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Research Progress of Naphthalimide Derivatives Optical Probes for Monitoring Physical and Chemical Properties of Microenvironment and Active Sulfur Substances

  • Pengpeng Xia ,
  • Jiangtai Chen ,
  • Gaofan Shi ,
  • Mengmeng Zhang ,
  • Wanchen Yao ,
  • Xiangde Lin ,
  • Dongdong Zeng
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  • aSchool of Health Science and Engineering, University of Shanghai for Science and Technology, Shanghai 200093
    bShanghai University of Medicine and Health Sciences, Shanghai 201318

Received date: 2022-05-06

  Revised date: 2022-06-13

  Online published: 2022-07-05

Supported by

Natural Science Foundation of Shanghai(19ZR1474300)

Abstract

Naphthalimide derivatives have been designed as optical probes and applied in various biological scenarios due to their excellent photophysical properties. As an important microenvironment and active sulfur substance in biology plays an important role in biological system, it is necessary to detect it efficiently. The detection of naphthalimide derivatives for microenvironment and active sulfur substances is reviewed. The detection of microenvironment is described from four aspects of pH value, viscosity, polarity and temperature, and the design scheme of the probe and the comparison of all kinds of fluorescence properties are discussed. From the point of view of detection strategy, the mechanism is divided into nucleophilic substitution strategy, nucleophilic addition strategy, substituent reduction strategy, heavy metal replacement strategy and other strategies, and the fluorescence properties of these probes are summarized and compared. Finally, some shortcomings in the design and practical application of this kind of probe are described, and the future prospect of this field is prospected.

Cite this article

Pengpeng Xia , Jiangtai Chen , Gaofan Shi , Mengmeng Zhang , Wanchen Yao , Xiangde Lin , Dongdong Zeng . Research Progress of Naphthalimide Derivatives Optical Probes for Monitoring Physical and Chemical Properties of Microenvironment and Active Sulfur Substances[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3620 -3639 . DOI: 10.6023/cjoc202205009

References

[1]
Zhou, K.; Ren, M. G..; Deng, B. B; Lin, W. L. New J. Chem. 2017, 41, 11507.
[2]
Li, X. L.; Zhao, R. R.; Wang, Y.; Huang, C. S. J. Mater. Chem. B 2018, 6, 6592.
[3]
Li, H. D.; Kim, H. J.; Xu, F.; Han, J. J.; Yao, Q. C.; Wang, J. Y.; Pu, K. Y.; Peng, X. J.; Yoon, J. Y. Chem. Soc. Rev. 2022, 51, 1795.
[4]
Li, M.; Fan, J. L.; Li, H. D.; Du, J. J.; Long, S. R.; Peng, X. J. Biomaterials 2018, 164, 98.
[5]
Liu, T.; Sun, L.; Zhang, Y. B..; Wang, Y. L; Zheng, J. J. Biochem. Mol. Toxicol. 2022, 36, e22942.
[6]
Lau, N.; Pluth, M. D. Curr. Opin. Chem. Biol. 2019, 49, 1.
[7]
Chen, W. J.; Ma, X. M.; Chen, H. J.; Liu, S. H.; Yin, J. Coord. Chem. Rev. 2021, 427, 213584.
[8]
He, X. Y.; Li, H.; Liu, S. S.; Li, Y.; Lin, X. D.; Zheng, H. Y.; Zhou, Z. L.; Zeng, D. D. ChemistrySelect 2022, 7, e202103821.
[9]
Ulla, H.; Kiran, M. R.; Garudachari, B.; Ahipa, T. N.; Tarafder, K.; Adhikari, A. V.; Umesh, G.; Satyanarayan, M. N. J. Mol. Struct. 2017, 1143, 344.
[10]
Shao, J. J.; Chang, J. J.; Chi, C. Y. Chem.-Asian J. 2014, 9, 253.
[11]
Li, L.; Zhang, Z. Q. Spectrochim. Acta, Part A 2022, 264, 120243.
[12]
Gao, C.; Liu, X. J.; Chen, W.; Wang, F. L.; Jiang, J. H. Methods Appl. Fluoresc. 2018, 7, 014002.
[13]
Jothi, D.; Munusamy, S.; Iyer, S. K. J. Photochem. Photobiol., A 2021, 420, 113491.
[14]
Shi, X. R.; Yin, C. X.; Wen, Y.; Huo, F. J. Dyes Pigm. 2019, 165, 38.
[15]
Hou, X. F.; Li, Z. S.; Li, Y. Q.; Zhou, Q. H.; Liu, C. H.; Fan, D.; Wang, J. J.; Xu, R. J.; Xu, Z. H. Spectrochim. Acta, Part A 2021, 246, 119030.
[16]
Wang, P.; Liu, J.; Lv, X.; Liu, Y. L.; Zhao, Y.; Guo, W. Org. Lett. 2012, 14, 520.
[17]
Hu, L.; Ju, M.; Gao, A. Q.; Chen, H. H.; Hou, A. Q. Dyes Pigm. 2022, 200, 110164.
[18]
Gopala, L.; Cha, Y. J.; Lee, M. H. Dyes Pigm. 2022, 201, 110195.
[19]
Qiu, K. Q.; Seino, R.; Han, G. Q.; Ishiyama, M.; Ueno, Y.; Tian, Z. Q.; Sun, Y. J.; Diao, J. J. Adv. Healthcare Mater. 2022, e2102185.
[20]
Tian, Y. Q.; Su, F. Y.; Weber, W.; Nandakumar, V.; Shumway, B. R.; Jin, Y. G.; Zhou, X. F.; Holl, M. R.; Johnson, R. H.; Meldrum, D. R. Biomaterials 2010, 31, 7411.
[21]
Lee, M. H.; Park, N.; Yi, C.; Han, J. H.; Hong, J. H.; Kim, K. P.; Kang, D. H.; Sessler, J. L.; Kang, C.; Kim, J. S. J. Am. Chem. Soc. 2014, 136, 14136.
[22]
Lee, M. H.; Kim, J. Y.; Han, J. H.; Bhuniya, S.; Sessler, J. L.; Kang, C.; Kim, J. S. J. Am. Chem. Soc. 2012, 134, 12668.
[23]
Zhou, X. F.; Su, F. Y.; Lu, H. G.; Willis, P. S.; Tian, Y. Q.; Johnson, R. H.; Meldrum, D. R. Biomaterials 2012, 33, 171.
[24]
Hu, F.; Huang, Y. X.; Xiao, Y. S.; Li, Y. C.; Luo, X.; Qian, X. H.; Yang, Y. J. Anal. Methods 2021, 13, 3012.
[25]
Liu, Q.; Liu, Y. Q.; Zhang, H.; Wen, Z. R. Spectrochim. Acta, Part A 2006, 65, 164.
[26]
Loukova, G. V.; Vasiliev, V. P.; Milov, A. A.; Smirnov, V. A.; Minkin, V. I. J. Photochem. Photobiol., A 2016, 327, 6.
[27]
Gonzalez, F. F.; Gutierrez, M. F.; Puentes, D. G.; Orte, A.; Gonzalez-Vera, J. A.; Herranz, R. Eur. J. Med. Chem. 2020, 200, 112407.
[28]
Xiao, H. B.; Chen, M. J.; Shi, G. H.; Wang, L.; Yin, H. Y.; Mei, C. Res. Chem. Intermed. 2010, 36, 1021.
[29]
Qian, M.; Zhang, L. W.; Pu, Z. J.; Zhang, C.; Chen, Q. X.; Sui, X. H.; Han, X.; Zeng, S.; Cui, H. Y.; Wang, J. Y.; Peng, X. J. Sens. Actuators, B 2021, 344, 130261.
[30]
Gai, F. Q.; Zuo, Y. J.; Lin, W. Y. Talanta 2021, 225, 122059.
[31]
Zhang, Z. H.; Li, C. C.; Cui, W. L.; Qu, J.; Zhang, H. T.; Liu, K. Y.; Zhu, X. Z.; Wang, J. Y. Eur. Polym. J. 2022, 166, 111030.
[32]
Stamentovic, V.; Collado, D.; Inestrosa, E. P. Spectrochim. Acta, Part A 2022, 267, 120546.
[33]
Dai, Y.; Lv, B. K.; Zhang, X. F.; Xiao, Y. Chin. Chem. Lett. 2014, 25, 1001.
[34]
Lan, H. C.; Li, Q.; Li, Y.; Xiao, S. Z.; Li, Y. Q.; Yan, X. J.; Yuan, S.; Zhu, P. C. Dyes Pigm. 2018, 155, 121.
[35]
Zhang, P. Y.; Chen, H. J.; Huang, H. Y.; Qiu, K. Q.; Zhang, C. X.; Chao, H.; Zhang, Q. L. Dalton Trans. 2019, 48, 3990.
[36]
Hou, L. L.; Ning, P.; Feng, Y.; Ding, Y. Q.; Bai, L.; Li, L.; Yu, H. Z.; Meng, X. M. Anal. Chem. 2018, 90, 7122.
[37]
Wang, L.; Wang, G.; Shang, C. D.; Kang, R.; Fang, Y. ACS Appl. Mater. Interfaces 2017, 9, 35419.
[38]
Kim, S. J.; Park, S. Y.; Yoon, S. A.; Kim, C.; Kang, C.; Lee, M. H. Anal. Chem. 2021, 93, 4391.
[39]
Wei, Y. F.; Zhang, X. Q.; Sun, R.; Xu, Y. J.; Ge, J. F. Dyes Pigm. 2021, 194, 109559.
[40]
Xia, T. K.; Wang, L. L.; Qu, Y. C.; Rui, Y. C.; Cao, J.; Hu, Y.; Yang, J.; Wu, J. W.; Xu, J. L. J. Mater. Chem. C 2016, 4, 5696.
[41]
Georgiev, N. I.; Marinova, N. V.; Bojinov, V. B. J. Photochem. Photobiol., A 2020, 401, 112733.
[42]
Zhu, L. Q.; Fu, M. L.; Yin, B.; Wang, L.; Chen, Y. J.; Zhu, Q. Dyes Pigm. 2020, 172, 107859.
[43]
Wu, N.; Sun, Y. S.; Kong, M. Y.; Lin, X.; Cao, C.; Li, Z. X.; Feng, W.; Li, F. Y. Small 2022, e2107963.
[44]
Qiao, J.; Mu, X. Y.; Qi, L. Biosens. Bioelectron. 2016, 85, 403.
[45]
Wen, Y.; Zhang, W. J.; Liu, T.; Huo, F. J.; Yin, C. X. Anal. Chem. 2017, 89, 11869.
[46]
Zhang, W. J.; Huo, F. J.; Yue, Y. K.; Zhang, Y. B.; Chao, J. B.; Cheng, F. Q.; Yin, C. X. J. Am. Chem. Soc. 2020, 142, 3262.
[47]
Qiao, J.; Wu, D. Y.; Song, Y. Y.; Ji, W. L.; Yue, Q. W.; Mao, L. Q.; Qi, L. Anal. Chem. 2021, 93, 14743.
[48]
Christopherson, C. J.; Mayder, D. M.; Poisson, J.; Paisley, N. R.; Tonge, C. M.; Hudson, Z. M. ACS Appl. Mater. Interfaces 2020, 12, 20000.
[49]
Rani, K.; Sengupta, S. Chem. Sci. 2021, 12, 15533.
[50]
Zhu, Y. Q.; Romero, E. L.; Ren, X. D.; Sanca, A. J.; Du, C. K.; Liu, C.; Karim, Z. A.; Alshbool, F. Z.; Khasawneh, F. T.; Zhou, J.; Zhong, D. F.; Geng, B. Nat. Commun. 2018, 9, 3952.
[51]
Lv, B.; Chen, S.; Tang, C. S.; Jin, H. F.; Du, J. B.; Huang, Y. Q. J. Adv. Res. 2021, 27, 85.
[52]
Park, C. S.; Ha, T. H.; Choi, S. A.; Nguyen, D. N.; Noh, S.; Kwon, O. S.; Lee, C. S.; Yoon, H. Biosens. Bioelectron. 2017, 89, 919.
[53]
Chen, W.; Pacheco, A.; Takano, Y.; Day, J. J.; Hanaoka, K.; Xian, M. Angew. Chem., Int. Ed. 2016, 55, 9993.
[54]
Zhang, Y. Q.; Zhang, L. Microchem. J. 2020, 159, 105394.
[55]
Shi, D. T.; Zhou, D.; Zang, Y.; Li, J.; Chen, G. R.; James, T. D.; He, X. P.; Tian, H. Chem. Commun. 2015, 51, 3653.
[56]
Velusamy, N.; Thirumalaivasan, N.; Bobba, K. N.; Podder, A.; Wu, S. P.; Bhuniya, S. J. Photochem. Photobiol., B 2019, 191, 99.
[57]
Tian, M. J.; Xu, J. H.; Ma, Q. J.; Li, L. K.; Yuan, H. M.; Sun, J. G.; Zhu, N. N.; Liu, S. Z. Spectrochim. Acta, Part A 2022, 268, 120708.
[58]
Han, Q. X.; Ru, J. X.; Wang, X. C.; Dong, Z.; Wang, L.; Jiang, H.; Liu, W. S. ACS Appl. Bio Mater. 2019, 2, 1987.
[59]
Singh, N.; Sharma, S.; Singh, R.; Rajput, S.; Chattopadhyay, N.; Tewari, D.; Joshi, K. B.; Verma, S. Chem. Sci. 2021, 12, 16085.
[60]
Gao, B. Z..; Cui, L. X; Pan, Y.; Xue, M. J.; Zhu, B. Y.; Zhang, G. M.; Zhang, C. H.; Shuang, S. M.; Dong, C. Spectrochim. Acta, Part A 2017, 173, 457.
[61]
Liu, W. J.; Chen, J.; Xu, Z. C. Coord. Chem. Rev. 2021, 429, 213638.
[62]
Li, Y.; Liu, W. M.; Zhang, P. P.; Zhang, H. Y.; Wu, J. S.; Ge, J. C.; Wang, P. F. Biosens. Bioelectron. 2017, 90, 117.
[63]
Yin, C. X.; Xiong, K. M.; Huo, F. J.; Salamanca, J. C.; Strongin, R. M. Angew. Chem., Int. Ed. 2017, 56, 13188.
[64]
Li, X. M.; Zheng, Y. J.; Tong, H. J.; Qian, R.; Zhou, L.; Liu, G. X.; Tang, Y.; Li, H.; Lou, K. Y.; Wang, W. Chem.-Eur. J. 2016, 22, 9247.
[65]
Qian, J.; Zhang, G.; Cui, J.; Zhou, L.; Chen, Z.; Zhang, Z.; Zhang, W. Sens. Actuators, B 2020, 311, 127923.
[66]
Liang, B. B.; Wang, B. Y.; Ma, Q. J.; Xie, C. X.; Li, X.; Wang, S. P. Spectrochim. Acta, Part A 2018, 192, 67.
[67]
Zhu, B. C.; Guo, B. P.; Zhao, Y. Z.; Zhang, B.; Du, B. Biosens. Bio- electron. 2014, 55, 72.
[68]
Song, L.; Jia, T.; Lu, W. J.; Jia, N. Q.; Zhang, W. B.; Qian, J. H. Org. Biomol. Chem. 2014, 12, 8422.
[69]
Shen, R. H.; Bai, J.; Qian, Y. J. Mater. Chem. B 2021, 9, 2462.
[70]
Wang, Y. P.; Chen, J.; Shu, Y.; Wang, J. H.; Qiu, H. D. Spectrochim. Acta, Part A 2022, 266, 120409.
[71]
Huang, J.; Chen, Y. N.; Qi, J. G.; Zhou, X. M.; Niu, L. Q.; Yan, Z. J.; Wang, J. H.; Zhao, G. X. Spectrochim. Acta, Part A 2018, 201, 105.
[72]
Cao, M. J.; Chen, H. Y.; Chen, D.; Xu, Z. Q.; Liu, S. H.; Chen, X. Q.; Yin, J. Chem. Commun. 2016, 52, 721.
[73]
Han, X.; Liu, Y. H.; Liu, G. T.; Luo, J. T.; Liu, S. H.; Zhao, W. B.; Yin, J. Chem.-Asian J. 2019, 14, 890.
[74]
Kwon, N.; Lim, C. S.; Ko, G.; Ha, J.; Lee, D.; Yin, J.; Kim, H. M.; Yoon, J. Anal. Chem. 2021, 93, 11612.
[75]
Shi, Y. G.; Yao, J. H.; Duan, Y. L.; Mi, Q. L.; Chen, J. H.; Xu, Q. Q.; Gou, G. Z.; Zhou, Y.; Zhang, J. F. Bioorg. Med. Chem. Lett. 2013, 23, 2538.
[76]
Luxami, V.; Verma, M.; Rani, R.; Paul, K.; Kumar, S. Org. Biomol. Chem. 2012, 10, 8076.
[77]
Zeng, Q. B.; Guo, Q. N.; Yuan, Y. P.; Yang, Y. Q.; Zhang, B.; Ren, L. L.; Zhang, X. X.; Luo, Q.; Liu, M. L.; Bouchard, L. S.; Zhou, X. Anal. Chem. 2017, 89, 2288.
[78]
Song, A. G.; Feng, T.; Shen, X.; Gai, S. C.; Zhai, Y. M.; Chen, H. Chem. Commun. 2019, 55, 7219.
[79]
Fujikawa, Y.; Terakado, K.; Nampo, T.; Mori, M.; Inoue, H. Talanta 2019, 204, 633.
[80]
Zhang, J.; Jin, Z.; Hu, X. X.; Meng, H. M.; Li, J.; Zhang, X. B.; Liu, H. W.; Deng, T. G.; Yao, S.; Feng, L. L. Anal. Chem. 2017, 89, 8097.
[81]
Tong, H. J.; Zheng, Y. J.; Zhou, L.; Li, X. M.; Qian, R.; Wang, R.; Zhao, J. H.; Lou, K. Y.; Wang, W. Anal. Chem. 2016, 88, 10816.
[82]
Lu, J.; Holmgren, A. Free Radical Biol. Med. 2014, 66, 75.
[83]
Zhang, L. W.; Duan, D. Z.; Liu, Y. P.; Ge, C. P.; Cui, X. M.; Sun, J. Y.; Fang, J. G. J. Am. Chem. Soc. 2014, 136, 226.
[84]
Lee, M. H.; Han, J. H.; Lee, J. H.; Choi, H. G.; Kang, C.; Kim, J. S. J. Am. Chem. Soc. 2012, 134, 17314.
[85]
Wi, Y. J.; Le, H. T.; Verwilst, P.; Sunwoo, K.; Kim, S. J.; Song, J. E.; Yoon, H. Y.; Han, G.; Kim, J. S.; Kang, C.; Kim, T. W. Chem. Commun. 2018, 54, 8897.
[86]
Huang, C. S.; Jia, T.; Tang, M. F.; Yin, Q.; Zhu, W. P.; Zhang, C.; Yang, Y.; Jia, N. Q.; Xu, Y. F.; Qian, X. H. J. Am. Chem. Soc. 2014, 136, 14237.
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