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Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction

Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents,...

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Detalles Bibliográficos
Autores principales: Chen, Kuo‐Ting, Ieritano, Christian, Seimbille, Yann
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838389/
https://www.ncbi.nlm.nih.gov/pubmed/29531889
http://dx.doi.org/10.1002/open.201700191
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author Chen, Kuo‐Ting
Ieritano, Christian
Seimbille, Yann
author_facet Chen, Kuo‐Ting
Ieritano, Christian
Seimbille, Yann
author_sort Chen, Kuo‐Ting
collection PubMed
description Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents, including fluorophores and radioisotope‐containing prosthetic groups. We investigated the feasibility of an early‐stage incorporation of dipeptide 1 into targeting vectors, such as c[RGDyK(C)] and HER2 pep, during solid‐phase peptide synthesis. Then, the utility of the click reaction to label bioactive peptides with a CBT‐modified imaging agent (FITC–CBT, 9) was assessed. The ligation reaction was found to be highly selective and efficient under various conditions. The fluorescently labeled peptides 2 and 3 were obtained in respective yields of 88 and 82 % under optimized conditions.
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spelling pubmed-58383892018-03-12 Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction Chen, Kuo‐Ting Ieritano, Christian Seimbille, Yann ChemistryOpen Communications Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents, including fluorophores and radioisotope‐containing prosthetic groups. We investigated the feasibility of an early‐stage incorporation of dipeptide 1 into targeting vectors, such as c[RGDyK(C)] and HER2 pep, during solid‐phase peptide synthesis. Then, the utility of the click reaction to label bioactive peptides with a CBT‐modified imaging agent (FITC–CBT, 9) was assessed. The ligation reaction was found to be highly selective and efficient under various conditions. The fluorescently labeled peptides 2 and 3 were obtained in respective yields of 88 and 82 % under optimized conditions. John Wiley and Sons Inc. 2018-02-06 /pmc/articles/PMC5838389/ /pubmed/29531889 http://dx.doi.org/10.1002/open.201700191 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Chen, Kuo‐Ting
Ieritano, Christian
Seimbille, Yann
Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title_full Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title_fullStr Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title_full_unstemmed Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title_short Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
title_sort early‐stage incorporation strategy for regioselective labeling of peptides using the 2‐cyanobenzothiazole/1,2‐aminothiol bioorthogonal click reaction
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838389/
https://www.ncbi.nlm.nih.gov/pubmed/29531889
http://dx.doi.org/10.1002/open.201700191
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