近红外荧光生物成像技术由于具有深的组织穿透性、低背景荧光干扰、最小生物样本光损伤等特点引起人们越来越多的关注。开发高荧光效率、低毒性的近红外荧光染料是近红外荧光成像技术发展的关键所在。本文综述了五类主要的有机近红外荧光染料(菁类、BODIPY类、罗丹明类、方酸类、卟啉类)的研究进展,重点分析其结构与光学性质等构效关系,为近红外荧光染料的设计和制备提供指导。另外,总结了有机近红外荧光材料功能化修饰的主要方法以改善生物相容性、靶向性能等,最后对近红外荧光染料存在的主要问题以及未来的热点方向进行了分析和展望。
[1] Weissleder R, Pittet M J. Nature, 2008, 452: 580.
[2] Chen M, Yin M. Prog. Polym. Sci., 2014, 39: 365.
[3] Yuan L, Lin W, Zheng K, He L, Huang W. Chem. Soc. Rev., 2012, 42: 622.
[4] Yuan A, Wu J, Tang X, Zhao L, Xu F, Hu Y. J. Pharm. Sci. Us., 2013, 102: 6.
[5] Luo S, Zhang E, Su Y, Cheng T, Shi C. Biomaterials, 2011, 32: 7127.
[6] Guo Z Q, Park S, Yoon J, Shin I. Chem. Soc. Rev., 2012, 41: 15.
[7] Han J, Burgess K. Chem. Rev., 2010, 110: 2709.
[8] Ni Y, Wu J. Org. Biomol. Chem., 2014, 12: 3774.
[9] Hayashi K, Nakamura M, Miki H, Ozaki S, Abe M, Matsumoto T, Ishimura K. Adv. Funct. Mater., 2012, 22: 3539.
[10] Hilderbrand S A, Weissleder R. Curr. Opin. Chem. Biol., 2010, 14: 71.
[11] Qian G, Wang Z Y. Chem. Asian J., 2010, 5: 1006.
[12] Mishra A, Behera R K, Behera P K, Mishra B K, Behera G B. Chem. Rev., 2000,100: 1973.
[13] James N S, Chen Y, Joshi P, Ohulchanskyy T Y, Ethirajan M, Henary M, Strekowsk L, Pandey R K. Theranostics, 2013, 3: 692.
[14] Peng X, Yang Z, Wang J, Fan J, He Y, Song F, Wang B, Sun S, Qu J, Qi J, Yang M. J. Am. Chem. Soc., 2011, 133: 6626.
[15] Cao J, Hu C, Sun W, Xu Q, Fan J, Song F, Sun S, Peng X. RSC. Adv., 2014, 4: 13385.
[16] Wang L Y, Chen Q W, Zhai G H, Wen Z Y, Zhang Z X. J. Mol. Struct: THEOCHEM, 2006, 778: 15.
[17] Desmettre T, Devoisselle J M, Mordon S. Surv. Ophthalmol., 2000, 45: 15.
[18] Strekowski L, Lipowska M, Patonay G. J.Org. Chem., 1992, 57: 4578.
[19] Yu L, Li T, Wang Q, Li L, Chen L. Res. Chem. Intermediat., 2014, 40: 1469.
[20] Samanta A, Vendrell M, Das R, Chang Y. Chem. Commun., 2010, 46: 7406.
[21] Silva G L, Ediz V, Yaron D, Armitage B A. J. Am. Chem. Soc., 2007, 129: 5710.
[22] Wu X, Chang S, Sun X, Guo Z, Li Y, Tang J, Shen Y, Shi J, Tian H, Zhu W. Chem. Sci., 2013, 4: 1221.
[23] Bouteiller C, Clavé G, Bernardin A, Chipon B, Massonneau M, Renard P. Bioconjugate Chem., 2007, 18: 1303.
[24] Luo S, Tan X, Qi Q, Guo Q, Ran X, Zhang L, Zhang E, Liang Y, Weng L, Zheng H, Cheng T, Su Y, Shi C. Biomaterials, 2013, 34: 2244.
[25] Zhu S, Zhang J, Vegesna G, Tiwari A, Luo F, Zeller M, Luck R, Li H, Green S, Liu H. RSC Adv., 2011, 2: 404.
[26] Boens N, Leen V, Dehaen W. Chem. Soc. Rev., 2012, 41: 1130.
[27] Killoran J, Allen L, Gallagher J F, Gallagher W M,O Shea D F. Chem. Commun., 2002, 17: 1862.
[28] Bellier Q, Dalier F, Jeanneau E, Maury O, Andraud C. New J. Chem., 2012, 36: 768.
[29] Hall M J, McDonnell S O, Killoran J, O'Shea D F. J. Org. Chem., 2005, 70: 5571.
[30] Zhang X, Yu H, Xiao Y. J. Org. Chem., 2012, 77: 669.
[31] Zhang X, Wang C, Han Z, Xiao Y. ACS. Appl. Mater. Interfaces, 2014, 6: 21669.
[32] Ulrich G, Goeb S, De Nicola A, Retailleau P, Ziessel R. J.Org. Chem., 2011, 76: 4489.
[33] Sarma T, Panda P K, Setsune J. Chem. Commun., 2013, 49: 9806.
[34] Zeng L, Jiao C, Huang X, Huang K, Chin W, Wu J. Org. Lett., 2011, 13: 6026.
[35] Zhao W, Carreira E M. Angew. Chem. Int. Ed., 2005, 44: 1677.
[36] Zhao W, Carreira E M. Chem. Eur. J., 2006, 12: 7254.
[37] Chen J, Burghart A, Derecskei-Kovacs A, Burgess K. J. Org. Chem., 2000, 65: 2900.
[38] Jiao L, Wu Y, Wang S, Hu X, Zhang P, Yu C, Cong K, Meng Q, Hao E, Vicente M. J. Org. Chem., 2014, 79: 1830.
[39] Gorman A, Killoran J, O'Shea C, Kenna T, Gallagher W M, O'Shea D F. J. Am. Chem. Soc., 2004, 126: 10619.
[40] Pastierik T, Šebej P, Medalová J, Štacko P, Klán P. J. Org. Chem., 2014, 79: 3374.
[41] Yang Y K, Cho H J, Lee J, Shin I, Tae J. Org. Lett., 2009, 11: 859.
[42] Beija M, Afonso C, Martinho J. Chem. Soc. Rev., 2009, 38: 2410.
[43] Liu J, Diwu Z, Leung W, Lu Y, Patch B, Haugland R P. Tetrahedron Lett., 2003, 44: 4355.
[44] Alessi A, Salvalaggio M, Ruzzon G. J. Lumin., 2013, 134: 385.
[45] Detty M R, Prasad P N, Donnelly D J, Ohulchanskyy T, Gibson S L, Hilf R. Bioorgan. Med. Chem., 2004, 12: 2537.
[46] Yuan L, Lin W, Chen H. Biomaterials, 2013, 34: 9566.
[47] Sun Y, Liu J, Lv X, Liu Y, Zhao Y, Guo W. Angew. Chem. Int. Ed., 2012, 51: 7634.
[48] Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T. ACS Chem. Biol., 2011, 6: 600.
[49] Yuan L, Lin W, Yang Y, Chen H. J. Am. Chem. Soc., 2012, 134: 1200.
[50] Fu M, Xiao Y, Qian X, Zhao D, Xu Y. Chem. Commun., 2008, 15: 1780.
[51] 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.
[52] Hu L, Yan Z, Xu H. RSC Adv., 2013, 3: 7667.
[53] Avirah R R, Jayaram D T, Adarsh N, Ramaiah D. Org. Biomol. Chem., 2012, 10: 911.
[54] Markova L I, Terpetschnig E A, Patsenker L D. Dyes Pigments, 2013, 99: 561.
[55] Mayerhöffer U, Fimmel B, Würthner F. Angew. Chem. Int. Ed., 2012, 51: 164.
[56] Mayerhöffer U, Gsänger M, Stolte M, Fimmel B, Würthner F. Chem. Eur. J., 2013, 19: 218.
[57] Umezawa K, Citterio D, Suzuki K. Anal. Sci., 2008, 24: 213.
[58] Mori H, Tanaka T, Osuka A. J. Mater. Chem. C, 2013, 1: 2500.
[59] Toganoh M, Kimura T, Furuta H. Chem. Eur. J., 2008, 14: 10585.
[60] Yoon M, Misra R, Yoon Z S, Kim K S, Lim J M, Chandrashekar T K, Kim D. J. Phys. Chem. B, 2008, 112: 6900.
[61] Zhu S, Dorh N, Zhang J, Vegesna G, Li H, Luo F, Tiwari A, Liu H. J. Mater. Chem., 2012, 22: 2781.
[62] Schädlich A, Caysa H, Mueller T, Tenambergen F, Rose C, Göpferich A, Kuntsche J, Mäder K. ACS Nano, 2011, 5: 8710.
[63] Cheng L, He W, Gong H, Wang C, Chen Q, Cheng Z, Liu Z. Adv. Funct. Mater., 2013, 23: 5893.
[64] Xu Y, Li Z, Malkovskiy A, Sun S, Pang Y. J. Phys. Chem. B, 2010, 114: 8574.
[65] Gao F P, Lin Y X, Li L L, Liu Y, Mayerhoffer U, Spenst P, Su J G, Li J Y, Wurthner F, Wang H. Biomaterials, 2014, 35: 1004.
[66] Liu F, Deng D, Chen X, Qian Z, Achilefu S, Gu Y. Mol. Imaging Biol., 2010, 12: 595.
[67] Harada T, Sano K, Sato K, Watanabe R, Yu Z, Hanaoka H, Nakajima T, Choyke P L, Ptaszek M, Kobayashi H. Bioconjugate Chem., 2014, 25: 362.
[68] Alexander V M, Sano K, Yu Z, Nakajima T, Choyke P L, Ptaszek M, Kobayashi H. Bioconjugate Chem., 2012, 23: 1671.
[69] Mitsunaga M, Ogawa M, Kosaka N, Rosenblum L T, Choyke P L, Kobayashi H. Nat. Med., 2011, 17: 1685.
[70] Nakajima T, Mitsunaga M, Bander N H, Heston W, Choyke P L, Kobayashi H. Bioconjugate Chem., 2011, 22: 1700.
[71] Guo Z, Park S, Yoon J, Shin I. Chem. Soc. Rev., 2014, 43: 16.
[72] Yu F, Li P, Li G, Zhao G, Chu T, Han K. J. Am. Chem. Soc., 2011, 133: 11030.
[73] Cheng G, Fan J, Sun W, Cao J, Hu C, Peng X. Chem. Commun., 2014, 50: 1018.
[74] Wang T, Zhao Q, Hu H, Yu S, Liu X, Liu L, Wu Q. Chem. Commun., 2012, 48: 8781.
[75] Benniston A, Harriman A, Whittle V L, Zelzer M. Eur. J. Org. Chem., 2010, 3: 523.
[76] Yang Z, He Y, Lee J, Park N, Suh M, Chae W, Cao J, Peng X, Jung H, Kang C, Kim J S. J. Am. Chem. Soc., 2013, 135: 9181.
[77] Wang L, Xiao Y, Tian W, Deng L. J. Am. Chem. Soc., 2013, 135: 2903.
[78] Kuimova M K, Yahioglu G, Levitt J A, Suhling K. J. Am. Chem. Soc., 2008, 130: 6672.
[79] Koenig M, Bottari G, Brancato G, Barone V, Guldi D M, Torres T. Chem. Sci., 2013, 4: 2502.
[80] Ryu J H, Shin M, Kim S A, Lee S, Kim H, Koo H, Kim B S, Song H K, Kim S H, Choi K, Kwon I C, Jeon H, Kim K. Biomaterials, 2013, 34: 9149.
[81] Cao W, Ng K K, Corbin I, Zhang Z, Ding L, Chen J, Zheng G. Bioconjugate Chem., 2009, 20: 2023.
[82] Kelderhouse L E, Chelvam V, Wayua C, Mahalingam S, Poh S, Kularatne S A, Low P S. Bioconjugate Chem., 2013, 24: 1075.
[83] Wu X, Sun X, Guo Z, Tang J, Shen Y, James T D, Tian H, Zhu W. J. Am. Chem. Soc., 2014, 136: 3579.
[84] Li S, Goins B, Zhang L, Bao A. Bioconjugate Chem., 2012, 23: 1322.
[85] Chen J, Guo Z, Wang H, Gong M, Kong X, Xia P, Chen Q. Biomaterials, 2013, 34: 571.
[86] Ni D, Zhang J, Bu W, Xing H, Han F, Xiao Q, Yao Z, Chen F, He Q, Liu J, Zhang S, Fan W, Zhou L, Peng W, Shi J. ACS Nano, 2014, 8: 1231.