A Long-wavelength Emissive Phenothiazine Derived Fluorescent Probe for Detecting HOCl Upregulation in 5-FU Stimulated Living Cells

Abstract

The endogenous hypochlorous acid(HOCl) has been evidenced in a variety of cellular courses. However, the role of HOCl in most pathophysiological processes still keeps unclear because of the limited detecting tools. In this work, we presented the preparation of a phenothiazine-derived fluorescent probe ClO-1 for HOCl detection with a cyanopyridinium moiety to improve its water solubility and lengthen its emission wavelength. The HOCl-promoted oxidation of sulfur atom in the probe resulted in a 460-fold emission intensity enhancement at 635 nm with high selectivity and sensitivity(detection limit: 1.12 nmol/L). The rapid response(5 s) also endowed the probe with real-time detection ability. Successfully, ClO-1 was devoted to the bioimaging of endogenous HOCl in inflamed RAW 264.7 cells and 5-fluorouracil-treated MCF-7 cells.

Keywords

Fluorescent probe / Phenothiazine / Hypochlorous acid / 5-Fluorouracil / Bioimaging

References

[1] Dickinson B C, Chang C J. Nat. Chem. Biol., 2011, 7: 504.

[2] Prokopowicz Z M, Arce F, Biedron R, Chiang C L-L, Ciszek M, Katz D R, Nowakowska M, Zapotoczny S, Marcinkiewicz J, Chain B M. J. Immunol., 2010, 184: 824.

[3] Hadjigogos K. Panminerva. Med., 2003, 45: 7.

[4] Wang J, Cheng D, Zhu L, Wang P, Liu H-W, Chen M, Yuan L, Zhang X B. Chem. Commun., 2019, 55: 10916.

[5] Gorrini C, Harris I S, Mak T W. Nat. Rev. Drug Discovery, 2013, 12: 931.

[6] Steinbeck M J, Nesti L J, Sharkey P F, Parvizi J. J. Orthop. Res., 2007, 25: 1128.

[7] Zhang R, Song B, Yuan J. Trends Anal. Chem., 2018, 99: 1.

[8] Sedgwick A C, Wu L, Han H-H, Bull S D, He X-P, James T D, Sessler J L, Tang B Z, Tian H, Yoon J. Chem. Soc. Rev., 2018, 47: 8842.

[9] Hou J-T, Yu K-K, Sunwoo K, Kim W Y, Koo S, Wang J, Ren W X, Wang S, Yu X-Q, Kim J S. Chem, 2020, 6: 832.

[10] Yang L, Guo L, Yu H, Wang G, Sun J, Zhang P, Gu X, Tang B Z. Chem. Res. Chinese Universities, 2021, 37(1): 129.

[11] Huang L, Chen Y, Zhao Y, Wang Y, Xiong J, Zhang J, Wu X, Zhou Y. Chin. Chem. Lett., 2020, 31: 2941.

[12] Wu D, Chen L, Xu Q, Chen X, Yoon J. Acc. Chem. Res., 2019, 52: 2158.

[13] Hou J-T, Zhang M, Liu Y, Ma X, Duan R, Cao X, Yuan F, Liao Y-X, Wang S, Ren W X. Coord. Chem. Rev., 2020, 421: 213457.

[14] Zhou Y, Hua J, Zhang H-P, Tang Y. Chem. Res. Chinese Universities, 2021, 37(1): 110.

[15] Song X, Bai S, He N, Wang R, Xing Y, Lv C, Yu F. ACS Sens., 2021, 6: 1228.

[16] Xing Y, Cheng Z, Wang R, Lv C, James T D, Yu F. Coord. Chem. Rev., 2020, 424: 213506.

[17] Ren M, Zhou K, He L, Lin W. J. Mater. Chem. B, 2018, 6: 1716.

[18] Hou J-T, Kim H S, Duan C, Ji M S, Wang S, Zeng L, Ren W X, Kim J S. Chem. Commun., 2019, 55: 2533.

[19] Huang Y, Zhang P, Gao M, Zeng F, Qin A, Wu S, Tang B Z. Chem. Commun., 201, 52: 7288.

[20] Pak Y L, Park S J, Wu D, Cheon B, Kim H M, Bouffard J, Yoon J. Angew. Chem. Int. Ed., 2018, 57: 1567.

[21] Xiong H, He L, Zhang Y, Wang J, Song X, Yang Z. Chin. Chem. Lett., 2019, 30: 1075.

[22] Pak Y L, Park S J, Song G, Yim Y, Kang H, Kim H M, Bouffard J, Yoon J. Anal. Chem., 2018, 90: 12937.

[23] Nguyen V-N, Heo S, Kim S, Swamy K M K, Ha J, Park S, Yoon J. Sens. Actuators B, 2020, 317: 128213.

[24] Yuan L, Wang L, Agrawalla B K, Park S-J, Zhu H, Sivaraman B, Peng J, Xu Q-H, Chang Y-T. J. Am. Chem. Soc., 2015, 137: 5930.

[25] Feng H, Zhang Z, Meng Q, Jia H, Wang Y, Zhang R. Adv. Sci., 2018, 5: 1800397.

[26] Wei P, Yuan W, Xue F, Zhou W, Li R, Zhang D, Yi T. Chem. Sci., 2018, 9: 495.

[27] Zhang M, Zuo M, Wang C, Li Z, Cheng Q, Huang J, Wang Z, Liu Z. Anal. Chem., 2020, 92: 5569.

[28] Hou J-T, Wang B, Zou Y, Fan P, Chang X, Cao X, Wang S, Yu F. ACS Sens., 2020, 5: 1949.

[29] Liu L, Jiang L, Yuan W, Liu Z, Liu D, Wei P, Zhang X, Yi T. ACS Sens., 2020, 5: 2457.

[30] Shi D, Chen S, Dong B, Zhang Y, Sheng C, James T D, Guo Y. Chem. Sci., 2019, 10: 3715.

[31] Mao Z, Ye M, Hu W, Ye X, Wang Y, Zhang H, Li C, Liu Z. Chem. Sci., 2018, 9: 6035.

[32] Duan C, Won M, Verwilst P, Xu J, Kim H S, Zeng L, Kim J S. Anal. Chem., 2019, 91: 4172.

[33] Lu P, Zhang X, Ren T, Yuan L. Chin. Chem. Lett., 2020, 31: 2980.

[34] He L, Xiong H, Wang B, Zhang Y, Wang J, Zhang H, Li H, Yang Z, Song X. Anal. Chem., 2020, 92: 11029.

[35] Xiao H, Xin K, Dou H, Yin G, Quan Y, Wang R. Chem. Commun., 2015, 51: 1442.

[36] Li Y, Li H, Di G. New J. Chem., 2020, 44: 14286.

[37] Li H, Miao Y, Liu Z, Wu X, Piao C, Zhou X. Dyes Pigm., 2020, 176: 108192.

[38] Yue X, Wang J, Han J, Wang B, Song X. Chem. Commun., 2020, 56: 2849.

[39] Wang S, Zhu B, Wang B, Cao X, Zhu L, Hou J-T, Zeng L. Chin. Chem. Lett., 2021, 32: 1795.

[40] Liu C, Wang Q, Jiao X, Yao H, He S, Zhao L, Zeng X. Dyes Pigm., 2019, 160: 989.

[41] Hou J-T, Wang B, Fan P, Duan R, Cao X, Zhu L, Wang S. Dyes Pigm., 2020, 182: 108675.

[42] Jiao X, Huang K, He S, Liu C, Zhao L, Zeng X. Org. Biomol. Chem., 2019, 17: 108.

[43] Natarajan V, Thirumalaivasan N, Wu S P, Sivan V. Org. Biomol. Chem., 2019, 17: 3538.

[44] Vedamalai M, Kedaria D, Vasita R, Gupta I. Sens. Actuators B, 2018, 263: 137.

[45] Yuan L, Lin W, Zheng K, He L, Huang W. Chem. Soc. Rev., 2013, 42: 622.

[46] Hou J-T, Wang B, Zhang Y, Cui B, Cao X, Zhang M, Ye Y, Wang S. Chem. Commun., 2020, 56: 2759.

[47] Ferrer-Sueta G, Radi R. ACS Chem. Biol., 2009, 4: 161.

[48] McCall M R, Carr A C, Forte T M, Frei B. Arterioscler. Thromb. Vasc. Biol., 2001, 21: 1040.

[49] Yao L, Zhang S, Wang R, Li W, Shen F, Yang B, Ma Y. Angew. Chem. Int. Ed., 2014, 53: 2119.

[50] Boyer J, Maxwell P J, Longley D B, Johnston P G. Anticancer Res., 2004, 24: 41.