Citation: Kang Yao, Fan Jiangli, Jin Qiang, Shi Chenhui, Du Jianjun, Peng Xiaojun. A α-KA fluorescent probe for discrimination of blood cancer serum[J]. Chinese Chemical Letters, ;2017, 28(10): 1991-1993. doi: 10.1016/j.cclet.2017.08.054 shu

A α-KA fluorescent probe for discrimination of blood cancer serum

a.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
b.
Department of Hepatobiliary and Pancreatic Surgery, The First Affiliated Hospital of Zhengzhou University, Zhengzhou 450001, China

Corresponding author: Fan Jiangli, fanjl@dlut.edu.cn
Received Date: 15 June 2017
Revised Date: 22 August 2017
Accepted Date: 30 August 2017
Available Online: 1 October 2017

Figures(5)

α-Ketoglutaric acid (α-KA) is an important metabolic intermediate in tricarboxylic acid circle in our body. The mutations of isocitrate dehydrogenase-1 (IDH1) and isocitrate dehydrogenase-2 (IDH2), however, will lead to the transformation of α-KA into 2-hydroxyglutarate (2-HG), which is confirmed to closely related to actue myeloid leukemia (AML). Therefore it is of great significance to detect α-KA level changes in serum. In this paper, a fluorescent "off-on" probe CH for α-KA was designed based on naphthalimide fluorophore by introducing a hydrazine group for α-KA recognition and a long alkyl amino chain to enhance PET efficiency and water solubility. Cetyltrimethyl ammonium bromide (CTAB) was added toform self-assembly micelles for accelerating the recognition process. CH shows a 28-fold fluorescence enhancement ((I-I₀)/I₀ at 550 nm) over other biological species by optimizing the chemical recognition process of CH with α-KA. Significantly, CH was successfully applied for thefluorescence discrimination of all kinds of blood cancer serum samples. This work would provide a potential method that is quick and convenient for sensing α-KA and may promote fluorescence detection in clinical diagnosis.
- Biomarker,
- Fluorescent probe,
- α-Ketoglutaricacid,
- Actue myeloid leukemia (AML),
- Serum detection
1. [1]
  H.F. Shi, X.J. Chen, S.J. Liu, et al., ACS Appl. Mater. Interfaces 5(2013) 4562-4568. doi: 10.1021/am4000408
2. [2]
  T. Wang, J.E.F. Douglass, K.J. Fitzgerald, et al., J. Am. Chem. Soc. 135(2013) 12429-12433. doi: 10.1021/ja406077j
3. [3]
  H. Zhang, J.L. Fan, J.Y. Wang, et al., J. Am. Chem. Soc. 135(2013) 11663-11669. doi: 10.1021/ja4056905
4. [4]
  Y.J. Huang, W.J. Ouyang, X. Wu, et al., J. Am. Chem. Soc. 135(2013) 1700-1703. doi: 10.1021/ja311442x
5. [5]
  H. Zhang, J.L. Fan, J.Y. Wang, et al., J. Am. Chem. Soc. 135(2013) 17469-17475. doi: 10.1021/ja4085308
6. [6]
  P. Jin, C. Jiao, Z. Guo, et al., Chem. Sci. 5(2014) 4012-4016. doi: 10.1039/C4SC01378F
7. [7]
  T. Tang, Y.Q. Chen, B.S. Fu, et al., Chin. Chem. Lett. 27(2016) 540-544. doi: 10.1016/j.cclet.2016.01.024
8. [8]
  W. Zhang, X.Y. Zhou, Q.Y. Yu, et al., Chin. Chem. Lett. 27(2016) 185-189. doi: 10.1016/j.cclet.2015.12.002
9. [9]
  W. Sun, S.J. Guo, C. Hu, J.L. Fan, X.J. Peng, Chem. Rev. 116(2016) 7768-7817. doi: 10.1021/acs.chemrev.6b00001
10. [10]
  H. Zhu, J.L. Fan, J.J. Du, X.J. Peng, Acc. Chem. Res. 49(2016) 2115-2126. doi: 10.1021/acs.accounts.6b00292
11. [11]
  J.L. Fan, Z.C. Han, Y. Kang, X.J. Peng, Sci. Rep. 6(2016) 19562-19568. doi: 10.1038/srep19562
12. [12]
  H.D. Li, Q.C. Yao, J.L. Fan, et al., Dyes Pigm. 133(2016) 79-85. doi: 10.1016/j.dyepig.2016.05.039
13. [13]
  L.L. Zhang, H.K. Zhu, C.C. Zhao, X.F. Gu, Chin. Chem. Lett. 28(2017) 218-221. doi: 10.1016/j.cclet.2016.07.008
14. [14]
  W. He, F.J.P. Miao, D.C.H. Lin, et al., Nature 429(2004) 188-193. doi: 10.1038/nature02488
15. [15]
  P.S. Ward, J. Patel, D.R. Wise, et al., Cancer Cell 17(2010) 225-234. doi: 10.1016/j.ccr.2010.01.020
16. [16]
  A. Schulze, A.L. Harris, Nature 491(2012) 364-373. doi: 10.1038/nature11706
17. [17]
  W. Xu, H. Yang, Y. Liu, et al., Cancer Cell 19(2011) 17-30. doi: 10.1016/j.ccr.2010.12.014
18. [18]
  L. Dang, D.W. White, S. Gross, et al., Nature 462(2009) 739-744. doi: 10.1038/nature08617
19. [19]
  S. Gross, R.A. Cairns, M.D. Minden, et al., J. Exp. Med. 6(2010) 1-6.
20. [20]
  L. Kronberger, H.J. Semmelrock, R.J. Schaur, et al., J. Cancer Res. Clin. Oncol. 97(1980) 295-299. doi: 10.1007/BF00405781
21. [21]
  B.M. Wagner, F. Donnarumma, R. Wintersteiger, W. Windischhofer, H.J. Leis, Anal. Bioanal. Chem. 396(2010) 2629-2637. doi: 10.1007/s00216-010-3479-0
22. [22]
  K. Pailla, F. Blonde-Cynober, C. Aussel, J.P. De Bandt, L. Cynober, Clin. Chem. 46(2000) 848-853.
23. [23]
  J.C.J. Deutsch, J. Chromatogr. B:Biomed. Sci. Appl. 690(1997) 1-6. doi: 10.1016/S0378-4347(96)00411-2
24. [24]
  T. Nakahara, J. Ishida, M. Yamaguchi, M. Nakamura, Anal. Biochem. 190(1990) 309-313. doi: 10.1016/0003-2697(90)90199-J
25. [25]
  Y. He, Z.Q. Guo, P.W. Jin, et al., Ind. Eng. Chem. Res. 54(2015) 2886-2893. doi: 10.1021/acs.iecr.5b00263
26. [26]
  C. Jiao, Y. He, P. Jin, S. Zhu, W.H. Zhu, Imaging Sci. Photochem. 33(2015) 195-202.
27. [27]
  A.P. De Silva, H.Q. Gunaratne, J.L. Habib-Jiwan, et al., Angew. Chem. Int. Ed. 34(1995) 1728-1731. doi: 10.1002/(ISSN)1521-3773
28. [28]
  A.P. De Silva, H.Q. Gunaratne, T. Gunnlaugsson, et al., Chem. Rev. 97(1997) 1515-1566. doi: 10.1021/cr960386p
29. [29]
  R.M. Duke, E.B. Veale, F.M. Pfeffer, P.E. Kruger, T. Gunnlaugsson, Chem. Soc. Rev. 39(2010) 3936-3953. doi: 10.1039/b910560n
30. [30]
  C. Choi, S.K. Ganji, R.J. DeBerardinis, et al., Nat. Med. 18(2012) 624-629. doi: 10.1038/nm.2682
31. [31]
  L. Song, X.D. Sun, Y. Ge, et al., Chin. Chem. Lett. 27(2016) 1776-1780. doi: 10.1016/j.cclet.2016.05.007
32. [32]
  M.Y. Wu, K. Li, C.Y. Li, J.T. Hou, X.Q. Yu, Chem. Commun. 50(2014) 183-185. doi: 10.1039/C3CC46468G
33. [33]
  D. Jacquemin, E.A. Perpète, I. Ciofini, C. Adamo, Theor. Chem. Acc. 128(2011) 127-136. doi: 10.1007/s00214-010-0783-x
34. [34]
  Y.H. Tang, X.Q. Kong, A. Xu, B.L. Dong, W.Y. Lin, Angew. Chem. Int. Ed. 55(2016) 3356-3359. doi: 10.1002/anie.201510373
1. [1]
  Yao-Hua Gu , Yu Chen , Qing Li , Neng-Bin Xie , Xue Xing , Jun Xiong , Min Hu , Tian-Zhou Li , Ke-Yu Yuan , Yu Liu , Tang Tang , Fan He , Bi-Feng Yuan . Metabolome profiling by widely-targeted metabolomics and biomarker panel selection using machine-learning for patients in different stages of chronic kidney disease. Chinese Chemical Letters, 2024, 35(11): 109627-. doi: 10.1016/j.cclet.2024.109627
2. [2]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
3. [3]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
4. [4]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
5. [5]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
6. [6]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
7. [7]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
8. [8]
  Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
9. [9]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
10. [10]
  Xiaoxiao Wang , Bolun Wang , Fenfen Ji , Jie Yan , Jiacheng Fang , Doudou Zhang , Ji Xu , Jing Ji , Xinran Hao , Hemi Luan , Yanjun Hong , Shulan Qiu , Min Li , Zhu Yang , Wenlan Liu , Xiaodong Cai , Zongwei Cai . Discovery of plasma biomarkers for Parkinson’s disease diagnoses based on metabolomics and lipidomics. Chinese Chemical Letters, 2024, 35(11): 109653-. doi: 10.1016/j.cclet.2024.109653
11. [11]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
12. [12]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
13. [13]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
14. [14]
  Quan Zhang , Shunjie Xing , Jingqian Han , Li Feng , Jianchun Li , Zhaosheng Qian , Jin Zhou . Organic pollutant sensing for human health based on carbon dots. Chinese Chemical Letters, 2025, 36(1): 110117-. doi: 10.1016/j.cclet.2024.110117
15. [15]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
16. [16]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379
17. [17]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
18. [18]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
19. [19]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778
20. [20]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(762)
HTML views(40)

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