ON-OFF-ON Double Colorimetric and Fluorescent Probes Based on Phenanthro［9，10-d］imidazole Derivatives and Their Living Cells Imaging

doi:10.7503/cjcu20210089

Abstract

Abstract:

The symmetric fluorescent probe PIP-ph-PIP based on phenanthro［9，10-d］imidazole was designed and synthesized， and its structure was characterized and confirmed. As the increasing amount of water in the solution of PIP-ph-PIP， the fluorescence intensity of PIP-ph-PIP first increased and then quenched with the gradual aggregation. The results of the fluorescence spectra indicated that the probe PIP-ph-PIP could selectively and successively recognize Ag⁺ and SCN^-， Cu²⁺ and PO³₄^-， respectively， with an ON-OFF-ON mode in the aqueous system. Moreover， the continuous effect can be observed by the colorimetric naked eye. The probe PIP-ph-PIP offered a relatively low detection limits of 6.1 nmol/L for Ag⁺ ions. The probe PIP-ph-PIP was successfully applied to detect Ag⁺ and Cu²⁺ in living human cancer cells（HeLa cells） and quantitively analyze of Ag⁺ and Cu²⁺ in actual water samples.

Key words: Water phase, Phenanthro［9, 10-d］imidazole, Colorimetry, Fluorescent probe, Cell imaging

CLC Number:

O657.3

TrendMD:

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.

Figures/Tables 10

References 33

1	Bush A. I.， Trends Neurosci.， 2003， 26， 207—214
2	Multhaup G.， Masters C. L.， Met. Ions. Biol. Syst.， 1999， 36， 365—387
3	Kepp K. P.， Chem. Soc. Rev.， 2012， 351， 127—159
4	Carter K. P.， Young A. M.， Palmer A. E.， Chem. Rev.， 2014， 114， 4564—4601
5	Beutler E.， Blood Cells Mol. Dis.， 2007， 39， 140—147
6	Wu D.， Chen L.， Lee W.， Ko G.， Yin J.， Yoon J.， Coordin. Chem. Rev.， 2018， 354， 74—97
7	Arena G.， Mendola D. L.， Pappalardo G.， Sovago I.， Rizzarelli E.， Coordin. Chem. Rev.， 2012， 256， 2202—2218
8	Udhayakumari D.， Naha S.， Velmathi S.， Anal. Methods， 2017， 9， 552—578
9	Pal A.， Neurotoxicology， 2014， 40， 97—101
10	Wang Q. Q.， Zhou L. Y.， Qiu L. P.， Lu D. Q.， Wu Y. X.， Zhang X. B.， Analyst， 2015， 140， 5563—5569
11	Barman S.， Mukhopadhyay S. K.， Gangopadhyay M.， Biswas S.， Dey S.， Singh N. D. P.， J. Mater. Chem. B， 2015， 3， 3490—3497
12	Poon V. K.， Burd A.， Burns， 2004， 30， 140—147
13	Drake P. L.， Hazelwood K. J.， Ann. Occup. Hyg.， 2005， 49， 575—585
14	Maity D.， Kumar V.， Govindaraju T.， Org. Lett.， 2012， 14， 6008—6011
15	Yang C. Y.， Chen Y.， Wu K.， Wei T.， Wang J. L.， Zhang S. S.， Han Y. F.， Anal. Methods， 2015， 7， 3327—3330
16	Wang H.， Shi D. L.， Li J.， Tang H. Y.， Guo Y.， Sensor Actuat. B： Chem.， 2018， 256， 600—608
17	Shen Y. M.， Zhang X. Y.， Zhang C. X.， Zhang Y. Y.， Jin J. L.， Li H. T.， Spectrochim. Acta B， 2018， 191， 427—434
18	Hu J.， Cheng K.， Wu Q.， Ding D. S.， Li C. G.， Li Z.， Mater. Chem. Front.， 2018， 2， 1201—1206
19	Lei M. M.， Zhou Q. H.， Yang L.， Xu Z. H.， Yang F. L.， Chin. J. Org. Chem.， 2020， 40， 2798—2803
20	Zhang C. L.， Sun Y. D.， Wang J.， He Y. Zhang Y. P.， Zhang L.， Song F. L.， Chem. J. Chinese Universities， 2020， 41（8）， 1785—1791（张成路，孙越冬，王静，何钰，张彦鹏，张璐，宋府璐. 高等学校化学学报， 2020， 41（8）， 1785—1791）
21	Song C. Y.， Jiang X. Y.， Yang Y. J.， Zhang J. J.， Larson S.， Zhao Y. P.， Wang L. H.， ACS Appl. Mater. Inter.， 2020， 12， 31242—31254
22	Zhou S. H.， Li Q.， Zhang T.， Pang D. W.， Tang H. W.， Chem. J. Chinese Universities， 2019， 40（8）， 1593—1599（周思慧，李琼，张婷，庞代文，唐宏武. 高等学校化学学报， 2019， 40（8）， 1593—1599）
23	Gao W. L.， Song H. H.， Wang X.， Liu X. Q.， Pang X. B.， Zhou Y. M.， Gao B.， Peng X. J.， ACS Appl. Mater. Inter.， 2018， 10， 1147—1154
24	Yang Y. S.， Cao B. X.， Zhang Y. P.， Dong Y. Y.， Chin. J. Org. Chem.， 2017， 37（11）， 3024—3030（杨云裳，曹碧霞，张应鹏，董玉莹. 有机化学， 2017， 37（11）， 3024—3030）
25	Zhang Z. T.， Wang R. Y.， Huang X. X.， Zhu W. F.， He Y. J.， Liu W. Y.， Liu F. L.， Feng F.， Qu W.， Anal. Chem.， 2021， 93， 1627—1635
26	Hua B.， Zhang C.， Zhou W.， Shao L.， Wang Z. D.， Wang L. J.， Zhu H. M.， Huang F. H.， J. Am. Chem. Soc.， 2020， 142， 16557—16561
27	Liu H. W.， Li K.， Hu X. X.， Zhu L. M.， Rong Q. M.， Liu Y. C.， Zhang X. B.， Hasserodt J.， Qu F. L.， Tan W. H.， Angew. Chem. Int. Ed.， 2017， 56，11788—11792
28	Lotfi B.， Tarlani A.， Akbari⁃Moghaddam P.， Mirza⁃Aghayan M.， Zadmard R.， Biosens. Bioelectron.， 2017， 90， 290—297
29	Maurya N.， Bhardwaj S.， Singh A. K.， J. Mater. Sci. Eng.C： Mater.， 2017， 74， 55—61
30	Li Y.， Yu H. J.， Shao G.， Gan F.， J. Photochem. Photobiol. A： Chem.， 2015， 301， 14—19
31	Gao R. J.， Xu G.， Zheng L. S.， Xie Y. J.， Tao M. L.， Zhang W. Q.， J. Mater. Chem. C， 2016， 4， 5996—6006
32	Job P.， Chim. Appl.， 1928， 9， 113—203
33	He Y. Q.， Zhao B.， Kan W.， Ding L. M.， Yu Z. C.， Wang M. Y.， Song B.， Wang L. Y.， Analyst，2020， 145， 213—222

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]	SHU Xin, WANG Di, YUAN Chunling, QIN Xiu, WANG Yilin. Colorimetric Determination of Sarcosine with Carbon Quantum Dots as Mimetic Peroxidase [J]. Chem. J. Chinese Universities, 2021, 42(6): 1761.
[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]	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.
[15]	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.

Sample	Spiked c（Ag⁺）/ （μmol·L^-1）	Detected c（Ag⁺）/ （μmol·L^-1）	Recovery of Ag⁺（%）	Standard deviation（%）	Spiked c（Cu²⁺）/（μmol·L^-1）	Detected c（Cu²⁺）/ （μmol·L^-1）	Recovery of Cu²⁺（%）	Standard deviation（%）
Tap water	1	1.01	101.0	1	1	0.94	0.94	1
	4	3.86	96.5	0.32	4	3.74	3.74	0.32
	7	6.93	99.0	0.65	7	6.86	6.86	0.65
Lake water	1	0.98	98.1	1	1	1.02	1.02	1
	4	3.91	97.7	0.48	4	3.78	3.78	0.28
	7	6.91	98.7	1.74	7	6.96	6.96	0.71
River water	1	0.97	97.0	1.12	1	0.96	0.96	1.12
	4	3.95	98.8	0.52	4	3.85	3.85	0.32
	7	6.89	98.4	0.23	7	6.84	6.84	0.27

Sample	Spiked c（Ag⁺）/ （μmol·L^-1）	Detected c（Ag⁺）/ （μmol·L^-1）	Recovery of Ag⁺（%）	Standard deviation（%）	Spiked c（Cu²⁺）/（μmol·L^-1）	Detected c（Cu²⁺）/ （μmol·L^-1）	Recovery of Cu²⁺（%）	Standard deviation（%）
Tap water	1	1.01	101.0	1	1	0.94	0.94	1
	4	3.86	96.5	0.32	4	3.74	3.74	0.32
	7	6.93	99.0	0.65	7	6.86	6.86	0.65
Lake water	1	0.98	98.1	1	1	1.02	1.02	1
	4	3.91	97.7	0.48	4	3.78	3.78	0.28
	7	6.91	98.7	1.74	7	6.96	6.96	0.71
River water	1	0.97	97.0	1.12	1	0.96	0.96	1.12
	4	3.95	98.8	0.52	4	3.85	3.85	0.32
	7	6.89	98.4	0.23	7	6.84	6.84	0.27