Skip to main content
SpringerLink
Log in

Synthesis of 19-substituted steroids of the 16α,17α-cyclohexanopregnane series and study of their interactions with rat uterine cytosol and blood serum proteins

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New 16α,17α-cyclohexanopregnanes (pregna-D′6-pentaranes) containing alkyl or heteroatomic substituents in position 19, namely, 19-methylidene-, 19-methyl-, 19-methoxyimino-, and 19-(3-methoxycarbonylpropoxyimino)-16α,17α-cyclohexanopregn-4-ene-3,20-diones were synthesized, and their interactions with the progesterone receptor and pentarane-binding proteins of rat uterus cytosol and rat blood serum was studied. The same substituent in position 19 of the steroid molecule can affect in opposite direction its affinity to these proteins. These results suggest differences in the structures of the ligand-binding pockets of the three proteins in the region surrounding the C(10) atom of the steroid nucleus.

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

References

  1. A. V. Kamernitsky, I. S. Levina, Bioorgan. Khim., 2005, 31, 115 [Russ. J. Bioorg. Chem., 2005, 31, 115 (Engl. Transl.)].

    Google Scholar 

  2. A. V. Kamernitsky, I. S. Levina, Bioorgan. Khim., 2005, 31, 227 [Russ. J. Bioorg. Chem., 2005, 31, 227 (Engl. Transl.)].

    Google Scholar 

  3. T. A. Shchelkunova, P. M. Rubtsov, I. S. Levina, A. V. Kamernitsky, and A. N. Smirnov, Steroids, 2002, 67, 323.

    Article  CAS  Google Scholar 

  4. G. Teutsch and D. Philibert, Human Reprod., 1994, 9,Suppl. 1, 12.

    CAS  Google Scholar 

  5. A. N. Smirnov, Ross. Fiziol. Zhurn. im. I. M. Sechenova [I. M. Sechenov Russ. Physiol. J.], 1999, 85, 601 (in Russian).

    CAS  Google Scholar 

  6. E. V. Pokrovskaya, I. S. Levina, L. E. Kulikova, A. V. Kamernitsky, A. N. Smirnov, Bioorgan. Khim., 2004, 30, 301 [Russ. J. Bioorg. Chem., 2004, 30, 268 (Engl. Transl.)].

    Google Scholar 

  7. I. S. Levina, A. V. Kamernitsky, L. E. Kulikova, Izv. Akad. Nauk SSSR. Ser. Khim., 1990, 1636 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1486 (Engl. Transl.)].

  8. G. J. Martin and M. L. Martin, Progr. Nucl. Magn. Reson. Spectrosc., 1972, 8, 195, 243.

    Article  Google Scholar 

  9. J. Fajkos, V. Pouzar, and K. Veres, Collect. Czech. Chem. Commun., 1990, 55, 2086.

    CAS  Google Scholar 

  10. I. S. Levina, L. E. Kulikova, A. V. Kamernitsky, A. S. Shashkov, A. N. Smirnov, and E. V. Pokrovskaya, Izv. Akad. Nauk. Ser. Khim., 2002, 649 [Russ. Chem. Bull., Int. Ed., 2002, 51, 703].

    Google Scholar 

  11. R. M. Khomutov, M. Ya. Karpeiskii, and E. S. Severin, Izv. Akad. Nauk SSSR. Ser. Khim., 1962, 1074 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1962, 11 (Engl. Transl.)].

    Google Scholar 

  12. A. V. Kamernitsky, I. S. Levina, L. E. Kulikova, T. N. Galakhova, V. P. Shevchenko, I. Yu. Nagaev, N. F. Myasoedov, A. N. Smirnov, E. V. Pokrovskaya, and T. A. Shchelkunova, Izv. Akad. Nauk. Ser. Khim., 1997, 1532 [Russ. Chem. Bull., 1997, 46, 1468 (Engl. Transl.)].

    Google Scholar 

  13. A. N. Smirnov, A. R. Yakovenko, I. S. Levina, and A. V. Kamernitsky, Biokhimiya, 1996, 61, 1460 [Biochemistry (Moscow), 1996, 61, 1034 (Engl. Transl.)].

    CAS  Google Scholar 

  14. G. Bray, Analyt. Biochem., 1960, 1, 279.

    CAS  Google Scholar 

  15. M. M. Bradford, Analyt. Biochem., 1976, 72, 248.

    CAS  Google Scholar 

  16. A. N. Smirnov, E. V. Pokrovskaya, G. S. Kogteva, V. P. Shevchenko, I. S. Levina, L. E. Kulikova, and A. V. Kamernitsky, Steroids, 2000, 65, 163.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. S. Levina, L. E. Kulikova & A. V. Kamernitsky

  2. Department of Biology, M. V. Lomonosov Moscow State University, 1 Leninskie gory, 119992, Moscow, Russian Federation

    E. V. Pokrovskaya & A. N. Smirnov

Authors
  1. I. S. Levina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. E. Kulikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kamernitsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. V. Pokrovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. N. Smirnov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2579–2584, November, 2005.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Levina, I.S., Kulikova, L.E., Kamernitsky, A.V. et al. Synthesis of 19-substituted steroids of the 16α,17α-cyclohexanopregnane series and study of their interactions with rat uterine cytosol and blood serum proteins. Russ Chem Bull 54, 2664–2670 (2005). https://doi.org/10.1007/s11172-006-0174-6

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-006-0174-6

Key words

Search

Navigation