19F magnetic resonance probes for live-cell detection of peroxynitrite using an oxidative decarbonylation reaction

被引:36
作者
Bruemmer, Kevin J. [1 ]
Merrikhihaghi, Sara [1 ]
Lollar, Christina T. [1 ]
Morris, Siti Nur Sarah [2 ]
Bauer, Johannes H. [2 ,3 ]
Lippert, Alexander R. [1 ,3 ]
机构
[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
[2] So Methodist Univ, Dept Biol Sci, Dallas, TX 75275 USA
[3] So Methodist Univ, Ctr Drug Discovery Design & Delivery CD4, Dallas, TX 75275 USA
关键词
NITRIC-OXIDE; FLUORESCENT-PROBE; HYDROGEN-PEROXIDE; IN-VIVO; KINETICS; NMR; OXYGEN; CALCIUM; VITRO;
D O I
10.1039/c4cc04292a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a newly discovered oxidative decarbonylation reaction of isatins that is selectively mediated by peroxynitrite (ONOO-) to provide anthranilic acid derivatives. We have harnessed this rapid and selective transformation to develop two reaction-based probes, 5-fluoroisatin and 6-fluoroisatin, for the low-background readout of ONOO- using F-19 magnetic resonance spectroscopy. 5-fluoroisatin was used to non-invasively detect ONOO- formation in living lung epithelial cells stimulated with interferon-gamma (IFN-gamma).
引用
收藏
页码:12311 / 12314
页数:4
相关论文
共 39 条
  • [1] Proteomic method identifies proteins nitrated in vivo during inflammatory challenge
    Aulak, KS
    Miyagi, M
    Yan, L
    West, KA
    Massillon, D
    Crabb, JW
    Stuehr, DJ
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (21) : 12056 - 12061
  • [2] 19F NMR measurements of NO production in hypertensive ISIAH and OXYS rats
    Bobko, AA
    Sergeeva, SV
    Bagryanskaya, EG
    Markel, AL
    Khramtsov, VV
    Reznikov, VA
    Kolosova, NG
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2005, 330 (02) : 367 - 370
  • [3] Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: Implications for intracellular measurement of reactive nitrogen and oxygen species
    Crow, JP
    [J]. NITRIC OXIDE-BIOLOGY AND CHEMISTRY, 1997, 1 (02): : 145 - 157
  • [4] An adhesive 19F MRI chemical probe allows signal off-to-on-type molecular sensing in a biological environment
    Doura, Tomohiro
    Hata, Ryunosuke
    Nonaka, Hiroshi
    Sugihara, Fuminori
    Yoshioka, Yoshichika
    Sando, Shinsuke
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (97) : 11421 - 11423
  • [5] p-Aminophenyl Alkyl Ether-based 19F MRI Probe for Specific Detection and Imaging of Hypochlorite Ion
    Doura, Tomohiro
    An, Qi
    Sugihara, Fuminori
    Matsuda, Tetsuya
    Sando, Shinsuke
    [J]. CHEMISTRY LETTERS, 2011, 40 (12) : 1357 - 1359
  • [6] Chemical Biology of Peroxynitrite: Kinetics, Diffusion, and Radicals
    Ferrer-Sueta, Gerardo
    Radi, Rafael
    [J]. ACS CHEMICAL BIOLOGY, 2009, 4 (03) : 161 - 177
  • [7] Groeger G, 2009, ANTIOXID REDOX SIGN, V11, P2655, DOI 10.1089/ARS.2009.2728
  • [8] Increased nitrotyrosine in exhaled breath condensate of patients with asthma
    Hanazawa, T
    Kharitonov, SA
    Barnes, PJ
    [J]. AMERICAN JOURNAL OF RESPIRATORY AND CRITICAL CARE MEDICINE, 2000, 162 (04) : 1273 - 1276
  • [9] Paramagnetic 19F Chemical Shift Probes that Respond Selectively to Calcium or Citrate Levels and Signal Ester Hydrolysis
    Harvey, Peter
    Chalmers, Kirsten H.
    De Luca, Elena
    Mishra, Anurag
    Parker, David
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (28) : 8748 - 8757
  • [10] 19F NMR based pH probes:: lanthanide(III) complexes with pH-sensitive chemical shifts
    Kenwright, Alan M.
    Kuprov, Ilya
    De Luca, Elena
    Parker, David
    Pandya, Shashi U.
    Senanayake, P. Kanthi
    Smith, David G.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (22) : 2514 - 2516