Advertisement

Russian Journal of Bioorganic Chemistry

, Volume 32, Issue 2, pp 146–153 | Cite as

Peptide fragment 66–77 of monocyte chemoattractant protein 1 and its retro-enantio analogue inhibit the migration of cells in vitro and in vivo

  • M. V. Sidorova
  • A. S. Molokoedov
  • A. A. Az’muko
  • T. I. Aref’eva
  • M. G. Melekhov
  • N. B. Kukhtina
  • T. L. Krasnikova
  • Zh. D. Bespalova
  • V. N. Bushuev
Article

Abstract

The retro-enantio-analogue of peptide 66–77 of the chemokine MCP-1 and two hexapeptide fragments 66–71 and 72–77 of the C-terminal sequence of this protein were synthesized using the Fmoc strategy of solid phase peptide synthesis. The effect of the synthetic peptides upon the MCP-1-stimulated migration of THP-1 mononuclear cells was studied in vitro. The activity of the retro-enantio analogue was found to be comparable with that of the initial peptide 66–77: both peptides inhibit the migration of monocytes and granulocytes into inflammation zones of experimental animals.

Key words

MCP-1-stimulated cell migration monocyte monocyte chemoattractant protein 1 (MCP-1) solid phase peptide synthesis synthetic peptides transpeptidation 

Abbreviations

Ddm

4,4′-dimethoxy-diphenylmethyl

Fmoc

9-fluorenylmethyloxycarbonyl

HMP

hydroxymethylphenoxy

HOBt

1-hydroxybenzotriazol

MALDI MS

matrix-assisted laser desorption ionization mass spectrometry

MCP-1

monocyte chemoattractant protein 1

NMP

N-methylpyrrolidone

SPPS

solid phase peptide synthesis

TFA

trifluoroacetic acid

TIBS

triisobutylsilane

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Baggiolini, M., Nature, 1998, vol. 392, pp. 565–568.CrossRefPubMedGoogle Scholar
  2. 2.
    Libby, P., J. Intern. Med., 2000, vol. 247, pp. 349–358.CrossRefPubMedGoogle Scholar
  3. 3.
    Reckless, J. and Grainger, D.J., Biochem. J., 1999, vol. 340, pp. 803–811.CrossRefPubMedGoogle Scholar
  4. 4.
    Reckless, J., Tatalick, L.M., and Grainger, D.J., Immunology, 2001, vol. 103, pp. 1–17.CrossRefGoogle Scholar
  5. 5.
    Sidorova, M.V., Molokoedov, A.S., Aref’eva, T.I., Kukhtina, N.B., Krasnikova, T.L., Bespalova, Zh.D., and Bushuev, V.N., Russ. J. Bioorg. Chem., 2004, vol. 30, pp. 523–533.Google Scholar
  6. 6.
    Shemyakin, M.M., Ovchinnikov, Yu.A., and Ivanov, V.T., Angew. Chem., Int. Ed. Engl., 1969, vol. 8, pp. 492–499.CrossRefGoogle Scholar
  7. 7.
    Krasnikova, T.L., Sidorova, M.V., Molokoedov, A.S., Aref’eva, T.I., Kukhtina, N.B., Melekhov, M.G., and Bespalova, Zh.D., Abstracts of Papers, II Russian Symp. on Chemistry and Biology of Peptides, St. Petersburg, 2005, p. 75.Google Scholar
  8. 8.
    Barany, G. and Merrifield, R.B., in The Peptides: Analysis, Synthesis and Biology. Vol. 2, Gross, E. and Meienhofer, J., Eds., New York: Academic, 1980, pp. 1–284.Google Scholar
  9. 9.
    Lauer, J.L., Fields, C.G., and Fields, G.B., Lett. Peptide Sci., 1994, vol. 1, pp. 197–205.Google Scholar
  10. 10.
    Sidorova, M.V., Molokoedov, A.S., Az’muko, A.A., Kudryavtseva, E.V., Krauze, E., Ovchinnikov, M.V., and Bespalova, Zh.D., Russ. J. Bioorg. Chem., 2004, vol. 30, pp. 101–110.Google Scholar
  11. 11.
    Falk, W., Goodwin, R.H., and Leonard, E.J., J. Immunol. Methods, 1980, vol. 33, pp. 239–247.CrossRefPubMedGoogle Scholar
  12. 12.
    Isakova, O.L., Sepetov, N.F., Bushuev, V.N., Bespalova, Zh.D., Vinogradov, V.A., Ruuge, E.K., and Titov, M.I., Bioorg. Khim., 1986, vol. 12, pp. 106–111.PubMedGoogle Scholar
  13. 13.
    Geratz, D.J., Pryzwansky, K.B., Schwab, J.H., Anderle, S.K., and Tidwell, R.R., Am. J. Pathol., 1993, vol. 142, pp. 1227–1237.Google Scholar
  14. 14.
    Olson, T.S. and Ley, K., Am. J. Physiol., 2002, vol. 283.Google Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • M. V. Sidorova
    • 1
  • A. S. Molokoedov
    • 1
  • A. A. Az’muko
    • 1
  • T. I. Aref’eva
    • 1
  • M. G. Melekhov
    • 1
  • N. B. Kukhtina
    • 1
  • T. L. Krasnikova
    • 1
  • Zh. D. Bespalova
    • 1
  • V. N. Bushuev
    • 1
  1. 1.Federal Agency for Healthcare and Social DevelopmentRussian Cardiological Research and Production AssociationMoscowRussia

Personalised recommendations