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Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors
Fifteen new peptide derivatives of ɛ-aminocaproic acid (EACA) containing the known fragment –Ala–Phe–Lys– with an affinity for plasmin were synthesised in the present study. The synthesis was carried out a solid phase. The following compounds were synthesised: H–Phe–Lys–EACA–X, H–d-Ala–Phe–Lys–EACA–...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer Netherlands
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5401710/ https://www.ncbi.nlm.nih.gov/pubmed/28491013 http://dx.doi.org/10.1007/s10989-016-9555-3 |
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author | Purwin, Maciej Markowska, Agnieszka Bruzgo, Irena Rusak, Tomasz Surażyński, Arkadiusz Jaworowska, Urszula Midura-Nowaczek, Krystyna |
author_facet | Purwin, Maciej Markowska, Agnieszka Bruzgo, Irena Rusak, Tomasz Surażyński, Arkadiusz Jaworowska, Urszula Midura-Nowaczek, Krystyna |
author_sort | Purwin, Maciej |
collection | PubMed |
description | Fifteen new peptide derivatives of ɛ-aminocaproic acid (EACA) containing the known fragment –Ala–Phe–Lys– with an affinity for plasmin were synthesised in the present study. The synthesis was carried out a solid phase. The following compounds were synthesised: H–Phe–Lys–EACA–X, H–d-Ala–Phe–Lys–EACA–X, H–Ala–Phe–Lys–EACA–X, H–d-Ala–Phe–EACA–X and H–Ala–Phe–EACA–X, where X = OH, NH(2) and NH–(CH(2))(5)–NH(2). All peptides, except for those containing the sequence H–Ala–Phe–EACA–X, displayed higher inhibitory activity against plasmin than EACA. The most active and selective inhibitor of plasmin was the compound H–d-Ala–Phe–Lys–EACA–NH(2) which inhibited the amidolytic activity of plasmin (IC(50) = 0.02 mM), with the antifibrinolytic activity weaker than EACA. The resulting peptides did not affect the viability of fibroblast cells, colon cancer cell line DLD-1, breast MCF-7 and MDA-MB-231 cell lines. |
format | Online Article Text |
id | pubmed-5401710 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Springer Netherlands |
record_format | MEDLINE/PubMed |
spelling | pubmed-54017102017-05-08 Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors Purwin, Maciej Markowska, Agnieszka Bruzgo, Irena Rusak, Tomasz Surażyński, Arkadiusz Jaworowska, Urszula Midura-Nowaczek, Krystyna Int J Pept Res Ther Article Fifteen new peptide derivatives of ɛ-aminocaproic acid (EACA) containing the known fragment –Ala–Phe–Lys– with an affinity for plasmin were synthesised in the present study. The synthesis was carried out a solid phase. The following compounds were synthesised: H–Phe–Lys–EACA–X, H–d-Ala–Phe–Lys–EACA–X, H–Ala–Phe–Lys–EACA–X, H–d-Ala–Phe–EACA–X and H–Ala–Phe–EACA–X, where X = OH, NH(2) and NH–(CH(2))(5)–NH(2). All peptides, except for those containing the sequence H–Ala–Phe–EACA–X, displayed higher inhibitory activity against plasmin than EACA. The most active and selective inhibitor of plasmin was the compound H–d-Ala–Phe–Lys–EACA–NH(2) which inhibited the amidolytic activity of plasmin (IC(50) = 0.02 mM), with the antifibrinolytic activity weaker than EACA. The resulting peptides did not affect the viability of fibroblast cells, colon cancer cell line DLD-1, breast MCF-7 and MDA-MB-231 cell lines. Springer Netherlands 2016-09-19 2017 /pmc/articles/PMC5401710/ /pubmed/28491013 http://dx.doi.org/10.1007/s10989-016-9555-3 Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. |
spellingShingle | Article Purwin, Maciej Markowska, Agnieszka Bruzgo, Irena Rusak, Tomasz Surażyński, Arkadiusz Jaworowska, Urszula Midura-Nowaczek, Krystyna Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title | Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title_full | Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title_fullStr | Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title_full_unstemmed | Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title_short | Peptides with 6-Aminohexanoic Acid: Synthesis and Evaluation as Plasmin Inhibitors |
title_sort | peptides with 6-aminohexanoic acid: synthesis and evaluation as plasmin inhibitors |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5401710/ https://www.ncbi.nlm.nih.gov/pubmed/28491013 http://dx.doi.org/10.1007/s10989-016-9555-3 |
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