Chemistry of Natural Compounds

, Volume 46, Issue 6, pp 841–847 | Cite as

Synthesis and functional pharmacological effects on human bronchi of 20-hydroxyeicosatetraenoic acid

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We have synthesized 20-hydroxyeicosatetraenoic acid (20-HETE) following a new route and delineated its functional effects in human bronchi. Isometric tension measurements were performed, and they demonstrated that synthetic 20-HETE induced a concentration-dependent relaxant effect in ASM on resting tone and on bronchi pre-contracted with methacholine.

Keywords

20-hydroxyeicosatetraenoic acid synthesis human bronchi Cu-mediated C-C bond formation histamine methacholine 
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Notes

Acknowledgment

The authors are grateful to the FMSS for financing this work via a transition grant. NSERC Canada and the Respiratory Health Network of the FRSQ Quebec are also acknowledged for supplying a PhD studentship to C.M. and support to E.R. (http://rsr.chus.qc.ca).

References

  1. 1.
    B. Escalante, D. Erlij, J. R. Falck, and J. C. McGiff, Science, 251, 799 (1991).PubMedCrossRefGoogle Scholar
  2. 2.
    R. J. Roman, Physiol. Rev., 82, 131 (2002).PubMedGoogle Scholar
  3. 3.
    D. C. Zeldin, J. D. Plitman, J. Kobayashi, R. F. Miller, J. R. Snapper, J. R. Falck, J. L. Szarek, R. M. Philpot, and J. H. Capdevila, J. Clin. Invest., 95, 2150 (1995).PubMedCrossRefGoogle Scholar
  4. 4.
    N. Miyata and R. J. Roman, J. Smooth Muscle Res., 41, 175 (2005).PubMedCrossRefGoogle Scholar
  5. 5.
    M. Cloutier, S. Campbell, N. Basora, S. Proteau, M. D. Payet, and E. Rousseau,Am. J. Physiol. Lung Cell. Mol. Physiol., 285, L560 (2003).PubMedGoogle Scholar
  6. 6.
    E. Rousseau, M. Cloutier, C. Morin, and S. Proteau, Am. J. Physiol. Lung Cell. Mol. Physiol., 288, L460 (2005).PubMedCrossRefGoogle Scholar
  7. 7.
    C. Morin, M. Sirois, V. Echave, M. M. Gomes, and E. Rousseau, Am. J. Physiol. Lung Cell. Mol. Physiol.,293, L1037 (2007).PubMedCrossRefGoogle Scholar
  8. 8.
    M. Yu, M. Alonso-Galicia, C.-W. Sun, R. J. Roman, N. Ono, H. Hirano, T. Ishimoto, Y. K. Reddy, K. R. Katipally, K. M. Reddy, V. R. Gopal, J. Yu, M. Takhi, and J. R. Falck, Bioorg. Med. Chem., 11, 2803 (2003).PubMedCrossRefGoogle Scholar
  9. 9.
    L. Qi, M. M. Meijler, S.-H. Lee, C. Sun, and K. D. Janda, Org. Lett., 6, 1673 (2004).PubMedCrossRefGoogle Scholar
  10. 10.
    R. A. Earl and K. P. Vollhardt, J. Org. Chem., 49, 4786 (1984).CrossRefGoogle Scholar
  11. 11.
    O. Dasse, A. Mahadevan, L. Han, B. R. Martin, V. Di Marzo, and R. K. Razdan, Tetrahedron, 56, 9195 (2000).CrossRefGoogle Scholar
  12. 12.
    C. Li, W. Xu, S. K. Vadivel, P. Fan, and A. Makriyannis, J. Med. Chem., 48, 6423 (2005).PubMedCrossRefGoogle Scholar
  13. 13.
    B. W. Gung, C. Gibeau, and A. Jones, Tetrahedron: Asymmetry, 16, 3107 (2005).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  1. 1.Laboratory of Supramolecular Synthesis, Department of Chemistry, Institute of PharmacologyUniversity of SherbrookeSherbrookeCanada
  2. 2.Le Biliarium, Department of Physiology and Biophysics, Faculty of Medicine and Health SciencesUniversity of SherbrookeSherbrookeCanada

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