Water-soluble Supramolecular Fluorescent Probe for Sensing Carbendazim and Its Application in Living Cell Imaging†

doi:10.7503/cjcu20180319

Abstract

Abstract:

A host-guest complex between cucurbit[8]uril(Q[8]) and acridine orange(AO) was used as a fluorescent probe for detecting the carbendazim(CBZ). 2AO@Q[8] fluorescent probe was designed and used to detect carbendazim with high sensitivity and selectivity with a detection limit of ca. 10^-8 mol/L. A good linear relationship of emission intensity at ca. 529 nm for CBZ at concentrations of 0.4—5.0 μmol/L was observed. The proposed sensing mechanism was investigated via ¹H NMR spectroscopy combined with density functional theory calculations at the B3LYP/6-31G(d) level. The cell imaging study showed that the 2AO@Q[8] complex could be used to detect carbendazim in prostate cancer(PC3) cells, which may help to sense carbendazim in biological system.

Key words: Cucurbit[8]uril, Acridine orange, Fluorescent probe, Carbendazim, Cell imaging

CLC Number:

O657

TrendMD:

YANG Mei,LIU Qing,TANG Qing,WANG Chenghui,YANG Meixiang,SUN Tao,HUANG Ying,TAO Zhu. Water-soluble Supramolecular Fluorescent Probe for Sensing Carbendazim and Its Application in Living Cell Imaging^†[J]. Chem. J. Chinese Universities, 2018, 39(12): 2665.

Figures/Tables 11

Fig.1 Possible action mode of 2AO@Q[8] and CBZ

Fig.2 Fluorescence changes(λex=495 nm)(A), fluorescence images of 2AO@Q[8](10 μmol/L) upon addition of CBZ and other interfering pesticides(10 μmol/L) under UV lamp irradiation(365 nm) in Tris-HCl solution(pH=7)(B) and images of 2AO@Q[8](10 μmol/L) upon addition of CBZ and other interfering pesticides(10 μmol/L) under natural light in Tris-HCl solution(pH=7)(C)

Fig.3 UV-Vis absorption spectra(A) and fluorescence spectra of 2AO@Q[8](10 μmol/L) upon addition of increasing amounts of CBZ in Tris-HCl solution(pH=7)(λex=495 nm)(B)c(CBZ)/(μmol·L-1): a—k: 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Insets of (B): fluorescence color of AO(left), 2AO@Q[8](middle) and 2AO@Q[8]-CBZ(right) under UV lamp irradiation(365 nm).

Fig.4 1H NMR spectra(400 MHz) of AO(a), Q[8]-AO(1:2)(b), Q[8]-AO-CBZ(1:1:1)(c), Q[8]-CBZ(1:2)(d) and CBZ(e) in Tris-HCl solution(pH=7)

Fig.5 Computationally optimized structures by B3LYP/6-31G(d) for 2CBZ@Q[8](1:2)(A) and Q[8]:AO:CBZ(1:1:1)(B) complexes

Fig.6 Change in fluorescence intensity of 2AO@Q[8](a, 10 μmol/L) and 2AO@Q[8]-CBZ(b, 10 μmol/L) under different time in Tris-HCl solution(pH=7)(λex=495 nm)

Fig.7 Fluorescence intensity of 2AO@Q[8](a, 10 μmol/L) and 2AO@Q[8]-CBZ(b, 10 μmol/L) under different pH values in Tris-HCl solution(λex=495 nm)(A) and fluorescence intensity of 2AO@Q[8](10 μmol/L) and 2AO@Q[8]-CBZ(10 μmol/L) with different metal ions in Tris-HCl solution(pH=7)(λex=495 nm)(B)(B) a. Blank; b. Fe3+; c. Mn2+; d. Al3+; e. Na+; f. Cu2+; g. Hg2+; h. Ca2+; i. Mg2+; j. Li+; k. K+; l. Zn2+.

Fig.8 Plot of fluorescence intensity of 2AO@Q[8](10 μmol/L) with increasing concentrations of CBZ(0.4—5 μmol/L) in Tris-HCl solution(pH=7)(λex=495 nm)

Table 1 Analytical results of CBZ in sample(river water)

10⁶ Addition/(mol·L^-1)	10⁶ Measure/(mol·L^-1)	Recovery(%)	RSD(%)
1.50	1.58	105.33	2.98
3.00	2.86	95.33	3.05
4.50	4.33	96.22	2.21

Fig.9 Cytotoxicity test of probe

Fig.10 Fluorescence brightfield imaging(A, B) and fluorescence imaging(C, D) of cells treated with 2AO@Q[8] complex(5 μmol/L)(A, C) and 2AO@Q[8](5 μmol/L) in the presence of CBZ(5 μmol/L)(B, D)

References 33

[1]	Fernandez-Suarez M., Ting A.Y., Nat. Rev. Mol. Cell. Bio.,2008, 9(12), 929—943
[2]	Bates M., Huang B., Dempsey G.T., Zhuang X., Science,2007, 317(5845), 1749—1753
[3]	Itoh R.E., Kurokawa K., Ohba Y., Yoshizaki H., Mochizuki N., Matsuda1 M., Mol. Cell.Biol., 2002, 22(18), 6582—6591
[4]	Wang Q.L., He D., Zheng X.D., Mei L.H., Microbiol. China,2002, 29(4), 81—85
	(王庆利, 何丹, 郑晓冬, 梅乐和. 微生物学通报, 2002, 29(4), 81—85)
[5]	Liu Q.K., Zhu G. L., New Pesticide Manual(The Second Edition), Shanghai: Shanghai Scientific & Technical Publishers, 1999, 309
	(刘乾开, 朱国念. 新编农药使用手册(第二版). 上海: 上海科学技术出版社, 1999, 309)
[6]	Jindal K.K., Sharma R.C., Gupta V.K., Indian. J. Agr. Sci.,1989, 59(11), 754—755
[7]	Bhatt H.R., Jadeja K.B., Indian Phytopathology,2010, 63(1), 103—105
[8]	Indra N., J. Mycol. Pl.Pathol., 2013, 43(4), 419—422
[9]	Jatav N.K., Rana R.S., Verma J.R., Verma S. K.B., Afr. J. Microbiol.Res., 2014, 8(22), 2202—2207
[10]	Kumar J., Watpade S., Pramanick K.K., Shukla A.K., Kumar J., Int. J. Trop. Agr.,2015, 33(2), 1549—1551
[11]	Venkateswarlua P., Mohan K.R., Kumar C.R., Seshaiah K., Food Chem.,2007, 105(4), 1760—1766
[12]	Lu S.Y., Liao J.W., Kuo M.L., Wan S.C., Hwang J.S., Ueng T.H., J. Toxicol. Env. Heal. A,2004, 67(19), 1501—1515
[13]	Aire T.A., Anat. Embryol., 2005, 210(1), 43—49
[14]	Bushway R.J., Hurst H.L., Kugabalasooriar J., Perkins L.B., J. Chromatogr.,1991, 587(2), 321—324
[15]	Li G. F., Hao Z. H., Dong S. M., Li C. S., J. Instru. Anal., 1998, 17(3), 69—71
	(李桂凤, 郝征红, 董淑敏, 李传胜. 分析测试学报, 1998, 17(3), 69—71)
[16]	Nozal M.J., Bernal J.L., Jiménez J.J., Martín M.T., Bernal J., J. Chromatogr.,2005, 1076(1), 90—96
[17]	Vega A.B., Frenich A.G., Vidal J. L.M., Anal. Chim. Acta,2005, 538(1), 117—127
[18]	Bushway R.J., Paradis L.R., Perkins L.B., Fan T.S., Young B.E., Walser P.E., J. Assoc. Off. Anal. Chem.,1993, 76(4), 851—856
[19]	Praetorius A., Bailey D.M., Schwarzlose T., Nau W.M., Org. Lett.,2008, 10(18), 4089—4092
[20]	Ji H.F., Dabestani R., Brown G.M., J. Am. Chem.Soc., 2000, 122, 9306—9307
[21]	Leray I., Valeur B., Eur. J. Inorg.Chem., 2009, 2009(24), 3525—3535
[22]	Valeur B., Leray I., Inorg. Chim. Acta,2007, 360(3), 765—744
[23]	Nau W.M., Ghale G., Hennig A., Bakirci H., Bailey D.M., J. Am. Chem. Soc.,2009, 131(32), 11558—11570
[24]	Tang Q., Zhang J., Sun T., Wang C.H., Huang Y., Zhou Q.D., Wei G., Spectrochim. Acta A,2017, 191, 372—376
[25]	Freeman W.A., Mock W.L., Shih N.Y., J. Am. Chem.Soc., 1981, 103(24), 7367—7368
[26]	Kim J., Jung I.S., Kim S.Y., Lee E., Kang J.K., Sakamoto S., Yamaguchi K., Kim K., J. Am. Chem.Soc., 2000, 122, 540—541
[27]	Kim K., Selvapalam N., Ko Y.H., Park K.M., Kim D., Kim J., Chem. Soc.Rev., 2007, 36(2), 267—279
[28]	Florea M., Nau W.M., Angew. Chem. Int.Ed., 2011, 50(40), 9338—9342
[29]	Dsouza R.N., Pischel U., Nau W.M., Chem. Rev., 2011, 111(12), 7941—7980
[30]	Hennig A., Bakirci H., Nau W.M., Nat. Methods,2007, 4(8), 629—632
[31]	Baumes L.A., Sogo M.B., Navajas P.M., Corma A., Garcia H., Tetrahedron Lett.,2009, 50(50), 7001—7004
[32]	Navajas P.M., Corma A., Garcia H., Chem. Phys. Chem.,2008, 9(5), 713—720
[33]	Day A.I., Blanch R.J., Arnold A.P., Lorenzo S., Lewis G.R., Dance I., Angew. Chem. Int.Ed., 2002, 41(2), 275—277

Related Articles 15

[1]	ZHAO Yongmei, MU Yeshu, HONG Chen, LUO Wen, TIAN Zhiyong. Bis-naphthalimide Derivatives for Picronitric Acid Detection in Aqueous Solution [J]. Chem. J. Chinese Universities, 2022, 43(3): 20210765.
[2]	TANG Qian, DAN Feijun, GUO Tao, LAN Haichuang. Synthesis and Application of Quinolinone-coumarin-based Colorimetric Fluorescent Probe for Recognition of Hg²⁺ [J]. Chem. J. Chinese Universities, 2022, 43(2): 20210660.
[3]	WANG Di, ZHONG Keli, TANG Lijun, HOU Shuhua, LYU Chunxin. Synthesis of Schiff-based Covalent Organic Framework and Its Recognition of I ^‒ [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220115.
[4]	HUANG Shan, YAO Jiandong, NING Gan, XIAO Qi, LIU Yi. Efficient Determination of Alkaline Phosphatase Activity Based on Graphene Quantum Dots Fluorescent Probes [J]. Chem. J. Chinese Universities, 2021, 42(8): 2412.
[5]	LI Anran, ZHAO Bing, KAN Wei, SONG Tianshu, KONG Xiangdong, BU Fanqiang, SUN Li, YIN Guangming, WANG Liyan. ON-OFF-ON Double Colorimetric and Fluorescent Probes Based on Phenanthro［9，10-d］imidazole Derivatives and Their Living Cells Imaging [J]. Chem. J. Chinese Universities, 2021, 42(8): 2403.
[6]	YANG Xinjie, LAI Yanqiong, LI Qiuyang, ZHANG Yanli, WANG Hongbin, PANG Pengfei, YANG Wenrong. An Enzyme-free and Label-free Fluorescent Probe for Detection of Microcystin-LR Based on Circular DNA-Silver Nanoclusters [J]. Chem. J. Chinese Universities, 2021, 42(12): 3600.
[7]	CHEN Weiju, CHEN Shiya, XUE Caoye, LIU Bo, ZHENG Jing. Fluorescent Probe for Hypoxia-triggered Imaging and Cancer Therapy [J]. Chem. J. Chinese Universities, 2021, 42(11): 3433.
[8]	HUANG Jialing,LIU Fengjiao,WANG Tingting,LIU Cuie,ZHENG Fengying,WANG Zhenhong,LI Shunxing. Nitrogen and Sulfur co-Doped Carbon Quantum Dots for Accurate Detection of pH in Gastric Juice^† [J]. Chem. J. Chinese Universities, 2020, 41(7): 1513.
[9]	WU Qian, CHENG Dan, LÜ Yun, YUAN Lin, ZHANG Xiaobing. Monitoring of Peroxynitrite Variation During Liver Injury Adopting a Far Red to Near-infrared Fluorescent Probe with Large Stokes Shift [J]. Chem. J. Chinese Universities, 2020, 41(11): 2426.
[10]	WANG Jinjin,QI Shaolong,DU Jianshi,YANG Qingbiao,SONG Yan,LI Yaoxian. Synthesis of Benzothiazole Fluorescent Probe for Detection of N₂H₄·H₂O and HS $O 3 - †$ [J]. Chem. J. Chinese Universities, 2019, 40(7): 1397.
[11]	MU Yaxin,A Li,ZHUANG Qianfen,WANG Yong,NI Yongnian. Hydrothermal Synthesis of Ultrasmall Fluorescent Tungsten Disulfide Quantum Dots and Their Application in Cell imaging^† [J]. Chem. J. Chinese Universities, 2019, 40(4): 693.
[12]	Yong ZHANG,Cheng SHEN,Zhirong XING,Guiqi CHEN,Zi LU,Zhibing HOU,Xuemei CHEN. Benzimidazole-Derived Fluorescence Enhancement Probe for Visual Detection of HClO ^† [J]. Chem. J. Chinese Universities, 2019, 40(12): 2480.
[13]	YU Zhaochuan, MA Wenhui, WU Tao, WEN Jing, ZHANG Yong, WANG Liyan, CHU Hongtao. Preparation of B, N, S co-Doped Graphene Quantum Dots for Fluorescence Detection of Fe ³⁺ and H₂P $O 4 - †$ [J]. Chem. J. Chinese Universities, 2019, 40(11): 2286.
[14]	WANG Fengyan, YAN Ni, WEI Junji, XIA Huiyun, SONG Lifang, SONG Jiale, GAO Lining, YAN Luke. Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative^† [J]. Chem. J. Chinese Universities, 2018, 39(11): 2594.
[15]	HE Xiaoqin, HE Junlin, XU Hua, GUO Lei, XIE Jianwei. Active Conformation of DNA Aptamer Against Recombinant Human Erythropoietin-α^† [J]. Chem. J. Chinese Universities, 2018, 39(1): 48.