Progress and Challenges of Water-soluble NIR-II Organic Fluorophores for Fluorescence Imaging In vivo

doi:10.1007/s40242-024-3264-9

摘要/Abstract

摘要： The small-molecule fluorophores for the second near-infrared (NIR-II, 1000—1700 nm) window have attracted increasing attention in basic scientific research and preclinical practice owing to their deep-photo penetration, minimal physiological toxicity and simplicity of chemical modification. However, most of the reported small-molecule NIR-II fluorophores suffered from poor water solubility, which can easily cause organ toxicity. In addition, the aggregation caused by their poor water solubility in the aqueous solution would also result in weak fluorescence of these NIR-II fluorophores. Thus, it is highly desirable and valuable to develop water-soluble small-molecule NIR-II fluorophores with excellent photophysical properties for high-contrast in vivo imaging. In this review, we summarize the recent research advances in water-soluble small-molecule NIR-II fluorophores and highlight the representative bioimaging applications. Moreover, the potential challenges and perspectives of water-soluble small-molecule NIR-II fluorophores are discussed as well. We anticipate this review can help researchers to grab the latest information of water-soluble small-molecule fluorophores for NIR-II imaging, sequentially boosting their further development.

关键词: Organic fluorophore, Fluorescent imaging, Imaging reagent, Fluorescent probe, The second near-infrared (NIR-II) imaging

Abstract: The small-molecule fluorophores for the second near-infrared (NIR-II, 1000—1700 nm) window have attracted increasing attention in basic scientific research and preclinical practice owing to their deep-photo penetration, minimal physiological toxicity and simplicity of chemical modification. However, most of the reported small-molecule NIR-II fluorophores suffered from poor water solubility, which can easily cause organ toxicity. In addition, the aggregation caused by their poor water solubility in the aqueous solution would also result in weak fluorescence of these NIR-II fluorophores. Thus, it is highly desirable and valuable to develop water-soluble small-molecule NIR-II fluorophores with excellent photophysical properties for high-contrast in vivo imaging. In this review, we summarize the recent research advances in water-soluble small-molecule NIR-II fluorophores and highlight the representative bioimaging applications. Moreover, the potential challenges and perspectives of water-soluble small-molecule NIR-II fluorophores are discussed as well. We anticipate this review can help researchers to grab the latest information of water-soluble small-molecule fluorophores for NIR-II imaging, sequentially boosting their further development.

Key words: Organic fluorophore, Fluorescent imaging, Imaging reagent, Fluorescent probe, The second near-infrared (NIR-II) imaging

XIE Yuxin, QIN Zuojia, QIAN Ming, REN Tianbing, YUAN Lin. Progress and Challenges of Water-soluble NIR-II Organic Fluorophores for Fluorescence Imaging In vivo[J]. 高等学校化学研究, 2024, 40(2): 190-201.

XIE Yuxin, QIN Zuojia, QIAN Ming, REN Tianbing, YUAN Lin. Progress and Challenges of Water-soluble NIR-II Organic Fluorophores for Fluorescence Imaging In vivo[J]. Chemical Research in Chinese Universities, 2024, 40(2): 190-201.

参考文献

[1] Hu Z., Fang C., Li B., Zhang Z., Cao C., Cai M., Su S., Sun X., Shi X., Li C., Zhou T., Zhang Y., Chi C., He P., Xia X., Chen Y., Gambhir S. S., Cheng Z., Tian J., Nat. Biomed. Eng., 2020, 4, 259
[2] Thomas J. A., Chem. Soc. Rev., 2015, 44, 4494
[3] Li C., Pang Y., Xu Y., Lu M., Tu L., Li Q., Sharma A., Guo Z., Li X., Sun Y., Chem. Soc. Rev., 2023, 52, 4392
[4] Pratt E. C., Skubal M., McLarney B., Causa-Andrieu P., Das S., Sawan P., Araji A., Riedl C., Vyas K., Tuch D., Grimm J., Nat. Biomed. Eng., 2022, 6, 559
[5] Chen L., Lyu Y., Zhang X., Zheng L., Li Q., Ding D., Chen F., Liu Y., Li W., Zhang Y., Huang Q., Wang Z., Xie T., Zhang Q., Sima Y., Li K., Xu S., Ren T., Xiong M., Wu Y., Song J., Yuan L., Yang H., Zhang X.-B., Tan W., Sci. China Chem., 2023, 66, 1336
[6] Ou Y.-F., Ren T.-B., Yuan L., Zhang X.-B., Chem.Biomed.Imaging, 2023, 1, 220
[7] Chen Y., Wang S., Zhang F., Nat. Rev. Bioeng., 2023, 1, 60
[8] Xu Y., Li C., An J., Ma X., Yang J., Luo L., Deng Y., Kim J. S., Sun Y., Sci. China Chem., 2023, 66, 155
[9] Tu L., Li C., Xiong X., Kim H. J., Li Q., Mei L., Li J., Liu S., Kim S. J., Sun Y., Angew. Chem. Int. Ed., 2023, 62, e202301560
[10] Welsher K., Liu Z., Sherlock S. P., Robinson J. T., Chen Z., Daranciang D., Dai H., Nat. Nanotechnol., 2009, 4, 773
[11] Qin Z., Ren T.-B., Zhou H., Zhang X., He L., Li Z., Zhang X.-B., Yuan L., Angew. Chem. Int. Ed., 2022, 61, e202201541
[12] Wan H., Du H., Wang F., Dai H., Adv. Funct. Mater., 2019, 29, 1900566
[13] He S., Song J., Qu J., Cheng Z., Chem. Soc. Rev., 2018, 47, 4258
[14] Soo Choi H., Liu W., Misra P., Tanaka E., Zimmer J. P., Itty Ipe B., Bawendi M. G., Frangioni J. V., Nat. Biotechnol., 2007, 25, 1165
[15] Lorenzo I., Serra-Prat M., Yébenes J. C., Nutrients, 2019, 11, 1857
[16] Cheng Q., Tian Y., Dang H., Teng C., Xie K., Yin D., Yan L., Adv. Healthc. Mater., 2022, 11, 2101697
[17] Li B., Lu L., Zhao M., Lei Z., Zhang F., Angew. Chem. Int. Ed., 2018, 57, 7483
[18] Yao C., Chen Y., Zhao M., Wang S., Wu B., Yang Y., Yin D., Yu P., Zhang H., Zhang F., Angew. Chem. Int. Ed., 2022, 61, e202114273
[19] Li B., Zhao M., Feng L., Dou C., Ding S., Zhou G., Lu L., Zhang H., Chen F., Li X., Li G., Zhao S., Jiang C., Wang Y., Zhao D., Cheng Y., Zhang F., Nat. Commun., 2020, 11, 3102
[20] Antaris A. L., Chen H., Diao S., Ma Z., Zhang Z., Zhu S., Wang J., Lozano A. X., Fan Q., Chew L., Zhu M., Cheng K., Hong X., Dai H., Cheng Z., Nat. Commun., 2017, 8, 15269
[21] Cheng P., Pu K., Nat. Rev. Mater., 2021, 6, 1095
[22] Cosco E. D., Caram J. R., Bruns O. T., Franke D., Day R. A., Farr E. P., Bawendi M. G., Sletten E. M., Angew. Chem. Int. Ed., 2017, 56, 13126
[23] Cosco E. D., Spearman A. L., Ramakrishnan S., Lingg J. G. P., Saccomano M., Pengshung M., Arús B. A., Wong K. C. Y., Glasl S., Ntziachristos V., Warmer M., McLaughlin R. R., Bruns O. T., Sletten E. M., Nat. Chem., 2020, 12, 1123
[24] Bhalani D. V., Nutan B., Kumar A., Singh Chandel A. K., Biomedicines, 2022, 10, 2055
[25] Tenchov R., Bird R., Curtze A. E., Zhou Q., ACS Nano, 2021, 15, 16982
[26] Yang Y., Sun C., Wang S., Yan K., Zhao M., Wu B., Zhang F., Angew. Chem. Int. Ed., 2022, 61, e202117436
[27] Zeng Z., Ouyang J., Sun L., Zeng C., Zeng F., Wu S., Anal. Chem., 2020, 92, 9257
[28] Bai L., Hu Z., Han T., Wang Y., Xu J., Jiang G., Feng X., Sun B., Liu X., Tian R., Sun H., Zhang S., Chen X., Zhu S., Theranostics, 2022, 12, 4536
[29] Zhang Y., Jia Y., Zhu S., SmartMat, 2023, DOI: 10.1002/smm2.1245
[30] Lei Z., Sun C., Pei P., Wang S., Li D., Zhang X., Zhang F., Angew. Chem. Int. Ed., 2019, 58, 8166
[31] Tao Z., Hong G., Shinji C., Chen C., Diao S., Antaris A. L., Zhang B., Zou Y., Dai H., Angew. Chem. Int. Ed., 2013, 52, 13002
[32] Shi Y., Yuan W., Liu Q., Kong M., Li Z., Feng W., Hu K., Li F., ACS Mater. Lett., 2019, 1, 418
[33] Zhao M., Wang J., Lei Z., Lu L., Wang S., Zhang H., Li B., Zhang F., Angew. Chem. Int. Ed., 2021, 60, 5091
[34] Wang S., Fan Y., Li D., Sun C., Lei Z., Lu L., Wang T., Zhang F., Nat. Commun., 2019, 10, 1058
[35] Lu X., Zhu Y., Bai R., Wu Z., Qian W., Yang L., Cai R., Yan H., Li T., Pandey V., Liu Y., Lobie P. E., Chen C., Zhu T., Nat. Nanotechnol., 2019, 14, 719
[36] de Castro C. E., Panico K., Stangherlin L. M., Ribeiro C. A. S., da Silva M. C. C., Carneiro-Ramos M. S., Dal-Bó A. G., Giacomelli F. C., Bioconjugate Chem., 2020, 31, 2638
[37] Huang J., Xie C., Zhang X., Jiang Y., Li J., Fan Q., Pu K., Angew. Chem. Int. Ed., 2019, 58, 15120
[38] Ouyang J., Sun L., Zeng F., Wu S., Analyst, 2022, 147, 410
[39] Chen Y., Pei P., Lei Z., Zhang X., Yin D., Zhang F., Angew. Chem. Int. Ed., 2021, 60, 15809
[40] Yan D., Li T., Yang Y., Niu N., Wang D., Ge J., Wang L., Zhang R., Wang D., Tang B. Z., Adv. Mater., 2022, 34, 2206643
[41] Sun Y., Qu C., Chen H., He M., Tang C., Shou K., Hong S., Yang M., Jiang Y., Ding B., Xiao Y., Xing L., Hong X., Cheng Z., Chem. Sci., 2016, 7, 6203
[42] Bandi V. G., Luciano M. P., Saccomano M., Patel N. L., Bischof T. S., Lingg J. G. P., Tsrunchev P. T., Nix M. N., Ruehle B., Sanders C., Riffle L., Robinson C. M., Difilippantonio S., Kalen J. D., Resch-Genger U., Ivanic J., Bruns O. T., Schnermann M. J., Nat. Methods, 2022, 19, 353
[43] Li D.-H., Gamage R. S., Oliver A. G., Patel N. L., Muhammad Usama S., Kalen J. D., Schnermann M. J., Smith B. D., Angew. Chem. Int. Ed., 2023, 62, e202305062
[44] Choi H. S., Nasr K., Alyabyev S., Feith D., Lee J. H., Kim S. H., Ashitate Y., Hyun H., Patonay G., Strekowski L., Henary M., Frangioni J. V., Angew. Chem. Int. Ed., 2011, 50, 6258
[45] Jia S., Lin E. Y., Mobley E. B., Lim I., Guo L., Kallepu S., Low P. S., Sletten E. M., Chem, 2023, 9, 3648
[46] Ding B., Xiao Y., Zhou H., Zhang X., Qu C., Xu F., Deng Z., Cheng Z., Hong X., J. Med. Chem., 2019, 62, 2049
[47] de Valk K. S., Handgraaf H. J., Deken M. M., Sibinga Mulder B. G., Valentijn A. R., Terwisscha van Scheltinga A. G., Kuil J., van Esdonk M. J., Vuijk J., Bevers R. F., Peeters K. C., Holman F. A., Frangioni J. V., Burggraaf J., Vahrmeijer A. L., Nat. Commun., 2019, 10, 3118
[48] Choi H. S., Gibbs S. L., Lee J. H., Kim S. H., Ashitate Y., Liu F., Hyun H., Park G., Xie Y., Bae S., Henary M., Frangioni J. V., Nat. Biotechnol., 2013, 31, 148
[49] Wang H., Kang H., Dinh J., Yokomizo S., Stiles W.R., Tully M., Cardenas K., Srinivas S., Ingerick J., Ahn S., Bao K., Choi H. S., Biomater. Res., 2022, 26, 51
[50] Chen S., Brunskill E. W., Potter S. S., Dexheimer P. J., Salomonis N., Aronow B. J., Hong C. I., Zhang T., Kopan R., Dev. Cell, 2015, 35, 49
[51] Perazella M. A., Coca S. G., Nat. Rev. Nephrol., 2013, 9, 484
[52] Chen C., Tian R., Zeng Y., Chu C., Liu G., Bioconjugate Chem., 2020, 31, 276
[53] Chen Z., Zhang Z., Zeng F., Wu S., Chem. Biomed. Imaging, 2023, 1, 716
[54] Zeng C., Tan Y., Sun L., Long Y., Zeng F., Wu S., ACS Appl. Mater. Interfaces, 2023, 15, 17664
[55] Ridker P. M., Cook N. R., Lancet, 2013, 382, 1762
[56] Dong Y., Lu X., Li Y., Chen W., Yin L., Zhao J., Hu X., Li X., Lei Z., Wu Y., Chen H., Luo X., Qian X., Yang Y., Chin. Chem. Lett., 2023, 34, 108154
[57] Antaris A. L., Chen H., Cheng K., Sun Y., Hong G., Qu C., Diao S., Deng Z., Hu X., Zhang B., Zhang X., Yaghi O. K., Alamparambil Z. R., Hong X., Cheng Z., Dai H., Nat. Mater., 2016, 15, 235
[58] Luo X., Li J., Zhao J., Gu L., Qian X., Yang Y., Chin. Chem. Lett., 2019, 30, 839
[59] Li D.-H., Smith B. D., J. Org. Chem., 2022, 87, 5893
[60] Xu W., Leary E., Sangtarash S., Jirasek M., González M. T., Christensen K. E., Abellán Vicente L., Agraït N., Higgins S. J., Nichols R. J., Lambert C. J., Erson H. L., J. Am. Chem. Soc., 2021, 143, 20472
[61] Tolbert L. M., Zhao X., J. Am. Chem. Soc., 1997, 119, 3253
[62] Grüneboom A., Hawwari I., Weidner D., Culemann S., Müller S., Henneberg S., Brenzel A., Merz S., Bornemann L., Zec K., Wuelling M., Kling L., Hasenberg M., Voortmann S., Lang S., Baum W., Ohs A., Kraff O., Quick H. H., Jäger M., Landgraeber S., Dudda M., Danuser R., Stein J. V., Rohde M., Gelse K., Garbe A. I., Adamczyk A., Westendorf A. M., Hoffmann D., Christiansen S., Engel D. R., Vortkamp A., Krönke G., Herrmann M., Kamradt T., Schett G., Hasenberg A., Gunzer M., Nat. Metab., 2019, 1, 236
[63] Sivaraj K. K., Adams R. H., Development, 2016, 143, 2706
[64] Mi C., Zhang X., Yang C., Wu J., Chen X., Ma C., Wu S., Yang Z., Qiao P., Liu Y., Wu W., Guo Z., Liao J., Zhou J., Guan M., Liang C., Liu C., Jin D., Nat. Commun., 2023, 14, 6287
[65] Chen P., Qu F., He L., Li M., Sun P., Fan Q., Zhang C., Li D., J. Nanobiotechnol., 2023, 21, 230
[66] Yan R., Guo Y., Wang X., Liang G., Yang A., Li J., ACS Nano, 2022, 16, 8399
[67] Zaheer A., Lenkinski R. E., Mahmood A., Jones A. G., Cantley L. C., Frangioni J. V., Nat. Biotechnol., 2001, 19, 1148
[68] Bhushan K. R., Misra P., Liu F., Mathur S., Lenkinski R. E., Frangioni J. V., J. Am. Chem. Soc., 2008, 130, 17648
[69] Hyun H., Wada H., Bao K., Gravier J., Yadav Y., Laramie M., Henary M., Frangioni J. V., Choi H. S., Angew. Chem. Int. Ed., 2014, 53, 10668
[70] Feng Y., Zhu S., Antaris A. L., Chen H., Xiao Y., Lu X., Jiang L., Diao S., Yu K., Wang Y., Herraiz S., Yue J., Hong X., Hong G., Cheng Z., Dai H., Hsueh A. J., Chem. Sci., 2017, 8, 3703
[71] Lin J., Li Q., Zeng X., Chen Z., Ding Q., Li Y., Zhou H., Meng X., Chen D., Deng Z., Hong X., Xiao Y., Sci. China: Chem., 2020, 63, 766
[72] Zhang X., Ji A., Wang Z., Lou H., Li J., Zheng L., Zhou Y., Qu C., Liu X., Chen H., Cheng Z., J. Med. Chem., 2021, 64, 11543
[73] Terenziani F., Przhonska O. V., Webster S., Padilha L. A., Slominsky Y. L., Davydenko I. G., Gerasov A. O., Kovtun Y. P., Shandura M. P., Kachkovski A. D., Hagan D. J., Van Stryland E. W., Painelli A., J. Phys. Chem. Lett., 2010, 1, 1800