Development of a fluorogenic small substrate for dipeptidyl peptidase-4

被引:4
|
作者
Ogawa, Futa [1 ]
Takeda, Masanori [1 ]
Miyanaga, Kanae [2 ]
Tani, Keita [2 ]
Yamazawa, Ryuji [1 ]
Ito, Kiyoshi [1 ]
Tarui, Atsushi [1 ]
Sato, Kazuyuki [1 ]
Omote, Masaaki [1 ]
机构
[1] Setsunan Univ, Fac Pharmaceut Sci, 45-1 Nagaotoge Cho, Hirakata, Osaka 5730101, Japan
[2] Osaka Kyoiku Univ, Div Nat Sci, Osaka 5828582, Japan
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷
关键词
dipeptidyl peptidase-4; fluorogenic substrate; fluorometry; small fluorescent molecule; SOLID-STATE; FLUORESCENT-PROBE; IN-VIVO; CELLS; DESIGN; VIOLET; TUMOR; IV;
D O I
10.3762/bjoc.13.267
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:2690 / 2697
页数:8
相关论文
共 50 条
  • [11] Cardiovascular effects of dipeptidyl peptidase-4 inhibitors
    Papagianni, M.
    Tziomalos, K.
    HIPPOKRATIA, 2015, 19 (03) : 195 - 199
  • [12] The Nonglycemic Actions of Dipeptidyl Peptidase-4 Inhibitors
    Kim, Na-Hyung
    Yu, Taeyang
    Lee, Dae Ho
    BIOMED RESEARCH INTERNATIONAL, 2014, 2014
  • [13] Dipeptidyl peptidase-4 and kidney fibrosis in diabetes
    Shi, Sen
    Koya, Daisuke
    Kanasaki, Keizo
    FIBROGENESIS & TISSUE REPAIR, 2016, 9
  • [14] Tolerability of Dipeptidyl Peptidase-4 Inhibitors: A Review
    Richard, Kathleen R.
    Shelburne, Jamie S.
    Kirk, Julienne K.
    CLINICAL THERAPEUTICS, 2011, 33 (11) : 1609 - 1629
  • [15] Dipeptidyl peptidase-4 inhibitors and cardiovascular safety
    Davis, Timothy M. E.
    MEDICAL JOURNAL OF AUSTRALIA, 2014, 200 (08) : 450 - 451
  • [16] Pharmacology of Dipeptidyl Peptidase-4 InhibitorsSimilarities and Differences
    Roberta Baetta
    Alberto Corsini
    Drugs, 2011, 71 : 1441 - 1467
  • [17] Nonglycemic effects of dipeptidyl peptidase-4 inhibitors
    Ametov, A. S.
    Kamynina, L. L.
    TERAPEVTICHESKII ARKHIV, 2013, 85 (01) : 98 - 102
  • [18] Increasing Age Associated with Higher Dipeptidyl Peptidase-4 Inhibition Rate Is a Predictive Factor for Efficacy of Dipeptidyl Peptidase-4 Inhibitors
    Hong, Sangmo
    Jung, Chang Hee
    Han, Song
    Park, Cheol-Young
    DIABETES & METABOLISM JOURNAL, 2022, 46 (01) : 63 - +
  • [19] Development of a Scalable Synthesis of Dipeptidyl Peptidase-4 Inhibitor ABT-279
    McDermott, Todd S.
    Bhagavatula, Lakshmi
    Borchardt, Thomas B.
    Engstrom, Kenneth M.
    Gandarilla, Jorge
    Kotecki, Brian J.
    Kruger, Albert W.
    Rozema, Michael J.
    Sheikh, Ahmad Y.
    Wagaw, Seble H.
    Wittenberger, Steven J.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (06) : 1145 - 1155
  • [20] Dipeptidyl peptidase-4 inhibitors and angioedema: a class effect?
    Saisho, Y.
    Itoh, H.
    DIABETIC MEDICINE, 2013, 30 (04) : e149 - e150