相比于基于非共价键的超分子相互作用的传统荧光探针,反应型荧光探针的识别过程不是通过配位和氢键的相互作用,而是通过与目标物发生化学反应,使得光谱性质或颜色改变,生成不同结构的光活性化合物。近年来,反应型荧光探针主要有三种化学反应类型:底物与受体通过共价键连接;底物作为催化剂,与受体发生不可逆的反应;基于置换反应使底物与受体络合。正是反应型荧光探针利用选择反应的优势识别特定物质,因而提供了方便、快捷、专一的分析检测目标物的方法,具有很高的灵敏度和选择性,受到越来越多的关注。本文综述了近六年来基于反应型罗丹明荧光探针用于检测金属阳离子、活性氧化物和阴离子诱导β-内酰胺开环的最新研究进展,评述其结构和检测性能之间的关系,并展望这类荧光探针的应用前景与发展趋势。
[1] Park S, Kim W, Swamy K M K, Lee H Y, Jung J Y, Kim G, Kim Y, Kim S J, Yoon J. Dyes Pigments, 2013, 99: 323.
[2] Sun T, Moon J O, Choi M G, Cho Y, Ham S W, Chang S K. Sensor and Actuat B, 2013, 182: 755.
[3] Wei L, Yi L, Song F, Wei C, Wang B F, Xi Z. Sci. Rep., 2014, 4 : 4521.
[4] Adhikari S, Ghosh A, Mandal S, Sengupta A, Chattopadhyay A, Matalobos J S, Lohar S, Das D. Dalton Trans., 2014, 43: 7747.
[5] 冷冰(Leng B), 田禾(Tian H). 化学进展(Progress in Chemistry), 2010, 22(5): 837.
[6] Wang M, Yan F Y, Zou Y, Chen L, Yang N, Zhou X G. Sensor and Actuat B, 2014, 192: 512.
[7] Yan F Y, Wang M, Cao D L, Yang N, Fu Y, Chen L, Chen L G. Dyes Pigments, 2013, 98: 42.
[8] Yan F Y, Cao D L, Yang N, Yu Q H, Wang M, Chen L. Sensor and Actuat B, 2012, 162: 313.
[9] Zhang D, Li M, Wang M, Wang J H, Yan X, Ye Y, Zhao Y F. Sensor and Actuat B, 2013, 177: 997.
[10] Lavis L D, Raines R T. ACS Chem. Biol., 2008, 3: 142.
[11] 孙伟 (Sun W), 胡德禹 (Hu D Y), 吴志兵 (Wu Z B), 宋宝安 (Song B A), 杨松 (Yang S). 有机化学(Chinese Journal of Organic Chemistry), 2011, 31(7): 997.
[12] Jun M E, Roy B, Ahn K H. Chem. Commun., 2011, 47: 7583.
[13] 刘云龙(Liu Y L). 山西大学博士论文(Doctoral Dissertation of Shanxi University), 2012.
[14] Kim H N, Lee M H, Kim H J, Kim J S, Yoon J. Chem. Soc. Rev., 2008, 37: 1465.
[15] Duong T Q, Kim J S. Chem. Rev., 2010, 110: 6280.
[16] Barceloux D G. J. Toxicol. Clin. Toxicol., 1999, 37: 217.
[17] Georgopoulos P G, Roy A, Yonone-Lioy M J, Opiekun R E, Lioy P J. J. Toxicol. Environ. Health Part B., 2001, 4: 341.
[18] 袁跃华(Yuan Y H), 田茂忠(Tian M Z), 冯锋(Feng F), 孟双明(Meng S M), 白云峰(Bai Y F). 化学进展(Progress in Chemistry), 2010, 22(10): 1929.
[19] Dujols V, Ford F, Czarnik A W. J. Am. Chem. Soc., 1997, 119: 7386.
[20] Chen X Q, Jia J, Ma H M, Wang S J, Wang X C. Anal. Chim. Acta, 2009, 632: 9.
[21] Hua Z Q, Wang X M, Feng Y C, Ding L, Lu H Y. Dyes and Pigments, 2011, 88: 257.
[22] Kumar M, Kumar N, Bhalla V, Sharma P R, Kaur T. Org. Lett., 2011, 14: 406.
[23] Tang L J, Guo J J, Cao Y H, Zhao N. J. Fluoresc., 2012, 22: 1603.
[24] Wang J L, Li H, Long L P, Xiao G Q, Xie D. J. Lumin., 2012, 132: 2456.
[25] Xiang Y, Tong A J. J. Lumin., 2008, 23: 28.
[26] Yu M X, Shi M, Chen Z G, Li F Y, Li X X, Gao Y H, Xu J, Yang H, Zhou Z G, Yi T, Huang C H. Chem. Eur. J., 2008, 14: 6892.
[27] Huang L, Hou F P, Xi P X, Bai D C, Xu M, Li Z P, Xie G Q, Shi Y J, Liu H Y, Zeng Z Z. J. Inorg. Biochem., 2011, 105: 800.
[28] Ilobet J M, Falco G, Teixido A, Domingo J L. J. Agric. Food Chem., 2003, 51: 838.
[29] Harris H H, Pickering I J, George G N. Science, 2003, 301: 1203.
[30] Pandurangappa M, Kumar K S. Anal. Methods, 2011, 3: 715.
[31] Yang Y K, Ko S K, Shin I, Tae J. Org. Bio. Chem., 2009, 7: 4590.
[32] Liu W M, Xu L W, Zhang H Y, You J J, Zhang X L, Sheng R L, Li H P, Wu S K, Wang P F. Org. Bio. Chem., 2009, 7: 660.
[33] Wu J S, Hwang I C, Kim K S, Kim J S. Org. Lett., 2007, 9(5): 907.
[34] Zhang J F, Lim C S, Cho B R, Kim J S. Talanta, 2010, 83: 658.
[35] Xi P X, Huang L, Liu H, Jia P F, Chen F J, Xu M, Zeng Z Z. J. Biol. Inorg. Chem., 2009, 14: 815.
[36] Gong Y J, Zhang X B, Chen Z, Yuan Y, Jin Z, Mei L, Zhang J, Tan W H, Shen G L, Yu R Q. Analyst, 2012, 137: 932.
[37] Zhang D, Li M, Wang M, Wang J H, Yang X, Ye Y, Zhao Y F. Sensor and Actuat B, 2013, 177: 977.
[38] Hu Z Q, Zhuang W M, Li M, Liu M D, Wen L R, Li C X. Dyes and Pigments, 2013, 98: 286.
[39] Nishizawa M, Imagawa H, Yamamoto H. Org. Biomol. Chem., 2010, 8: 511.
[40] Lin W Y, Cao X W, Ding Y D, Yuan L, Long L L. Chem. Commun, 2010, 46: 3529.
[41] Zhu M, Yuan M, Liu X, Xu J, Lv J, Huang C. Org. Lett., 2008, 10: 1481.
[42] Coskun A, Yilmaz M D, Akkaya E U. Org. Lett., 2007, 9: 607.
[43] Avirah R R, Jyothish K, Ramaiah D. Org. Lett., 2007, 9: 121.
[44] Zhang X, Shiraishi Y, Hirai T. Org. Lett., 2007, 9: 5039.
[45] Wang L N, Yan J X, Qin W W, Liu W S, Wang R. Dyes and Pigments, 2012, 92: 1083.
[46] Du J J, Fan J L, Peng X J, Sun P P, Wang J Y, Li H L, Sun S G. Org. Lett., 2010, 12(3): 476.
[47] Shi W, Sun S N, Li X H, Ma H M. Inorg. Chem., 2010, 49: 1206.
[48] Autreáux B, Tucker N P, Dixon R, Spiro S A. Nature, 2005, 437: 769.
[49] Swaminathan S, Fonseca V A, Alam M G, Shah S V. Diabetes Care, 2007, 30: 1926.
[50] Galaris D, Skiada V, Barbouti A. Cancer Lett., 2008, 266: 21.
[51] Lee M H, Giap T V, Kim S H, Lee Y H, Kang C, Kim J S. Chem. Commun., 2010, 46: 1407.
[52] Chen X P, Hong H J, Han R, Zhang D, Ye Y, Zhao Y F. J. Fluoresc., 2012, 22: 789.
[53] Cho D G, Sessler J L. Chem. Soc. Rev., 2009, 38: 1647.
[54] Carey J S, Laffan D, Thomson C, Williams M T. Org. Biomol. Chem., 2006, 4: 2337.
[55] International Programme on Chemical Safety. Environmental Health Criteria Series 226-Palladium.2nd ed. Geneva: World Health Organization, 2002.
[56] Jun M E, Ahn K H. Org. Lett., 2010, 12: 2790.
[57] Asharani P V, Wu Y L, Gong Z, Valiyaveettil S. Nanotechnology, 2008, 19: 1.
[58] Chatterjee A, Santra M, Won N, Kim S J, Kim J K, Kim S B, Ahn K H. J. Am. Chem. Soc., 2009, 131: 2040.
[59] Danscher G. Histochem. Cell Biol., 2002, 117: 447.
[60] Goodman C M, McCusker C D, Yilmaz T, Rotello V M. Bioconjug. Chem., 2004, 15: 897.
[61] Habib A, Tabata M. J. Inorg. Biochem., 2004, 98: 1696.
[62] Nyarko E, Hara T, Grab D J, Habib A, Kim Y, Nikolskaia O, Fukuma T, Tabata M. Chem. Biol. Interact., 2004, 148: 19.
[63] Jou M J, Chen X Q, Swamy K M K, Kim H N, Kim H J, Lee S G, Yoon J Y. Chem. Commun, 2009, 7218.
[64] Yang Y K, Lee S H, Tae J S. Org. Lett., 2009, 11: 5610.
[65] Egorova O A, Seo H, Chatterjee A, Ahn K H. Org. Lett., 2010, 12: 401.
[66] Yuan L, Lin W Y, Yang Y T, Song J Z. Chem. Comm., 2011, 47: 4703.
[67] D'Autréaux B, Toledano M B. Nat. Rev. Mol. Cell. Biol., 2007, 8: 813.
[68] Oushiki D, Kojima H, Terai T, Arita M, Hanaoka K, Urano Y, Nagano T. J. Am. Chem. Soc., 2010, 132: 2795.
[69] Yap Y W, Whiteman M, Cheung N S. Cell Signal, 2007, 19: 219.
[70] Pattison D I, Davies M. J. Biochemistry, 2006, 45: 8152.
[71] Sugiyama S, Kugiyama K, Aikawa M, Nakamura S, Ogawa H, Libby P. Vasc. Biol., 2004, 24: 1309.
[72] Podrez E A, AbuSoud H M, Hazen S L. Free Radical Biol. Med., 2000, 28: 1717.
[73] Sun Z N, Liu F Q, Chen Y, Tam P K H, Yang D. Org. Lett., 2008, 10: 2171.
[74] Yang Y K, Cho H J, Lee J, Shin I, Tae J. Org. Lett., 2009, 11: 859.
[75] Zhan X Q, Yan J H, Su J H, Wang Y C, He J, Wang S Y, Zheng H, Xu J G. Sensor and Actuat B, 2010, 150: 774.
[76] Zhang Z, Zheng Y, Hang W, Yan X M, Zhao Y F. Talanta, 2011, 85: 779.
[77] Wei F F, Lu Y, He S, Zhao L C, Zeng X S. Anal. Methods, 2012, 4: 616.
[78] Zhang Y R, Chen X P, Shao J, Zhang J Y, Yuan Q, Miao J Y, Zhao B X. Chem. Commun, 2014, 50: 14241.
[79] Halliwell B, Gutteridge J M C. Free Radicals in Biology and Medicine. 2nd ed. NY: Oxford University Press, 1989.
[80] Yapici N B, Jockusch S, Moscatelli A, Mandalapu S R, Itagaki Y, Bates D K, Wiseman S, Gibson K M, Turro N J, Bi L. Org. Lett., 2012, 14: 50.
[81] Kim M, Ko S K, Kim H, Shin I, Tae J. Chem. Commun., 2013, 49: 7959.
[82] Paulsen C E, Carroll K S. ACS Chem. Biol., 2010, 5: 47.
[83] Galaris D, Skiada V, Barbouti A. Cancer Lett., 2008, 266: 21.
[84] Yuan L, Lin W Y, Xie Y N, Chen B, Zhu S S. J. Am. Chem. Soc., 2012, 134: 1305.
[85] Ratner A J, Prince A. Am. J. Respir. Cell Mol. Biol., 2006, 22: 642.
[86] McFeeters R F. J. Food Protect., 1998, 61: 885.
[87] Fazio T, Warner C R. Food Addit. Contam., 1990, 7: 433.
[88] Yang X F, Zhao M L, Wang G. Sensor and Actuat B, 2010, 152: 8.
[89] Banerjee A, Sahana A, Lohar S, Hauli I, Mukhopadhyay S K, Safin D A, Babashkina M G, Bolte M, Garcia Y, Das D. Chem. Commun., 2013, 49: 2527.