Skip to main content

The solid-state catalytic isotope exchange of hydrogen in dalargin

Abstract

A [3H]Dalargin preparation with a molar radioactivity of 52 Ci/mmol was obtained by the high temperature solid-state catalytic isotope exchange (HSCIE) of tritium for hydrogen at 150°C. This tritium-labeled peptide was shown to completely retain its biological activity in the test of binding to opioid receptors from rat brain. The dissociation constant of the Dalargin-opioid receptor complex was found to be 4.3 nM. The dependences of the chemical yield and the molar radioactivity on the reaction time and temperature of HSCIE were determined. The activation energy of the HSCIE reaction for the peptide was calculated to be 32 kcal/mol. The amino acid analysis showed that tritium is distributed between all the amino acid residues of [3H]Dalargin at the HSCIE reaction, with the temperature growth significantly increasing the total tritium incorporation and, especially, enhancing the radioactivity incorporation into aromatic residues.

This is a preview of subscription content, access via your institution.

Abbreviations

DALG:

Dalargin, Tyr-D-Ala-Gly-Phe-Leu-Arg

DADLE:

[D-Ala2,D-Leu5]enkephalin

HSCIE:

high temperature solid state catalytic isotope exchange

OR:

opioid receptors

RRA:

radioreceptor assay

HS:

hydrogen spillover

References

  1. Zolotarev, Yu.A., Petrenik, B.V., Myasoedov, N.F., Bespalova, Zh.D., Molokoedov, A.S., and Yarygin, K.I.,Bioorg. Khim., 1982, vol. 8, pp. 1615–1619.

    Google Scholar 

  2. Darula, Z., Peter, A., and Toth, G.,J. Labelled Compd. Radiopharm., 1998, vol. 29, pp. 817–826.

    Google Scholar 

  3. Zolotarev, Yu.A., Kozik, V.S., Zaitsev, D.A., Dorokhova, E.M., and Myasoedov, N.F.,Dokl. Akad. Nauk SSSR, 1989, vol. 308, pp. 1146–1151.

    CAS  Google Scholar 

  4. Zolotarev, Yu.A., Kozic, V.S., Dorokhova, E.M., Zaitsev, D.A., and Myasoedov, N.F.,J. Radioanal. Nucl. Chem. Art., 1992, vol. 162, pp. 3–14.

    Article  CAS  Google Scholar 

  5. Sermon, P.A. and Bond, D.C.,Catalysis Reviews, 1973, vol. 8, pp. 211–245.

    Article  CAS  Google Scholar 

  6. Zolotarev, Yu.A., Borisov, Yu.A., and Myasoedov, N.F.,J. Phys. Chem., 1999, vol. 103, pp. 4861–4864.

    CAS  Google Scholar 

  7. Zolotarev, Yu.A., Laskatelev, E.V., Dorokhova, E.M., Borisov, Yu.A., and Myasoedov, N.F.,Izv. Ross. AN, Ser. Khim., 1997, no. 8, pp. 1611–1617.

  8. Zozulya, A.A., Kost, N.V., Toropov, A.V., Meshavkin, V.K., Butenko, O.B., and Barsegyan, G.G.,Immunologiya, 1996, vol. 5, pp. 25–29.

    Article  Google Scholar 

  9. Zozulya, A.A., Meshavkin, V.K., Toropov, A.V., Gurevich, K.G., and Kost, N.V.,Byull. Eksp. Biol. Med., 1999, vol. 127, pp. 211–214.

    Article  Google Scholar 

  10. Pencheva, N., Bocheva, A., Dimitrov, E., Ivancheva, C., and Radomirov, R.,Eur. J. Pharmacol., 1996, vol. 304, pp. 99–108.

    PubMed  Article  CAS  Google Scholar 

  11. Leslie, F.M.,Pharmacol. Rev., 1987, vol. 39, pp. 197–249.

    PubMed  CAS  Google Scholar 

  12. Zolotarev, Yu.A., Dorokhova, E.M., Nezavibatko, V.N., Borisov, Yu.A., Rosenberg, S.G., and Myasoedov, N.F.,Amino Acids, 1995, vol. 8, pp. 353–365.

    Article  CAS  Google Scholar 

  13. Simantov, R., Childers, S.R., and Snyder, S.H.,Eur. J. Pharmacol., 1978, vol. 47, pp. 319–331.

    PubMed  Article  CAS  Google Scholar 

  14. Bradford, M.M.,Anal. Biochem., 1976, vol. 72, pp. 248–254.

    PubMed  Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. A. Zolotarev.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Zolotarev, Y.A., Dadayan, A.K., Vas’kovskii, B.V. et al. The solid-state catalytic isotope exchange of hydrogen in dalargin. Russ J Bioorg Chem 26, 457–460 (2000). https://doi.org/10.1007/BF02758615

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02758615

Key words

  • Dalargin
  • enkephalins
  • hydrogen isotope exchange
  • hydrogen spillover
  • opioid receptors