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Falck, J.R. et al.

John R. Falck, Gerd Wallukat, Narender Puli, Mohan Goli, Cosima Arnold, Anne Konkel, Michael Rothe, Robert Fischer, Dominik N. Müller, Wolf-Hagen Schunck,

17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.

17(R),18(S)-epoxyeicosatetraenoic acid [17(R),18(S)-EETeTr], a cytochrome P450 epoxygenase metabolite of eicosapentaenoic acid (EPA), exerts negative chronotropic effects and protects neonatal rat cardiomyocytes against Ca(2+)-overload with EC(50) ≈ 1-2 nM. Structure-activity studies revealed that a cis-Δ(11,12)- or Δ(14,15)-olefin and a 17(R),18(S)-epoxide are minimal structural elements for antiarrhythmic activity whereas antagonist activity was often associated with the combination of a Δ(14,15)-olefin and a 17(S),18(R)-epoxide. Compared with natural material, the agonist and antagonist analogues are chemically and metabolically more robust and several show promise as templates for future development of clinical candidates.[1]

References

17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues. Falck, J.R., Wallukat, G., Puli, N., Goli, M., Arnold, C., Konkel, A., Rothe, M., Fischer, R., Müller, D.N., Schunck, W.H. J. Med. Chem. (2011) [Pubmed]

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