Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging

doi:10.11944/j.issn.1000-0518.2017.12.170319

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (12): 1450-1456.DOI: 10.11944/j.issn.1000-0518.2017.12.170319

• Full Papers • Previous Articles Next Articles

Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging

Jia ZHOU,Yun NI,Chengwu ZHANG(),Xinghan QIU,Yanfei ZHAO,Lei BAI,Gaobin ZHANG(),Lin LI()

Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM),Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM),Nanjing Tech University(Nanjing Tech),Nanjing 211816,China

Received:2017-09-05 Accepted:2017-10-23 Published:2017-12-04 Online:2017-12-04
Contact: Chengwu ZHANG,Gaobin ZHANG,Lin LI
Supported by:
Supported by the National Natural Science Foundation of China(No.81672508, No.61505076), the Major Projects of Natural Science Research in Colleges and Universities in Jiangsu(No.16KJA180004)

Abstract

Abstract:

In the field of biological imaging, two-photon fluorescent dyes with stable optical properties under physiological conditions have broad application prospects. Herein, we designed and synthesized a two-photon fluorescent dye 2-[(1E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-4(3H)-pyrimidinone(NHP). NHP was obtained by condensation between 2,4-dismethyl-6-pyrimidinol and 4-dimethylaminobenzaldehyde. The chemical structure and optical properties of NHP was characterized by mass spectrometry(MS), nuclear magnetic resonance spectroscopy(NMR), ultraviolet-visible(UV-Vis) absorption spectra and fluorescence emission spectra method as well as the external environment change effect on the emission spectrum. The results show that the absorption peak of NHP is around 400 nm, and the emission peak of which is around 550 nm. The fluorescence emission of NHP is stable in various pH, ions and amino acids conditions. Furthermore, biological experimental results show that NHP is able to image HepG2/SH-SY5Y cells and Drosophila brains with negligible cytotoxicity. All of those indicate that NHP is an ideal two-photon fluorescence dye for bioimaging.

Key words: pyrimidine derivatives, two-photon imaging, fluorescent probes, bioimaging

Jia ZHOU, Yun NI, Chengwu ZHANG, Xinghan QIU, Yanfei ZHAO, Lei BAI, Gaobin ZHANG, Lin LI. Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging[J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1450-1456.

References

[1]	Ray P C. Size and Shape Dependent Second Order Nonlinear Optical Properties of Nanomaterials and Their Application in Biological and Chemical Sensing[J]. Chem Rev,2010,110(9):5332-5365.
[2]	Ellinger S,Graham K R,Shi P,et al.Donor-Acceptor-Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission[J]. Chem Mater,2011,23(17):3805-3817.
[3]	Sumalekshmy S,Fahrni C J. Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy[J]. Chem Mater,2011,23(3):483-500.
[4]	Yang Y M,Zhao Q,Feng W,et al.Luminescent Chemodosimeters for Bioimaging[J]. Chem Rev,2013,113(1):192-270.
[5]	Yong K T,Qian J,Roy I,et al.Quantum Rod Bioconjugates as Targeted Probes for Confocal and Two-Photon Fluorescence Imaging of Cancer Cells[J]. Nano Lett,2007,7(3):761-765.
[6]	Coenjarts C, Garci'a O,Llauger L, et al. Mapping Photogenerated Radicals in Thin Polymer Films:Fluorescence Imaging Using a Prefluorescent Radical Probe[J]. J Am Chem Soc,2003,125(3):620-621.
[7]	Yanez C O,Andrade C D,Yao S,et al.Photosensitive Polymeric Materials for Two-Photon 3D Worm Optical Data Storage Systems[J]. Appl Mater Interfaces,2009,1(10):2219-2229.
[8]	Corredor C C,Huang Z L,Belfield K D,et al.Photochromic Polymer Composites for Two-Photon 3D Optical Data Storage[J]. J Chem Mater,2007,19(21):5165-5173.
[9]	Dvornikov A S,Walker E P,Rentzepis P M,et al.Two-Photon Three-Dimensional Optical Storage Memory[J]. J Phys Chem,2009,113(49):13633-13644.
[10]	Jhaveri S J, McMullen J D,Sijbesma R, et al. Direct Three-Dimensional Microfabrication of Hydrogels via Two-Photon Lithography in Aqueous Solution[J]. J Chem Mater,2009,21(10):2003-2006.
[11]	Zhou W H,Kuebler S M,Braun K L,et al.An Efficient Two-Photon-Generated Photoacid Applied to Positive-Tone 3D Microfabrication[J]. Science,2002,296(55700):1106-1109.
[12]	ZHANG Yong,LI Wei,WANG Qiang,et al.A Benzoxazole-Based Fluorescent Probe for Visual Detection of Hg2+[J]. Acta Chim Sin,2013,71(11):1496-1499(in Chinese). 张勇,李伟,王强,等. 一种基于苯并噁唑类的可视化检测汞离子的荧光探针[J]. 化学学报,2013,71(5):1496-1499.
[13]	Jasieniak J J,Fortunati I,Gardin S,et al.Highly Efficient Amplified Stimulated Emission from CdSe-CdS-ZnS Quantum Dot Doped Waveguides with Two-Photon Infrared Optical Pumping[J]. Adv Mater,2008,20(1):69-73.
[14]	Beverina L,Crippa M,Landenna M,et al.Assessment of Water-Soluble π-Extended Squaraines as One- and Two-Photon Singlet Oxygen Photosensitizers:Design, Synthesis, and Characterization[J]. J Am Chem Soc,2008,130(6):1894-1902.
[15]	Akdas K H,Roisnel T,Ledoux I,et al.A New Class of Bipyrimidine Based Octupolar Chromophores:Synthesis, Fluorescent and Quadratic Nonlinear Optical Properties[J]. New J Chem,2009,33(7):1470-1473.
[16]	Liu B,Zhang H L,Liu J,et al.Novel Pyrimidine-based Amphiphilic Molecules:Synthesis, Spectroscopic Properties and Applications in Two-photon Fluorescence Microscopic Imaging[J]. J Mater Chem,2007,17(28):2921-2929.
[17]	Liu Z J,Chen T,Liu B,Huang Z L,et al.Two-photon Absorption of a Series of V-shape Molecules:The Influence of Acceptor's Strength on Two-photon Absorption in a Noncentrosymmetric D-π-A-π-D System[J]. J Mater Chem,2007,17(44): 4685-4689.
[18]	JING Yinzhi,ZHOU Jun,LIANG Dawei,et al.Synthesis and Biological Activities of 4,6-Diary l-2-Aminopyrimidine Derivatives[J]. Chinese J Appl Chem,2011,28(2):209-213(in Chinese). 江银枝,周俊,梁大伟,等. 4,6- 二芳基-2- 氨基嘧啶类衍生物的合成与生物活性[J]. 应用化学,2011,28(2):209-213.
[19]	Hillesheim P C,Mahurin S M,Fulvio P F,et al.A New Class of Bipyrimidine Based Octupolar Chromophores:Synthesis, Fluorescent and Quadratic Nonlinear Optical Properties[J]. Chem Rev,2012,51(11):530-537.
[20]	Klingele J,Dechert S,Meyer F. Polynuclear Transition Metal Complexes of Metal/metal-bridging Compartmental Pyrazolate Ligands[J]. Coord Chem Rev,2009,253(21):2698-2741.
[21]	Viciano-Chumillas M, Tanase S,de Jongh L J, et al. Coordination Versatilityof Pyrazole-based Ligands Towards High-nuclearity Transition-metal and Rareearth Clusters[J]. Eur J Inorg Chem,2010,41(44):3403-3418.
[22]	Kruidenier L,Chung C W,Cheng Z J,et al.A Selective Jumonji H3K27 Demethylase Inhibitor Modulates the Proinflammatory Macrophage Response[J]. Nature,2012,488(7411):404-408.
[23]	Liu B,Hu X L,Liu J,et al.Synthesis and Photophysical Properties of Novel Pyrimidine-based Two-photon Absorption Chromophores[J]. Tetrahedron Lett,2007,48(34):5958-5962.
[24]	YANG Tingting,GUO Zhiqian,SHAO Andong,et al.A Turn-On Fluorescent Probe for Cysteine Based on Benzopyran[J]. Chinese J Appl Chem,2016,33(4):397-405(in Chinese). 杨婷婷,郭志前,邵安东,等. 基于苯并吡喃腈的激活型半胱氨酸荧光探针[J]. 应用化学,2016,33(4):397-405.
[25]	Bilbrey J A,Sontag S K,Huddleston N E,et al.On the Role of Disproportionation Energy in Kumada Catalyst-Transfer Polycondensation[J]. ACS Macro Lett,2012,1(8):995-1000.
[26]	Shi Q Q,Chen W Q,Xiang J F,et al.A Low-Bandgap Conjugated Polymer Based on Squaraine with Strong Two-Photon Absorption[J]. Macromolecules,2011,44(10):3759-3765.
[27]	Yu Z P,Duan Y Y,Cheng L H,et al.Aggregation Induced Emission in the Rotatable Molecules:The Essential Role of Molecular Interaction[J]. J Mater Chem,2012,22:16927-16932.
[28]	Hu R R,Maldonado J L,Rodriguez M,et al.Luminogenic Materials Constructed from Tetraphenylethene Building Blocks:Synthesis, Aggregation-induced Emission, Two-photon Absorption, Light Refraction, and Explosive Detection[J]. J Mater Chem,2012,22:232-240.
[29]	Gao Y H,Wu J Y,Li Y M,et al.A Sulfur-Terminal Zn(Ⅱ) Complex and Its Two-Photon Microscopy Biological Imaging Application[J]. J Am Chem Soc,2009,131(14):5208-5213.
[30]	Li D M,Tian X H,Hu G J,et al.Synthesis, Crystal Structures, Photophysical Properties, and Bioimaging of Living Cells of Bis-β-Diketonate Phenothiazine Ligands and Its Cyclic Dinuclear Complexes[J]. Inorg Chem,2011,50(17):7997-8006.
[31]	Wang X C,Tian X H,Zhang Q,et al.Optimal Design for the Maximum Load of Three-Point Bending Concrete Beam Based on the Analyzing of Critical Crack-Mouth Opening Displacement[J]. J Chem Mater,2012,24(193/194):954-957.
[32]	Kim J Y,Kim D,Kang S Y,et al.Bioorganic & Medicinal[J]. Chem Lett,2010,256(20):6439-6442.
[33]	Li L,Zhang C W,Chen G Y,et al.A Sensitive Two-photon Probe to Selectively Detect Monoamine Oxidase B Activity in Parkinson's Disease Models[J]. Nat Commun,2014,5(25):3276.

Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 10

Recommended Articles

Metrics

Comments

[1]	Jia-Mei GENG, Su-Fang MA, Wen LIU, Hai-Peng DIAO, Zhi-Fang WU, Si-Jin LI. Liver-Targeted Fluorescent Probes for Specific Detection of ONOO^- in HepG2 Cells [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 441-448.
[2]	Hui DU, Chen-Yang YAO, Hao PENG, Bo JIANG, Shun-Xiang LI, Jun-Lie YAO, Fang ZHENG, Fang YANG, Ai-Guo WU. Applications of Transition Metal⁃doped Iron⁃based Nanoparticles in Biomedicine [J]. Chinese Journal of Applied Chemistry, 2022, 39(3): 391-406.
[3]	HUANG Zike, LIU Chao, FU Qiangqiang, LI Jin, ZOU Jianmei, XIE Sitao, QIU Liping. Aptamer-based Fluorescence Probe for Bioanalysis and Bioimaging [J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 28-39.
[4]	LI Na,LI Hui. Synthesis and Antitumor Activity of Hexahydro-1H-pyrrolo [3,4-d] Pyrimidine Derivatives [J]. Chinese Journal of Applied Chemistry, 2017, 34(5): 541-549.
[5]	YAO Qianfang,CHENG Wenyu,YIN Meizhen. Host-Guest Supramolecular Fluorescent Probes Based on Macrocyclic Molecules [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1344-1354.
[6]	BU Lulu,WANG Qing,XIE Yongshu. Research Progress of Fluorescent Zinc Probes [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1355-1369.
[7]	CHEN Jianhua,LI Dongyang,LIU Shenghua,TAN Ying,YIN Jun. Recent Advances in Phosgene and Nerve Agents Responsive Fluorescent Probes [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1413-1432.
[8]	Jia ZHOU, Yun NI, Chengwu ZHANG, Xinghan QIU, Yanfei ZHAO, Lei BAI, Gaobin ZHANG, Lin LI. Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging [J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 0-0.
[9]	LI Haidong,YAO Qichao,FAN Jiangli,DU Jianjun,PENG Xiaojun. Research Advance on the Fluorescent Probe of Palladium Ions [J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1099-1114.
[10]	WANG Haitao, WANG Hongyan, YANG Liangru , MAO Pu, QU Lingbo. Process Optimization of 4-Hydroxyl-2-(methylsulfanyl)-pyrimidine-5-carboxylic Acid Ethyl Ester Synthesis [J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 412-415.