Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties
Background: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between α,β-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 <i>S<...
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MDPI AG
2021-02-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/4/2168 |
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| author | Paweł Lenartowicz Mateusz Psurski Aleksandra Kotynia Aleksandra Pieniężna Monika Cuprych Klaudia Poniatowska Justyna Brasuń Paweł Kafarski |
| author_facet | Paweł Lenartowicz Mateusz Psurski Aleksandra Kotynia Aleksandra Pieniężna Monika Cuprych Klaudia Poniatowska Justyna Brasuń Paweł Kafarski |
| author_sort | Paweł Lenartowicz |
| collection | DOAJ |
| description | Background: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between α,β-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 <i>S</i>-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-(<i>Z</i>)-β-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 <i>S</i>-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. |
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| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T00:39:15Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-443fa0d2bf30442bb2e1982e43e20d9e2023-12-11T17:57:06ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-02-01224216810.3390/ijms22042168Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative PropertiesPaweł Lenartowicz0Mateusz Psurski1Aleksandra Kotynia2Aleksandra Pieniężna3Monika Cuprych4Klaudia Poniatowska5Justyna Brasuń6Paweł Kafarski7Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-052 Opole, PolandLaboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wrocław, PolandDepartment of Inorganic Chemistry, Wrocław Medical University, ul. Borowska 211 A, 50-556 Wrocław, PolandDepartment of Inorganic Chemistry, Wrocław Medical University, ul. Borowska 211 A, 50-556 Wrocław, PolandLaboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wrocław, PolandLaboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, ul. R. Weigla 12, 53-114 Wrocław, PolandDepartment of Inorganic Chemistry, Wrocław Medical University, ul. Borowska 211 A, 50-556 Wrocław, PolandDepartment of Bioorganic Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandBackground: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between α,β-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 <i>S</i>-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-(<i>Z</i>)-β-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 <i>S</i>-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.https://www.mdpi.com/1422-0067/22/4/2168dehydrocysteinedehydropeptidesaddition-elimination reactioncomplexing agentantiproliferative activity |
| spellingShingle | Paweł Lenartowicz Mateusz Psurski Aleksandra Kotynia Aleksandra Pieniężna Monika Cuprych Klaudia Poniatowska Justyna Brasuń Paweł Kafarski Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties International Journal of Molecular Sciences dehydrocysteine dehydropeptides addition-elimination reaction complexing agent antiproliferative activity |
| title | Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties |
| title_full | Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties |
| title_fullStr | Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties |
| title_full_unstemmed | Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties |
| title_short | Dipeptides of <i>S</i>-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties |
| title_sort | dipeptides of i s i substituted dehydrocysteine as artzyme building blocks synthesis complexing abilities and antiproliferative properties |
| topic | dehydrocysteine dehydropeptides addition-elimination reaction complexing agent antiproliferative activity |
| url | https://www.mdpi.com/1422-0067/22/4/2168 |
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