Citation: CHEN Li-Yan,  WU Di. An Excited-state Intramolecular Proton Transfer-based Ratiometric Fluorescence Probe for Detection of Hypochlorite[J]. Chinese Journal of Analytical Chemistry, ;2021, 49(8): 1350-1356. doi: 10.19756/j.issn.0253-3820.201579 shu

An Excited-state Intramolecular Proton Transfer-based Ratiometric Fluorescence Probe for Detection of Hypochlorite

  • Corresponding author: CHEN Li-Yan, clyan@mail.ccnu.edu.cn
  • Received Date: 22 September 2020
    Revised Date: 25 March 2021

    Fund Project: Supported by the National Natural Science Foundation of China (No.22007034).

  • A new ratiometric fluorescence probe (HBT-CN) was developed with familiar excited state intramolecular proton transfer (ESIPT) fluorophore 2-(2'-hydroxyphenyl)-benzothiazole (HBT) as framework and diaminomeleonitrile (DMN) group as reactive site. The performance of this probe to monitor HOCl was further investigated. This probe possessed good sensitivity and with the ability to rapidly detect HOCl within seconds with a detection limit as low as 1.1×10-7 mol/L. Furthermore, this probe displayed high specificity for sensing HOCl over other relevant analytes including reactive oxygen species (H2O2, tBuO, ROO·) and reactive nitrogen species (NO2-, NO3-, ONOO-, NO·). Importantly, the cell experiments demonstrated that the probe HBT-CN had good cell membrane permeability and could monitor HOCl in live cells by dual-channel.
  • 加载中
    1. [1]

      JUDD S J, JEFFREY J A. Water Res., 1995, 29(4): 1203-1206.

    2. [2]

      SHEPHERD J, HILDERBRAND S A, WATERMAN P, HEINECKE J W, WEISSLEDER R, LIBBY P. Chem. Biol., 2007, 14(11): 1221-1231.

    3. [3]

      WINTERBOURN C C. Biochim. Biophys. Acta, 2014, 1840(2): 730-738.

    4. [4]

      YAP Y W, WHITEMAN M, CHEUNG N S. Cell. Signalling, 2007, 19(2): 219-228.

    5. [5]

      WHITEMAN M, ROSE P, SIAU J L, CHEUNG N S, TAN G S, HALLIWELL B, ARMSTRONG J S. Free Radical Biol. Med., 2005, 38(12): 1571-1584.

    6. [6]

      HESSE S J A, RUIJTER G J G, DIJKEMA C, VISSER J. J. Biotechnol., 2000, 77(1): 5-15.

    7. [7]

      ORDEIG O, MAS R, GONZALO J, DEL CAMPO F J, MUNOZ F J, DE HARO C. Electroanalysis, 2005, 17(18): 1641-1648.

    8. [8]

      ZHANG R G, KELEN S G, LAMANNA J C. J. Appl. Phys., 1990, 68(3): 1101-1106.

    9. [9]

      BONANNI A, CAMPANELLA L, GATTA T, GREGORI E, TOMASSETTI M. Food Chem., 2007, 102(3): 751-758.

    10. [10]

    11. [11]

    12. [12]

    13. [13]

    14. [14]

    15. [15]

      KANG J, HUO F J, YUE Y K, WEN Y, CHAO J B, ZHANG Y B, YIN C X. Dyes Pigm., 2017, 136: 852-858.

    16. [16]

      CHENG G H, FAN J L, SUN W, SUI K, JIN X, WANG J Y, PENG X J. Analyst, 2013, 138(20): 6091-6096.

    17. [17]

      CHEN X Q, LEE K, REN X T, RYU J, KIM G. Nat. Protoc., 2016, 11: 1219-1228.

    18. [18]

      XU Q L, LEE K, LEE S, LEE K. M, LEE W, YOON J. J. Am. Chem. Soc., 2013, 135(26): 9944-9949.

    19. [19]

      ZHOU J, LI L H, SHI W, GAO X H, LI X H, MA H M. Chem. Sci., 2015, 6(3): 4884-4888.

    20. [20]

      ZHANG Y R, ZHAO Z M, MIAO J Y, ZHAO B X. Sens. Actuators, B, 2016, 229: 408-413.

    21. [21]

      CAO L Y, ZHANG R, ZHANG W Z, DU Z B, LIU C J, YE Z Q, SONG B, YUAN J L. Biomaterials, 2015, 68: 21-31.

    22. [22]

      XU C, ZHOU Y, ZHOU Y, LI Z, PENG X J. Sens. Actuators, B, 2020, 325: 128766.

    23. [23]

      FAN J L, MU H Y, ZHU H, WANG J Y, PENG X J. Analyst, 2015, 140(13): 4594-4598.

    24. [24]

      LIU F, WU T, CAO J, CUI S, YANG Z, QIANG X, SUN S, SONG F, FAN J, WANG J, PENG X J. Chem. -Eur. J., 2013, 19(5): 1548-1553.

    25. [25]

      LEE M H, KIM J S, SESSLER J L. Chem. Soc. Rev., 2015, 44(13): 4185-4191.

    26. [26]

      HE L, XIONG H, WANG B, ZHANG Y, WANG J, ZHANG H, LI H, YANG Z, SONG X. Anal. Chem., 2020, 92(16): 11029-11034.

    27. [27]

      PARK J, KIM H, CHOI Y, KIM Y. Analyst, 2013, 138(12): 3368-3371.

    28. [28]

      ZHANG Y R, CHEN X P, SHAO J, ZHANG J Y, YUAN Q, MIAO J Y, ZHAO B X. Chem. Commun., 2014, 50(91): 14241-14244.

    29. [29]

      HOU J T, LI K, YANG J, YU K K, LIAO Y X, RAN Y Z, LIU Y H, ZHOU X D, YU X D. Chem. Commun. 2015, 51(31): 6781-6784.

    30. [30]

      ZHANG D, YANG Z, LI H, PEI Z, SUN S, XU Y. Chem. Commun., 2016, 52(4): 749-752.

    31. [31]

      HEYER E, BENELHADJ K, BUDZAK S, JACQUEMIN D, MASSUE J, ULRICH G. Chem. -Eur. J., 2017, 23(30): 7324-7336.

    32. [32]

      CHEN L, PARK S J, WU D, KIM H M, YOON J. Dyes Pigm., 2018, 158: 526-532.

    33. [33]

      AFFELDT R F, BORGES A C S, RUSSOWSKY D, RODEMBUSCH F S. New. J. Chem., 2014, 38(9): 4607-4614.

    34. [34]

      CHENG X, JIA H, LONG T, FENG J, QIN J, LI Z. Chem. Commun., 2011, 47(43): 11978-11980.

  • 加载中
    1. [1]

      Yanglin Jiang Mingqing Chen Min Liang Yige Yao Yan Zhang Peng Wang Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027

    2. [2]

      Yanxi LIUMengjia XUHaonan CHENQuan LIUYuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423

    3. [3]

      Jinlong YANWeina WUYuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154

    4. [4]

      Yuting DUJing YUANPeiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461

    5. [5]

      Jiakun BAITing XULu ZHANGJiang PENGYuqiang LIJunhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002

    6. [6]

      Yingpeng ZHANGXingxing LIYunshang YANGZhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064

    7. [7]

      Jun LUOBaoshu LIUYunchang ZHANGBingkai WANGBeibei GUOLan SHETianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240

    8. [8]

      Wei GAOMeiqi SONGXuan RENJianliang BAIJing SUJianlong MAZhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112

    9. [9]

      Lei ZHANGCheng HEYang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081

    10. [10]

      Yu SUXinlian FANYao YINLin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126

    11. [11]

      Siyi ZHONGXiaowen LINJiaxin LIURuyi WANGTao LIANGZhengfeng DENGAo ZHONGCuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093

    12. [12]

      Linfang ZHANGWenzhu YINGui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405

    13. [13]

      Meirong HANXiaoyang WEISisi FENGYuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150

    14. [14]

      Yuan ZHUXiaoda ZHANGShasha WANGPeng WEITao YI . Conditionally restricted fluorescent probe for Fe3+ and Cu2+ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232

    15. [15]

      Shuwen SUNGaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399

    16. [16]

      Zhifeng CAIYing WUYanan LIGuiyu MENGTianyu MIAOYihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394

    17. [17]

      Qingjun PANZhongliang GONGYuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365

    18. [18]

      Caixia Lin Zhaojiang Shi Yi Yu Jianfeng Yan Keyin Ye Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

    19. [19]

      Benhua Wang Chaoyi Yao Yiming Li Qing Liu Minhuan Lan Guipeng Yu Yiming Luo Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070

    20. [20]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

Metrics
  • PDF Downloads(12)
  • Abstract views(1012)
  • HTML views(89)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return