Skip to main content
SpringerLink
Log in

Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

The convergent synthesis of biosynthetic precursors of brassinosteroids with a Δ2-bond in cycle A—secasterol and 24-episecasterol—was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Δ22-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

(DHQD)2-PHAL:

hydroquinidine 1,4-phthalazinediyl diether

MTT:

3-(4,5-dimethylthiazolyl-2)-2,5 diphenyltetrazolium bromide

References

  1. Khripach, V.A., Zhabinskii, V.N., and de Groot, A., Brassinosteroids: A New Class of Plant Hormones, San Diego: Academic, 1999.

    Google Scholar 

  2. Wachsman, M.B., Lopez, E.M.F., Ramirez, J.A., Galagovsky, L.R., and Coto, C.E., Antivir. Chem. Chemother., 2000, vol. 11, pp. 71–77.

    CAS  PubMed  Google Scholar 

  3. Talarico, L.B., Ramirez, J.A., Galagovsky, L.R., and Wachsman, M.B., Med. Chem. Res., 2002, vol. 11, pp. 434–444.

    CAS  Google Scholar 

  4. Wachsman, M.B., Ramírez, J.A., Galagovsky, L.R., and Coto, C.E., Antivir. Chem. Chemother., 2002, vol. 13, pp. 61–66.

    CAS  PubMed  Google Scholar 

  5. Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., and Coto, C.E., Curr. Med. Chem. Anti-Infect. Agents, 2004, vol. 3, pp. 163–179.

    Article  CAS  Google Scholar 

  6. Wachsman, M.B., Castilla, V., Talarico, L.B., Ramírez, J.A., Galagovsky, L.R., and Coto, C.E., Int. J. Antimicrob. Agents, 2004, vol. 23, pp. 524–526.

    Article  CAS  PubMed  Google Scholar 

  7. Castilla, V., Larzabal, M., Sgalippa, N.A., Wachsman, M.B., and Coto, C.E., Antiviral Res., 2005, vol. 68, pp. 88–95.

    Article  CAS  PubMed  Google Scholar 

  8. Talarico, L.B., Castilla, V., Ramírez, J.A., Galagovsky, L.R., and Wachsman, M.B., Chemotherapy, 2005, vol. 52, pp. 38–42.

    Article  PubMed  Google Scholar 

  9. Franek, F., Eckschlager, T., and Kohout, L., Collect. Czech. Chem. Commun., 2003, vol. 68, pp. 2190–2200.

    Article  CAS  Google Scholar 

  10. Ramírez, J.A., Centurion, O.M.T., Gros, E.G., and Galagovsky, L.R., Steroids, 2000, vol. 65, pp. 329–337.

    Article  PubMed  Google Scholar 

  11. Michelini, F.M., Ramírez, J.A., Berra, A., Galagovsky, L.R., and Alche, L.E., Steroids, 2004, vol. 69, pp. 713–720.

    CAS  PubMed  Google Scholar 

  12. Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E., and Galagovsky, L.R., Bioorg. Med. Chem., 2007, vol. 15, pp. 7538–7544.

    Article  PubMed  Google Scholar 

  13. Swaczynová J., Šíša M., Hnilicková J., Kohout L., and Strnad M., Polish. J. Chem., 2006, vol. 80, pp. 629–635.

    Google Scholar 

  14. Wu, Y.D. and Lou, Y.J., Pharmazie, 2007, vol. 62, pp. 392–395.

    CAS  PubMed  Google Scholar 

  15. Malíková J., Swaczynová J., Kolár, Z., and Strnad, M., Phytochemistry, 2008, vol. 69, pp. 418–426.

    Article  PubMed  Google Scholar 

  16. Eignerova, B., Slavíkova, B., Budesínsky, M., Dracínsky, M., Klepetarova, B., Stastna, E., and Kotora, M., J. Med. Chem., 2009, vol. 52, pp. 5753–5757.

    Article  CAS  PubMed  Google Scholar 

  17. Drozdov, F.V., Mekhtiev, A.R., Morozevish, G.E., Timofeev, V.R., and Misharin, A.Yu., Bioorg. Khim., 2007, vol. 33, pp. 349–356 [Russ. J. Bioorg. Chem., 2007, vol. 33, pp. 326–333].

    CAS  PubMed  Google Scholar 

  18. Misharin, A.Y., Mekhtiev, A.R., Morozevich, G.E., Tkachev, Y.V., and Timofeev, V.P., Bioorg. Med. Chem., 2008, vol. 16, pp. 1460–1473.

    Article  CAS  PubMed  Google Scholar 

  19. Choe, S., Physiologia Plant., 2006, vol. 126, pp. 539–548.

    Article  CAS  Google Scholar 

  20. Hamdy, A.-H.A., Aboutabl, E.A., Sameer, S., Hussein, A.A., Díaz-Marrero, A.R., Darias, J., and Cueto, M., Steroids, 2009, vol. 74, pp. 927–930.

    Article  CAS  PubMed  Google Scholar 

  21. Antonchick, A.P., Schneider, B., Zhabinskii, V.N., Konstantinova, O.V., and Khripach, V.A., Phytochemistry, 2003, vol. 63, pp. 771–776.

    Article  CAS  PubMed  Google Scholar 

  22. Khripach, V.A., Zhabinskii, V.N., Ol’khovik, V.K., and Lakhvich, F.A., Zh. Org. Khim., 1990, vol. 26, pp. 1966–1976.

    CAS  Google Scholar 

  23. Sharpless, K.B., Amberg, W., Bennani, Y.L., Crispino, G.A., Hartung, J., Jeong, K.-S., Kwong, H.-L., Morikawa, K., Wang, Z.-M., Xu, D., and Zhang, X.-L., J. Org. Chem., 1992, vol. 57, pp. 2768–2771.

    Article  CAS  Google Scholar 

  24. Marino, J.P., de Dios, A., Anna, L.J., and de la Pradilla, R.F., J. Org. Chem., 1996, vol. 61, pp. 109–117.

    Article  CAS  Google Scholar 

  25. Anastasia, M., Allevi, P., Ciuffreda, P., and Oleotti, A., Steroids, 1985, vol. 45, pp. 561–564.

    Article  CAS  PubMed  Google Scholar 

  26. McMorris, T.C. and Patil, P.A., J. Org. Chem., 1993, vol. 58, pp. 2338–2339.

    Article  CAS  Google Scholar 

  27. Chang, G., Guida, W.C., and Still, W., J. Am. Chem. Soc., 1989, vol. 111, pp. 4379–4386.

    Article  CAS  Google Scholar 

  28. HyperChem™ H., Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA.

  29. Humphrey, W., Dalke, A., and Schulten, K., J. Mol. Graphics, 1996, vol. 14, pp. 33–38.

    Article  CAS  Google Scholar 

  30. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, pp. 55–63.

    Article  CAS  PubMed  Google Scholar 

  31. Tkachev, Ya.V., Mekhtiev, A.R., Nikolaeva, I.A., Zhabinskii, V.N., Khripach, V.A., Timofeev, V.P., and Misharin, A.Yu., Bioorg. Khim., 2010, vol. 36 [Russ. J. Bioorg. Chem., 2010, vol. 36] (in press).

  32. Huang, L.F., Zhou, W.S., Sun, L.Q., and Pan, X.F., J. Chem. Soc., Perkin Trans., 1993, pp. 1683–1686.

  33. Voigt, B., Takatsuto, S., Yokota, T., and Adam, G., J. Chem. Soc., Perkin Trans., 1995, pp. 1495–1498.

Download references

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220141, Belarus

    V. A. Khripach, V. N. Zhabinskii, O. V. Gulyakevich & O. V. Konstantinova

  2. Orekhovich Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, Moscow, Russia

    A. Yu. Misharin & A. R. Mekhtiev

  3. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia

    V. P. Timofeev & Ya. V. Tkachev

Authors
  1. V. A. Khripach
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. N. Zhabinskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Gulyakevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. V. Konstantinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. Yu. Misharin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. R. Mekhtiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. P. Timofeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ya. V. Tkachev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Khripach.

Additional information

Original Russian Text © V.A. Khripach, V.N. Zhabinskii, O.V. Gulyakevich, O.V. Konstantinova, A.Yu. Misharin, A.R. Mekhtiev, V.P. Timofeev, Ya.V. Tkachev, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 6, pp. 815–824.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khripach, V.A., Zhabinskii, V.N., Gulyakevich, O.V. et al. Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells. Russ J Bioorg Chem 36, 746–754 (2010). https://doi.org/10.1134/S1068162010060117

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162010060117

Keywords

Search

Navigation