Citation: Yanying Wang, Ronghui Zhou, Wenxue Liu, Chao Liu, Peng Wu. Comparison of benzothiazole-based dyes for sensitive DNA detection[J]. Chinese Chemical Letters, ;2020, 31(11): 2950-2954. doi: 10.1016/j.cclet.2020.01.023 shu

Comparison of benzothiazole-based dyes for sensitive DNA detection

Yanying Wang ^a ,
Ronghui Zhou ^b ,
Wenxue Liu ^a ,
Chao Liu ^{c, *,} ,
Peng Wu ^{a, c, *,}

a.
College of Chemistry, Sichuan University, Chengdu 610064, China
b.
State Key Laboratory of Oral Diseases, West China Hospital of Stomatology, Sichuan University, Chengdu 610041, China
c.
State Key Laboratory of Hydraulics and Mountain River Engineering, College of Water Resource & Hydropower, Sichuan University, Chengdu 610065, China

liuchao@scu.edu.cn (C. Liu), wupeng@scu.edu.cn (P. Wu).

Received Date: 11 December 2019
Revised Date: 8 January 2020
Accepted Date: 8 January 2020
Available Online: 21 January 2020

Figures(4)

For efficient and quantitative DNA detection, fluorescence staining is the most often explored approach, which relies on non-covalent binding of dyes with double stranded DNA (dsDNA). Ethidium bromide (EB) is the most classic DNA stain, but suffers from its high carcinogenicity. A series of less toxic alternatives were developed, many of which contain the core structure of the benzothiazole ring. However, the relationship between the structure and the DNA detection performance was not illustrated. Herein, five benzothiazole dyes, namely thiazole orange, SYBR Green Ⅰ, PicoGreen, SYBR Safe, and thioflavine-T, were compared for DNA detection through direct fluorescence and gel electrophoresis, with particular focus on the structure-performance relationship. It turned out that SYBR Green Ⅰ is currently the best choice for DNA detection. The results in this work may be useful for future DNA-staining dye developments.
- DNA quantitative detection,
- Benzothiazole,
- SYBR Green Ⅰ,
- Gel electrophoresis
1. [1]
  C. Ramakers, J.M. Ruijter, R.H.L. Deprez, et al., Neurosci. Lett. 339(2003) 62-66. doi: 10.1016/S0304-3940(02)01423-4
2. [2]
  T.Y. Dong, G.A. Wang, M.W. Li, et al., Anal. Methods 11(2019) 5376-5380. doi: 10.1039/C9AY01383K
3. [3]
  A.M. Haines, S.S. Tobe, H.J. Kobus, et al., Electrophoresis 36(2015) 941-944. doi: 10.1002/elps.201400496
4. [4]
  F. Vitzthum, G. Geiger, H. Bisswanger, et al., Anal. Biochem. 276(1999) 59-64. doi: 10.1006/abio.1999.4298
5. [5]
  X.Y. Luo, B.B. Xue, G.F. Feng, et al., J. Am. Chem. Soc. 141(2019) 5182-5191. doi: 10.1021/jacs.8b10265
6. [6]
  Y.S. Ding, X.T. Liu, J. Zhu, et al., Talanta 125(2014) 393-399. doi: 10.1016/j.talanta.2014.03.032
7. [7]
  P.J. Zhu, Y.Y. Zhang, S.X. Xu, et al., Chin. Chem. Lett. 30(2019) 58-62. doi: 10.1016/j.cclet.2018.02.003
8. [8]
  G.Y. Park, S.K. Chakkarapani, S. Ju, et al., Chin. Chem. Lett. 29(2018) 505-508. doi: 10.1016/j.cclet.2017.08.018
9. [9]
  J.B. Lepecq, C. Paoletti, Anal. Biochem. 17(1966) 100-107. doi: 10.1016/0003-2697(66)90012-1
10. [10]
  J.B. Lepecq, C. Paoletti, J. Mol. Bio. 27(1967) 87-106. doi: 10.1016/0022-2836(67)90353-1
11. [11]
  A.N. Glazer, H.S. Rye, Nature 359(1992) 859-861. doi: 10.1038/359859a0
12. [12]
  L.G. Lee, C.H. Chen, L.A. Chiu, Cytometry 7(1986) 508-517. doi: 10.1002/cyto.990070603
13. [13]
  H.S. Rye, M.A. Quesada, K. Peck, et al., Nucleic Acids Res. 19(1991) 327-333. doi: 10.1093/nar/19.2.327
14. [14]
  D.L. Boger, B.E. Fink, S.R. Brunette, et al., J. Am. Chem. Soc. 123(2001) 5878-5891. doi: 10.1021/ja010041a
15. [15]
  H. Zipper, H. Brunner, J. Bernhagen, et al., Nucleic Acids Res. 32(2004) e103. doi: 10.1093/nar/gnh101
16. [16]
  X. Jin, S. Yue, K.S. Wells, et al., FASEB J. 8(1994) 1266.
17. [17]
  W. Ma, S. Lu, D. Zhu, et al., Chin. Chem. Lett. 25(2014) 482-484. doi: 10.1016/j.cclet.2013.12.013
18. [18]
  H. Hu, J.Y. Zhang, Y. Ding, et al., Anal. Chem. 89(2017) 5101-5106. doi: 10.1021/acs.analchem.7b00666
19. [19]
  X.F. Zhang, C.P. Huang, S.X. Xu, et al., Chem. Commun. 51(2015) 14465-14468. doi: 10.1039/C5CC06105A
20. [20]
  X.Y. Fan, Y.Y. Wang, L. Deng, et al., Anal. Chem. 91(2019) 9407-9412. doi: 10.1021/acs.analchem.9b01675
21. [21]
  X.S. Ren, Q.H. Xu, Langmuir 25(2009) 43-47. doi: 10.1021/la803430g
22. [22]
  V.L. Singer, L.J. Jones, S.T. Yue, et al., Anal. Biochem. 249(1997) 228-238. doi: 10.1006/abio.1997.2177
23. [23]
  S.J. Ahn, J. Costa, J.R. Emanuel, Nucleic Acids Res. 24(1996) 2623-2625. doi: 10.1093/nar/24.13.2623
24. [24]
  A. Dragan, E. Bishop, J.R. Casas-Finet, et al., Anal. Biochem. 396(2010) 8-12. doi: 10.1016/j.ab.2009.09.010
25. [25]
  D. Marie, D. Vaulot, F. Partensky, Appl. Environ. Microbiol. 62(1996) 1649-1655. doi: 10.1128/AEM.62.5.1649-1655.1996
26. [26]
  C. Martineau, L.G. Whyte, C.W. Greer, J. Microbiol.Methods 73(2008) 199-202. doi: 10.1016/j.mimet.2008.01.016
27. [27]
  W.E.Evenson, L.M.Boden, K.A.Muzikar, et al., J.Org.Chem.77(2012)10967-10971. doi: 10.1021/jo3021659
28. [28]
  G.T. Westermark, K.H. Johnson, P. Westermark, Thioflavin Stains, in:R. Wetzel (Ed.), Methods in Enzymology, Academic Press, Amsterdam, 1999, pp. 3-25.
29. [29]
  X.H. Li, L.J. Gan, Q.S. Ou, et al., Biosens. Bioelectron. 66(2015) 399-404. doi: 10.1016/j.bios.2014.11.049
30. [30]
  J. Mohanty, N. Barooah, V. Dhamodharan, et al., J. Am. Chem. Soc. 135(2013) 367-376. doi: 10.1021/ja309588h
31. [31]
  H. Hilal, J. Taylor, Dyes Pigment. 75(2007) 483-490. doi: 10.1016/j.dyepig.2006.06.032
32. [32]
  M.J. Frisch, G.W. Truck, H.B. Schlegel, et al., Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2013.
33. [33]
  D. Su, C.L. Teoh, L. Wang, et al., Chem. Soc. Rev. 46(2017) 4833-4844. doi: 10.1039/C7CS00018A
34. [34]
  N. Amdursky, Y. Erez, D. Huppert, Acc. Chem. Res. 45(2012) 1548-1557. doi: 10.1021/ar300053p
35. [35]
  C.S. O'Neil, J.L. Beach, T.D. Gruber, Electrophoresis 39(2018) 1474-1477. doi: 10.1002/elps.201700489
36. [36]
  K. Hirakawa, S. Kawanishi, T. Hirano, Chem. Res. Toxicol.18(2005) 1545-1552. doi: 10.1021/tx0501740
37. [37]
  H.S. Rye, M.A. Quesada, P. Konan, et al., Nucleic Acids Res. 19(1991) 327-333. doi: 10.1093/nar/19.2.327
38. [38]
  A.I. Dragan, R. Pavlovic, J.B. McGivney, et al., J. Fluoresc. 22(2012) 1189-1199. doi: 10.1007/s10895-012-1059-8
39. [39]
  Z.Z. Shao, C. Zhang, X.H. Zhu, et al., Chin. Chem. Lett. 30(2019) 2169-2172. doi: 10.1016/j.cclet.2019.06.023
40. [40]
  S.S. Long, W.J. Chi, L. Miao, et al., Chin. Chem. Lett. 30(2019) 601-604. doi: 10.1016/j.cclet.2018.12.008
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