Citation: Ying He, Mengjia Liu, Shun Teng, Lukasz Wojtas, Guangxin Gu, Xiaodong Shi. Synthesis and characterization of fluorescence active G₄-quartet and direct evaluation of self-assembly impact on emission[J]. Chinese Chemical Letters, ;2022, 33(9): 4203-4207. doi: 10.1016/j.cclet.2022.03.007 shu

Synthesis and characterization of fluorescence active G₄-quartet and direct evaluation of self-assembly impact on emission

Ying He ^a ,
Mengjia Liu ^a ,
Shun Teng ^a ,
Lukasz Wojtas ^a ,
Guangxin Gu ^{b, *,} ,
Xiaodong Shi ^{a, *,}

a.
Department of Chemistry, University of South Florida, Tampa, FL 33620, United States
b.
Department of Materials Science, Fudan University, Shanghai 200438, China

Guangxingu@fudan.edu.cn

xmshi@usf.edu

Received Date: 22 October 2021
Revised Date: 27 February 2022
Accepted Date: 2 March 2022
Available Online: 5 March 2022

Figures(6)

Fluorescence (FL) active 8-aryl guanosine derivatives were prepared and applied for cation mediated self-assembly to form the H-bonded G₈-quadruplexes. The p-cyano (p-CN) and 8-anthracene (8-An) substituted guanosines were identified to give the strongest fluorescence with the formation of G₈-octamers (G₈) both in solution (NMR) and solid state (X-ray). This well-defined G₈-octamer system has provided the first direct evidence on the self-assembled G-quadruplex fluorescence emission with aggregation-induced emission (AIE), which could be applied as the foundation for FL molecular probe design toward G-quadruplex recognition.
- Self-assembly,
- H-bonding,
- G₄-quartet,
- Fluorescence,
- Aggregation induced emission
1. [1]
  J.T. Davis, G.P. Spada, Chem. Soc. Rev. 36 (2007) 296–313. doi: 10.1039/B600282J
2. [2]
  J.T. Davis, Angew. Chem. Int. Ed. 43 (2004) 668–698. doi: 10.1002/anie.200300589
3. [3]
  M. Martín-Arroyo, A. Del Prado, R. Chamorro, N. Bilbao, D. González-Rodríguez, Angew. Chem. Int. Ed. 59 (2020) 9041–9046. doi: 10.1002/anie.201916261
4. [4]
  A.N. Lane, J.B. Chaires, R.D. Gray, J.O. Trent, Nucleic Acids Res. 36 (2008) 5482–5515. doi: 10.1093/nar/gkn517
5. [5]
  G. Biffi, D. Tannahill, J. McCafferty, S. Balasubramanian, Nat. Chem. 5 (2013) 182–186. doi: 10.1038/nchem.1548
6. [6]
  M.L. Bochman, K. Paeschke, V.A. Zakian, Nat. Rev. Genet. 13 (2012) 770–780. doi: 10.1038/nrg3296
7. [7]
  S. Xiao, W. Lee, F. Chen, et al., Chem. Commun. 56 (2020) 6981–6984. doi: 10.1039/d0cc02926b
8. [8]
  S. Xiao, P.J. Paukstelis, R.D. Ash, P.Y. Zavalij, J.T. Davis, Angew. Chem. Int. Ed. 58 (2019) 18434–18437. doi: 10.1002/anie.201910872
9. [9]
  K.B. Sutyak, W. Lee, P.V. Zavalij, O. Gutierrez, J.T. Davis, Angew. Chem. Int. Ed. 57 (2018) 17146–17150. doi: 10.1002/anie.201811202
10. [10]
  D. Luo, Y. Mu, J. Phys. Chem. 119 (2015) 4955–4967. doi: 10.1021/acs.jpcb.5b01107
11. [11]
  M. Sproviero, R.A. Manderville, Chem. Commun. 50 (2014) 3097–3099. doi: 10.1039/C3CC49560D
12. [12]
  G.M. Peters, L.P. Skala, J.T. Davis, J. Am. Chem. Soc. 138 (2016) 134–139. doi: 10.1021/jacs.5b08769
13. [13]
  M.I. Umar, D. Ji, C.Y. Chan, C.K. Kwok, Molecules 24 (2019) 2416. doi: 10.3390/molecules24132416
14. [14]
  P. Zhu, Y. Zhang, S. Xu, X. Zhang, Chin. Chem. Lett. 30 (2019) 58–62. doi: 10.1016/j.cclet.2018.02.003
15. [15]
  H. Cai, C. Zhou, Q. Yang, et al., Chin. Chem. Lett. 29 (2018) 531–534. doi: 10.1016/j.cclet.2017.09.010
16. [16]
  L. Yu, Q. Yang, Y. Tang, Chin. Chem. Lett. 30 (2019) 694–697. doi: 10.1016/j.cclet.2018.10.011
17. [17]
  Y. Saito, R.H.E. Hudson, J. Photochem. Photobiol. C 36 (2018) 48–73. doi: 10.1016/j.jphotochemrev.2018.07.001
18. [18]
  D.J.M. Blanchard, T.Z. Cservenyi, R.A. Manderville, Chem. Commun. 51 (2015) 16829–16831. doi: 10.1039/C5CC07154B
19. [19]
  D.J.M. Blanchard, K.L. Fadock, M. Sproviero, et al., Chem. Comm. 4 (2016) 2915–2924. doi: 10.1039/C5TC03354C
20. [20]
  K.L. Fadock, R.A. Manderville, P. Sharma, S.D. Wetmore, Org. Biomol. Chem. 14 (2016) 4409–4419. doi: 10.1039/C6OB00474A
21. [21]
  A. Dumas, N.W. Luedtke, Nucleic Acids Res. 39 (2011) 6825–6834. doi: 10.1093/nar/gkr281
22. [22]
  A.A. Tanpure, S.G. Srivatsan, Nucleic Acids Res. 43 (2015) 149-149. doi: 10.1093/nar/gkv743
23. [23]
  T.X. Chen, F. Ning, H.S. Liu, et al., Chin. Chem. Lett. 28 (2017) 1380–1384. doi: 10.1016/j.cclet.2017.01.006
24. [24]
  Y. He, Y. Zhang, L. Wojtas, et al., Chem. Sci. 10 (2019) 4192–4199. doi: 10.1039/c9sc00190e
25. [25]
  Y. He, Y. Zhang, L. Wojtas, Chem Asian J. 15 (2020) 1030–1034. doi: 10.1002/asia.202000016
26. [26]
  Y. Zhang, Y. He, L. Wojtas, X. Shi, H. Guo, Cell Rep. Phys. Sci. 1 (2020) 100211. doi: 10.1016/j.xcrp.2020.100211
27. [27]
  Y. He, Y. Zhang, M. Liu, et al., Cell Rep. Phys. Sci. 2 (2021) 100519. doi: 10.1016/j.xcrp.2021.100519
28. [28]
  A. Jablonski, Nature, 131 (1933) 839–840. doi: 10.1038/131839b0
29. [29]
  Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Soc. Rev. 40 (2011) 5361–5388. doi: 10.1039/c1cs15113d
30. [30]
  M.H. Lee, A. Sharma, M.J. Chang, et al., Chem. Soc. Rev. 47 (2018) 28–52. doi: 10.1039/C7CS00557A
31. [31]
  R.T.K. Kwok, C.W.T. Leung, J.W.Y. Lam, B.Z. Tang, Chem. Soc. Rev. 44 (2015) 4228–4238. doi: 10.1039/C4CS00325J
32. [32]
  Y. Hong, M. Haubler, J.W. e. Y. Lam, et al., Chem. Eur. J. 14 (2008) 6428–6437. doi: 10.1002/chem.200701723
1. [1]
  Yuanpeng Ye , Longfei Yao , Guofeng Liu . Engineering circularly polarized luminescence through symmetry manipulation in achiral tetraphenylpyrazine structures. Chinese Journal of Structural Chemistry, 2025, 44(2): 100460-100460. doi: 10.1016/j.cjsc.2024.100460
2. [2]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
3. [3]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
4. [4]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
5. [5]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
6. [6]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
7. [7]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
8. [8]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
9. [9]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
10. [10]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
11. [11]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
12. [12]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
13. [13]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
14. [14]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
15. [15]
  Xian Yan , Huawei Xie , Gao Wu , Fang-Xing Xiao . Boosted solar water oxidation steered by atomically precise alloy nanocluster. Chinese Chemical Letters, 2025, 36(1): 110279-. doi: 10.1016/j.cclet.2024.110279
16. [16]
  Feng Cao , Chunxiang Xian , Tianqi Yang , Yue Zhang , Haifeng Chen , Xinping He , Xukun Qian , Shenghui Shen , Yang Xia , Wenkui Zhang , Xinhui Xia . Gelation-pyrolysis strategy for fabrication of advanced carbon/sulfur cathodes for lithium-sulfur batteries. Chinese Chemical Letters, 2025, 36(3): 110575-. doi: 10.1016/j.cclet.2024.110575
17. [17]
  Fengying Ye , Ming Hu , Jun Luo , Wei Yu , Zhirong Xu , Jinjin Fu , Yansong Zheng . Significantly boosting circularly polarized luminescence by synergy of helical and planar chirality. Chinese Chemical Letters, 2025, 36(5): 110724-. doi: 10.1016/j.cclet.2024.110724
18. [18]
  Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
19. [19]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
20. [20]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(636)
HTML views(39)

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

Synthesis and characterization of fluorescence active G4-quartet and direct evaluation of self-assembly impact on emission

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis and characterization of fluorescence active G₄-quartet and direct evaluation of self-assembly impact on emission