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Review
. 2021 Apr 27;26(9):2538.
doi: 10.3390/molecules26092538.

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Michał Zimecki  1 , Krzysztof Kaczmarek  2
Affiliations
Review

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Michał Zimecki et al. Molecules. .

Abstract

The consequences of manipulations in structure and amino acid composition of native cyclolinopeptide A (CLA) from linen seeds, and its linear precursor on their biological activities and mechanisms of action, are reviewed. The modifications included truncation of the peptide chain, replacement of amino acid residues with proteinogenic or non-proteinogenic ones, modifications of peptide bond, and others. The studies revealed changes in the immunosuppressive potency of these analogs investigated in a number of in vitro and in vivo experimental models, predominantly in rodents, as well as differences in their postulated mechanism of action. The modified peptides were compared with cyclosporine A and parent CLA. Some of the synthesized and investigated peptides show potential therapeutic usefulness.

Keywords: PGE2; cis-peptide bond; cyclolinopeptide A (CLA); cyclosporine A; edge-to-face; homo amino acids; immunosuppression.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The structure of Cyclolinopeptide A (CAS 33302-55-5).
Figure 2
Figure 2
The structure of the cyclic tetrapeptide, cyclo-(L-Pro-L-Pro-L-β3hPhe-L-Phe-). (3S,9S,13S,16S)-9,13-dibenzyl-1,7,10,14-tetraazatricyclo[14.3.0.03,7]nonadecane- 2,8,11,15-tetrone (IUPAC name).
See this image and copyright information in PMC

References

    1. Kaufmann H.P., Tobschirbel A. Über ein Oligopeptid aus Leinsamen. Chem. Ber. 1959;92:2805–2809. doi: 10.1002/cber.19590921122. - DOI
    1. Ansari R., Zarshenas M.M., Dadbakhsh A.H. A Review on Pharmacological and Clinical Aspects of Linum usitatissimum L. Curr. Drug Discov. Technol. 2019;16:148–158. doi: 10.2174/1570163815666180521101136. - DOI - PubMed
    1. Shim Y.Y., Song Z., Jadhav P.D., Reaney M.J. Orbitides from flaxseed (Linum usitatissimum L.): A comprehensive review. Trends Food Sci. Technol. 2019;93:197–211. doi: 10.1016/j.tifs.2019.09.007. - DOI
    1. Wieczorek Z., Bengtsson B., Trojnar J., Siemion I.Z. Immunosuppressive activity of cyclolinopeptide A. Pept. Res. 1991;4:275–283. - PubMed
    1. Siemion I.Z., Pedyczak A., Strug I., Wieczorek Z. Synthesis and biological studies on analogs of cyclolinopeptide A with a shortened peptide chain. Arch. Immunol. Ther. Exp. 1994;42:459–465. - PubMed