Skip to main content
SpringerLink
Log in

Calix[4]arenes C-136 and C-137 hyperpolarize myometrium mitochondria membranes

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

Abstract

Calixarenes are supramolecular compounds interacting with bioactive molecules and ions, causing changes in biochemical and biophysical processes. The aim of this work was to study the effects of calix[4]arenes C-136, C-137, and C-138 at the level of polarization of the rat myometrium mitochondria membrane. The structure of synthesized calix[4]arene molecules was confirmed by the methods of 1H NMR and infrared spectroscopy. Calix[4]arenes C-136 and C-137 each possess two chalcone amide moieties at the lower rim, while calix[4]arene C-138, only one. Calix[4]arenes C-136 and C-137 differ by the presence of ether or hydroxyl groups, respectively, at the lower rim of calix[4]arene skeleton, as well as the length of alkyl spacer between chalcone amide group and the macrocycle. It was shown that calix[4]arenes C-136, C-137, and C-138 form micelles in aqueous medium and in dimethylformamide (DMF). Irradiation of micelles with an argon laser on the flow cytometer results in the rise of autofluorescence. In an aqueous medium, calix[4]arene micelles interact with a positively charged voltage-sensitive fluorescent probe TMRM, which can testify to the presence of negative charge in these structures. However, calix[4]arene micelles do not interact with TMRM in DMF solution. The mitochondrial membrane potential was measured using fluorescent dyes MTG and TMRM with confocal microscopy and fluorescent dye TMRM with flow cytometry. Experiments were conducted on myometrium cells in culture and on suspension of digitonin-permeabilized uterus myocytes. It was shown that the fluorescent signal was stable during the time of experiment. Calix[4]arenes C-136 and C-137 (10 μM) hyperpolarize mitochondria membranes. At maximum, the effect was 173% relative to the control. At the same time, calix[4]arene C-138 did not influence the mitochondria membrane potential. The relationship between the structural organization of investigated calix[4]arene molecules and their effect on polarization of the mitochondria membrane is discussed.

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

CCCP:

carbonyl cyanide m-chlorophenylhydrazone

DMEM:

Dulbecco’s modified Eagle’s medium

DMF:

dimethylformamide

FBS:

fetal bovine serum

MTG:

MitoTracker Green

TMRM:

tetramethylrhodamine methyl ether

C[4]A:

calix[4]arenes

References

  1. Duchen, M.R., Mol. Aspects Med., 2004, vol. 4, pp. 365–451.

    Article  Google Scholar 

  2. Nicholls, D.G., Cell Calcium, 2005, vol. 38, pp. 311–317.

    Article  PubMed  CAS  Google Scholar 

  3. Kostyuk, P.G., Kostyuk, O.P., and Luk’yanets’, O.O., Calcium Ions and Brain Functions: From Physiology to Pathology, Kyiv: Naukova dumka, 2005.

    Google Scholar 

  4. Divakaruni, A.S. and Brand, M.D., Physiology (Bethesda), 2011, vol. 26, pp. 192–205.

    Article  CAS  Google Scholar 

  5. Scatena, R., Adv. Exp. Med. Biol., 2012, vol. 942, pp. 329–346.

    Article  PubMed  CAS  Google Scholar 

  6. Gutsche, C.D., Calixarenes Revisited, Cambridge: The Royal Society of Chemistry, 1998.

    Google Scholar 

  7. Gutshe, C.D. and Igbal, M., Org. Synt., 1990, vol. 68, pp. 234–236.

    Google Scholar 

  8. Rodic, R.V., Boyko, V.I., and Kalchenko, V.I., Carr. Med. Chem., 2009, vol. 16, pp. 1630–1655.

    Article  Google Scholar 

  9. Klyachina, M.A., Boyko, V.I., Yakovenko A.V., Babich L.G., Shlykov S.G., Kosterin S.O., Khilya V.P., and Kalchenko V.I, J. Inclus. Phenom. Macrocycl. Chem., 2008, vol. 60, pp. 131–137.

    Article  CAS  Google Scholar 

  10. Iwamoto, K. and Shinkai, S., Org. Chem., 1992, vol. 57, pp. 7066–7073.

    Article  CAS  Google Scholar 

  11. Ehrenberg, B., Montana, V., Wei, M.D., Wuskell, J.P., and Loew, L.M., Biophys. J., 1988, vol. 53, pp. 785–794.

    Article  PubMed  CAS  Google Scholar 

  12. Mattiasson, G., Cytometry A, 2004, vol. 60, pp. 145–154.

    Article  PubMed  Google Scholar 

  13. Antonenko, Y.N., Avetisyan, A.V., Cherepanov, D.A., Knorre, D.A., Korshunova, G.A., Markova, O.V., Ojovan, S.M., Perevoshchikova, I.V., Pustovidko, A.V., Rokitskaya, T.I., Severina, I.I., Simonyan, R.A., Smirnova, E.A., Sobko, A.A., Sumbatyan, N.V., Severin, F.F., and Skulachev, V.P., J. Biol. Chem., 2011, vol. 286, pp. 17831–17840.

    Article  PubMed  CAS  Google Scholar 

  14. Hockenbery, D.M., Environ. Mol. Mutagen., 2010, vol. 51, pp. 476–489.

    Article  PubMed  CAS  Google Scholar 

  15. Skulachev, V.P., Apoptosis, 2006, vol. 11, pp. 473–485.

    Article  PubMed  CAS  Google Scholar 

  16. Giovannini, C., Matarrese, P., Scazzocchio, B., Sanchez, M., Masella, R., and Malorni, W., FEBS Lett., 2002, vol. 523, pp. 200–206.

    Article  PubMed  CAS  Google Scholar 

  17. Sommer, S.P., Sommer, S., Sinha, B., Wiedemann, J., Otto, C., Aleksic, I., Schimmer, C., and Leyh, R.G., J. Heart. Lung Transplant., 2011, vol. 30, pp. 811–818.

    Article  PubMed  Google Scholar 

  18. Ralph, S.J., Low, P., Dong, L., Lawen, A., and Neuzil, J., Recent Pat. Anticancer Drug Discov., 2006, vol. 1, pp. 327–346.

    Article  PubMed  CAS  Google Scholar 

  19. Babich, L.G., Shlykov, S.G., Borisova, L.A., and Kosterin, S.O., Biokhimiya, 1994, vol. 59, pp. 1218–1229.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Palladin Institute of Biochemistry, National Academy of Sciences of Ukraine, ul. Leontovicha 9, Kiev, 01601, Ukraine

    L. G. Babich, S. G. Shlykov & S. A. Kosterin

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanska 5, Kiev, 02660, Ukraine

    V. I. Boyko & M. A. Klyachina

Authors
  1. L. G. Babich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Shlykov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Boyko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. A. Klyachina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. A. Kosterin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. G. Babich.

Additional information

Original Russian Text © L.G. Babich, S.G. Shlykov, V.I. Boyko, M.A. Klyachina, S.A. Kosterin, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 6, pp. 728–735.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Babich, L.G., Shlykov, S.G., Boyko, V.I. et al. Calix[4]arenes C-136 and C-137 hyperpolarize myometrium mitochondria membranes. Russ J Bioorg Chem 39, 649–655 (2013). https://doi.org/10.1134/S1068162013050026

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162013050026

Keywords

Search

Navigation