Citation: Li Haimei, Luo Huajian, Xiao Qi, Yang Liyun, Huang Shan, Liu Yi. Investigations of Interactions and Mechanisms of Chiral Graphene Quantum Dots with DNA[J]. Acta Chimica Sinica, ;2020, 78(6): 577-586. doi: 10.6023/A20040109 shu

Investigations of Interactions and Mechanisms of Chiral Graphene Quantum Dots with DNA

Li Haimei ^a ,
Luo Huajian ^a ,
Xiao Qi ^a ,
Yang Liyun ^a ,
Huang Shan ^a,b,, ,
Liu Yi ^a,b,,

a.
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning 530001, China
b.
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China

Corresponding author: Huang Shan, huangs@nnnu.edu.cn Liu Yi, yiliuchem@whu.edu.cn
Received Date: 17 April 2020
Available Online: 1 June 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21873075, 21864006, 21763005, 21673166, 21563006)the National Natural Science Foundation of China 21873075the National Natural Science Foundation of China 21763005the National Natural Science Foundation of China 21563006the National Natural Science Foundation of China 21673166the National Natural Science Foundation of China 21864006

Figures(10)

As one of the most important characteristics of nature, chirality is closely related to life activities. Therefore, chiral nanomaterials have caused great attention in material, biology and some related fields. In this paper, a new preparation method for chiral graphene quantum dots (L-GQDs and D-GQDs) was proposed via one-step hydrothermal method. This method used citric acid and L(or D)-tryptophan as raw materials to synthesize chiral graphene quantum dots. Circular dichroism spectroscopy proved that the two chiral graphene quantum dots had two chiral signals with high symmetry, and the absorption peaks were located at 230 nm and 305 nm, respectively. A lot of thermodynamic parameters have been obtained by using fluorescence. The results of viscosity measurement, DNA melting experiments and multi-spectroscopic methods indicated that there was a large chiral difference between the combination of chiral graphene quantum dots and ctDNA. UV-Vis absorption spectrometry proved that the two different chiral graphene quantum dots caused the slightly red shift of absorption peak and hypochromic effect of ctDNA. These quantum dots increased the melting temperature of DNA, but reduced the relative viscosity of ctDNA. Through hydrogen bonding and van der Waals interaction, both graphene quantum dots were inserted into the G-C base pair of ctDNA, which affected the right-handed B-form helicity of ctDNA significantly. The steric hindrance effects of L-GQDs and D-GQDs were different, resulting in the differences of them in their intercalation and binding with ctDNA. Comparably, D-GQDs with right-handedness exhibited the strongest intercalative binding ability with ctDNA, and were easier to intercalate into ctDNA with the right-handed B-helical structure, causing the significant influence on right-handed B-helical structure of ctDNA. These results revealed the molecular mechanisms of the intercalative binding interactions between chiral graphene quantum dots and DNA, which provided valuable information for the development of chiral nanomaterials in chemistry, biology, and medicine areas.
- chiral graphene quantum dot,
- calf thymus DNA,
- spectroscopy,
- interaction mechanism,
- thermodynamic parameter,
- steric hindrance
1. [1]
  Crassous, J. Chem. Soc. Rev. 2009, 38, 830. doi: 10.1039/b806203j
2. [2]
  Li, Q.; Jia, Y.; Li, J. B. Acta Chim. Sinica 2019, 77, 1173.
3. [3]
  Xiong, F.; Li, L. Chinese J. Org. Chem. 2018, 38, 2927.
4. [4]
  Cai, J.; Hao, C.; Sun, M.; Ma, W.; Xu, C.; Kuang, H. Small 2018, 14, 1703931. doi: 10.1002/smll.201703931
5. [5]
  Mohammadi, E.; Tsakmakidis, K. L.; Askarpour, A. N.; Dehkhoda, P.; Tavakkoli, A.; Altug, H. ACS Photonics 2018, 5, 2669. doi: 10.1021/acsphotonics.8b00270
6. [6]
  Liu, G. J.; Shi, H. Chinese J. Org. Chem. 2016, 36, 2583. doi: 10.6023/cjoc201603037
7. [7]
  Liu, Q.; Guo, B. D.; Rao, Z. Y.; Zhang, B. H.; Gong, J. R. Nano Lett. 2013, 13, 2436. doi: 10.1021/nl400368v
8. [8]
  Ge, S. Y.; He, J. B.; Ma, C. T.; Liu, J. Y.; Xi, F. N.; Dong, X. P. Talanta 2019, 199, 581. doi: 10.1016/j.talanta.2019.02.098
9. [9]
  Lu, H. T.; Li, W. J.; Dong, H. F.; Wei, M. L. Small 2019, 15, 1902136. doi: 10.1002/smll.201902136
10. [10]
  Sajjadi, S.; Khataee, A.; Soltani, R. D. C.; Hasanzadeh, A. J. Phys. Chem. Solids 2019, 127, 140. doi: 10.1016/j.jpcs.2018.12.014
11. [11]
  Zhou, X. Q.; Sun, Q.; Jiang, L.; Li, S. T.; Gu, W.; Tian, J. L.; Liu, X.; Yan, S. P. Dalton Trans. 2015, 44, 9516. doi: 10.1039/C5DT00931F
12. [12]
  Carrillo-Carrión, C.; Cárdenas, S.; Simonet, B. M.; Simonet, B. M.; Valcárcel, M. Anal. Chem. 2009, 81, 4730. doi: 10.1021/ac900034h
13. [13]
  Zeng, C. J.; Jin, R. C. Chem 2017, 12, 1839.
14. [14]
  Jiang, S.; Chekini, M.; Qu, Z. B.; Wang, Y. C.; Yeltik, A.; Liu, Y. G.; Kotlyar, A.; Zhang, T. Y.; Li, B.; Demir, H. V.; Kotov, N. A. J. Am. Chem. Soc. 2017, 139, 13701. doi: 10.1021/jacs.7b01445
15. [15]
  Li, F.; Li, Y. Y.; Yang, X.; Han, X. X.; Yang, J.; Wei, T. T.; Yang, D. Y.; Xu, H. P.; Nie, G. J. Angew. Chem., Int. Ed. 2018, 57, 2377. doi: 10.1002/anie.201712453
16. [16]
  Suzuki, N.; Wang, Y. C.; Elvati, P.; Qu, Z. B.; Kim, K.; Jiang, S.; Baumeister, E.; Lee, J.; Yeom, B. J.; Bahng, J. H.; Lee, J.; Violi, A.; Kotov, N. A. ACS Nano 2016, 10, 1744. doi: 10.1021/acsnano.5b06369
17. [17]
  Xu, L. G.; Xu, Z.; Ma, W.; Liu, L. Q.; Wang, L. B.; Kuang, H.; Xu, C. H. J. Mater. Chem. B 2013, 1, 4478. doi: 10.1039/c3tb20692k
18. [18]
  Gan, Z.; Xu, H.; Hao, Y. Nanoscale 2016, 8, 7794. doi: 10.1039/C6NR00605A
19. [19]
  Xu, M. H.; He, G. L.; Li, Z. H.; He, F. J.; Gao, F.; Su, Y. J.; Zhang, L. Y.; Yang, Z.; Zhang, Y. F. Nanoscale 2014, 6, 10307. doi: 10.1039/C4NR02792B
20. [20]
  Singh, H.; Sreedharan, S.; Tiwari, K.; Green, N. H.; Smythe, C.; Pramanik, S. K.; Thomas, J. A.; Das, A. Chem. Commun. 2019, 55, 52.
21. [21]
  SimoEs, E. F. C.; Da Silva, J. C. G. E.; LeitaO, J. M. M. Anal. Chim. Acta 2014, 852, 174. doi: 10.1016/j.aca.2014.08.050
22. [22]
  Liu, Z. G.; Xiao, J. C.; Wu, X. W.; Lin, L. Q.; Weng, S. H.; Chen, M.; Cai, X. H.; Lin, X. H. Sens. Actuators, B 2016, 229, 217. doi: 10.1016/j.snb.2016.01.127
23. [23]
  Peng, J.; Gao, W.; Gupta, B. K.; Liu, Z.; Romero-Aburto, R.; Ge, L. H.; Song, L.; Alemany, L. B.; Zhan, X. B.; Gao, G. H.; Vithayathil, S. A.; Kaipparettu, B. A.; Marti, A. A.; Hayashi, T.; Zhu, J. J.; Ajayan, P. M. Nano Lett. 2012, 12, 844. doi: 10.1021/nl2038979
24. [24]
  Zhou, X.; Zhang, G.; Wang, L. J. Lumin. 2014, 154, 116. doi: 10.1016/j.jlumin.2014.04.017
25. [25]
  Kurbanoglu, S.; Dogan-Topal, B.; Hlavata, L.; Labuda, J.; Ozkan, S. A.; Uslu, B. Electrochim. Acta 2015, 169, 233. doi: 10.1016/j.electacta.2015.04.087
26. [26]
  Kumar, C. V.; Turner, R. S.; Asuncion, E. H. J. Photochem. Photobiol., A 1993, 74, 231. doi: 10.1016/1010-6030(93)80121-O
27. [27]
  Li, Y.; Zhang, G. W.; Pan, J. H.; Zhang, Y. Sens. Actuators, B 2014, 191, 464. doi: 10.1016/j.snb.2013.10.022
28. [28]
  Cohen, G.; Eisenberg, H. Biopolymers 1969, 8, 45. doi: 10.1002/bip.1969.360080105
29. [29]
  Coury, J. E.; Mcfail-Isom, L.; Williams, L. D. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 12283. doi: 10.1073/pnas.93.22.12283
30. [30]
  Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed., Springer, New York, 2006.
31. [31]
  Leckband, D. Annu. Rev. Biophys. Biomol. Struct. 2000, 29, 1. doi: 10.1146/annurev.biophys.29.1.1
32. [32]
  Ross, P. D.; Subramanian, S. Biochemistry 1981, 20, 3096. doi: 10.1021/bi00514a017
33. [33]
  Huang, S.; Liang, Y.; Huang, C. S.; Su, W.; Lei, X. L.; Liu, Y.; Xiao, Q. Luminescence 2016, 31, 1384. doi: 10.1002/bio.3119
34. [34]
  Blackburn, G. M.; Gait, M. J. Nucleic Acids in Chemistry and Biology, 2nd ed., Oxford University Press, New York, 1996.
35. [35]
  Barton, J. K. Science 1986, 233, 727. doi: 10.1126/science.3016894
36. [36]
  Hanczyc, P.; Lincoln, P.; Norden, B. J. Phys. Chem. B 2013, 117, 2947. doi: 10.1021/jp311952x
37. [37]
  Jangir, D. K.; Charak, S.; Mehrotra, R.; Kundu, S. J. Photochem. Photobiol., B 2011, 105, 143. doi: 10.1016/j.jphotobiol.2011.08.003
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