Citation: Yuyu Wang, Houna Duan, Hongyuan Shi, Shiwei Zhang, Yufang Xu, Weiping Zhu, Xuhong Qian. A highly sensitive fluorescent probe for tracking intracellular zinc ions and direct imaging of prostatic tissue in mice[J]. Chinese Chemical Letters, ;2020, 31(11): 2933-2936. doi: 10.1016/j.cclet.2020.05.028 shu

A highly sensitive fluorescent probe for tracking intracellular zinc ions and direct imaging of prostatic tissue in mice

Yuyu Wang ^{a, 1} ,
Houna Duan ^{a, 1} ,
Hongyuan Shi ^{b, *,} ,
Shiwei Zhang ^a ,
Yufang Xu ^a ,
Weiping Zhu ^{a, *,} ,
Xuhong Qian ^a

a.
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
Department of Radiology, Jiangsu Province Hospital, First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, China

shy1188@126.com

wpzhu@ecust.edu.cn

Received Date: 18 April 2020
Revised Date: 18 May 2020
Accepted Date: 18 May 2020
Available Online: 15 November 2020

Figures(4)

A highly sensitive fluorescent sensor ZnDN was designed, synthesized and used for tracking intracellular zinc ions in various living cells and direct imaging of prostatic tissue in mice. ZnDN was prepared from the heterocyclic-fused naphthalimide fluorophore, and the zinc receptor, N, N-bis(2-pyridylmethyl)ethylenediamine (BPEN). Upon addition of Zn²⁺ to the solutions of ZnDN, a remarkable fluorescence enhancement was observed, which could be attributed to the photo-induced electron transfer (PET) mechanism. Since ZnDN exhibited high sensitivity toward Zn²⁺ in phosphate buffer solution, with a limit of detection of 4.0×10^-9 mol/L, it was further applied for the imaging of exogenous and endogenous Zn²⁺ in different living cells. Living cells imaging experiments suggested that ZnDN could image the changes of intracellular free zinc ions, and could be used for two-photon imaging. Moreover, flow cytometry suggested that ZnDN could distinguish cancerous prostate cells from normal cells. Animal experiments indicated that ZnDN had the potential in imaging prostate tissue in vivo.
- Fluorescent probe,
- Zinc ion,
- Prostate cells,
- Naphthalimide,
- In vivo imaging
1. [1]
  Y. Chen, Y. Bai, Z. Han, W. He, Z. Guo, Chem. Soc. Rev. 44(2015) 4517-4546. doi: 10.1039/C5CS00005J
2. [2]
  W. Maret, Y. Li, Chem. Rev. 109(2009) 4682-4707. doi: 10.1021/cr800556u
3. [3]
  Y. Qin, P.J. Dittmer, J.G. Park, K.B. Jansen, A.E. Palmer, Proc. Natl. Acad. Sci. U. S. A. 108(2011) 7351-7356. doi: 10.1073/pnas.1015686108
4. [4]
  C.E. Outten, T.V. O'Halloran, Science 292(2001) 2488-2492. doi: 10.1126/science.1060331
5. [5]
  A. Changela, K. Chen, Y. Xue, et al., Science 301(2003) 1383-1387. doi: 10.1126/science.1085950
6. [6]
  J. Wang, Y. Xiao, Z. Zhang, et al., J. Mater. Chem. 15(2005) 2836-2839. doi: 10.1039/b500766f
7. [7]
  L.A. Lichten, R. Cousins, Annu. Rev. Nutr. 29(2009) 153-176. doi: 10.1146/annurev-nutr-033009-083312
8. [8]
  W. Maret, J. Nutr. 130(2000) 1455-1458. doi: 10.1093/jn/130.5.1455S
9. [9]
  E. Bossy-Wetzel, M.V. Talantova, W.D. Lee, M.N. Schölzke, S.A. Lipton, Neuron 41(2004) 351-365. doi: 10.1016/S0896-6273(04)00015-7
10. [10]
  E. Aizenman, A.K. Stout, K.A. Hartnett, et al., J. Neurochem. 75(2000) 1878-1888.
11. [11]
  C.J. Frederickson, W. Maret, M.P. Cuajungco, Neuroscientist 10(2004) 18-25. doi: 10.1177/1073858403255840
12. [12]
  R.J. Cousins, J.P. Liuzzi, L.A. Lichten, J. Biol. Chem. 281(2006) 24085-24089. doi: 10.1074/jbc.R600011200
13. [13]
  C.J. Frederickson, J.Y. Koh, A.I. Bush, Nat. Rev. Neurosci. 6(2005) 449-462. doi: 10.1038/nrn1671
14. [14]
  D.A. Scott, A.M. Fisher, J. Clin. Invest. 17(1938) 725-728. doi: 10.1172/JCI101000
15. [15]
  A.I. Bush, W.H. Pettingell, G. Multhaup, et al., Science 265(1994) 1464-1467. doi: 10.1126/science.8073293
16. [16]
  M.P. Cuajungco, G.J. Lees, Neurobiol. Dis. 4(1997) 137-169. doi: 10.1006/nbdi.1997.0163
17. [17]
  S.K. Ghosh, P. Kim, X.A. Zhang, et al., Cancer Res. 70(2010) 6119-6127. doi: 10.1158/0008-5472.CAN-10-1008
18. [18]
  W. Chyan, D.Y. Zhang, S.J. Lippard, R.J. Radford, Proc. Natl. Acad. Sci. U. S. A. 111(2014) 143-148. doi: 10.1073/pnas.1310583110
19. [19]
  L.C. Costello, R.B. Franklin, J. Biol. Inorg. Chem. 16(2011) 3-8. doi: 10.1007/s00775-010-0736-9
20. [20]
  A. Banas, W.M. Kwiatek, K. Banas, et al., J. Biol. Inorg. Chem.15(2010) 1147-1155. doi: 10.1007/s00775-010-0675-5
21. [21]
  C.G. Taylor, Biometals 18(2005) 305-312. doi: 10.1007/s10534-005-3686-x
22. [22]
  X. Qian, Y. Xiao, Y. Xu, et al., Chem. Commun. 46(2010) 6418-6436. doi: 10.1039/c0cc00686f
23. [23]
  L. Zhou, Z. Jin, X. Fan, et al., Chin. Chem. Lett. 29(2018) 1500-1502. doi: 10.1016/j.cclet.2018.07.018
24. [24]
  J. Zhu, X. Liu, J. Huang, L. Xu, Chin. Chem. Lett. 30(2019) 1767-1774. doi: 10.1016/j.cclet.2019.08.027
25. [25]
  C.B. Huang, L. Xu, J.L. Zhu, et al., J. Am. Chem. Soc. 139(2017) 9459-9462. doi: 10.1021/jacs.7b04659
26. [26]
  J. Zhu, P. Jia, N. Li, et al., Chin. Chem. Lett. 29(2018) 1445-1450. doi: 10.1016/j.cclet.2018.09.002
27. [27]
  Y. Yan, X. Zhang, X. Zhang, et al., Chin. Chem. Lett. 31(2020) 1091-1094. doi: 10.1016/j.cclet.2019.10.025
28. [28]
  L. Zhou, L. Xie, C. Liu, Y. Xiao, Chin. Chem. Lett. 30(2019) 1799-1808. doi: 10.1016/j.cclet.2019.07.051
29. [29]
  X. Guo, X. Qian, L. Jia, J. Am. Chem. Soc. 126(2004) 2272-2273. doi: 10.1021/ja037604y
30. [30]
  L. Cui, Y. Zhong, W. Zhu, Y. Xu, X. Qian, Chem. Comm. 46(2010) 7121-7123. doi: 10.1039/c0cc01000f
31. [31]
  H. Duan, D. Yu, C. Huang, et al., Chin. Chem. Lett. 30(2019) 55-57. doi: 10.1016/j.cclet.2018.03.016
32. [32]
  J. Zhang, C. Wang, L. Zhang, et al., RSC Adv. 6(2016) 71624-71627. doi: 10.1039/C6RA13226J
33. [33]
  L. Xue, G. Li, D. Zhu, Q. Liu, H. Jiang, Inorg. Chem. 51(2012) 10842-10849. doi: 10.1021/ic301307v
34. [34]
  E. Casero, J.A.M. Gago, F. Pariente, E. Lorenzo, Eur. Biophys. J. 33(2004) 726-731. doi: 10.1007/s00249-004-0418-z
35. [35]
  W. Chyan, D.Y. Zhang, S.J. Lippard, R.J. Radford, Proc. Natl. Acad. Sci. U. S. A. 111(2014) 143-148. doi: 10.1073/pnas.1310583110
1. [1]
  Duan Houna , Ding Yu , Huang Chusen , Zhu Weiping , Wang Rui , Xu Yufang . A lysosomal targeting fluorescent probe and its zinc imaging in SH-SY5Y human neuroblastoma cells. Chinese Chemical Letters, 2019, 30(1): 55-57. doi: 10.1016/j.cclet.2018.03.016
2. [2]
  Lina Huang , Yu Chen , Yuqiang Zhao , Yumin Wang , Junwei Xiong , Junfeng Zhang , Xianghua Wu , Ying Zhou . A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe²⁺ in vivo. Chinese Chemical Letters, 2020, 31(11): 2941-2944. doi: 10.1016/j.cclet.2020.06.006
3. [3]
  Xue-Mei Li , Rui-Rui Zhao , Yu-Ling Wei , Dan Yang , Zhang-Jian Zhou , Jun-Feng Zhang , Ying Zhou . A rhodamine derivative for Hg²⁺-selective colorimetric and fluorescent sensing and its application to in vivo imaging. Chinese Chemical Letters, 2016, 27(6): 813-816. doi: 10.1016/j.cclet.2016.04.001
4. [4]
  Qing Liu , Lin Xue , Dong-Jian Zhu , Guo-Ping Li , Hua Jiang . Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells. Chinese Chemical Letters, 2014, 25(1): 19-23.
5. [5]
  Ning Zhang , Yi Su , Miao Yu . A novel cell-impermeable fluorescent zinc sensor containing poly(ethylene glycol) chain. Chinese Chemical Letters, 2011, 22(7): 863-866. doi: 10.1016/j.cclet.2011.01.006
6. [6]
  Feng Wei , Qiao Qing-Long , Leng Shuang , Miao Lu , Yin Wen-Ting , Wang Li-Qiu , Xu Zhao-Chao . A 1, 8-naphthalimide-derived turn-on fluorescent probe for imaging lysosomal nitric oxide in living cells. Chinese Chemical Letters, 2016, 27(9): 1554-1558. doi: 10.1016/j.cclet.2016.06.016
7. [7]
  Xiu Ying Zhang , Zuo Hui Wang , Lin Yang . A highly selective and sensitive fluorescent chemosensor for Zn²⁺. Chinese Chemical Letters, 2008, 19(10): 1240-1243. doi: 10.1016/j.cclet.2008.07.006
8. [8]
  Zhou Langping , Jin Zechen , Fan Xiaoxiang , Yao Yuhua , Chen Zhaoyang , Zhang Weibing , Qian Junhong . Synthesis of 1, 8-naphthalimide-based fluorescent nano-probes and their application in pH detection. Chinese Chemical Letters, 2018, 29(10): 1500-1502. doi: 10.1016/j.cclet.2018.07.018
9. [9]
  Tun Tang , Yu-Qi Chen , Bo-Shi Fu , Zhi-Yong He , Heng Xiao , Fan Wu , Jia-Qi Wang , Shao-Ru Wang , Xiang Zhou . A novel resorufin based fluorescent “turn-on” probe for the selective detection of hydrazine and application in living cells. Chinese Chemical Letters, 2016, 27(4): 540-544.
10. [10]
  Song Lun , Sun Xu-Dong , Ge Yu , Yao Yu-Hua , Shen Jie , Zhang Wei-Bing , Qian Jun-Hong . Anaphthalimide-based fluorescent probe for mercaptocontaining compounds. Chinese Chemical Letters, 2016, 27(12): 1776-1780. doi: 10.1016/j.cclet.2016.05.007
11. [11]
  Hui Chen , Hui Wang , Xiao-Jun Qin , Chen Chen , Lu Feng , Lai-Zhong Chen , Lu-Pei Du , Min-Yong Li . A bestatin-based fl uorescent probe for aminopeptidase N cell imaging. Chinese Chemical Letters, 2015, 26(5): 513-516. doi: 10.1016/j.cclet.2015.01.023
12. [12]
  Zhang Baoxin , Zhang Haijuan , Zhong Miao , Wang Song , Xu Qianhe , Cho Dong-Hyung , Qiu Hongdeng . A novel off-on fluorescent probe for specific detection and imaging of cysteine in live cells and in vivo. Chinese Chemical Letters, 2020, 31(1): 133-135. doi: 10.1016/j.cclet.2019.05.061
13. [13]
  Hui-Ying Liu , Miao Zhao , Qing-Long Qiao , Hai-Jing Lang , Jing-Zhe Xu , Zhao-Chao Xu . Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging. Chinese Chemical Letters, 2014, 25(7): 1060-1064. doi: 10.1016/j.cclet.2014.05.010
14. [14]
  Shuang-Yong Lin , Hui-Jun Zhu , Wen-Jian Xu , Gui-Mei Wang , Nan-Yan Fu . A squaraine based fl uorescent probe for mercury ion via coordination induced deaggregation signaling. Chinese Chemical Letters, 2014, 25(9): 1291-1295. doi: 10.1016/j.cclet.2014.04.027
15. [15]
  Zhao Wu Xu , Jin Tang , He Tian . A highly sensitive colorimetric and ratiometric sensor for fluoride ion. Chinese Chemical Letters, 2008, 19(11): 1353-1357. doi: 10.1016/j.cclet.2008.09.005
16. [16]
  Shuangzhe Zhang , Haidong Li , Qichao Yao , Sahar Ghazali , Jiangli Fan , Jianjun Du , Jingyun Wang , Fengli Gao , Miao Li , Haibo Wang , Chengyong Dong , Xiaojun Peng . A unique two-photon fluorescent probe based on ICT mechanism for imaging palladium in living cells and mice. Chinese Chemical Letters, 2020, 31(11): 2913-2916. doi: 10.1016/j.cclet.2020.01.006
17. [17]
  Ke-Rang Wang , Feng Qian , Xiao-Man Wang , Guan-Hai Tan , Rui-Xue Rong , Zhi-Ran Cao , Hua Chen , Ping-Zhu Zhang , Xiao-Liu Li . Cytotoxic activity and DNA binding of naphthalimide derivatives with amino acid and dichloroacetamide functionalizations. Chinese Chemical Letters, 2014, 25(7): 1087-1093. doi: 10.1016/j.cclet.2014.04.020
18. [18]
  Bo Gao , Yang Li , He Tian . Synthesis and near-infrared characteristics of novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores. Chinese Chemical Letters, 2007, 18(3): 283-286. doi: 10.1016/j.cclet.2007.01.014
19. [19]
  Ming SUN , Di Hua SHANG GUAN , Hui Min MA , Li Hua NIE , Xiao Hua LIShao Xiang XIONG . A Novel Fluorescent Probe for Lead Ions. Chinese Chemical Letters, 2003, 14(10): 1024-1026.
20. [20]
  Chena Yahui , Wei Tingwen , Zhang Zhijie , Zhang Wei , Lv Jing , Chen Tiantian , Chi Bo , Wang Fang , Chen Xiaoqiang . A mitochondria-targeted fluorescent probe for ratiometric detection of hypochlorite in living cells. Chinese Chemical Letters, 2017, 28(10): 1957-1960. doi: 10.1016/j.cclet.2017.05.010

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(30)
HTML views(2)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142