水溶性苝酰亚胺类材料的合成及其生物应用

吴锦钧, 杨震, 焦剑梅, 孙鹏飞, 范曲立, 黄维

doi:10.7536/PC160717

化学进展 ›› 2017, Vol. 29 ›› Issue (2/3) :216-230 DOI: 10.7536/PC160717

综述

扫码查看或转发全文

水溶性苝酰亚胺类材料的合成及其生物应用

吴锦钧, 杨震, 焦剑梅, 孙鹏飞, 范曲立, 黄维

作者信息 +

The Synthesis and Biological Applications of Water-Soluble Perylene Diimides

Jinjun Wu, Zhen Yang, Jianmei Jiao, Pengfei Sun, Quli Fan, Wei Huang

Author information +

文章历史 +

摘要

3，4，9，10-苝四甲酰二亚胺及其衍生物（PDIs）因其光、热、化学稳定性好，荧光量子效率高的优点，已经在有机场效应晶体管（OFET）、有机太阳能电池（OPV）、染料激光和有机电致发光器件（OLED）等方面使用，但其自身结构容易π-π堆积，导致水溶性差，限制了其在生物领域的进一步运用。因此，对PDIs进行修饰，获得可以用于生物体的水溶性PDIs显得尤为重要。本文综述了对PDIs进行水溶性修饰的各种方法：使用阴离子取代基、阳离子取代基和非离子取代基等在PDIs酰亚胺的氮原子位置或者湾位置进行修饰，利用取代基的水溶性、静电排斥作用或者空间位阻效应来实现PDIs的水溶性。同时，进一步阐述了水溶性PDIs在新型荧光探针、光声成像、化学治疗和光动态治疗等方面的应用。

Abstract

Perylene diimide and its derivatives (PDIs) have been widely used as organic field-effect transistor (OFET), organic photovoltaic cell (OPV), dye laser and organic light emitting diode (OLED) in the field of optoelectronic materials due to their photo, thermal, chemical stability and high fluorescence quantum yields. However, because of their inherent structure, PDIs have poor water-solubility and easily form aggregates, which has limited their applications in biological fields. So, it's essential to synthesize water-soluble PDIs. This paper systematically presents the synthetic methods for obtaining water-soluble PDIs by introducing anionic substituent, cationic substituent or non-ionic substituent into the imide-position or bay-region of PDIs. Some of these substituents are water-soluble, and the others will achieve the water-solubility of PDIs through electrostatic repulsion or steric hindrance. In addition, several novel biological applications have been listed, such as chemotherapy,photodynamic therapy and fluorescence imaging.PDIs can also be used as a promising photo-acoustic contrast agents due to their good light absorption and photostability.

Contents
1 Introduction
2 Modification of PDIs
3 Modification of water-soluble PDIs
3.1 Anionic substituent
3.2 Cationic substituent
3.3 Non-ionic substituent
4 Biological application of water-soluble PDIs
4.1 Fluorescence probe
4.2 Contrast agent of photo-acoustic imaging
4.3 Chemotherapy
4.4 Photo-sensitizer of photodynamic therapy
5 Conclusion

Graphical abstract

关键词

3,4,9,10-苝四甲酰二甲胺 / 水溶性 / 修饰 / 生物应用

Key words

PDIs / water-soluble / modify / biological application

引用本文

引用格式 ▾

吴锦钧, 杨震, 焦剑梅, 孙鹏飞, 范曲立, 黄维. 水溶性苝酰亚胺类材料的合成及其生物应用[J]. 化学进展, 2017, 29(2/3): 216-230 DOI:10.7536/PC160717

Jinjun Wu, Zhen Yang, Jianmei Jiao, Pengfei Sun, Quli Fan, Wei Huang. The Synthesis and Biological Applications of Water-Soluble Perylene Diimides[J]. Progress in Chemistry, 2017, 29(2/3): 216-230 DOI:10.7536/PC160717

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[1] Huang C, Barlow S, Marder S R. J. Org. Chem., 2011, 76:2386.
[2] Kazmaier P M, Hoffmannr R. J. Am. Chem. Soc., 1994, 116:9684.
[3] Wurthner F. Chem. Commun., 2004, (14):1564.
[4] Ahrens M J, Fuller M J, Wasielewski M R. Chem. Mater., 2003, 15:2684.
[5] Serin J M, Brousmiche D W, Frechet J M J. Chem. Commun., 2002, (22):2605.
[6] Gronheid R, Hofkens J, Köhn F, Weil T, Reuther E, Müllen K, Schryver F C D. J. Am. Chem. Soc., 2002, 124:2418.
[7] An Z, Yu J, Jones S C, Barlow S, Yoo S, Domercq B, Prins P, Siebbeles L D A, Kippelen B, Marder S R. Adv. Mater., 2005, 17:2580.
[8] Jones B A, Facchetti A, Wasielewski M R, Marks T J. J. Am. Chem. Soc., 2007, 129:15259.
[9] Sadrai M, Bird G R. Opt. Commun., 1984, 51:62.
[10] Ford W E, Kamat P V. J. Phys. Chem., 1987, 91:6373.
[11] Seybold G, Wagenblast G. Dyes Pigments, 1989, 11:303.
[12] Zhan X W, Tan Z, Domercq B, An Z S, Zhang X, Barlow S, Li Y F, Zhu D B, Kippelen B, Marder S R. J. Am. Chem. Soc., 2007, 129:7246.
[13] Lindner S M, Kaufmann N, Thelakkat M. Org. Electr., 2007, 8:69.
[14] Jones B A, Ahrens M J, Yoon M H, Facchetti A, Marks T J, Wasielewski M R. Angew. Chem. Int. Ed., 2004, 43:6363.
[15] Zhan X W, Facchetti A, Barlow S, Marks T J, Ratner M A, Wasielewski M R, Marder S R. Adv. Mater., 2011, 23:268.
[16] Schmidt-Mende L, Fechtenkotter A, Mullen K, Moons E, Friend R H, MacKenzie J D. Science, 2001, 293:1119.
[17] Tan Z A, Zhou E, Zhan X, Wang X, Li Y, Barlow S, Marder S R. Appl. Phys. Lett., 2008, 93:073309.
[18] Qu J Q, Zhang J Y, Grimsdale A C, Mullen K, Jaiser F, Yang X H, Neher D. Macromolecules, 2004, 37:8297.
[19] Langhals H, Jona W, Einsiedl F, Wohnlich S. Adv. Mater., 1998, 10:1022.
[20] Gorl D, Zhang X, Wurthner F. Angew. Chem. Int. Ed., 2012, 51:6328.
[21] Wang B, Yu C. Angew. Chem., 2010, 122:1527.
[22] Wang B, Zhu Q K, Liao D L, Yu C. J. Mater. Chem., 2011, 21:4821.
[23] Wang B, Jiao H P, Li W Y, Liao D L, Wang F Y, Yu C. Chem. Commun., 2011, 47:10269.
[24] Fan Q L, Cheng K, Yang Z, Zhang R P, Yang M, Hu X, Ma X M, Bu L H, Lu X M, Xiong X X, Huang W, Zhao H, Cheng Z. Adv. Mater., 2015, 27:843.
[25] Zhao Q, Zhang H Y. Dyes Pigments, 2005, 66:15.
[26] Icli S, Demic S, Dindar B, Doroshenko A O, Timur C. J. Photochem. Photobiol. A, 2000, 136:15.
[27] Langhals H. Heterocycles, 1995, 40:477.
[28] Syebold G, Wagenblast G. Dyes Pigments, 1989, 11:303.
[29] Langhals H, Demmig S, Huber H. Spectrochim. Acta Part A, 1988, 44:1189.
[30] Fan L Q, Xu Y P, Tian H. Tetrahedron Lett., 2005, 46:4443.
[31] Chen Z J, Baumeister U, Tschierske C, Wurthner F. Chem. Eur. J., 2007, 13:450.
[32] Sadrai M, Hadel L, Saners R R. J. Phys. Chem., 1992, 96:7988.
[33] Wang K, Wang Y, Li J, An H, Zhang L, Zhang J, Li X. Bioorg. Med. Chem. Lett., 2013, 23:480.
[34] Qu J, Kohl C, Pottek M, Müllen K. Angew. Chem. Int. Ed., 2004, 43:1528.
[35] Frank D, Vos M, Antonietti M, Sommerdijk N A J M, Faul C F J. Chem. Mater., 2006, 18:1839.
[36] Kohl C, Weil T, Qu J, Müllen K. Chem. Eur. J., 2004, 10:5297.
[37] Ehli C, Oelsner C, Guldi D M, Mateo-Alonso A, Prato M, Schmidt C, Backes C, Hauke F, Hirsch A. Nat. Mater., 2014, 1:243.
[38] Backes C, Schmidt C D, Hauke F, Bottcher C, Hirsch A. J. Am. Chem. Soc., 2009, 131:2172.
[39] Zheng Y, You S S, Ji C D, Yin M Z, Yang W T, Shen J. Adv. Mater., 2016, 28:1375.
[40] Battagliarin G, Davies M, Mackowiak S, Li C, Müllen K. Chem. Phys., 2012, 13:923.
[41] Wang B, Yu C. Angew. Chem. Int. Ed., 2010, 49:1485.
[42] Xu Z, Cheng W, Guo K, Yu J, Shen J, Tang J, Yang W T, Yin M. ACS Appl. Mater. Inter., 2015, 7:9784.
[43] You S S, Cai Q, Zheng Y, He B C, Shen J, Yang W T, Yin M Z. ACS Appl. Mater. Inter., 2014, 6:16327.
[44] Yin M Z, Shen J, Gert O P, Mullen K. J. Am. Chem. Soc., 2008, 130:7806.
[45] You S, Cai Q, Müllen K, Yang W, Yin M. Chem. Commun., 2014, 50:823.
[46] Yin M T, Feng C L, Shen J, Yu Y M, Xu Z J, Yang W T, Knoll W, Müllen K. Small, 2011, 7:1629.
[47] Xu Z J, He B C, Shen J, Yang W T, Yin M Z. Chem. Commun., 2014, 50:823.
[48] Du F F, Tian J, Wang H, Liu B, Jin B K, Bai R. Macromolecules, 2012, 45:3086.
[49] Forgan R S, Sauvage J P, Stoddart J F. Chem. Rev., 2011, 111:5434.
[50] Sun H, Guo B, Cheng R, Meng F, Liu H, Zhong Z. Biomaterials, 2009, 30:6358.
[51] Biedermann F, Elmalem E, Ghosh I, Nau W M, Scherman O A. Angew. Chem., 2012, 124:7859.
[52] Liu K, YaoY X, Kang Y T, Liu Y, Han Y C, Wang Y L, Li Z B, Zhang X. Sci. Rep., 2013, 3:2372.
[53] Casado A G, Jonkheijm P, Huskens J. Langmuir, 2011, 27:11508.
[54] Biedermann F, Elmalem E, Ghosh I, Nau W M, Scherman O A. Angew. Chem. Int. Ed., 2012, 51:7739.
[55] Yang S K, Shi X H, Park S, Doganay S, Ha T, Zimmerman S C. J. Am. Chem. Soc., 2011, 133:9964.
[56] Rauwald U, Biedermann F, Deroo S, Robinson C V, Scherman O A. J. Phys. Chem. B, 2010, 114:8606.
[57] Zhang X, Rehm S, Safont-Sempere M M, Wurthner F. Nat. Mater., 2009, 1:263.
[58] Wang L, Xu L Q, Neoh K G, Kang E T. J. Mater. Chem., 2011, 21:6502.
[59] Xu L Q, Wang L, Zhang B, Lim C H, Chen Y, Neoh K G, Kang E T, Fu G D. Polymer, 2011, 52:2376.
[60] Ustinov A V, Dubnyakova V V, Korshun V A. Tetrahedron, 2008, 64:1467.
[61] Heek T, Nikolaus J, Schwarzer R, Fasting C, Welker P, Licha K, Herrmann K, Haag R. Bioconjugate Chem., 2013, 24:153.
[62] Li Z, Wei L, Gao M, Lei H. Adv. Mater., 2005, 17:1001.
[63] Gref R, Domb A, Quellec P, Blunk T, Muller R H, Verbavatz J M, Langer R. Adv. Drug. Delivery. Rev., 2012, 64:316.
[64] Shirman E, Ustinov A, Ben-Shitrit N, Weissman H, Iron M A, Cohen R, Rybtchinski B. J. Phys. Chem. B, 2008, 112:8855.
[65] Gao B X, Li H X, Liu H M, Zhang L C, Bai Q Q, Ba X W. Chem. Commun., 2011, 47:3894.
[66] Heek T, Fasting C, Rest C, Zhang X, Wurthner F, Haag R. Chem. Commun., 2010, 46:1884.
[67] Heek T, Wurthner F, Haag R. Chem. Eur. J., 2013, 19:10911.
[68] Chen M J, Yin M Z. Progress in Polymer Science, 2014, 39:365.
[69] Liu K L, Xu Z J, Yin M Z. Progress in Polymer Science, 2015, 46:25.
[70] Sun M M, Mullen K, Yin M Z. Chem. Soc. Rev., 2016, 45:1513.
[71] Jeong Y, Yoon J. Inorg. Chim. Acta., 2012, 381:2.
[72] Langner C, Denk H. Virchows Archiv, 2004, 445:111.
[73] Zhong L N, Xing F F, Bai Y L, Zhao Y M, Zhu S R. Spectrochim. Acta Part A, 2013, 115:370.
[74] Willner I, Zayats M. Angew. Chem., 2007, 119:6528.
[75] Zhao W A, Ali M M, Aguirre S D, Brook M A, Li Y F. Anal. Chem., 2008, 80:8431.
[76] Yang Z, Yuan Y, Jiang R C, Fu N N, Lu X M, Tian C C, Hu W B, Fan Q L, Huang W. Polym. Chem., 2014, 5:1372.
[77] Ma Y S, Zhang F X, Zhang J F, Jiang T Y, Li X M, Wu J S, Ren H X. Luminscence, 2016, 31:102.
[78] Wang L, Sun C, Li S F, Jia N, Li J, Qu F R, Goh K L, Chen Y. Polymer, 2016, 82:172.
[79] Kaloyanova S, Zagranyarski Y, Ritz S, Hanulova M, Koynov K, Vonderheit A, Mullen K, Peneva K. J. Am. Chem. Soc., 2016, 138:2881.
[80] Wang X, Pang Y, Ku G, Stoica G, Wang L V. Opt. Lett., 2003, 28:1739.
[81] Xiang L, Xing D, Gu H, Yang D, Yang S, Zeng L, Chen W R. J. Biomed. Opt., 2007, 12:14001.
[82] Taruttis A, van Dam G M, Ntziachristos V. Cancer Res., 2015, 75:1548.
[83] Zackrisson S, van de Ven S M W Y, Gambhir S S. Cancer Res., 2014, 74:979.
[84] Yuan Z, Jiang H. Med. Phys., 2007, 34:538.
[85] Xu M, Wang L V. IEEE Trans. Med. Imaging, 2002, 21:814.
[86] Xu M, Xu Y, Wang L V. IEEE Trans. Biomed. Eng., 2003, 50:1086.
[87] Homan K A, Souza M, Truby R, Luke G P, Green C, Vreeland E, Emelianov S. ACS Nano, 2012, 6:641.
[88] Yu J, Yang C, Li J D S, Ding Y C, Zhang L, Yousaf M Z, Li J, Pang R, Wei L B, Xu L L, Sheng F G, Li C H, Li G J, Zhao L Y, Hou Y L. Adv. Mater., 2014, 26:4114.
[89] De la Zerda A, Zavaleta C, Keren S, Vaithilingam S, Bodapati S, Liu Z, Levi J, Smith B R, Ma T J, Oralkan O, Cheng Z, Chen X, Dai H, Khuri-Yakub B T, Gambhir S S. Nat. Nanotechnol., 2008, 3:557.
[90] Xu Z J, Guo K R, Yu J S, Sun H L, Tang J, Shen J, Mullen K, Yang W T, Yin M Z. Small, 2014, 10:4087.
[91] Sun M M, Yin W Y, Dong X H, Yang W T, Zhao Y L, Yin M Z. Nanoscale, 2016, 8:5302.
[92] Ikeda N, Usuda J, Kato H, Ishizumi T, Ichinose S, Otani K, Honda H, Furukawa K, Okunaka T, Tsutsui H. Laser. Surg. Med., 2011, 43:749.
[93] Capella M A M, Capella L S J. Biomed. Sci., 2003, 10:361.
[94] Ethirajan M, Chen Y H, Joshi P, Pandey R K. Chem. Soc. Rev., 2011, 40:340.
[95] Lucky S S, Soo K C, Zhang Y. Chem. Rev., 2015, 115:1990.
[96] Debele T A, Peng S, Tsai H C. Mol. Sci., 2015, 16:22094.
[97] Yukruk F, Dogan A L, Canpinar H, Guc D, Akkaya E U. Org. Lett., 2005, 7:2885.
[98] Dincalp H, K?z?lok S, Icli S. J. Fluoresc., 2014, 24:917.
[99] Cao G J, Rong R X, Wang Y N, Xu Q, Wang K R, Li X L. Dyes Pigments, 2017, 136:569.