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

Russian Journal of Bioorganic Chemistry volume 32, pages 146–153 (2006)Cite this 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.

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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

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Authors and Affiliations

  1. Federal Agency for Healthcare and Social Development, Russian Cardiological Research and Production Association, Tret’ya Cherepkovskaya ul. 15a, Moscow, 121552, Russia

    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

Authors
  1. M. V. Sidorova
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  2. A. S. Molokoedov
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  3. A. A. Az’muko
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  4. T. I. Aref’eva
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  5. M. G. Melekhov
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  6. N. B. Kukhtina
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  7. T. L. Krasnikova
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  8. Zh. D. Bespalova
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  9. V. N. Bushuev
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Corresponding author

Correspondence to M. V. Sidorova.

Additional information

Original Russian Text © 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, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 2, pp. 161–168.

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Sidorova, M.V., Molokoedov, A.S., Az’muko, A.A. et al. Peptide fragment 66–77 of monocyte chemoattractant protein 1 and its retro-enantio analogue inhibit the migration of cells in vitro and in vivo. Russ J Bioorg Chem 32, 146–153 (2006). https://doi.org/10.1134/S1068162006020063

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  • DOI: https://doi.org/10.1134/S1068162006020063

Key words

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