Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation

[Image: see text] A self-immolative bioorthogonal conditionally cleavable linker based on Grob fragmentation is described. It is derived from 1,3-aminocyclohexanols and allows the release of sulfonate-containing compounds in aqueous media. Modulation of the amine pK(a) promotes fragmentation even at...

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Autores principales: Ferhati, Xhenti, Salas-Cubero, Marina, Garrido, Pablo, García-Sanmartín, Josune, Guerreiro, Ana, Avenoza, Alberto, Busto, Jesús H., Peregrina, Jesús M., Martínez, Alfredo, Jiménez-Moreno, Ester, Bernardes, Gonçalo J. L., Corzana, Francisco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576835/
https://www.ncbi.nlm.nih.gov/pubmed/34694118
http://dx.doi.org/10.1021/acs.orglett.1c03299
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author Ferhati, Xhenti
Salas-Cubero, Marina
Garrido, Pablo
García-Sanmartín, Josune
Guerreiro, Ana
Avenoza, Alberto
Busto, Jesús H.
Peregrina, Jesús M.
Martínez, Alfredo
Jiménez-Moreno, Ester
Bernardes, Gonçalo J. L.
Corzana, Francisco
author_facet Ferhati, Xhenti
Salas-Cubero, Marina
Garrido, Pablo
García-Sanmartín, Josune
Guerreiro, Ana
Avenoza, Alberto
Busto, Jesús H.
Peregrina, Jesús M.
Martínez, Alfredo
Jiménez-Moreno, Ester
Bernardes, Gonçalo J. L.
Corzana, Francisco
author_sort Ferhati, Xhenti
collection PubMed
description [Image: see text] A self-immolative bioorthogonal conditionally cleavable linker based on Grob fragmentation is described. It is derived from 1,3-aminocyclohexanols and allows the release of sulfonate-containing compounds in aqueous media. Modulation of the amine pK(a) promotes fragmentation even at slightly acidic pH, a common feature of several tumor environments. The Grob fragmentation can also occur under physiological conditions in living cells, highlighting the potential bioorthogonal applicability of this reaction.
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spelling pubmed-85768352021-11-10 Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation Ferhati, Xhenti Salas-Cubero, Marina Garrido, Pablo García-Sanmartín, Josune Guerreiro, Ana Avenoza, Alberto Busto, Jesús H. Peregrina, Jesús M. Martínez, Alfredo Jiménez-Moreno, Ester Bernardes, Gonçalo J. L. Corzana, Francisco Org Lett [Image: see text] A self-immolative bioorthogonal conditionally cleavable linker based on Grob fragmentation is described. It is derived from 1,3-aminocyclohexanols and allows the release of sulfonate-containing compounds in aqueous media. Modulation of the amine pK(a) promotes fragmentation even at slightly acidic pH, a common feature of several tumor environments. The Grob fragmentation can also occur under physiological conditions in living cells, highlighting the potential bioorthogonal applicability of this reaction. American Chemical Society 2021-10-25 2021-11-05 /pmc/articles/PMC8576835/ /pubmed/34694118 http://dx.doi.org/10.1021/acs.orglett.1c03299 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ferhati, Xhenti
Salas-Cubero, Marina
Garrido, Pablo
García-Sanmartín, Josune
Guerreiro, Ana
Avenoza, Alberto
Busto, Jesús H.
Peregrina, Jesús M.
Martínez, Alfredo
Jiménez-Moreno, Ester
Bernardes, Gonçalo J. L.
Corzana, Francisco
Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title_full Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title_fullStr Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title_full_unstemmed Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title_short Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation
title_sort bioorthogonal self-immolative linker based on grob fragmentation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576835/
https://www.ncbi.nlm.nih.gov/pubmed/34694118
http://dx.doi.org/10.1021/acs.orglett.1c03299
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