Citation: Zhen-Shuo YAN, Yan-Hui KANG, Yang-Ling CHEN, Li-Ni HUO. Synthesis, Crystal Structure and Its Application in Living Cells Imaging of Benz(c)acridine-1, 2, 3-triazole Derivatives[J]. Chinese Journal of Structural Chemistry, ;2021, 40(10): 1309-1316. doi: 10.14102/j.cnki.0254–5861.2011–3159 shu

Synthesis, Crystal Structure and Its Application in Living Cells Imaging of Benz(c)acridine-1, 2, 3-triazole Derivatives

a.
Guangxi University of Chinese Medicine, Nanning 530001, China
b.
Hebei University of Engineering, Handan 056038, China

Corresponding author: Li-Ni HUO, huolini@126.com
Received Date: 25 February 2021
Accepted Date: 16 April 2021

Fund Project: the National Natural Science Foundation of China 22067001Natural Science Foundation of Guangxi Province 2018GXNSFAA281189Graduate Education Innovation Project of Guangxi University of Chinese Medicine YCSY20190027the Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine (2013) No. 20Collaborative Innovation Center of Zhuang and Yao Ethnic Medicine (2014) No. 32Guangxi Key Discipline Zhuang Pharmacology (2013) No. 16First-class Discipline in Guangxi of traditional Chinese Pharmacology (Direction of Ethnic Medicine) (2018) No. 12

Figures(7)

A highly selective iron ions fluorescent probe based on the benz(c)acridine-1, 2, 3-triazole derivatives was produced by multi-step reactions. 1-(7-Benz[c]acridinyl)-4-(4-methylphenyl)-1, 2, 3-triazole (4a), C₂₆H₁₈N₄, was structurally determined by single-crystal X-ray diffraction. It crystallizes in the trigonal system, space group R-3 with a = 36.230(10), b = 36.230(10), c = 7.993(3) Å, β = 90°, V = 9086(6) Å³, Z = 18, D_c = 1.271 g/cm³, F(000) = 3636, μ = 0.602 mm^-1, the final R = 0.0865 and wR = 0.1619 for 3951 observed reflections (I > 2σ(I)). X-ray analysis indicated that all four rings of benz(c)acridine are in the same plane, and the 1, 2, 3-triazole ring and the corresponding linked benzene (C(1)–C(6)–C(7)–C(8)–C(9)–N(1)) are approximately perpendicular with a dihedral angle of 106.5°. The crystal packing of the compound was stabilized by two weak interactions between C(11)–H(10)···N(4) and C(18)–H(18)···N(1). In fluorescence spectra studies, compound 4c was exhibited good selectivity and sensitivity towards iron ions in DMSO: mops buffer solution. Furthermore, 4c was successfully used for imaging iron ions in living HeLa cervical cancer cells.
- benz(c)acridine-1, 2, 3-triazole,
- crystal structure,
- fluorescent probe,
- iron ions
1. [1]
  Raymond, K. N.; Dertz, E. A.; Kim, S. S. Enterobactin: an archetype for microbial iron transport. Proc. Natl. Acad. Sci. U. S. A 2003, 100, 3584−3588. doi: 10.1073/pnas.0630018100
2. [2]
  Pantopoulos, K.; Porwal, S. K.; Tartakoff, A.; Devireddy, L. Mechanisms of mammalian iron homeostasis. Biochemistry 2012, 51, 5705−5724. doi: 10.1021/bi300752r
3. [3]
  Abbaspour, N.; Hurrell, R.; Kelishadi, R. Review on iron and its importance for human health. J. Res. Med. Sci. 2014, 19, 164−174.
4. [4]
  Kindra, L. R.; Eggers, C. J.; Liu, A. T.; Mendoza, K.; Mendoza, J.; Myers, A. R. K.; Penner, R. M. Lithographically patterned PEDOT nanowires for the detection of iron(III) with nanomolar sensitivity. Anal. Chem. 2015, 87, 11492−11500. doi: 10.1021/acs.analchem.5b03255
5. [5]
  Guo, C. H.; Hsu, G. S. W.; Chuang, C. J.; Chen, P. C. Aluminum accumulation induced testicular oxidative stress and altered selenium metabolism in mice. Environ. Toxicol. Pharmacol. 2009, 27, 176−181. doi: 10.1016/j.etap.2008.10.001
6. [6]
  Li, Q.; Song, P.; Dai, Y.; Wang, C.; Xu, K. Progress in fluorescent chemical sensors based on acridine. Chem. Res. 2015, 26, 433−440.
7. [7]
  Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M. H. Chemical sensors that incorporate click-derived triazoles. Chem. Soc. Rev. 2011, 40, 2848−2866. doi: 10.1039/c0cs00143k
8. [8]
  Ng, D. K. P.; Shi, W. J.; Liu, J. Y.; Lo, P. C. Selective detection of Hg²⁺ ion with boron dipyrromethene-based fluorescent probes appended with a bis(1, 2, 3-triazole)amino receptor. Chem. Asian J. 2019, 14, 1059−1065. doi: 10.1002/asia.201900166
9. [9]
  Xiao, L.; Ren, P.; Jing, X.; Ren, L.; Li, Z.; Dai, F. Application in molecular recognition of 1, 2, 3-trizole derivatives. Chin. J. Org. Chem. 2017, 37, 3085−3095. doi: 10.6023/cjoc201705043
10. [10]
  Chen, Y.; Zheng, C.; Peng, X.; Fu, Q.; Wu, L.; Lin, Q. Research progress in the synthesis of 1, 2, 3-triazole under transition-metal-free. Chin. J. Org. Chem. 2016, 36, 1779−1789. doi: 10.6023/cjoc201601020
11. [11]
  Chen, R.; Huo, L. N.; Jaiswal, Y.; Huang, J. Y.; Zhong, Z. G.; Zhong, J.; Leonard, W.; Xia, X.; Liang, Y.; Yan, Z. S. Design, synthesis, antimicrobial, and anticancer activities of acridine thiosemicarbazides derivatives. Molecules 2019, 24, 2065−15. doi: 10.3390/molecules24112065
12. [12]
  Huo, L. N.; Chen, R.; Li, P. Y.; Su, W.; Lu, R. M. The preparation method of 1-(7-benz[c]acridinyl)-4-(4-methylphenyl)-1, 2, 3-triazole. CN Patent, C07D401/04. 2015108702191. 2016−03−23.
13. [13]
  Huo, L. N.; Chen, R.; Liao, Y. F.; Liu, H. G.; Li, P. Y.; Lu, R. M.; Zhong, Z. G. Synthesis, crystal structure and biological evaluation of acridine-1, 2, 3-triazole derivatives. Chin. J. Struct. Chem. 2016, 35, 698−704.
14. [14]
  Sheldrick, G. M. A short history of SHELX. Acta Cryst. 2008, A64, 112−122.
15. [15]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. 2015, C71, 3−8.
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沈阳化工大学材料科学与工程学院沈阳 110142