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An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues

Abstract

A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me4-BODIPY) fluorophore at co-position of fatty acid residue was carried out. The key stage of the synthesis is hydrolysis of corresponding sphingomyelins catalyzed by phospholipase D from Streptomyces chromofuscus; the enzymatic yield has been raised to 50–70% by appliance of organic solvent in the incubation medium.

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Abbreviations

AV:

9-anthrylvinyl

C1P:

ceramide-1-phosphate

DIPEA:

diisopropylethylamine

Me4BODIPY:

4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl

PLD:

phospholipase D

SM:

sphingomyelin

References

  1. Bajjalieh, S.M., Martin, T.F.J., and Floor, E., J. Biol. Chem., 1989, vol. 264, pp. 14354–14360.

    PubMed  CAS  Google Scholar 

  2. Gómez-Muñoz, A., FEBS Letters, 2004, vol. 562, pp. 5–10.

    PubMed  Article  Google Scholar 

  3. Fyrst, H. and Saba, J.D., Nat. Chem. Biol., 2010, vol. 6, pp. 489–497.

    PubMed  Article  CAS  Google Scholar 

  4. Bornancin, F., Cell. Signal., 2011, vol. 23, pp. 999–1008.

    PubMed  Article  CAS  Google Scholar 

  5. Byun, H.-S., Erukulla, R.K., and Bittman, R., J. Org. Chem., 1994, vol. 59, pp. 6495–6498.

    Article  CAS  Google Scholar 

  6. Szulc, Z.M., Hannun, Y.A., and Bielawska, A., Tetrahedron Lett., 2000, vol. 41, pp. 7821–7824.

    Article  CAS  Google Scholar 

  7. Nussbaumer, P., Hornillos, V., Ghobrial, M., and Ullrich, T., Chem. Phys. Lipids, 2008, vol. 151, pp. 125–128.

    PubMed  Article  CAS  Google Scholar 

  8. Schneider, E.G. and Kennedy, E.P., J. Biol. Chem., 1973, vol. 248, pp. 3739–3741.

    PubMed  CAS  Google Scholar 

  9. Preiss, J., Loomis, C.R., Bishop, W.R., Stein, R., Niedel, J.E., and Bell, R.M., J. Biol. Chem., 1986, vol. 261, pp. 8597–8600.

    PubMed  CAS  Google Scholar 

  10. Don, A.S. and Rosen, H., Anal. Biochem., 2008, vol. 375, pp. 265–271.

    PubMed  Article  CAS  Google Scholar 

  11. Gómez-Muñoz, A., Frago, L.M., Alvarez, L., and Varela-Nieto, I., Biochem. J., 1997, vol. 325, pp. 435–440.

    PubMed  Google Scholar 

  12. Tauzin, L., Graf, C., Sun, M., Rovina, P., Bouveyron, N., Jaritz, M., Winiski, A., Hartmann, N., Staedtler, F., Billich, A., Baumruker, T., Zhang, M., and Bornancin, F., J. Lipid, Res., 2007, vol. 48, pp. 66–76.

    Article  CAS  Google Scholar 

  13. Heller, M., Adv. Lipid Res., 1978, vol. 16, pp. 267–326.

    PubMed  CAS  Google Scholar 

  14. Davidson, F.M. and Long, C., Biochem. J., 1958, vol. 69, pp. 458–466.

    PubMed  CAS  Google Scholar 

  15. Selvy, P.E., Lavieri, R.R., Lindsley, C.W., and Brown, H.A., Chem. Rev., 2011, vol. 111, pp. 6064–6119.

    PubMed  Article  CAS  Google Scholar 

  16. Imamura, S. and Horiuti, Y., J. Biochem., 1979, vol. 85, pp. 79–95.

    PubMed  CAS  Google Scholar 

  17. Estrada, R., Stolowich, N., and Yappert, M.C., Anal. Biochem., 2008, vol. 380, pp. 41–50.

    PubMed  Article  CAS  Google Scholar 

  18. Uesugi, Y. and Hatanaka, T., Biochim. Biophys. Acta, 2009, vol. 1791, pp. 962–969.

    PubMed  Article  CAS  Google Scholar 

  19. Molotkovsky, J.G., Manevich, Y.M., Babak, V.I., and Bergelson, L.D., Biochim. Biophys. Acta, 1984, vol. 778, pp. 281–288.

    Article  Google Scholar 

  20. Boldyrev, I.A. and Molotkovsky, J.G., Russ. J. Bioorg. Chem., 2006, vol. 32, pp. 78–83.

    Article  CAS  Google Scholar 

  21. El Kirat, K., Prigent, A.F., Chauvet, J.P., Roux, B., and Besson, F., Eur. J. Biochem., 2003, vol. 270, pp. 4523–4530.

    PubMed  Article  Google Scholar 

  22. Hirche, F. and Ulbrich-Hofmann, R., Biochim. Biophys. Acta, 1999, vol. 1436, pp. 383–389.

    PubMed  Article  CAS  Google Scholar 

  23. Sachl, R., Boldyrev, I., and Johansson, L., Phys. Chem. Chem. Phys., 2010, vol. 12, pp. 6027–6034.

    PubMed  Article  CAS  Google Scholar 

  24. Bittman, R. and Verbicky, C.A., J. Lipid Res., 2000, vol. 41, pp. 2089–2093.

    PubMed  CAS  Google Scholar 

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Correspondence to J. G. Molotkovsky.

Additional information

Published in Russian in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 5, pp. 604–608.

The article was translated by the authors.

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Boldyrev, I.A., Brown, R.E. & Molotkovsky, J.G. An expedient synthesis of fluorescent labeled ceramide-1-phosphate analogues. Russ J Bioorg Chem 39, 539–542 (2013). https://doi.org/10.1134/S106816201305004X

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  • DOI: https://doi.org/10.1134/S106816201305004X

Keywords

  • fluorescent lipid probes
  • ceramide-1-phosphate
  • BODIPY
  • anthrylvinyl
  • synthesis
  • phospholipase D