metabolites dramatically reduce the bioactivity of this class of compounds and render them poor potential pharmacological agents. In light of the findings associated with the stabilisation and market value of the synthetic prostaglandin and prostacyclin analogues, it was thought that a similar approach could be beneficial with respect to the native Lipoxins (LX).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Collins PW, Djuric SW (1993) Chem Rev 93:1533

    Article  CAS  Google Scholar 

  2. Phillips ED, Chang H-F, Holmquist CR, McCauley JP (2003) Bioorg Med Chem Lett 13:3223

    Article  CAS  Google Scholar 

  3. O’Sullivan TP, Vallin KSA, Shah STA, Fakhry J, Maderna P, Scannell M, Sampaio ALF, Perretti M, Godson C, Guiry PJ (2007) J Med Chem 50:5894

    Article  Google Scholar 

  4. Petasis NA, Keledjian R, Sun Y-P, Nagulapalli KC, Tjonahen E, Yang R, Serhan CN (2008) Bioorg Med Chem Lett 18:1382

    Article  CAS  Google Scholar 

  5. Guilford WJ, Bauman JG, Skuballa W, Bauer S, Wei GP, Davey D, Schaefer C, Mallari C, Terkelsen J, Tseng J-L, Shen J, Subramanyam B, Schottelius AJ, Parkinson JF (2004) J Med Chem 47:2157

    Article  CAS  Google Scholar 

  6. Nicolaou KC, Ramphal JY, Petasis NA, Serhan CN (1991) Angew Chem Int Ed Engl 30:1100

    Article  Google Scholar 

  7. Petasis NA, Akritopoulou-Zanze I, Fokin VV, Bernasconi G, Keledjian R, Yang R, Uddin J, Nagulapalli KC, Serhan CN (2005) Prostaglandins Leukot Essent Fat Acids 73:301

    Article  CAS  Google Scholar 

  8. Serhan CN, Maddox JF, Petasis NA, Akritopoulou-Zanze I, Papayianni A, Brady HR, Colgan SP, Madara JL (1995) Biochemistry 34:14609–14615

    Article  CAS  Google Scholar 

  9. Webber SE, Veale CA, Nicolaou KC (1988) Adv Exp Med Biol 229:61

    CAS  Google Scholar 

  10. Clish CB, O’Brien JA, Gronert K, Stahl GL, Petasis NA, Serhan CN (1999) Proc Natl Acad Sci U S A 96:8247

    Article  CAS  Google Scholar 

  11. Fierro IM, Kutok JL, Serhan CN (2002) J Pharmacol Exp Ther 300:385

    Article  CAS  Google Scholar 

  12. Rodríguez AR, Spur BW (2001) Tetrahedron Lett 42:6057

    Article  Google Scholar 

  13. Nicolaou KC, Veale CA, Webber SE, Katerinopoulos H (1985) J Am Chem Soc 107:7515

    Article  CAS  Google Scholar 

  14. Boland W, Schroer N, Sieler C, Feigel M (1987) Helv Chim Acta 70:1025

    Article  CAS  Google Scholar 

  15. Takano T, Fiore S, Maddox JF, Brady HR, Petasis NA, Serhan CN (1997) J Exp Med 185:1693

    Article  CAS  Google Scholar 

  16. Duffy CD, Maderna P, McCarthy C, Loscher CE, Godson C, Guiry PJ (2010) Chem Med Chem 5:517

    CAS  Google Scholar 

  17. Singh S, Duffy CD, Shah STA, Guiry PJ (2008) J Org Chem 7:6429

    Article  Google Scholar 

  18. Singh S, Guiry PJ (2009) Eur J Org Chem

    Google Scholar 

  19. Singh S, Guiry PJ (2009) J Org Chem 74:5758

    Article  CAS  Google Scholar 

  20. Maderna P, Cottell DC, Berlasconi G, Petasis NA, Brady HR, Godson C (2002) Am J Pathol 160:2275

    Article  CAS  Google Scholar 

  21. Maddox JF, Serhan CN (1996) J Exp Med 183:137

    Article  CAS  Google Scholar 

  22. Maddox JF, Hachicha M, Takano T, Petasis NA, Fokin VV, Serhan CN (1997) J Biol Chem 272:6972

    Article  CAS  Google Scholar 

  23. Chiang N, Serhan C, Dahlén S-E, Drazen JM, Hay DWP, Rovati GN, Shimizu T, Yokomiao T, Brink C (2006) Pharmacol Rev 58:463

    Article  CAS  Google Scholar 

  24. Bannenberg G, Moussignac R-L, Gronert K, Devchand PR, Schmidt BA, Guilford WJ, Bauman JG, Subramanyam B, Perez HD, Parkinson JF, Serhan CN (2004) Br J Pharmacol 143:43

    Article  CAS  Google Scholar 

  25. Sun Y-P, Tjonahen E, Keledjian R, Zhu M, Yang R, Recchiuti A, Pillai PS, Petasis NA, Serhan CN (2009) Prostaglandins Leukot Essent Fat Acids 81:357

    Article  CAS  Google Scholar 

  26. Nicolaou KC, Webber SE (1984) J Am Chem Soc 106:5734

    Article  CAS  Google Scholar 

  27. Midland MM, McDowell DC, Hatch RL, Tramontano A (1980) J Am Chem Soc 102:867

    Article  CAS  Google Scholar 

  28. Petasis NA, Bzowej EI (1990) J Am Chem Soc 112:6392

    Article  CAS  Google Scholar 

  29. Jeffery T (1996) Tetrahedron 52:10113

    Article  CAS  Google Scholar 

  30. Soundararajan R, Matteson DS (1990) J Org Chem 55:2274

    Article  CAS  Google Scholar 

  31. Petasis NA, Zavialov IA (1996) Tetrahedron Lett 37:567

    Article  CAS  Google Scholar 

  32. Hong S, Gronert K, Devchand PR, Moussignac R-L, Serhan CN (2003) J Biol Chem 278:14677

    Article  CAS  Google Scholar 

  33. Serhan CN, Hong S, Gronert K, Colgan SP, Devchand PR, Mirick G, Moussignac R-L (2002) J Exp Med 196:1025

    Article  CAS  Google Scholar 

  34. Sodin-Semrl S, Taddeo B, Tseng D, Varga J, Fiore S (2000) J Immunol 164:2660

    CAS  Google Scholar 

  35. Samuelsson B, Dahlen SE, Lindgren JA, Rouzer CA, Serhan CN (1987) Science 237:1171

    Article  CAS  Google Scholar 

  36. Ellis CK, Smigel MD, Oates JA, Oelz O, Sweetman BJ (1979) J Biol Chem 254:4152

    CAS  Google Scholar 

  37. Guindon Y, Delorme D, Lau CK, Zamboni R (1988) J Org Chem 53:267

    Article  CAS  Google Scholar 

  38. Robinson RA, Clark JS, Holmes AB (1993) J Am Chem Soc 115:10400

    Article  CAS  Google Scholar 

  39. Schottelius AJ, Giesen C, Asadullah K, Fierro IM, Colgan SP, Bauman J, Guilford W, Perez HD, Parkinson JF (2002) J Immunol 169:7063

    CAS  Google Scholar 

  40. Fiorucci S, Wallace JL, Mencarelli A, Distrutti E, Rizzo G, Farneti S, Morelli A, Tseng J-L, Suramanyam B, Guilford WJ, Parkinson JF (2004) Proc Natl Acad Sci U S A 101:15736

    Google Scholar 

  41. Guilford WJ, Parkinson JF (2005) Prostaglandins Leukot Essent Fat Acids 73:245

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Colm Duffy .

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Duffy, C. (2012). Recent Advances in the Chemistry and Biology of Stable Synthetic Lipoxin Analogues. In: Heteroaromatic Lipoxin A4 Analogues. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-24632-6_2

Download citation

Publish with us

Policies and ethics