用于二肽基肽酶-4的荧光小分子底物的开发。

Ogawa Futa, Takeda Masanori, Miyanaga Kanae, Tani Keita, Yamazawa Ryuji, Ito Kiyoshi, Tarui Atsushi, Sato Kazuyuki, Omote Masaaki

Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.

Division of Natural Sciences, Osaka Kyoiku University, Asahigaoka, Kashiwara, Osaka 582-8582, Japan.

Beilstein J Org Chem. 2017 Dec 14;13:2690-2697. doi: 10.3762/bjoc.13.267. eCollection 2017.

A series of aniline and -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 to the non-fluorescent dipeptide analogue H-Gly-Pro- for the use as a fluorogenic substrate for dipeptidyl peptidase-4 (DPP-4). The progress of the enzymatic hydrolysis of H-Gly-Pro- with DPP-4 was monitored by fluorometric determination of released into the reaction medium. The results suggest that could be used as fluorophore in OFF-ON-type fluorogenic probes.

合成了一系列带有吸电子3,3,3-三氟丙烯基取代基的苯胺和对苯二胺衍生物，作为小分子且化学稳定的荧光有机化合物。通过将2,4-二取代苯胺转化为非荧光二肽类似物H-Gly-Pro-，用作二肽基肽酶-4（DPP-4）的荧光底物，对它们的荧光性能进行了评估。通过荧光测定法监测释放到反应介质中的H-Gly-Pro-与DPP-4的酶促水解过程。结果表明，可作为开-关型荧光探针中的荧光团。