Development of a fluorogenic small substrate for dipeptidyl peptidase-4

A series of aniline and m-phenylenediamine derivatives with electron-withdrawing 3,3,3-trifluoropropenyl substituents were synthesized as small and chemically stable fluorescent organic compounds. Their fluorescence performances were evaluated by converting 2,4-disubstituted aniline 1 to the non-flu...

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Autores principales: Ogawa, Futa, Takeda, Masanori, Miyanaga, Kanae, Tani, Keita, Yamazawa, Ryuji, Ito, Kiyoshi, Tarui, Atsushi, Sato, Kazuyuki, Omote, Masaaki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753067/
https://www.ncbi.nlm.nih.gov/pubmed/29564006
http://dx.doi.org/10.3762/bjoc.13.267
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author Ogawa, Futa
Takeda, Masanori
Miyanaga, Kanae
Tani, Keita
Yamazawa, Ryuji
Ito, Kiyoshi
Tarui, Atsushi
Sato, Kazuyuki
Omote, Masaaki
author_facet Ogawa, Futa
Takeda, Masanori
Miyanaga, Kanae
Tani, Keita
Yamazawa, Ryuji
Ito, Kiyoshi
Tarui, Atsushi
Sato, Kazuyuki
Omote, Masaaki
author_sort Ogawa, Futa
collection PubMed
description A series of aniline and m-phenylenediamine derivatives with electron-withdrawing 3,3,3-trifluoropropenyl substituents were synthesized as small and chemically stable fluorescent organic compounds. Their fluorescence performances were evaluated by converting 2,4-disubstituted aniline 1 to the non-fluorescent dipeptide analogue H-Gly-Pro-1 for the use as a fluorogenic substrate for dipeptidyl peptidase-4 (DPP-4). The progress of the enzymatic hydrolysis of H-Gly-Pro-1 with DPP-4 was monitored by fluorometric determination of 1 released into the reaction medium. The results suggest that 1 could be used as fluorophore in OFF–ON-type fluorogenic probes.
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spelling pubmed-57530672018-03-21 Development of a fluorogenic small substrate for dipeptidyl peptidase-4 Ogawa, Futa Takeda, Masanori Miyanaga, Kanae Tani, Keita Yamazawa, Ryuji Ito, Kiyoshi Tarui, Atsushi Sato, Kazuyuki Omote, Masaaki Beilstein J Org Chem Full Research Paper A series of aniline and m-phenylenediamine derivatives with electron-withdrawing 3,3,3-trifluoropropenyl substituents were synthesized as small and chemically stable fluorescent organic compounds. Their fluorescence performances were evaluated by converting 2,4-disubstituted aniline 1 to the non-fluorescent dipeptide analogue H-Gly-Pro-1 for the use as a fluorogenic substrate for dipeptidyl peptidase-4 (DPP-4). The progress of the enzymatic hydrolysis of H-Gly-Pro-1 with DPP-4 was monitored by fluorometric determination of 1 released into the reaction medium. The results suggest that 1 could be used as fluorophore in OFF–ON-type fluorogenic probes. Beilstein-Institut 2017-12-14 /pmc/articles/PMC5753067/ /pubmed/29564006 http://dx.doi.org/10.3762/bjoc.13.267 Text en Copyright © 2017, Ogawa et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ogawa, Futa
Takeda, Masanori
Miyanaga, Kanae
Tani, Keita
Yamazawa, Ryuji
Ito, Kiyoshi
Tarui, Atsushi
Sato, Kazuyuki
Omote, Masaaki
Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_full Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_fullStr Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_full_unstemmed Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_short Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_sort development of a fluorogenic small substrate for dipeptidyl peptidase-4
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753067/
https://www.ncbi.nlm.nih.gov/pubmed/29564006
http://dx.doi.org/10.3762/bjoc.13.267
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