基于嘌呤席夫碱荧光探针检测Al3+及细胞实验应用

doi:10.6023/cjoc202112002

摘要/Abstract

基于嘌呤母体的席夫碱, 设计合成并评价了一种新型的检测Al³⁺的开启式荧光探针(E)-2-((2-(8,9-二(萘-1-基)-9H-嘌呤-6-基)腙)甲基)-5-(二乙氨基)苯酚(DNHP). DNHP在MeOH/H₂O (V∶V=9∶1, pH=7.4)中对Al³⁺表现出显著的选择性和快速响应, 并且伴随着从淡黄色到亮蓝色的荧光颜色变化. DNHP的发射强度与Al³⁺的浓度(2~6 µmol/L)之间存在良好的线性关系(R²=0.98367), 最低检出限为588.0 nmol/L. 利用Job’s plot、¹H NMR和密度泛函理论(DFT)研究证明了DNHP对Al³⁺的传感机理. 更重要的是, DNHP表现出细胞渗透性, 并被成功应用于存活的HepG-2细胞内对铝离子的检测.

关键词: 荧光传感器, 嘌呤, 铝, 实际应用

A new “turn-on” fluorescent probe (E)-2-((2-(8,9-di(naphthalen-1-yl)-9H-purin-6-yl)hydrazono)methyl)-5-(diethylamino)phenol (DNHP) for detecting Al³⁺ was designed, synthesized and evaluated based on purine schiff base. DNHP exhibited remarkable selectivity and rapid response towards Al³⁺ in MeOH/H₂O (V∶V=9∶1, pH=7.4), accompanying with a fluorescent color change from yellow to bright blue. A good linear relationship (R²=0.98367) was obtained between the emission intensity of DNHP and the concentration of Al³⁺ (2~6 µmol/L) with a detection limit of 588 nmol/L. The sensing mechanism of DNHP to Al³⁺ was investigated through the Job’s plot, ¹H NMR and density functional theory (DFT) study. More importantly, the sensor DNHP exhibits permeability and could be successfully applied for detection of intracellular cadmium ions in living HepG-2 cells.

Key words: fluorescent sensor, purine, aluminum, practical application

引用此文

鞠立鑫, 邵琦, 陆临川, 陆鸿飞. 基于嘌呤席夫碱荧光探针检测Al³⁺及细胞实验应用[J]. 有机化学, 2022, 42(6): 1706-1712.

Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu. A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1706-1712.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 11

Scheme 1. Synthetic route of DNHP

Figure 1. (a) Fluorescence emission spectra of DNHP (10 μmol/L) in the presence of different metal ions (5.0 equiv.) and (b) UV-Vis absorption (left) and fluorescence spectra (right) of DNHP (red line) and DNHP-Al3+ (black line) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mol/L)

Figure 2. Fluorescence response of DNHP (10 μmol/L) to addition of 5.0 equiv. of other metal ions (the blank bar portion) and the mixture of 5.0 equiv. of other metal ions with 5.0 equiv. of Al3+ (the red bar portion, left to right: Co2+, Pd2+, Ni2+, Cu2+, Cr3+, Zn2+, Cu+, Mn2+, Mg2+, Ba2+, Pb2+, Fe3+, Sn2+, Fe2+, K+, Ca2+, Na+, Ag+, Hg2+ and Cd2+)

Figure 3. Fluorescence changes of DNHP (10 μmol/L) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mmol/L) with the addition of Al3+ (0~6 equiv.) (Inset: photographic fluorescence images of DNHP and DNHP-Al3+. Excitation is at 380 nm; Emission is at 468 nm)

Figure 4. Effect of pH on the fluorescence intensity at 468 nm of DNHP (10 μmol/L) in the absence and presence of 5 equiv. of Al3+

Figure 5. Time profile of DNHP (10 μmol/L) in the presence of Al3+ (5 equiv., 50 μmol/L) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mmol/L)

Figure 6. Job’s plot between DNHP+Al3+ and Al3+ in MeOH/H2O buffer solution

Figure 7. Fluorescence color changes of test strips for Al3+ at different concentrations under a UV lamp

Figure 8. HOMO and LUMO distributions of DNHP and DNHP-Al3+ complex

Figure 9. Cytotoxic nature of DNHP in HepG-2 cells

Figure 10. Fluorescence imaging of DNHP (8 μmol/L) in HepG-2 cells in the absence and presence of Al3+ (20 μmol/L)

参考文献 22

[1]	Liu, T.-T.; Li, S. J.; Fu, H.; Tian, Z. N.; Sun, X. J.; Xing, Z. Y. J. Photochem. Photobiol., 2020, 403, 112865. doi: 10.1016/j.jphotochem.2020.112865
[2]	Gupta, A.; Kumar, N. RSC Adv. 2016, 6, 106413. doi: 10.1039/C6RA23682K
[3]	Yin, P.-C.; Niu, Q. F.; Wei, T.; Li, T. D.; Li, Y.; Yang, Q. X. J. Photochem. Photobiol., 2020, 389, 112249. doi: 10.1016/j.jphotochem.2019.112249
[4]	Gupta, R.; Malak, S. S.; Kumar, V.; Kumar, P. New J. Chem. 2020, 44, 13285. doi: 10.1039/D0NJ00517G
[5]	Wu, Y.; Rahman, F.; Bhatti, M.; Yu, S.; Yang, B.; Wang, H.; Li, Z.; Zhang, D. New J. Chem. 2018, 42, 14978. doi: 10.1039/C8NJ02474J
[6]	Crapper, D.; Krishnan, S.; Dalton, A. Science 1973, 180, 511. pmid: 4735595
[7]	Savory, J.; Ghribi, O.; Forbes, M. S. J. Inorg. Biochem. 2001, 87, 15. pmid: 11709208
[8]	McLachlan, D. R. C.; Bergeron, C.; Alexandrov, P. N.; Walsh, W. J.; Pogue, A. I.; Percy, M. E.; Kruck, T. P. A.; Fang, Z. D.; Sharfman, N. M.; Jaber, V.; Zhao, Y. H.; Li, W. H.; Lukiw, W. J. Mol. Neurobiol. 2019, 56, 1531. doi: 10.1007/s12035-018-1441-x pmid: 30706368
[9]	Wang, B.; Xing, W.; Zhao, Y.; Deng, X. Environ. Toxicol. Pharmacol. 2010, 29, 308. doi: 10.1016/j.etap.2010.03.007
[10]	Peng, H.-N.; Liu, Y. Q.; Huang, J. Q.; Wang, S. X.; Cai, X. P.; Xu, S. J.; Huang, A.; Zeng, Q.; Xu, M. J. Mol. Struct. 2021, 1229, 129866. doi: 10.1016/j.molstruc.2020.129866
[11]	Li, B.; Mei, H. H.; Chang, Y. X.; Xu, K. X.; Yang, L. Spectrochim. Acta, Part A 2020, 239, 118552.
[12]	Wang, Y.; Ma, Z. Y.; Zhang, D. L.; Deng, J. L.; Chen, X.; Xie, C. Z.; Qiao, X.; Li, Q. Z.; Xu, J. Y. Spectrochim. Acta, Part A 2018, 195, 157.
[13]	Purkait, R.; Dey, A.; Dey, S.; Ray, P. P.; Sinha, C. New J. Chem. 2019, 43, 14979. doi: 10.1039/c9nj03377g
[14]	Aydin, D.; Gunay, I. B.; Elmas, S. N. K.; Savran, T.; Arslan, F. N.; Sadi, G.; Yilmaz, I. New J. Chem. 2020, 44, 12079. doi: 10.1039/D0NJ02487B
[15]	Carlos, F. D. S.; Monteiro, R. F.; Silva, L. A.; Zanlorenzi, C.; Nunes, F. S. Spectrochim. Acta, Part A 2020, 231, 118119.
[16]	Roy, S. B.; Rajak, K. K. J. Photochem. Photobiol., A 2017, 332, 505.
[17]	Zhu, G.; Huang, Y.; Wang, C.; Lu, L.; Sun, T.; Wang, M.; Tang, Y.; Shan, D.; Wen, S.; Zhu, J. Spectrochim. Acta, Part A 2019, 210, 105.
[18]	Suresh, S.; Bhuvanesh, N.; Prabhu, J.; Thamilselvan, A.; Raj-kumar, S. R. J.; Kannan, K.; Rajesh, K. V.; Nandhakumar, R. J. Photochem. Photobiol., A 2018, 359, 172.
[19]	Kaur, R.; Saini, S.; Kaur, N.; Singh, N.; Jang, D. Spectrochim. Acta, Part A 2020, 225, 117523.
[20]	Wu, Y.; Rahman, F. U.; Bhatti, M. Z.; Yu, S. B.; Yang, B.; Wang, H.; Li, Z. T.; Zhang, D. W. New J. Chem. 2018, 42, 14978. doi: 10.1039/C8NJ02474J
[21]	Das, S.; Dutta, M.; Das, D. Anal. Methods 2013, 5, 6262. doi: 10.1039/c3ay40982a
[22]	Zhang, W.-X.; Jin, X. X.; Chen, W.; Jiang, C. H.; Lu, H. F. Anal. Methods 2019, 11, 2396. doi: 10.1039/C9AY00380K

基于嘌呤席夫碱荧光探针检测Al³⁺及细胞实验应用

A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 11

参考文献 22

相关文章 15

编辑推荐

相关统计

本文评价

[1]	赵怡玲, 陈志康, 李磊, 刘聪磊, 朱红平. 硅宾/有机铝的Lewis酸碱对体系及其丙烯酸酯聚合的引发性能[J]. 有机化学, 2023, 43(10): 3590-3597.
[2]	汪蕾, 于淑晶, 杨娜, 王宝雷. 新型含二氢喹唑啉酮的咖啡因衍生物的合成及生物活性研究[J]. 有机化学, 2023, 43(1): 299-307.
[3]	楚治良, 陈晖娟, 单帅, 王晓娜, 高春芳, 渠桂荣, 刘忠于, 郭海明. 一步法合成1,2,4-三氮唑[3,4-i]嘌呤类化合物[J]. 有机化学, 2022, 42(5): 1551-1556.
[4]	白冰, 徐芳琳, 杨静, 张改红, 毛多斌, 王宁. AlCl₃催化3-(2-氨基乙基)吡咯的合成[J]. 有机化学, 2021, 41(6): 2335-2342.
[5]	刘航, 张舒昀, 李欢, 张燕, 李正名, 王宝雷. 8-[(3,4,4-三氟丁-3-烯-1-基)硫基]取代的新型甲基黄嘌呤及其衍生物的合成和生物活性[J]. 有机化学, 2021, 41(5): 2091-2098.
[6]	李清寒, 罗瑞强, 吴川, 肖红柳, 郭少鹏, 张志豪, 黄哲耀, 周林. 烷基铝试剂与亲电试剂的偶联反应研究进展[J]. 有机化学, 2021, 41(4): 1489-1497.
[7]	贾俊辉, 温娟娟. 基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al³⁺检测性质研究[J]. 有机化学, 2021, 41(4): 1728-1733.
[8]	夏超, 王东超, 郭海明. 三氟甲磺酸钪催化嘌呤与邻羟基苄醇反应构建非环核苷[J]. 有机化学, 2021, 41(11): 4391-4399.
[9]	张舒昀, 刘航, 汪蕾, 李正名, 王宝雷. 新型含取代哌嗪的咖啡因衍生物的合成、结构表征及生物活性研究[J]. 有机化学, 2021, 41(10): 4075-4082.
[10]	马学林, 韩利民, 张骁勇, 郝占忠, 杨威, 张玉恒, 王丽. 多响应锆基金属有机框架荧光传感器对Fe³⁺,Cr₂O₇^2-离子和有机小分子的识别[J]. 有机化学, 2020, 40(9): 2938-2948.
[11]	袁康宁, 赵玉英, 常宏宏, 田俊, 高文超. AlCl₃促进的有机反应研究进展[J]. 有机化学, 2020, 40(9): 2607-2625.
[12]	张继东, 詹妍, 李胡月雯, 齐怡, 王瑞鹏, 孟莉. 硒化合物荧光传感器研究进展[J]. 有机化学, 2020, 40(7): 1847-1859.
[13]	姚明, 张静静, 杨森, 熊航行. γ-三氧化二铝促进的炔烃碘代反应研究[J]. 有机化学, 2020, 40(7): 2153-2158.
[14]	马学林, 韩利民, 张骁勇, 张玉恒, 王丽, 杨坤, 冀婕. 三嗪衍生物荧光探针对Zr^4＋，Fe^3＋和丙酮的识别[J]. 有机化学, 2020, 40(6): 1745-1751.
[15]	曹西颖, 罗时荷, 杨崇岭, 肖颖, 李晓燕, 张钧如, 汪朝阳. 有机聚合物荧光传感器的研究进展[J]. 有机化学, 2020, 40(12): 4046-4059.