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基于硅杂蒽类染料的荧光探针及其应用

杜曼, 霍宝龙, 刘杰民*, 李梦文, 房乐秋, 杨运旭*

化学进展 ›› 2018, Vol. 30 ›› Issue (6) :809-830

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化学进展 ›› 2018, Vol. 30 ›› Issue (6) :809-830 DOI: 10.7536/PC171025
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基于硅杂蒽类染料的荧光探针及其应用

    杜曼, 霍宝龙, 刘杰民*, 李梦文, 房乐秋, 杨运旭*
作者信息 +

Fluorescent Probes Based on Silicon-Substituted Xanthene Dyes and Their Applications in Bioimaging

  • Man Du, Baolong Huo, Jiemin Liu*, Mengwen Li, Leqiu Fang, Yunxu Yang*
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摘要

近年来,荧光成像技术为人们研究活体细胞及组织内的化学生物学过程提供了有效的研究工具,可以无损、实时、原位地以高时空分辨率实现对目标物进行生物荧光成像与分析。荧光成像技术在生物学、环境监测、临床诊断和药物发现等诸多研究领域发挥着越来越重要的作用。生物荧光成像技术的最新进展对发展新型小分子荧光染料及探针提出了更高的要求。激发和发射波长位于近红外光区(600~900 nm)的荧光染料及探针由于具有光毒性低、生物分子自发荧光干扰小、光散射低、组织穿透能力强等优点,非常适合用于生物荧光成像领域。通过将罗丹明分子中O桥原子用Si代替,得到了一类新型的探针分子——硅杂蒽类荧光探针。这类染料分子在保留了氧杂蒽荧光染料优越的光学性质的同时,光谱发生明显红移,满足了近红外荧光检测的要求,具有良好的生物相容性。本文综述了近年来基于硅杂蒽及其衍生物荧光探针的合成及在金属离子、pH值、小分子、生物酶等检测方面的研究进展,并且简要阐述了基于硅杂蒽类探针分子的识别检测机理以及其在生物成像等方面的应用。

Abstract

During the past several years, fluorescence imaging techniques have provided a powerful technique for studying chemical and biological events and processes in living system in a noninvasive and real time manner in situ with high spatial and temporal resolution. Fluorescence imaging has been becoming a more and more powerful tool in diverse research fields ranging from biology, environmental monitoring, clinical diagnosis, to drug discovery. Recent advances in fluorescence bioimaging have spurred a higher demand for developing new small-molecule fluorescent probes. Fluorescent probes whose excitation and emission wavelengths are in the near-infrared(NIR) region (650~900 nm) are favorable for biological applications due to the low phototoxicity, minimum interference from the background autofluorescence of biomolecules, low light scattering and deep tissue penetration. Recent research has shown that the Si-substituted xanthenes, in which the O atom in xanthenes is replaced by the Si atom, have attracted considerable interest on account of their excellent NIR photophysical properties as well as biocompatible characteristics. Fluorescent probes based on Si-substituted xanthenes or their derivatives in literatures in recent years are summarized. The progress of the application of Si-substituted xanthenes in metal ions, pH, small molecules, enzymes, and biological imaging are expounded elaborately.
Contents
1 Introduction
2 The synthesis of SiRs
2.1 The synthesis of TMDHS
2.2 The synthesis of SiRs
3 Fluorescent probes for cations
3.1 Fluorescent probes for Zn2+
3.2 Fluorescent probes for Ca2+
3.3 Fluorescent probes for Cu2+
3.4 Fluorescent probes for Hg2+
4 Fluorescent probes for pH
5 Fluorescent probes for molecules
5.1 Fluorescent probes for HCHO
5.2 Fluorescent probes for HClO and ROS
6 Fluorescent probes for enzymes
6.1 Fluorescent probes for β-galactosidase
6.2 Fluorescent probes for MMPs
6.3 Fluorescent probes for caspase and LAP
6.4 Fluorescent probes for Btk
7 Fluorescent probes for gases
7.1 Fluorescent probes for O2
7.2 Fluorescent probes for 1O2
7.3 Fluorescent probes for NO
8 Applications of biological imaging
8.1 Imaging of cellular proteins
8.2 Imaging of the Golgi in live cells
8.3 Imaging of GFP cells
8.4 Imaging of tumor cells
8.5 Imaging of mouse transplantation tumor
8.6 Imaging of neurons
8.7 Imaging of bacterial peptidoglycan
8.8 Imaging of cytoskeletal filaments
8.9 DNA stains
8.10 Imaging of mitochondria in myeloma cells
9 Conclusion and outlook

Graphical abstract

关键词

硅杂蒽 / 荧光探针 / 合成 / 近红外 / 生物成像

Key words

Si-substituted xanthenes / fluorescent probe / synthesis / near-infrared (NIR) / biological imaging

引用本文

引用格式 ▾
杜曼, 霍宝龙, 刘杰民*, 李梦文, 房乐秋, 杨运旭*. 基于硅杂蒽类染料的荧光探针及其应用[J]. 化学进展, 2018, 30(6): 809-830 DOI:10.7536/PC171025
Man Du, Baolong Huo, Jiemin Liu*, Mengwen Li, Leqiu Fang, Yunxu Yang*. Fluorescent Probes Based on Silicon-Substituted Xanthene Dyes and Their Applications in Bioimaging[J]. Progress in Chemistry, 2018, 30(6): 809-830 DOI:10.7536/PC171025

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参考文献

[1] Summerield S, Miller J N. Anal. Proc., 1993, 30:131.
[2] Patony G, Antoine M D. Anal. Chem., 1991, 63:321A.
[3] Imasaka T, Tsukamoto A, Ishibashi N. Anal. Chem., 1989, 61:2285.
[4] Yuan L, Lin W, Zheng K, He L, Huang W. Chem. Soc. Rev., 2013, 42:622.
[5] Morris M C. ACS Med. Chem. Lett., 2014, 5:99.
[6] Kobayashi H, Ogawa M, Alford R, Choyke P L, Urano Y. Chem. Rev., 2010, 110:2620.
[7] Sun Y Q, Liu J, Lv X, Liu Y, Zhao Y, Guo W. Angew. Chem. Int. Edit., 2012, 51:7634.
[8] Frangioni J V. Curr. Opin. Chem. Biol., 2003, 7:626.
[9] Tsien R Y, Harootunian A T. Cell Calcium, 1990, 11:93.
[10] Minta A, Kao J P, Tsien R Y. J. Biol. Chem., 1989, 264:8171.
[11] Keereweer S, Kerrebijn J D, von Driel P B, Xie B, Kaijzel E L, Snoeks T J, Que I, Hutteman M, van der Vorst J R, Vahrmeijer A L, van de velde C J, Baatenburg de Jong R J, Löwik C W. Mol. Imaging Biol., 2011, 13:199.
[12] Vendrell M, Zhai D, Er J C, Chang Y T. Chem. Rev., 2012, 112:4391.
[13] Terai T, Nagano T. Curr. Opin. Chem. Biol., 2008, 12:515.
[14] Chan J, Dodani S C, Chang C J. Nat. Chem., 2012, 4:973.
[15] Fu M, Xiao Y, Qian X, Zhao D, Xu Y. Chem. Commun., 2008, (15):1780.
[16] Yamaguchi S, Tamao K. J. Chem. Soc. Dalton Trans., 1998, (22):3693.
[17] Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T. ACS Chem. Biol., 2011, 6:600.
[18] Egawa T, Koide Y, Hanaoka K, Komatsu T, Terai T, Nagano T. Chem. Commun., 2011, 47:4162.
[19] Wang B G, Chai X Y, Zhu W W, Wang T, Wu Q Y. Chem. Commun., 2014, 50:14374.
[20] Grimm J B, Brown T A, Tkachuk A N, Lavis L D. ACS Cent. Sci., 2017, 3:975.
[21] Prodi L, Bolletta F, Montalti M, Zaccheroni N. Coord. Chem. Rev., 2000, 205:59.
[22] Silva A P, Gunaratne H Q, Gunnlaugsson T, Huxley A J, McCoy C P, Rademacher J T, Rice T E. Chem. Rev., 1997, 97:1515.
[23] Hirano T, Kikuchi K, Urano Y, Higuchi T, Nagano T. J. Am. Chem. Soc., 2000, 122:12399.
[24] Clapham D E. Cell, 2007, 131:1047.
[25] Egawa T, Hanaoka K, Koide Y, Ujita S, Takahashi N, Ikegaya Y, Matsuki N, Terai T, Ueno T, Komatsu T, Nagano T. J. Am. Chem. Soc., 2011, 133:14157.
[26] Wang B G, Cui X Y, Zhang Z Q, Chai X Y, Ding H, Wu Q Y, Guo Z W, Wang T. Org. Biomol. Chem., 2016, 14:6720.
[27] Wang A Z, Yang Y X, Yu F F, Xue L W, Hu B W, Fan W P, Dong Y J. Talanta, 2015, 132:864.
[28] Wang T, Zhao Q J, Hu H G, Yu S C, Liu X, Liu L, Wu Q Y. Chem. Commun., 2012, 48:8781.
[29] Tao J, Wan X C, Chen X Q, Li T C, Diao Q P, Yu H F, Wang T. Dyes and Pigments, 2017, 137:601.
[30] Zhu W W, Chai X Y, Wang B G, Zou Y, Wang T, Meng Q G, Wu Q Y. Chem. Commun., 2015, 51:9608.
[31] Hirabayashi K, Hanaoka K, Takayanagi T, Toki Y, Egawa T, Kamiya M, Komatsu T, Ueno T, Terai T, Yoshida K, Uchiyama M, Nagano T, Urano Y. Anal. Chem., 2015, 87:9061.
[32] Brewer T F, Chang C J. J. Am. Chem. Soc., 2015, 137:10886.
[33] Roth A, Li H, Anorma C, Chan J. J. Am. Chem. Soc., 2015, 137:10890.
[34] Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T. J. Am. Chem. Soc., 2011, 133:5680.
[35] Quinn A B, Narsimha S, Daniel J D, Colleen N S, Matthew E M. J. Am. Chem. Soc., 2013, 135:13365
[36] Zhang H X, Liu J, Liu C L, Yu P C, Sun M J, Yan X H, Guo J P, Guo W. Biomaterials, 2017, 133:60.
[37] Myochin T, Hanaoka K, Komatsu T, Terai T, Nagano T. J. Am. Chem. Soc., 2012, 134:13730.
[38] Myochin T, Hanaoka K, Iwaki S, Ueno T, Komatsu T, Terai T, Nagano T, Urano Y. J. Am. Chem. Soc., 2015, 137:4759.
[39] Kushida Y, Hanaoka K, Komatsu T, Terai T, Ueno T, Yoshida K, Uchiyama M, Nagano T. Bioorg. Med. Chem. Lett., 2012, 22:3908.
[40] Kim E, Yang K S, Kohler R H, Dubach J M, Mikula H, Weissleder R. Bioconjugate Chem., 2015, 26:1513.
[41] Piao W, Tsuda S, Tanaka Y, Maeda S, Liu F, Takahashi S, Kushida Y, Komatsu T, Ueno T, Terai T, Nakazawa T, Uchiyama M, Morokuma K, Nagano T, Hanaoka K. Angew. Chem. Int. Edit., 2013, 52:13028.
[42] Kim S, Tachikawa T, Fujitsuka M, Majima T. J. Am. Chem. Soc., 2014, 136:11707.
[43] Wang B G, Yu S C, Chai X Y, Li T J, Wu Q Y, Wang T. Chem. Eur. J., 2016, 22:5649.
[44] Mao Z Q, Jiang H, Song X J, Hu W, Liu Z H. Anal. Chem., 2017, 89:9620.
[45] Lukinavicius G, Umezawa K, Olivier N, Honigmann A, Yang G, Plass T, Mueller V, Reymond L, Correa I R, Luo Z G, Schultz C, Lemke E A, Heppenstall P, Eggeling C, Manley S, Johnsson K. Nat. Chem., 2013, 5:132.
[46] Lukinavicius G, Reymond L, D'este E, Masharina A, Gottfert F, Ta H, Guther A, Fournier M, Rizzo S, Waldmann H, Blaukopf C, Sommer C, Gerlich D W, Arndt H D, Hell S W, Johnsson K. Nat. Methods, 2014, 11:731.
[47] Lukinavicius G, Reymond L, Umezawa K, Sallin O, D'Este E, Göttfert F, Ta H, Hell S W, Urano Y, Johnsson K. J. Am. Chem. Soc., 2016, 138:9365.
[48] Uno S, Kamiya M, Yoshihara T, Sugawara K, Okabe K, Tarhan M C, Fujita H, Funatsu T, Okada Y, Tobita S, Urano Y. Nat. Chem., 2014, 6:681.
[49] Grimm J B, Klein T, Kopek B G, Shtengel G, Hess H F, Sauer M, Lavis L D. Angew. Chem. Int. Edit., 2016, 55:1723.
[50] Erdmann R S, Takakura H, Thompson A D, Riveramolina F, Allgeyer E S, Bewersdorf J, Toomre D, Schepartz A. Angew. Chem. Int. Edit., 2014, 53:10242.
[51] Kim E, Yang K S, Giedt R J, Weissleder R. Chem. Commun., 2014, 50:4504.
[52] Kim S Y, Fujitsuka M, Tohnai N, Tachikawa T, Hisaki I, Miyata M, Majima T. Chem. Commun., 2015, 51:11580.
[53] Kim S Y, Fujitsuka M, Miyata M, Majima T. Phys. Chem. Chem. Phys., 2016, 18:2097.
[54] Shen S X, Yu J R, Lu Y M, Zhang S C, Yi X G, Gao B X. RSC Adv., 2017, 7:10922.
[55] McCann T E, Kosaka N, Koide Y, Mitsunaga M, Choyke P L., Nagano T, Urano Y, Kobayashi H. Bioconjugate Chem., 2011, 22:2531.
[56] Koide Y, Urano Y, Hanaoka K, Piao W, Kusakabe M, Saito N, Terai T, Okabe T, Nagano T. J. Am. Chem. Soc., 2012, 134:5029.
[57] Huang Y L, Walker A S, Miller E W. J. Am. Chem. Soc., 2015, 137:10767.
[58] Shieh P, Siegrist M S, Cullen A J, Bertozzi C R. Proc.Natl.Acad.Sci.U.S.A., 2014, 111:5456.
[59] Butkevich A N, Mitronova G Y, Sidenstein S C, Klocke J L, Kamin D, Meineke D N, D'Este E, Kraemer P T, Danzl J G, Belov V N, Hell S W. Angew. Chem. Int. Ed., 2016, 55:3290.
[60] Lukinavicius G, Blaukopf C, Pershagen E, Schena A, Reymond L, Derivery E, Marcos G G, D'este E, Hell S W, Wolfram G D, Johnsson K. Nat. Commun., 2015, 6:8497.
[61] Pastierik T, Šebej P, Medalova J, Štacko P, Klan P. J. Org. Chem., 2014, 79:3374.
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