A reversible near-infrared fluorescence probe for reactive oxygen species based on Te-rhodamine

被引：143

作者：

Koide, Yuichiro ^{[1
]}

Kawaguchi, Mitsuyasu ^{[1
]}

Urano, Yasuteru ^{[2
]}

Hanaoka, Kenjiro ^{[1
]}

Komatsu, Toru ^{[1
]}

Abo, Masahiro ^{[1
]}

Teraia, Takuya ^{[1
]}

Nagano, Tetsuo ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Univ Tokyo, Grad Sch Med, Bunkyo Ku, Tokyo 1130033, Japan

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 25期

关键词：

OXIDATIVE STRESS; HYDROGEN-PEROXIDE; TELLURIUM ANALOGS; FREE-RADICALS; NITRIC-OXIDE; MECHANISM; PEROXYNITRITE; DESIGN; DAMAGE; ACID;

D O I：

10.1039/c2cc18011a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have designed and synthesized a reversible near-infrared (NIR) fluorescence probe, 2-Me TeR, for reactive oxygen species (ROS), utilizing the redox properties of the tellurium (Te) atom. 2-Me TeR is oxidized to fluorescent 2-Me TeOR by various ROS, while the generated 2-Me TeOR is quickly reduced in the presence of glutathione to regenerate 2-Me TeR. This redox-induced reversible NIR-fluorescence response of 2-Me TeR allowed us to detect the endogenous production of ROS and subsequent homeostatic recovery of the intracellular reductive environment in hydrogen peroxide-stimulated HL-60 cells. This probe is expected to be useful for monitoring the dynamics of ROS production continuously in vivo.

引用

页码：3091 / 3093

页数：3

共 41 条

[1] Development of a Highly Sensitive Fluorescence Probe for Hydrogen Peroxide [J].

Abo, Masahiro ;

Urano, Yasuteru ;

Hanaoka, Kenjiro ;

Terai, Takuya ;

Komatsu, Toru ;

Nagano, Tetsuo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10629-10637

[2] Tellurium: an element with great biological potency and potential [J].

Ba, Lalla Aicha ;

Doering, Mandy ;

Jamier, Vincent ;

Jacob, Claus .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (19) :4203-4216

[3] Lipid oxidation products and atherosclerosis [J].

Berliner, J .

VASCULAR PHARMACOLOGY, 2002, 38 (04) :187-191

[4] Tellurium analogues of rosamine and rhodamine dyes:: Synthesis, structure, 125Te NMR, and heteroatom contributions to excitation energies [J].

Calitree, Brandon ;

Donnelly, David J. ;

Holt, Jason J. ;

Gannon, Michael K. ;

Nygren, Cara L. ;

Sukumaran, Dinesh K. ;

Autschbach, Jochen ;

Detty, Michael R. .

ORGANOMETALLICS, 2007, 26 (25) :6248-6257

[5] Regulation and measurement of oxidative stress in apoptosis [J].

Curtin, JF ;

Donovan, M ;

Cotter, TG .

JOURNAL OF IMMUNOLOGICAL METHODS, 2002, 265 (1-2) :49-72

[6] ROS as signalling molecules:: mechanisms that generate specificity in ROS homeostasis [J].

D'Autreaux, Benoit ;

Toledano, Michel B. .

NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2007, 8 (10) :813-824

[7] Biomarkers of oxidative damage in human disease [J].

Dalle-Donne, I ;

Rossi, R ;

Colombo, R ;

Giustarini, D ;

Milzani, A .

CLINICAL CHEMISTRY, 2006, 52 (04) :601-623

[8] 2,7-Bis-N,N-dimethylaminochalcogenoxanthen-9-ones via electrophilic cyclization with phosphorus oxychloride [J].

Del Valle, DJ ;

Donnelly, DJ ;

Holt, JJ ;

Detty, MR .

ORGANOMETALLICS, 2005, 24 (15) :3807-3810

[9] Dicationic Tellurium Analogues of the Classic N-Heterocyclic Carbene [J].

Dutton, Jason L. ;

Ragogna, Paul J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (41) :12454-12461

[10] Development of a fluorescein analogue, TokyoMagenta, as a novel scaffold for fluorescence probes in red region [J].

Egawa, Takahiro ;

Koide, Yuichiro ;

Hanaoka, Kenjiro ;

Komatsu, Toru ;

Terai, Takuya ;

Nagano, Tetsuo .

CHEMICAL COMMUNICATIONS, 2011, 47 (14) :4162-4164

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