Citation: Na Li, Qian Zhou, Kun Li, Ting Jiang, Xiao-Qi Yu. Qualitative and quantitative detection of aldehydes in DNA with 2-amino benzamidoxime derivative[J]. Chinese Chemical Letters, ;2023, 34(1): 107471. doi: 10.1016/j.cclet.2022.04.069 shu

Qualitative and quantitative detection of aldehydes in DNA with 2-amino benzamidoxime derivative

Na Li ^{a, 1} ,
Qian Zhou ^{b, 1} ,
Kun Li ^{a, *,} ,
Ting Jiang ^a ,
Xiao-Qi Yu ^{a, b, *,}

a.
Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu 610064, China
b.
Department of Chemistry, Xihua University, Chengdu 610039, China

kli@scu.edu.cn

xqyu@scu.edu.cn

Received Date: 11 March 2022
Revised Date: 20 April 2022
Accepted Date: 24 April 2022
Available Online: 28 April 2022

Figures(4)

An aldehyde-reactive probe based on 2-amino benzamidoxime (ABAO) framework was introduced, which can selectively label aldehydes in DNA through intramolecular ring closure under mild aqueous solutions. We screened ABAO derivatives that can undergo a cyclization with the formylated nucleobases to generate a fluorescence nucleoside, and of these derivatives 5-methoxy-ABAO (PMA) emerged as the optimal choice. PMA can sensitively and selectively react with 5fU, 5fC and AP to form fluorogenic dihydroquinazoline derivatives, which also can quantify DNA damages induced by γ-irradiation. PMA-initiated labeling strategy provides great convenience for qualitative and quantitative detection of aldehydes in DNA.
- Aldehydes in DNA,
- 2-Amino benzamidoxime derivative,
- Intramolecular ring closure,
- Fluorescent adducts,
- Quantitative analysis
1. [1]
  P.L. Arnold, Z.R. Turner, Nat. Rev. Chem.1 (2017) 1–16 doi: 10.1038/s41570-016-0001
2. [2]
  M.J. Booth, E.A. Raiber, S. Balasubramanian, Chem. Rev. 115 (2015) 2240–2254 doi: 10.1021/cr5002904
3. [3]
  J. Dietzsch, D. Feineis, C. Hoebartner, FEBS Lett. 592 (2018) 2032–2047 doi: 10.1002/1873-3468.13058
4. [4]
  T. Carell, M.Q. Kurz, M. Mueller, M. Rossa, F. Spada, Angew. Chem. Int. Ed. 57 (2018) 4296–4312 doi: 10.1002/anie.201708228
5. [5]
  H. Hong, H. Cao, Y. Wang, Y. Wang, Chem. Res. Toxicol. 19 (2006) 614–621 doi: 10.1021/tx060025x
6. [6]
  X. Wu, Y. Zhang, Nat. Rev. Genet. 18 (2017) 517–534 doi: 10.1038/nrg.2017.33
7. [7]
  C.S. Nabel, H. Jia, Y. Ye, et al., Nat. Chem. Biol. 8 (2012) 751–758 doi: 10.1038/nchembio.1042
8. [8]
  J. Cadet, K.J.A. Davies, M.H.G. Medeiros, P. Di Masciod, J. Richard Wagner, Free Radical Biol. Med. 107 (2017) 13–34 doi: 10.1016/j.freeradbiomed.2016.12.049
9. [9]
  W.P. Roos, B. Kaina, Cancer Lett. 332 (2013) 237–248 doi: 10.1016/j.canlet.2012.01.007
10. [10]
  K.S. Gates, Chem. Res. Toxicol. 22 (2009) 1747–1760 doi: 10.1021/tx900242k
11. [11]
  M. Su, A. Kirchner, S. Stazzoni, et al., Angew. Chem. Int. Ed. 55 (2016) 11797–11800 doi: 10.1002/anie.201605994
12. [12]
  Q. Dai, P.J. Sanstead, C.S. Peng, et al., ACS Chem. Biol. 11 (2016) 470–477 doi: 10.1021/acschembio.5b00762
13. [13]
  A.M. Deaton, A. Bird, Genes Dev. 25 (2011) 1010–1022 doi: 10.1101/gad.2037511
14. [14]
  M. Berney, J.F. McGouran, Nat. Rev. Chem. 2 (2018) 332–348 doi: 10.1038/s41570-018-0044-4
15. [15]
  P.A. Jones, Nat. Rev. Genet. 13 (2012) 484–492 doi: 10.1038/nrg3230
16. [16]
  X.F. Zhang, L. Wang, N. Li, Y. Xiao, Chin. Chem. Lett. 32 (2021) 2395–2399 doi: 10.1016/j.cclet.2021.02.031
17. [17]
  G.R. Zou, K.Y. Zhang, W. Yang, et al., Chin. Chem. Lett. 32 (2021) 3252–3256 doi: 10.1016/j.cclet.2021.02.036
18. [18]
  D.B. Gophane, S.T. Sigurdsson, Chem. Commun. 49 (2013) 999–1001 doi: 10.1039/C2CC36389E
19. [19]
  W. Hirose, K. Sato, A. Matsuda, Angew. Chem. Int. Ed. 49 (2010) 8392–8394 doi: 10.1002/anie.201004087
20. [20]
  S.R. Wang, J.Q. Wang, B.S. Fu, et al., J. Am. Chem. Soc. 140 (2018) 15842–15849 doi: 10.1021/jacs.8b09113
21. [21]
  S.R. Wang, Y.Y. Song, L. Wei, et al., J. Am. Chem. Soc. 139 (2017) 16903–16912 doi: 10.1021/jacs.7b09635
22. [22]
  T. Hong, T. Wang, P. Guo, et al., Anal. Chem. 85 (2013) 10797–10802 doi: 10.1021/ac4020676
23. [23]
  P. Guo, S. Yan, J. Hu, et al., Org. Lett. 15 (2013) 3266–3269 doi: 10.1021/ol401290d
24. [24]
  L. Xu, Y.C. Chen, S. Nakajima, et al., Chem. Sci. 5 (2014) 567–574 doi: 10.1039/C3SC51849C
25. [25]
  L. Xu, Y.C. Chen, J. Chong, et al., Angew. Chem. Int. Ed. 53 (2014) 11223–11227 doi: 10.1002/anie.201406220
26. [26]
  C. Liu, Y. Wang, X. Zhang, et al., Chem. Sci. 8 (2017) 4505–4510 doi: 10.1039/C7SC00637C
27. [27]
  J. Krim, C. Gruenewald, M. Taourirte, J.W. Engels, Bioorg. Med. Chem. 20 (2012) 480–486 doi: 10.1016/j.bmc.2011.10.041
28. [28]
  R.E. Hardisty, F. Kawasaki, A.B. Sahakyan, S. Balasubramanian, J. Am. Chem. Soc. 137 (2015) 9270–9272 doi: 10.1021/jacs.5b03730
29. [29]
  J. Hu, X. Xing, X. Xu, et al., Chem. Eur. J. 19 (2013) 5836–5840 doi: 10.1002/chem.201300082
30. [30]
  C. Liu, Y. Wang, W. Yang, et al., Chem. Sci. 8 (2017) 7443–7447 doi: 10.1039/C7SC03685J
31. [31]
  B. Samanta, J. Seikowski, C. Hoebartner, Angew. Chem. Int. Ed. 55 (2016) 1912–1916 doi: 10.1002/anie.201508893
32. [32]
  Y. Wang, C. Liu, X. Zhang, et al., Chem. Sci. 9 (2018) 3723–3728 doi: 10.1039/C8SC00493E
33. [33]
  C. Zhu, Y. Gao, H. Guo, et al., Cell Stem Cell 20 (2017) 720–731 doi: 10.1016/j.stem.2017.02.013
34. [34]
  B. Xia, D. Han, X. Lu, et al., Nat. Methods 12 (2015) 1047–1050 doi: 10.1038/nmeth.3569
35. [35]
  Q. Zhou, K. Li, K.K. Yu, et al., Chem. Commun. 56 (2020) 12158–12161 doi: 10.1039/d0cc04950f
36. [36]
  Q. Zhou, K. Li, L.L. Li, et al., Anal. Chem. 91 (2019) 9366–9370 doi: 10.1021/acs.analchem.9b02499
37. [37]
  Q. Zhou, K. Li, Y.H. Liu, et al., Chem. Commun. 54 (2018) 13722–13725 doi: 10.1039/c8cc07541g
38. [38]
  F. Kawasaki, P. Murat, Z. Li, T. Santner, S. Balasubramanian, Chem. Commun. 53 (2017) 1389–1392 doi: 10.1039/C6CC08670E
39. [39]
  A. Maiti, A.Z. Michelson, C.J. Armwood, J.K. Lee, A.C. Drohat, J. Am. Chem. Soc. 135 (2013) 15813–15822 doi: 10.1021/ja406444x
40. [40]
  S. Cortellino, J. Xu, M. Sannai, et al., Cell 146 (2011) 67–79 doi: 10.1016/j.cell.2011.06.020
41. [41]
  C. Liu, X. Luo, Y. Chen, et al., Anal. Chem. 90 (2018) 14616–14621 doi: 10.1021/acs.analchem.8b04822
42. [42]
  P.I. Kitov, D.F. Vinals, S. Ng, K.F. Tjhung, R. Derda, J. Am. Chem. Soc. 136 (2014) 8149–8152 doi: 10.1021/ja5023909
43. [43]
  A.K. Ressmann, D. Schwendenwein, S. Leonhartsberger, et al., Adv. Synth. Catal. 361 (2019) 2538–2543
44. [44]
  M. Muenzel, U. Lischke, D. Stathis, et al., Chem. Eur. J. 17 (2011) 13782–13788 doi: 10.1002/chem.201102782
45. [45]
  G.S. Madugundu, J. Cadet, J.R. Wagner, Nucleic Acids Res. 42 (2014) 7450–7460 doi: 10.1093/nar/gku334
1. [1]
  Wei Peng , Baoying Wen , Huamin Li , Yiru Wang , Jianfeng Li . Exploration and Practice on Raman Scattering Spectroscopy Experimental Teaching. University Chemistry, 2024, 39(8): 230-240. doi: 10.3866/PKU.DXHX202312062
2. [2]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
3. [3]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
4. [4]
  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
5. [5]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
6. [6]
  Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2023.100309
7. [7]
  Yuxin Xiao , Xiaowei Wang , Yutong Yin , Fangchao Yin , Jinchao Li , Zhiyuan Hou , Mashooq Khan , Rusong Zhao , Wenli Wu , Qiongzheng Hu . Distance-based lateral flow biosensor for the quantitative detection of bacterial endotoxin. Chinese Chemical Letters, 2024, 35(12): 109718-. doi: 10.1016/j.cclet.2024.109718
8. [8]
  Chang Liu , Tao Wu , Lijiao Deng , Xuzi Li , Xin Fu , Shuzhen Liao , Wenjie Ma , Guoqiang Zou , Hai Yang . Programmed DNA walkers for biosensors. Chinese Chemical Letters, 2024, 35(9): 109307-. doi: 10.1016/j.cclet.2023.109307
9. [9]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
10. [10]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
11. [11]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
12. [12]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
13. [13]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
14. [14]
  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
15. [15]
  Neng Shi , Haonan Jia , Jixiang Zhang , Pengyu Lu , Chenglong Cai , Yixin Zhang , Liqiang Zhang , Nongyue He , Weiran Zhu , Yan Cai , Zhangqi Feng , Ting Wang . Accurate expression of neck motion signal by piezoelectric sensor data analysis. Chinese Chemical Letters, 2024, 35(9): 109302-. doi: 10.1016/j.cclet.2023.109302
16. [16]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
17. [17]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
18. [18]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
19. [19]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
20. [20]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(548)
HTML views(56)

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