A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

被引:168
作者
Xu, Qingling [1 ]
Heo, Cheol Ho [2 ]
Kim, Jin A. [1 ]
Lee, Hye Sue [2 ]
Hu, Ying [1 ]
Kim, Dayoung [1 ]
Swamy, Kunemadihalli Mathada Kotraiah [1 ,3 ]
Kim, Gyoungmi [1 ]
Nam, Sang-Jip [1 ]
Kim, Hwan Myung [2 ]
Yoon, Juyoung [1 ]
机构
[1] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea
[2] Ajou Univ, Dept Energy Syst Res, Suwon 443749, Gyeonggi Do, South Korea
[3] VL Coll Pharm, Dept Pharmaceut Chem, Raichur 584103, Karnataka, India
基金
新加坡国家研究基金会;
关键词
INDUCED HOCL PRODUCTION; LIVE CELLS; REACTIVE OXYGEN; LIVING CELLS; CANCER-CELLS; IN-VIVO; PH; TISSUES; MYELOPEROXIDASE; CHEMISTRY;
D O I
10.1021/acs.analchem.6b01738
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Hypochlorite (OCl-) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl- at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl- recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl- in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl-, displayed a selective fluorescent off/on response to OCl- with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl- in live RAW 264.7 cells-via two-photon microscopy.
引用
收藏
页码:6615 / 6620
页数:6
相关论文
共 46 条
  • [1] Oxidative stress in neurodegeneration: cause or consequence?
    Andersen, JK
    [J]. NATURE MEDICINE, 2004, 10 (07) : S18 - S25
  • [2] A Ratiometric Two-Photon Fluorescent Probe Reveals Reduction in Mitochondrial H2S Production in Parkinson's Disease Gene Knockout Astrocytes
    Bae, Sung Keun
    Heo, Cheol Ho
    Choi, Dong Joo
    Sen, Debabrata
    Joe, Eun-Hye
    Cho, Bong Rae
    Kim, Hwan Myung
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (26) : 9915 - 9923
  • [3] pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination
    Best, Quinn A.
    Sattenapally, Narsimha
    Dyer, Daniel J.
    Scott, Colleen N.
    McCarroll, Matthew E.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) : 13365 - 13370
  • [4] Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species
    Chen, Xiaoqiang
    Tian, Xizhe
    Shin, Injae
    Yoon, Juyoung
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) : 4783 - 4804
  • [5] A specific and sensitive method for detection of hypochlorous acid for the imaging of microbe-induced HOCl production
    Chen, Xiaoqiang
    Lee, Kyung-Ah
    Ha, Eun-Mi
    Lee, Kyung Mi
    Seo, You Yeong
    Choi, Han Kyoung
    Kim, Ha Na
    Kim, Min Jung
    Cho, Chun-Seok
    Lee, Soo Young
    Lee, Won-Jae
    Yoon, Juyoung
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (15) : 4373 - 4375
  • [6] A highly specific BODIPY-based probe localized in mitochondria for HClO imaging
    Cheng, Guanghui
    Fan, Jiangli
    Sun, Wen
    Sui, Kun
    Jin, Xin
    Wang, Jingyun
    Peng, Xiaojun
    [J]. ANALYST, 2013, 138 (20) : 6091 - 6096
  • [7] Transformed target cell-derived superoxide anions drive apoptosis induction by myeloperoxidase
    Engelmann, I
    Dormann, S
    Saran, M
    Bauer, G
    [J]. REDOX REPORT, 2000, 5 (04) : 207 - 214
  • [8] Molecular mechanisms of macrophage activation and deactivation by lipopolysaccharide: roles of the receptor complex
    Fujihara, M
    Muroi, M
    Tanamoto, K
    Suzuki, T
    Azuma, H
    Ikeda, H
    [J]. PHARMACOLOGY & THERAPEUTICS, 2003, 100 (02) : 171 - 194
  • [9] Halliwell B, 1999, METHOD ENZYMOL, V301, P333
  • [10] Deep tissue two-photon microscopy
    Helmchen, F
    Denk, W
    [J]. NATURE METHODS, 2005, 2 (12) : 932 - 940