{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:50:45Z","timestamp":1760233845627,"version":"build-2065373602"},"reference-count":41,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,22]],"date-time":"2021-02-22T00:00:00Z","timestamp":1613952000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Centre, Poland (NCN)","award":["2016\/21\/B\/ST5\/00115","2017\/26\/D\/NZ7\/01152"],"award-info":[{"award-number":["2016\/21\/B\/ST5\/00115","2017\/26\/D\/NZ7\/01152"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Background: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between \u03b1,\u03b2-carbon atoms. Its presence provides unique structural properties and reaction centre for chemical modification. In this study, the series of new class of dipeptides containing S-substituted dehydrocysteine with variety of heterocyclic moieties was prepared. The compounds were designed as the building blocks for the construction of artificial metalloenzymes (artzymes). Therefore, the complexing properties of representative compounds were also evaluated. Furthermore, the acknowledged biological activity of natural dehydropeptides was the reason to extend the study for antiproliferative action of against several cancer cell lines. Methods: The synthetic strategy involves glycyl and phenylalanyl-(Z)-\u03b2-bromodehydroalanine as a substrate in one pot addition\/elimination reaction of thiols. After deprotection of N-terminal amino group the compounds with triazole ring were tested as complexones for copper(II) ions using potentiometric titration and spectroscopic techniques (UV-Vis, CD, EPR). Finally, the antiproliferative activity was evaluated by sulforhodamine B assay. Results and Conclusions: A simple and efficient procedure for preparation of dipeptides containing S-substituded dehydrocysteine was provided. The peptides containing triazole appeared to be strong complexones of copper(II) ions. Some of the peptides exhibited promising antiproliferative activities against number of cancer cell lines, including cell lines resistant to widely used anticancer agent.<\/jats:p>","DOI":"10.3390\/ijms22042168","type":"journal-article","created":{"date-parts":[[2021,2,22]],"date-time":"2021-02-22T14:23:27Z","timestamp":1614003807000},"page":"2168","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Dipeptides of S-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8515-4428","authenticated-orcid":false,"given":"Pawe\u0142","family":"Lenartowicz","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8866-7149","authenticated-orcid":false,"given":"Mateusz","family":"Psurski","sequence":"additional","affiliation":[{"name":"Laboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0730-8975","authenticated-orcid":false,"given":"Aleksandra","family":"Kotynia","sequence":"additional","affiliation":[{"name":"Department of Inorganic Chemistry, Wroc\u0142aw Medical University, ul. Borowska 211 A, 50-556 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aleksandra","family":"Pieni\u0119\u017cna","sequence":"additional","affiliation":[{"name":"Department of Inorganic Chemistry, Wroc\u0142aw Medical University, ul. Borowska 211 A, 50-556 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0750-0617","authenticated-orcid":false,"given":"Monika","family":"Cuprych","sequence":"additional","affiliation":[{"name":"Laboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Klaudia","family":"Poniatowska","sequence":"additional","affiliation":[{"name":"Laboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Justyna","family":"Brasu\u0144","sequence":"additional","affiliation":[{"name":"Department of Inorganic Chemistry, Wroc\u0142aw Medical University, ul. Borowska 211 A, 50-556 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8019-4797","authenticated-orcid":false,"given":"Pawe\u0142","family":"Kafarski","sequence":"additional","affiliation":[{"name":"Department of Bioorganic Chemistry, Wroc\u0142aw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1734","DOI":"10.1039\/C3CS60037H","article-title":"Supramolecular catalysis. Part 2: Artificial enzyme mimics","volume":"43","author":"Raynal","year":"2014","journal-title":"Chem. Soc. 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