水溶性聚噻吩衍生物的合成、表征及细胞成像
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摘要
采用FeCl_3氧化聚合制备了一种新型的水溶性聚噻吩衍生物:N,N,N-三甲基-2-(2-{2-[2-(3-噻吩)乙氧基]乙氧基}乙氧基)乙铵溴化物与(4-{[2-(2-{2-[2-(3-噻吩)乙氧基]乙氧基}乙氧基)乙基]氨基甲酰基}苯基)硼酸的无规共聚物(简称PT-2).在水溶液中对其紫外/可见吸收光谱以及荧光发射光谱进行了表征,其最大吸收波长为419 nm,最大发射波长为579 nm,摩尔吸光系数为4. 6×10~3L/(mol·cm),荧光量子产率为12%.动态光散射实验表明其在水溶液中所形成的聚集体平均粒径为234 nm. PT-2在100 W汞灯照射下表现出较好的光稳定性. 3-(4,5-二甲基噻唑-2)-2,5-二苯基四氮唑溴盐(MTT)实验证明,其对人肺癌A549细胞的毒性较低,细胞成像及共定位分析结果表明PT-2能够富集在溶酶体中,因此,在溶酶体特异性的细胞成像方面具有潜在的应用价值.
A new polythiophene derivative,random copolymer of N,N,N-trimethyl-2-(2-{ 2-[2-(thiophen-3-yl) ethoxy]ethoxy } ethoxy) ethanaminium bromide and(4-{ [2-(2-{ 2-[2-(thiophen-3-yl) ethoxy]ethoxy }ethoxy) ethyl]carbamoyl} phenyl) boronic acid,abbreviated as PT-2,was synthesized through FeCl3 oxidative polymerization reaction. Its optical properties and applications in cellular imaging were investigated. The UV-Vis absorption and fluorescence emission spectra were measured in water solution, the absorption maximum is 419 nm,emission maximum is 579 nm,molar absorption coefficient is 4. 6×10~3 L/(mol·cm),fluorescence quantum yield is 12%. Dynamic light scattering test showed that the average particle size of its aggregates formed in water was about 234 nm. Under the irradiation of mercury lamp(100 W),PT-2 exhibits a satisfactory photostability. Moreover,after co-culture with human lung cancer(A549) cells for 24 h,PT-2 shows low cytotoxicity and could be enriched in the cytoplasm. It's fluorescence image could superposed well with lysosome-specific dye(Lyso Tracker Blue DND-22). Thus,PT-2 has potential application value in lysosomal-specific cell imaging.
A new polythiophene derivative,random copolymer of N,N,N-trimethyl-2-(2-{ 2-[2-(thiophen-3-yl) ethoxy]ethoxy } ethoxy) ethanaminium bromide and(4-{ [2-(2-{ 2-[2-(thiophen-3-yl) ethoxy]ethoxy }ethoxy) ethyl]carbamoyl} phenyl) boronic acid,abbreviated as PT-2,was synthesized through FeCl3 oxidative polymerization reaction. Its optical properties and applications in cellular imaging were investigated. The UV-Vis absorption and fluorescence emission spectra were measured in water solution, the absorption maximum is 419 nm,emission maximum is 579 nm,molar absorption coefficient is 4. 6×10~3 L/(mol·cm),fluorescence quantum yield is 12%. Dynamic light scattering test showed that the average particle size of its aggregates formed in water was about 234 nm. Under the irradiation of mercury lamp(100 W),PT-2 exhibits a satisfactory photostability. Moreover,after co-culture with human lung cancer(A549) cells for 24 h,PT-2 shows low cytotoxicity and could be enriched in the cytoplasm. It's fluorescence image could superposed well with lysosome-specific dye(Lyso Tracker Blue DND-22). Thus,PT-2 has potential application value in lysosomal-specific cell imaging.
引文
[1]Zhou H.X.,Yang L.Q.,You W.,Macromolecules,2011,45(2),607-632
[2]Li W.W.,Roelofs W.S.,Turbiez M.,Wienk M.M.,Janssen R.A.,Advanced Materials,2014,26(20),3304-3309
[3]Günes S.,Neugebauer H.,Sariciftci N.S.,Chemical Reviews,2007,107(4),1324-1338
[4]Qin R.P.,Song G.L.,Jiang Y.R.,Bo Z.S.,Chem.J.Chinese Universities,2012,33(4),828-832(秦瑞平,宋桂林,蒋玉荣,薄志山.高等学校化学学报,2012,33(4),828-832)
[5]Burroughes J.H.,Bradley D.D.C.,Brown A.R.,Marks R.N.,Mackay K.,Friend R.H.,Burns P.L.,Holmes A.B.,Nature,1990,347(6293),539-541
[6]Alsalhi M.S.,Alam J.,Dass L.A.,Raja M.,International Journal of Molecular Sciences,2011,12(3),2036-2054
[7]Herguth P.,Jiang X.Z.,And M.S.L.,Jen A.K.Y.,Macromolecules,2002,35(16),6094-6100
[8]Lei T.,Cao Y.,Fan Y.L.,Liu C.J.,Yuan S.C.,Pei J.,J.Am.Chem.Soc.,2011,133(16),6099-6101
[9]Lim E.,Kim Y.M.,Lee J.I.,Jung B.J.,Cho N.S.,Lee J.,Do L.M.,Shim H.K.,Journal of Polymer Science,Part A:Polymer Chemistry,2010,44(16),4709-4721
[10]Wang C.L.,Dong H.L.,Hu W.P.,Liu Y.Q.,Zhu D.B.,Chemical Reviews,2012,112(4),2208-2267
[11]Yu M.H.,Tang Y.L.,He F.,Wang S.,Zheng D.G.,Li Y.L.,Zhu D.B.,Macromolecular Rapid Communications,2010,27(20),1739-1745
[12]Xie B.H.,Bagui M.,Guo R.Y.,Li K.,Wang Q.,Peng Z.H.,Journal of Polymer Science,Part A:Polymer Chemistry,2007,45(22),5123-5135
[13]Traina C.A.,Nd B.R.,Bazan G.C.,J.Am.Chem.Soc.,2011,133(32),12600-12607
[14]Yang X.H.,Wang S.F.,Wang K.M.,Luo X.M.,Tan W.H.,Cui L.,Chem.J.Chinese Universities,2009,30(5),899-902(羊小海,王胜锋,王柯敏,罗晓明,谭蔚泓,崔亮.高等学校化学学报,2009,30(5),899-902)
[15]Zhu C.L.,Liu L.B.,Yang Q.,Lv F.T.,Wang S.,Chemical Reviews,2012,112(8),4687-4735
[16]Li J.,Yuan Y.,Zeng G.S.,Li X.,Yang Z.,Li X.Z.,Jiang R.C.,Hu W.B.,Sun P.F.,Wang Q.,Polymer Chemistry,2016,7(45),6890-6894
[17]Li S.L.,Chen T.,Wang Y.X.,Liu L.B.,Lv F.T.,Li Z.L.,Huang Y.Y.,Schanze K.S.,Wang S.,Angewandte Chemie,2017,56(43),13455-13458
[18]Wang B.,Zhu C.L.,Liu L.B.,Lv F.T.,Yang Q.,Wang S.,Polymer Chemistry,2013,4(20),5212-5215
[19]Sista P.,Ghosh K.,Martinez J.S.,Rocha R.C.,Journal of Nanoscience&Nanotechnology,2014,14(1),250-272
[20]Tang H.W.,Xing C.F.,Liu L.B.,Yang Q.,Wang S.,Small,2011,7(10),1464-1470
[21]Otsuka H.,Uchimura E.,Koshino H.,Okano T.,Kataoka K.,J.Am.Chem.Soc.,2003,125(12),3493-3502
[22]Chen X.,Varki A.,ACS Chemical Biology,2010,5(2),163-176
[23]Schauer R.,Glycoconjugate Journal,2000,17(7-9),485-499
[24]Matsumoto A.,Sato N.,Kataoka K.,Miyahara Y.,J.Am.Chem.Soc.,2009,131(34),12022-12023
[25]Wen Q.S.,Zhu C.L.,Liu L.B.,Yang Q.,Wang S.,Zhu D.B.,Macromolecular Chemistry&Physics,2012,213(23),2486-2491
[26]Liu A.P.,Peng S.,Soo J.C.,Kuang M.,Chen P.,Duan H.W.,Analytical Chemistry,2011,83(3),1124-1130
[27]Wang F.Y.,Meng L.,Bing W.,Zhang J.Y.,Cheng Y.Q.,Liu L.B.,Lv F.T.,Shu W.,Scientific Reports,2015,5,7617
[28]Wang F.Y.,Liu Z.,Wang B.,Feng L.H.,Liu L.B.,Lv F.T.,Wang Y.L.,Wang S.,Angewandte Chemie International Edition,2014,53(2),424-428
[2]Li W.W.,Roelofs W.S.,Turbiez M.,Wienk M.M.,Janssen R.A.,Advanced Materials,2014,26(20),3304-3309
[3]Günes S.,Neugebauer H.,Sariciftci N.S.,Chemical Reviews,2007,107(4),1324-1338
[4]Qin R.P.,Song G.L.,Jiang Y.R.,Bo Z.S.,Chem.J.Chinese Universities,2012,33(4),828-832(秦瑞平,宋桂林,蒋玉荣,薄志山.高等学校化学学报,2012,33(4),828-832)
[5]Burroughes J.H.,Bradley D.D.C.,Brown A.R.,Marks R.N.,Mackay K.,Friend R.H.,Burns P.L.,Holmes A.B.,Nature,1990,347(6293),539-541
[6]Alsalhi M.S.,Alam J.,Dass L.A.,Raja M.,International Journal of Molecular Sciences,2011,12(3),2036-2054
[7]Herguth P.,Jiang X.Z.,And M.S.L.,Jen A.K.Y.,Macromolecules,2002,35(16),6094-6100
[8]Lei T.,Cao Y.,Fan Y.L.,Liu C.J.,Yuan S.C.,Pei J.,J.Am.Chem.Soc.,2011,133(16),6099-6101
[9]Lim E.,Kim Y.M.,Lee J.I.,Jung B.J.,Cho N.S.,Lee J.,Do L.M.,Shim H.K.,Journal of Polymer Science,Part A:Polymer Chemistry,2010,44(16),4709-4721
[10]Wang C.L.,Dong H.L.,Hu W.P.,Liu Y.Q.,Zhu D.B.,Chemical Reviews,2012,112(4),2208-2267
[11]Yu M.H.,Tang Y.L.,He F.,Wang S.,Zheng D.G.,Li Y.L.,Zhu D.B.,Macromolecular Rapid Communications,2010,27(20),1739-1745
[12]Xie B.H.,Bagui M.,Guo R.Y.,Li K.,Wang Q.,Peng Z.H.,Journal of Polymer Science,Part A:Polymer Chemistry,2007,45(22),5123-5135
[13]Traina C.A.,Nd B.R.,Bazan G.C.,J.Am.Chem.Soc.,2011,133(32),12600-12607
[14]Yang X.H.,Wang S.F.,Wang K.M.,Luo X.M.,Tan W.H.,Cui L.,Chem.J.Chinese Universities,2009,30(5),899-902(羊小海,王胜锋,王柯敏,罗晓明,谭蔚泓,崔亮.高等学校化学学报,2009,30(5),899-902)
[15]Zhu C.L.,Liu L.B.,Yang Q.,Lv F.T.,Wang S.,Chemical Reviews,2012,112(8),4687-4735
[16]Li J.,Yuan Y.,Zeng G.S.,Li X.,Yang Z.,Li X.Z.,Jiang R.C.,Hu W.B.,Sun P.F.,Wang Q.,Polymer Chemistry,2016,7(45),6890-6894
[17]Li S.L.,Chen T.,Wang Y.X.,Liu L.B.,Lv F.T.,Li Z.L.,Huang Y.Y.,Schanze K.S.,Wang S.,Angewandte Chemie,2017,56(43),13455-13458
[18]Wang B.,Zhu C.L.,Liu L.B.,Lv F.T.,Yang Q.,Wang S.,Polymer Chemistry,2013,4(20),5212-5215
[19]Sista P.,Ghosh K.,Martinez J.S.,Rocha R.C.,Journal of Nanoscience&Nanotechnology,2014,14(1),250-272
[20]Tang H.W.,Xing C.F.,Liu L.B.,Yang Q.,Wang S.,Small,2011,7(10),1464-1470
[21]Otsuka H.,Uchimura E.,Koshino H.,Okano T.,Kataoka K.,J.Am.Chem.Soc.,2003,125(12),3493-3502
[22]Chen X.,Varki A.,ACS Chemical Biology,2010,5(2),163-176
[23]Schauer R.,Glycoconjugate Journal,2000,17(7-9),485-499
[24]Matsumoto A.,Sato N.,Kataoka K.,Miyahara Y.,J.Am.Chem.Soc.,2009,131(34),12022-12023
[25]Wen Q.S.,Zhu C.L.,Liu L.B.,Yang Q.,Wang S.,Zhu D.B.,Macromolecular Chemistry&Physics,2012,213(23),2486-2491
[26]Liu A.P.,Peng S.,Soo J.C.,Kuang M.,Chen P.,Duan H.W.,Analytical Chemistry,2011,83(3),1124-1130
[27]Wang F.Y.,Meng L.,Bing W.,Zhang J.Y.,Cheng Y.Q.,Liu L.B.,Lv F.T.,Shu W.,Scientific Reports,2015,5,7617
[28]Wang F.Y.,Liu Z.,Wang B.,Feng L.H.,Liu L.B.,Lv F.T.,Wang Y.L.,Wang S.,Angewandte Chemie International Edition,2014,53(2),424-428