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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–...

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Autores principales: Purwin, Maciej, Markowska, Agnieszka, Bruzgo, Irena, Rusak, Tomasz, Surażyński, Arkadiusz, Jaworowska, Urszula, Midura-Nowaczek, Krystyna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Netherlands 2016
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.
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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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