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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Main Authors:	Futa Ogawa, Masanori Takeda, Kanae Miyanaga, Keita Tani, Ryuji Yamazawa, Kiyoshi Ito, Atsushi Tarui, Kazuyuki Sato, Masaaki Omote
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-12-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	dipeptidyl peptidase-4 fluorogenic substrate fluorometry small fluorescent molecule
Online Access:	https://doi.org/10.3762/bjoc.13.267

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spelling	doaj-a0ee4253a8324c1dabbf18db16b412cc2021-02-02T05:50:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-12-011312690269710.3762/bjoc.13.2671860-5397-13-267Development of a fluorogenic small substrate for dipeptidyl peptidase-4Futa Ogawa0Masanori Takeda1Kanae Miyanaga2Keita Tani3Ryuji Yamazawa4Kiyoshi Ito5Atsushi Tarui6Kazuyuki Sato7Masaaki Omote8Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanDivision of Natural Sciences, Osaka Kyoiku University, Asahigaoka, Kashiwara, Osaka 582-8582, JapanDivision of Natural Sciences, Osaka Kyoiku University, Asahigaoka, Kashiwara, Osaka 582-8582, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanA 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.https://doi.org/10.3762/bjoc.13.267dipeptidyl peptidase-4fluorogenic substratefluorometrysmall fluorescent molecule
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Futa Ogawa Masanori Takeda Kanae Miyanaga Keita Tani Ryuji Yamazawa Kiyoshi Ito Atsushi Tarui Kazuyuki Sato Masaaki Omote
spellingShingle	Futa Ogawa Masanori Takeda Kanae Miyanaga Keita Tani Ryuji Yamazawa Kiyoshi Ito Atsushi Tarui Kazuyuki Sato Masaaki Omote Development of a fluorogenic small substrate for dipeptidyl peptidase-4 Beilstein Journal of Organic Chemistry dipeptidyl peptidase-4 fluorogenic substrate fluorometry small fluorescent molecule
author_facet	Futa Ogawa Masanori Takeda Kanae Miyanaga Keita Tani Ryuji Yamazawa Kiyoshi Ito Atsushi Tarui Kazuyuki Sato Masaaki Omote
author_sort	Futa Ogawa
title	Development of a fluorogenic small substrate for dipeptidyl peptidase-4
title_short	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_sort	development of a fluorogenic small substrate for dipeptidyl peptidase-4
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2017-12-01
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.
topic	dipeptidyl peptidase-4 fluorogenic substrate fluorometry small fluorescent molecule
url	https://doi.org/10.3762/bjoc.13.267
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Development of a fluorogenic small substrate for dipeptidyl peptidase-4

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