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Cystein-containing peptides induce migration of monocytes

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Abstract

The automated Fmoc solid-phase technique was used to synthesize Cys-containing linear peptide fragments of monocyte chemoattractant protein-1, chemokine domain of fractalkine, and their analogues, with the Cys residue being either modified or replaced with Ser. Chimeric symmetric and asymmetric disulfides were also prepared from the linear precursors. A SAR study of a set of the newly synthesized peptides showed that the capacity to stimulate migration of monocytes and influence cell motility in vitro critically depends, in general, on the presence of free Cys thiol group in the molecule. Notably, all analogues, including chimeric disulfides, containing no SH groups demonstrated the lack of chemokinetic properties.

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Abbreviations

Acm:

acetamidomethyl

CCR2:

receptor MCP-1

CDF:

chemokine domain of fractalkine

DBU:

1,8-diazobicyclo[5.4.0]undec-7-en

DTT:

dithiothreitol

Fmoc:

9-fluorenylmethoxycarbonyl

HOBt:

1-hydroxybenzotriazol

MALDI:

matrix-assisted laser desorption/ionization

MCP-1:

monocyte chemoattractant protein-1

4-MePip:

4-methylpiperidin

NMM:

N-methylmorpholine

NADPH:

nicotinamide adenine dinucleotide phosphate

Nox:

NADPH oxydase

TBTU:

2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

Pbf:

2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl

PT:

pertussis toxin

TIS:

triisopropylsilane

Trt:

trityl

AOS:

active oxygen species

PB:

phosphate buffer

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Authors and Affiliations

  1. Russian Cardiological Research and Production Complex, Russian Ministry of Public Health, Tretya Cherepkovskaya ul. 15a, Moscow, 121552, Russia

    M. V. Sidorova, T. I. Arefieva, M. E. Palkeeva, A. S. Molokoedov, A. A. Az’muko, N. Yu. Ruleva, E. A. Pylaeva, T. L. Krasnikova & Zh. D. Bespalova

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  1. M. V. Sidorova
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  2. T. I. Arefieva
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  3. M. E. Palkeeva
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  4. A. S. Molokoedov
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  5. A. A. Az’muko
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  6. N. Yu. Ruleva
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  7. E. A. Pylaeva
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  8. T. L. Krasnikova
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  9. Zh. D. Bespalova
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Correspondence to M. V. Sidorova.

Additional information

Original Russian Text © M.V. Sidorova, T.I. Arefieva, M.E. Palkeeva, A.S. Molokoedov, A.A. Az’muko, N.Yu. Ruleva, E.A. Pylaeva, T.L. Krasnikova, Zh.D. Bespalova, 2015, published in Bioorganicheskaya Khimiya, 2015, Vol. 41, No. 1, pp. 13–22.

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Sidorova, M.V., Arefieva, T.I., Palkeeva, M.E. et al. Cystein-containing peptides induce migration of monocytes. Russ J Bioorg Chem 41, 10–18 (2015). https://doi.org/10.1134/S1068162015010124

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  • DOI: https://doi.org/10.1134/S1068162015010124

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