Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions
Self-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents <i>N</i>-methyl dimethyl methyl (i.e., trimethyl) carbamate as a new...
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doaj-7afbf365d0e84c2fba33f4dd7b7654f82020-11-25T03:29:39ZengMDPI AGMolecules1420-30492020-05-01252153215310.3390/molecules25092153Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme ReactionsNoriaki Nakamura0Shohei Uchinomiya1Kazuya Inoue2Akio Ojida3Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, JapanSelf-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents <i>N</i>-methyl dimethyl methyl (i.e., trimethyl) carbamate as a new class of self-immolative linker for the fluorescence detection of enzyme reactions. The trimethyl carbamate was shown to spontaneously undergo intramolecular cyclization upon formation of a carboxylate group, to liberate a fluorophore with the second time rapid reaction kinetics. Interestingly, the auto-cleavage reaction of trimethyl carbamate was also induced by the formation of hydroxyl and amino groups. Fluorescent probes with a trimethyl carbamate could be applicable for fluorescence monitoring of the enzyme reactions catalyzed by esterase, ketoreductase, and aminotransferase, and for fluorescence imaging of intracellular esterase activity in living cells, hence demonstrating the utility of this new class of self-immolative linker.https://www.mdpi.com/1420-3049/25/9/2153fluorescent probeself-immolative linkertrimethyl carbamateenzyme detection |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Noriaki Nakamura Shohei Uchinomiya Kazuya Inoue Akio Ojida |
spellingShingle |
Noriaki Nakamura Shohei Uchinomiya Kazuya Inoue Akio Ojida Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions Molecules fluorescent probe self-immolative linker trimethyl carbamate enzyme detection |
author_facet |
Noriaki Nakamura Shohei Uchinomiya Kazuya Inoue Akio Ojida |
author_sort |
Noriaki Nakamura |
title |
Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions |
title_short |
Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions |
title_full |
Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions |
title_fullStr |
Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions |
title_full_unstemmed |
Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions |
title_sort |
trimethyl-substituted carbamate as a versatile self-immolative linker for fluorescence detection of enzyme reactions |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2020-05-01 |
description |
Self-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents <i>N</i>-methyl dimethyl methyl (i.e., trimethyl) carbamate as a new class of self-immolative linker for the fluorescence detection of enzyme reactions. The trimethyl carbamate was shown to spontaneously undergo intramolecular cyclization upon formation of a carboxylate group, to liberate a fluorophore with the second time rapid reaction kinetics. Interestingly, the auto-cleavage reaction of trimethyl carbamate was also induced by the formation of hydroxyl and amino groups. Fluorescent probes with a trimethyl carbamate could be applicable for fluorescence monitoring of the enzyme reactions catalyzed by esterase, ketoreductase, and aminotransferase, and for fluorescence imaging of intracellular esterase activity in living cells, hence demonstrating the utility of this new class of self-immolative linker. |
topic |
fluorescent probe self-immolative linker trimethyl carbamate enzyme detection |
url |
https://www.mdpi.com/1420-3049/25/9/2153 |
work_keys_str_mv |
AT noriakinakamura trimethylsubstitutedcarbamateasaversatileselfimmolativelinkerforfluorescencedetectionofenzymereactions AT shoheiuchinomiya trimethylsubstitutedcarbamateasaversatileselfimmolativelinkerforfluorescencedetectionofenzymereactions AT kazuyainoue trimethylsubstitutedcarbamateasaversatileselfimmolativelinkerforfluorescencedetectionofenzymereactions AT akioojida trimethylsubstitutedcarbamateasaversatileselfimmolativelinkerforfluorescencedetectionofenzymereactions |
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