Peptides conjugated to 2-alkoxy-8-oxo-adenine as potential synthetic vaccines triggering TLR7
Copyright © 2019 The Authors. Published by Elsevier Ltd.. All rights reserved..
Covalent linking of immunogenic oligopeptides with synthetic Toll-like receptor ligands is a useful approach to develop self-adjuvanting vaccines. In particular, small-molecule based agonists of Toll-like receptor 7 (TLR7) that are derived from 8-oxo-adenine core are potentially promising because these chemically robust TLR7 ligands can be connected to peptide T-cell epitopes via straightforward solid-phase peptide synthesis. In this contribution we present the synthesis of a Boc-protected 9-benzyl-2-alkoxy-8-oxo-adenine building block and its application in the online solid phase synthesis of three peptide conjugates that differ in the position of the TLR7 ligand within the peptide. The conjugates are able to induce dendritic cell maturation and T cell proliferation while the position of the ligand impacts T cell proliferation potency.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
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| Enthalten in: |
Bioorganic & medicinal chemistry letters - 29(2019), 11 vom: 01. Juni, Seite 1340-1344 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Gential, Geoffroy P P [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 11.09.2020 Date Revised 11.09.2020 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bmcl.2019.03.048 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM295741791 |
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| 500 | |a published: Print-Electronic | ||
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| 520 | |a Copyright © 2019 The Authors. Published by Elsevier Ltd.. All rights reserved. | ||
| 520 | |a Covalent linking of immunogenic oligopeptides with synthetic Toll-like receptor ligands is a useful approach to develop self-adjuvanting vaccines. In particular, small-molecule based agonists of Toll-like receptor 7 (TLR7) that are derived from 8-oxo-adenine core are potentially promising because these chemically robust TLR7 ligands can be connected to peptide T-cell epitopes via straightforward solid-phase peptide synthesis. In this contribution we present the synthesis of a Boc-protected 9-benzyl-2-alkoxy-8-oxo-adenine building block and its application in the online solid phase synthesis of three peptide conjugates that differ in the position of the TLR7 ligand within the peptide. The conjugates are able to induce dendritic cell maturation and T cell proliferation while the position of the ligand impacts T cell proliferation potency | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a 9-Benzyl-2-butoxy-8-oxo-adenine | |
| 650 | 4 | |a Dendritic cells | |
| 650 | 4 | |a Synthetic peptide conjugates | |
| 650 | 4 | |a T cell proliferation | |
| 650 | 4 | |a TLR7 agonist | |
| 650 | 7 | |a Ligands |2 NLM | |
| 650 | 7 | |a Peptides |2 NLM | |
| 650 | 7 | |a TLR7 protein, human |2 NLM | |
| 650 | 7 | |a Toll-Like Receptor 7 |2 NLM | |
| 650 | 7 | |a Vaccines, Synthetic |2 NLM | |
| 650 | 7 | |a Adenine |2 NLM | |
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| 700 | 1 | |a Hogervorst, Tim P |e verfasserin |4 aut | |
| 700 | 1 | |a Tondini, Elena |e verfasserin |4 aut | |
| 700 | 1 | |a van de Graaff, Michel J |e verfasserin |4 aut | |
| 700 | 1 | |a Overkleeft, Herman S |e verfasserin |4 aut | |
| 700 | 1 | |a Codée, Jeroen D C |e verfasserin |4 aut | |
| 700 | 1 | |a van der Marel, Gijsbert A |e verfasserin |4 aut | |
| 700 | 1 | |a Ossendorp, Ferry |e verfasserin |4 aut | |
| 700 | 1 | |a Filippov, Dmitri V |e verfasserin |4 aut | |
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