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Synthesis and Properties of the retro-Analogue of Myelopeptide MP-2

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Abstract

The bone marrow myelopeptide MP-2 (Leu-Val-Val-Tyr-Pro-Trp), exhibiting antitumor activity, and its retro-analogue (Trp-Pro-Tyr-Val-Val-Leu) were synthesized, and their properties were studied. The in vitro and in vivo activities of retro-MP-2 were comparable with those of MP-2. Both peptides equally restored the functional activity of T-lymphocytes inhibited by toxins released by HL-60 cells and inhibited by 70–82% the growth of various types of transplantable solid tumors: Ca-755 adenocarcinoma of the mammary gland, Lewis adenocarcinoma of the lung, and S180 sarcoma. The positions and intensities of the Cotton effects in CD spectra of the MP-2 peptide and its retro-analogue in various solvents are almost indistinguishable. The positions of extrema and integral intensities of the amide I and amide A bands in IR spectra of both peptides were practically identical.

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Abbreviations

CM:

condition medium

DCHA:

dicyclohexylamine

DMF:

dimethylformamide

MP:

myelopeptides

PHA:

phytohemagglutinin

TFE:

trifluoroethanol

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Correspondence to L. A. Fonina.

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__________

Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 3, 2005, pp. 239–244.

Original Russian Text Copyright © 2005 by Fonina, Ovchinnikov, Gur’yanov, Sychev, Belevskaya, Treshchalina.

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Fonina, L.A., Ovchinnikov, M.V., Gur’yanov, S.A. et al. Synthesis and Properties of the retro-Analogue of Myelopeptide MP-2. Russ J Bioorg Chem 31, 210–215 (2005). https://doi.org/10.1007/s11171-005-0029-1

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  • DOI: https://doi.org/10.1007/s11171-005-0029-1

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