基于激发态分子内质子转移机理的比率型荧光探针的合成及对次氯酸的检测

陈黎艳 吴迪

引用本文: 陈黎艳, 吴迪. 基于激发态分子内质子转移机理的比率型荧光探针的合成及对次氯酸的检测[J]. 分析化学, 2021, 49(8): 1350-1356. doi: 10.19756/j.issn.0253-3820.201579 shu
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

基于激发态分子内质子转移机理的比率型荧光探针的合成及对次氯酸的检测

    通讯作者: 陈黎艳,E-mail:clyan@mail.ccnu.edu.cn
  • 基金项目:

    国家自然科学基金项目(No.22007034)资助。

摘要: 以常见的激发态分子内质子转移(ESIPT)类型的荧光团2-(2'-羟基苯基)-苯并噻唑(HBT)为主要骨架,以高反应活性的二氨基马来腈(DMN)结构单元为识别基团,构建了比率型荧光探针HBT-CN,并对其识别性能进行了研究。HBT-CN具有良好的灵敏度,可在几秒内对HOCl做出响应,检出限低至0.11 μmol/L。干扰实验表明,探针HBT-CN不受活性氧(如H2O2tBuO、ROO·)及活性氮(如NO2-、NO3-、ONOO-、NO·)等物质的干扰,具有优异的选择性。细胞成像实验表明,探针HBT-CN具有良好的细胞膜渗透性及在活体细胞中双通道比率型检测HOCl分子的能力。

English


    1. [1]

      JUDD S J, JEFFREY J A. Water Res., 1995, 29(4): 1203-1206.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.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.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.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.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.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.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.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.BONANNI A, CAMPANELLA L, GATTA T, GREGORI E, TOMASSETTI M. Food Chem., 2007, 102(3): 751-758.

    10. [10]

      CHEN Wei, MA Hui-Min. Chin. J. Anal. Chem., 2012, 40(9): 1311-1321. 陈巍, 马会民. 分析化学, 2012, 40(9): 1311-1321.

    11. [11]

      QI Shao-Long, DU Jian-Shi, LI Rong-Hang, LI Qiang, ZHU Lu-Bao, SHI Ya-Nan, WANG Xin-Yu, YANG Qing-Biao, ZHANG Gui-Rong, LI Yao-Xian. Chin. J. Anal. Chem., 2020, 48(3): 347-354. 戚少龙, 杜建时, 李容杭, 李强, 祝录宝, 时亚男, 王欣宇, 杨清彪, 张桂荣, 李耀先. 分析化学, 2020, 48(3): 347-354.

    12. [12]

      ZOU Xiao-Bo, JIANG Cai-Ping, LI Zhi-Hua, SUN Yue, SHI Ji-Yong, LI Yan-Xiao, HUANG Xiao-Wei, ZHANG Di, HU Xue-Tao, ZHAI Xiao-Dong, WEI Xiao-Ou. Chin. J. Anal. Chem., 2020, 48(4): 507-515. 邹小波, 蒋彩萍, 李志华, 孙悦, 石吉勇, 李艳肖, 黄晓玮, 张迪, 胡雪桃, 翟晓东, 魏晓鸥. 分析化学, 2020, 48(4): 507-515.

    13. [13]

      WANG Yan-Bao, ZHAO Bao-Xiang. Chin. J. Org. Chem., 2016, 36: 1539-1554. 王延宝, 赵宝祥. 有机化学, 2016, 36: 1539-1554.

    14. [14]

      HOU Ling-Yan, ZHANG Zhu-Jun, ZHOU Fu-Lin. Chin. J. Anal. Chem., 2007, 35(2): 285-288. 侯凌燕, 章竹君, 周福林. 分析化学, 2007, 35(2): 285-288.

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

  • 加载中
计量
  • PDF下载量:  12
  • 文章访问数:  905
  • HTML全文浏览量:  81
文章相关
  • 收稿日期:  2020-09-22
  • 修回日期:  2021-03-25
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

/

返回文章