A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging

doi:10.6023/cjoc201510028

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 774-781.DOI: 10.6023/cjoc201510028 Previous Articles Next Articles

ARTICLE

新型萘酰亚胺-氟硼二吡咯荧光分子的合成、荧光共振能量转移及细胞成像 2017-2018 Awarded

沈宝星, 钱鹰

东南大学化学化工学院南京 211189

收稿日期:2015-10-24 修回日期:2015-12-01 发布日期:2015-12-21
通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
基金资助:
国家自然科学基金(No.61178057)资助项目.

A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging

Shen Baoxing, Qian Ying

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2015-10-24 Revised:2015-12-01 Published:2015-12-21
Supported by:
Project supported by the National Natural Science Foundation of China (No. 61178057).

1. A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging.PDF(483KB)

Abstract

A novel fluorescent dye naphthalene imide-fluorine boron two pyrrole 1-(2-(4-(1,3,5,7-tetramethyl fluorine boron pyrrole)phenoxy)ethyl)-4-(4-N-butyl-1,8-naphthalene imide)-1,2,3-triazole (NP-BODIPY) has been synthesized by Click reaction and characterized by ¹H NMR, ¹³C NMR and HRMS techniques. NP-BODIPY has the property of intermolecule fluorescence resonance energy transfer from the naphthalene imide to BODIPY, the NP-BODIPY/SiO₂nanoparticles was prepared by positive phase microemulsion. In the test of the UV-vis absorption and fluorescence spectrum of NP-BODIP, purple fluorescence could be observed under ultraviolet lamp when NP-BODIPY was in solid state, green fluorescence could be observed when NP-BODIPY was in THF solution, fluorescence spectrum exhibited bimodal structure in 430 and 510 nm, the fluorescence quantum efficiency of NP-BODIPY was 67% and the ultraviolet absorption peaks were at 366 and 500 nm. The fluorescence quantum efficiency of NP-BODIPY in H₂O/THF mixture solution is 39%. It has strong fluorescence when water fraction is 80%, and the maximum fluorescence peaks are at 510 nm. When NP-BODIPY was co-incubated with michigan cancer foundation-7 cells (MCF-7) cells, the fluorescent dye penetrated into the MCF-7 cells and could be clearly observed. NP-BODIPY/SiO₂nanoparticles exhibit good water solubility, size controllable, low cytotoxicity and good biocompatibility. So NP-BODIPY can be widely used for biomarkers and fluorescence imaging.

Key words: Click reaction, naphthalene imide, BODIPY, fluorescent nanoparticles, cell imaging, fluorescence resonance energy transfer

Cite this article

Shen Baoxing, Qian Ying. A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging[J]. Chin. J. Org. Chem., 2016, 36(4): 774-781.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wang, L.-Y.; Fang, G.; Cao, D. Sens. and Actuators B. 2015, 207, 849.
[2] He, X. G.; Zhang, J.; Liu, X. G.; Dong, L.; Li, D.; Qiu, H. Y.; Yin, S. C. Sens. Actuators B. 2014, 192, 29.
[3] Vedamalai, M.; Wu, S. P. Org. Biomol. Chem. 2012, 10, 5410.
[4] Zhang, X.-L. Ph. D. Dissertation, Dalian University of Technology, Dalian, 2009 (in Chinese). (张晓琳, 博士论文, 大连理工大学, 大连, 2009.)
[5] Zhu, L.; Younes, A.; Yuan, Z.; Clark, R. J. J. Photochem. Photobiol. A: Chem. 2015, 311, 1.
[6] Sreenath, K.; Yuan, Z.; Allen, J. R.; Davidson, M. W.; Zhu, L. Chem. Eur. J. 2015, 21, 867.
[7] Peng, X.; Du, J.; Fan, J. J. Am. Chem. Soc. 2007, 129, 500.
[8] Zhang, X.; Xiao, Y.; Qian, X. Org. Lett. 2008, 10, 29.
[9] Wang, J. M.; Yu, H.; Li, Q. Talanta 2015, 144, 763.
[10] Azael Gomez-Duran, C. F.; Hu, R. R.; Feng, G. X.; Li, T. Z.; Bu, F.; Arseneault, M.; Liu, Bin.; Peña-Cabrera, E.; Tang, B. Z. ACS Appl. Mater. Interfaces. 2015, 7, 15168.
[11] Zhao, C.; Jiang, H. Chin. J. Chem. 2015, 33, 7.
[12] Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
[13] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. 2002, 41, 2596.
[14] Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302.
[15] Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278.
[16] Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
[17] Bevilacqua, V.; King, M.; Chaumontet, M.; Nothisen, M.; Gabillet, S.; Buisson, D.; Puente, C.; Wagner, A.; Taran, F. Angew. Chem., Int. Ed. 2014, 53, 5872.
[18] Ingale, S. A.; Seela, F. J. Org. Chem. 2013, 78, 3394.
[19] Yuan, Z.; Kuang, G. C.; Clark, R. J.; Zhu, L. Org. Lett. 2012, 14, 2590.
[20] Cheng, H. R.; Qian, Y. RSC Adv. 2015, 5, 86371.
[21] Cheng, H. R.; Qian, Y. RSC Adv. 2015, 5, 82887.
[22] Mukherjee, S.; Thilagar, P. Chem. Eur. J. 2014, 20, 9052.
[23] Duke, R. M.; Gunnlaugsson, T. Tetrahedron Lett. 2007, 48, 8043.
[24] Zhu, L.; Yuan, Z.; J. Tyler, S.; Kesavapillai, S. RSC Adv. 2014, 4, 20398.
[25] Xu, Z.-C.; Juyoung, Y.; David, R. S. Chem. Soc. Rev. 2010, 39, 1996.
[26] Xuan-Anh, T.; Victor, A.; Paolo, B.; Bernadette, T. S. B.; Karsten, H. Biosens. Bioelectron. 2015, 64, 359.
[27] Gan, J.-A.; Song, Q.-L.; Hou, X.-Y.; Chen, K.-C.; Tian, H. J. Photochem. Photobiol. A 2004, 162, 399.
[28] Jin, P.-W.; Jiao, C.-H.; Guo, Z.-Q.; He, Y.; Zhu, S.-Q.; Tian, H.; Zhu, W.-H. Chem. Sci. 2014, 5, 4012.
[29] Liu, X.-L.; Du, X.-J.; Dai, C.-G.; Song, Q.-H. J. Org. Chem. 2014, 79, 9481.
[30] Liu, Y.-B.; Liu, Y.-W; Liu, W.; Liang, S.-C. Spectrochim. Acta A 2015, 137, 509.
[31] Sun, J.-F.; Qian, Y. Chin. J. Org. Chem. 2015, 35, 1104 (in Chinese). (孙京府, 钱鹰, 有机化学, 2015, 35, 1104.)
[32] Jin, Y.; Qian, Y. New J. Chem. 2015, 39, 2872.
[33] Huimin, G.; Muro-Small, M. L.; Shaomin, J. Inorg. Chem. 2010, 49, 6802.
[34] Cheng, H. R.; Qian, Y. Sens. Actuators, B 2015, 219, 57.

新型萘酰亚胺-氟硼二吡咯荧光分子的合成、荧光共振能量转移及细胞成像 2017-2018 Awarded

A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[2]	Xiaolong Zhao, Liangwu Guo, Yuqing Li, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. Near-Infrared Visualization Fluoroboron Dipyrrole (BODIPY) Fluore-scent Probe with Large Stokes Shift for Detecting Na₂S₂O₄ in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2484-2491.
[3]	Yang Zhao, Panpan Chen, Gaonan Li, Zhigang Niu, Enju Wang. Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2156-2162.
[4]	Yifang Li, Yao Wang, Huawei Niu, Xiujin Chen, Zhaozhou Li, Yongguo Wang. Research Progress of Sulfur Dioxide Fluorescent Probe Targeting Mitochondria [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1952-1962.
[5]	Hongwei Tang, Chao Wang, Keli Zhong, Shuhua Hou, Lijun Tang, Yanjiang Bian. A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 712-717.
[6]	Meng Liu, Yanru Huang, Xiaofei Sun, Lijun Tang. An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClO^–Recognition [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 345-351.
[7]	Jiaxin Li, Ruyan He, Senlin Duan, Jinhua Li, Xiaojing Han, Yong Ye. Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO^– Detection [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2428-2432.
[8]	Xuerong Chen, Liang Qi, Jinpei Huang, Weiwei Zhu, Yifeng Zhou. Lewis Acid Promoted Intramolecular Nucleophilic Heterocyclization of Unsaturated Amides for the Synthesis of 2-Oxazolines and Their Applications in Imaging of Living Cells [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2155-2163.
[9]	Bin-Kai Liu, Kun-Xu Teng, Li-Ya Niu, Qing-Zheng Yang. Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1265-1285.
[10]	Xiaolong Zhao, Yuqing Li, Liangwu Guo, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu^2＋ Based on Boron-Dipyrromethene (BODIPY) Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3757-3765.
[11]	Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.
[12]	Chao Wang, Xin Wang, Keli Zhong, Shuhua Hou, Xiaomei Yan, Yanjiang Bian, Lijun Tang. A Long-Wavelength Fluorescent Probe for Naked Eye Recognition of HSO₃^-/SO₃^2- in Aqueous Solution and Its Application [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2417-2423.
[13]	Keli Zhong, Lulu Zhou, Lin Chen, Lijun Tang, Xue Gao, Xiuying Liu, Xiuxiu Pang, Xiaomei Yan. Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd²⁺ [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1124-1130.
[14]	Yang Min, Xia Lili, Zhou Xiaoqin, Jia Chengli, Ji Min, Wang Peng. A Ratiometric Fluorescent Probe for Imaging Hydrogen Peroxide in Living Cells [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2888-2894.
[15]	Mei Huihui, Yang Mingyang, Liu Xiaoyan, Tian Yuping, Xu Kuoxi. A Novel Phenanthroline-Based Fluorescent Probe for Pb(II) [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2508-2512.