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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

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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Correspondence to M. V. Sidorova.

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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