Design of Chemical Shift-Switching 19F Magnetic Resonance Imaging Probe for Specific Detection of Human Monoamine Oxidase A

被引：52

作者：

Yamaguchi, Koya ^{[1
]}

Ueki, Ryosuke ^{[1
]}

Nonaka, Hiroshi ^{[1
]}

Sugihara, Fuminori ^{[2
]}

Matsuda, Tetsuya ^{[2
]}

Sando, Shinsuke ^{[1
,3
]}

机构：

[1] Kyushu Univ, INAMORI Frontier Res Ctr, Nishi Ku, Fukuoka 8190395, Japan

[2] Kyoto Univ, Grad Sch Informat, Dept Syst Sci, Sakyo Ku, Kyoto 6068501, Japan

[3] Japan Sci & Technol Agcy, PRESTO, Kawaguchi, Saitama 3320012, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 36期

关键词：

FLUOROGENIC PROBES; BETA-GALACTOSIDASE; REPORTER MOLECULE; MAO-A; ASSAY;

D O I：

10.1021/ja2057506

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Monoamine inclose (MAO) A is a flavoenzyme that catalyzes the oxidation of biologically important monoamines and is thought to be associated with psychiatric disorders. Here, we report a strategy for rationally designing a F-19 magnetic resonance imaging probe for the specific detection of human MAO-A (hMAO-A) activity. Our designed F-19 probe was oxidized expeditiously by hMAO-A to produce 2-fluoro-4-nitrophenol via a spontaneous beta-elimination mechanism. Concomitant with the structural change of the probe to the product, the F-19 chemical shift changed by 4.2 ppm, which was enough to visualize the probe and enzymatic product separately. Importantly, our probe achieved excellent discrimination of hMAO-A from its isoform hMAO-B.

引用

页码：14208 / 14211

页数：4

共 31 条

[1]

Albers AE, 2007, CHEM COMMUN, P4647, DOI 10.1039/b713190a

[2] TURNOVER OF BRAIN MONOAMINE-OXIDASE MEASURED INVIVO BY POSITRON EMISSION TOMOGRAPHY USING L-[C-11]DEPRENYL [J].

ARNETT, CD ;

FOWLER, JS ;

MACGREGOR, RR ;

SCHLYER, DJ ;

WOLF, AP ;

LANGSTROM, B ;

HALLDIN, C .

JOURNAL OF NEUROCHEMISTRY, 1987, 49 (02) :522-527

[3] Synthesis and Characterization of 2-(2′-hydroxy-5′-chlorophenyl)-6-chloro-4(3H)-Quinazolinone-Based Fluorogenic Probes for Cellular Imaging of Monoamine Oxidases [J].

Aw, Junxin ;

Shao, Qing ;

Yang, Yanmei ;

Jiang, Tingting ;

Ang, Chungyen ;

Xing, Bengang .

CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (06) :1317-1321

[4] THE FUNCTIONAL-ROLE OF MONOAMINE OXIDASE-A AND OXIDASE-B IN THE MAMMALIAN CENTRAL-NERVOUS-SYSTEM [J].

BERRY, MD ;

JUORIO, AV ;

PATERSON, IA .

PROGRESS IN NEUROBIOLOGY, 1994, 42 (03) :375-391

[5] Synthesis and biological evaluation of MAO-A selective 1,4-disubstituted-1,2,3,6-tetrahydropyridinyl substrates [J].

Bissel, P ;

Bigley, MC ;

Castagnoli, K ;

Castagnoli, N .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :3031-3041

[6] Design of optical switches as metabolic indicators: New fluorogenic probes for monoamine oxidases (MAO A and B) [J].

Chen, G ;

Yee, DJ ;

Gubernator, NG ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4544-4545

[7] 19F NMR applications in chemical biology [J].

Cobb, Steven L. ;

Murphy, Cormac D. .

JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (02) :132-143

[8] NUCLEAR MAGNETIC-RESONANCE STUDIES OF AMINE STORAGE IN PIG PLATELETS [J].

COSTA, JL ;

DOBSON, CM ;

FAY, DD ;

KIRK, KL ;

POULSEN, FM ;

VALERI, CR ;

VECCHIONE, JJ .

FEBS LETTERS, 1981, 136 (02) :325-328

[9] Novel NMR approach to assessing gene transfection:: 4-fluoro-2-nitrophenyl-β-D-galactopyranoside as a prototype reporter molecule for β-galactosidase [J].

Cui, WN ;

Otten, P ;

Li, YM ;

Koeneman, KS ;

Yu, JX ;

Mason, RP .

MAGNETIC RESONANCE IN MEDICINE, 2004, 51 (03) :616-620

[10] Three-dimensional structure of human monoamine oxidase A (MAO A): Relation to the structures of rat MAO A and human MAO B [J].

De Colibus, L ;

Li, M ;

Binda, C ;

Lustig, A ;

Edmondson, DE ;

Mattevi, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (36) :12684-12689

← 1 2 3 4 →