点击化学法构筑新型小分子荧光探针的研究
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摘要
8-羟基喹啉是一种重要的金属离子鳌合剂，被广泛应用于构建具有高灵敏度的金属离子荧光分子探针，三唑的过渡金属配合物具有非常有趣的磁学和光学性质，点击化学提供了在温和条件下高效合成三唑类化合物的方法，本论文以8一羟基喹啉为主要构筑块，利用点击化学方法合成了1，2，3一三唑基喹啉小分子衍生物，研究了他们与金属离子的配位行为和相应的结构，探索了这类配合物作为荧光分子探针对特定离子的识别功能。取得以下一些结果：
1．利用Cu(I)催化的Huisgen 1，3一偶极环加成反应合成新型小分子cd荧光探针1a，探针1a在质子化的溶剂及水·乙腈(95：5)测试体系中的荧光吸收强度低，能克服Zn的干扰而选择性识别cd2．，测试工作的pH范围广。
2．用一锅法合成了一类小分子荧光探针2a。2d，此类探针在水-乙腈(5：95)的体系中能克服大多数碱金属、碱土金属及过度金属的干扰而对Fe有特定识别功能，其中化合物2d在水-乙腈(95：5)的体系中能选择性识别Zn~(2+)，此类探针工作的pH范围宽，对Fe的识别不受时间、温度的限制，且配位稳定、灵敏度高、响应快。
3．以8．羟基喹啉为主要的构筑块，利用一锅反应合成对维生素C有识别性的化合物4(DMF．Hepes Buffer=1：1，v／V)，绘制了定量分析的工作曲线，可能用于食品和药物中维生素C的定量分系。
8-hydroxyquinoline as an important metallic ion chelating agent，hasbeen widely applied to construct the highly sensitive metallic ionfluorescent probe．Click chemistry has provided the highly effectivesynthesis of triazole derivatives under the mild condition．In the presentpaper,we have synthesized several novel 8-hydroxyquinoline derivativesthrough“Click Chemistry'’and studied them as novel fluorescent probe．
1．A novel 1,2，3一triazolyl linked 8-hydroxyquinoline(8-HQ)dimer，as aselective turn．on fluorescent sensor for Cd was synthesized fromthe“click”reaction，and gave weaker fluorescence in protlc solventsand water—based mixture solvent(CH3CN/H20：5/95，v/v)．Thissensor showed highly selective tum-on fluorescence for CdoverZn within a broad pH range in aqueous solution rCH3CN/H20 5/95，v/v)．
2．A series of novel probes 2a．2d that exhibits good photophysicalprOperties，were synthesized and used as fluoroionophore for Fe”sensitive optochemical sensor．The sensor shows a working pHranre from 4 to 1 2 and excellent selectivity for Fe over a largenumber of cations such as alkali，alkaline earth and transitionalmetal ions．Compound 2d was also a selective“turn—on’’fluorescentsensor for zn in aqueous solution(CH3CN/H20=5/95，v/v)．
3．A probe that shows specific recognition to Vitamin C in aqueoussolution fDMF—Hepes Buffer=1：1，v/v)over a wide range of pH wasdeveloped and may be used to detect the content of Vitamin C inf00d and the medicine．
1．利用Cu(I)催化的Huisgen 1，3一偶极环加成反应合成新型小分子cd荧光探针1a，探针1a在质子化的溶剂及水·乙腈(95：5)测试体系中的荧光吸收强度低，能克服Zn的干扰而选择性识别cd2．，测试工作的pH范围广。
2．用一锅法合成了一类小分子荧光探针2a。2d，此类探针在水-乙腈(5：95)的体系中能克服大多数碱金属、碱土金属及过度金属的干扰而对Fe有特定识别功能，其中化合物2d在水-乙腈(95：5)的体系中能选择性识别Zn~(2+)，此类探针工作的pH范围宽，对Fe的识别不受时间、温度的限制，且配位稳定、灵敏度高、响应快。
3．以8．羟基喹啉为主要的构筑块，利用一锅反应合成对维生素C有识别性的化合物4(DMF．Hepes Buffer=1：1，v／V)，绘制了定量分析的工作曲线，可能用于食品和药物中维生素C的定量分系。
8-hydroxyquinoline as an important metallic ion chelating agent，hasbeen widely applied to construct the highly sensitive metallic ionfluorescent probe．Click chemistry has provided the highly effectivesynthesis of triazole derivatives under the mild condition．In the presentpaper,we have synthesized several novel 8-hydroxyquinoline derivativesthrough“Click Chemistry'’and studied them as novel fluorescent probe．
1．A novel 1,2，3一triazolyl linked 8-hydroxyquinoline(8-HQ)dimer，as aselective turn．on fluorescent sensor for Cd was synthesized fromthe“click”reaction，and gave weaker fluorescence in protlc solventsand water—based mixture solvent(CH3CN/H20：5/95，v/v)．Thissensor showed highly selective tum-on fluorescence for CdoverZn within a broad pH range in aqueous solution rCH3CN/H20 5/95，v/v)．
2．A series of novel probes 2a．2d that exhibits good photophysicalprOperties，were synthesized and used as fluoroionophore for Fe”sensitive optochemical sensor．The sensor shows a working pHranre from 4 to 1 2 and excellent selectivity for Fe over a largenumber of cations such as alkali，alkaline earth and transitionalmetal ions．Compound 2d was also a selective“turn—on’’fluorescentsensor for zn in aqueous solution(CH3CN/H20=5/95，v/v)．
3．A probe that shows specific recognition to Vitamin C in aqueoussolution fDMF—Hepes Buffer=1：1，v/v)over a wide range of pH wasdeveloped and may be used to detect the content of Vitamin C inf00d and the medicine．
引文
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[5] Kolb, H. C.; Finn, M. G..; Sharpless, K. B., Ang. Chem. Int. Ed. 2001, 40, 2004.
[6] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Ang. Chem. Int. Ed, 2002, 41, 2596-2599.
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[11] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Ang. Chem. Int .Ed. 2001, 40 (11):2004-2021.
[12]药物开发领域中的“点击化学”2005级博士生:葛广波,指导老师:杨凌研究员,2006, 05 (17), PPT.
[13]李娟等,化学通报. 2007, 19(11), 1754-1760.
[14] Lin, H.; Walsh, T. J. Am. Chem. Soc. 2004, 126, 13998-14003.
[15] Rossi, L. L.; Basu, A. Chem. Lett. 2005, 15, 3596-3599.
[16] Perez-Balderas, P.; Ortega-Munoz, M.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951-1954.
[17] (a)仇文卫等,生命科学. 2006, 18(3), 295: (b)Moses, J. E.; Moothouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262.
[18] Laurent, B. A.; Grayson, S. M.J. Am. Chem. Soc. 2006, 128, 4238-4239.
[19] Arosio, D; Bertoli, M.; Manzoni, L., et al. Tetra. Lett, 2006, 47: 3697-3700
[20] Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897-3899.
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[22] Orgueira, H. A.; Fokas, D.; Isome, Y.; Chane, P. C. M.; Baldino, C. M. Tetra. Lett. 2005, 46, 291l-1913.
[23] Sreedhar, B.; Reddy, P. S.; Kumar, N. S. Tetra. Lett. 2006, 47, 3055-3057.
[24] Beekinann, H. S. G.; Wittmann, V. Org. Lett. 2007, 9, 16-18.
[25] Kumar, D.; Reddy, V. B.; Varma, R. S. Tetr. Lett. 2009, 50, 2065.
[26] Attanasi, O. A.; Favi, G. E.; Mantellini, P. E.; Moseatelli, G.;. Perrulli, F.; R. Org. Lett. 2010, 12, 468.
[27] Landis, E. C.; Hamers, R. J. Chem. Mater. 2009, 21 (4): 724-730.
[28] Font, D.; Sayalero, S.; Bastero, A.; Jimeno, C.; Perieas, M. A.; Org. Lett., 2008, 10(2): 337-340.
[29] Zhou, C. H.; Zhang, F. F.; Gan, L. L.; Zhang, Y. Y.; Geng, R. X. Sci China Ser B-chem., 2009, 39(3): 208-252.
[30] Zhou, C. H.; Gan, L. L.; Zhang, Y. Y.; Zhang, F. F.; Geng, R. X. 2009, 52(4): 415-458.
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[34] Chauhan, R. S.; Kakkar, L. R. Chem. Anal. 1997, 42, 729-731.
[35] Zhu, R. H.; Kok, W. T. Anal. Chem. Acta, 1998, 371, 269-272.
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[53] Zhang, H.; Han, L. F.; Zachariasse, K. A.; Jiang, Y. B.Org. Lett. 2005, 7, 4217-4220.
[54] Bardez, E.; Devol, I.; Larrey, B.; Valeur, B.; J. Phys. Chem. B, 1997, 101, 7786-7793.
[55] Launay, F.; Alain, V.; Destandau, E.; Ramos, N.; Bardez, E.; Baret, P.; Pierre, J. L. New. J. Chem. 2001, 25, 1269-1280.
[56] Prodi, L.; Bolletta, F.;Montalti, M.; Zaceheroni, N.; Savage, P. B.; Bradshaw, J.; S.; Izatt, R. M.; Tetra. Lett. 1998, 39, 5451-5453.
[57] Farruggia, G.; Iotti, S.; Prodi, L.; Montalti. M.; Zaceheroni, N.; Savage, P. B.; Trapani, V.; Sale, P.; Wolf, F. I.; J. Am. Chem. Soc. 2006, 128, 344-347.
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[59] Zhang, X. X.; Bradshaw, J. S.; Bordunov, A. V.; Izatt, R. M.; J. Inet, Ph-enom.1997, 29, 259-261.
[60] Yang, Z.; Bradshaw, J. S.; Zhang, X. X.; Savage, P. B.; Krakowiak, K. E.; Dalley, N. K.; Su, N.; Bronson, R. T.; Izatt, R. M. J. Org. Chem., 19-99, 64, 3162-3165.
[61] Bordunov, A. V.; Bradshaw, J. S.; Zhang, X. X.; Dalley, K.; Kou, X.; Iz-att, R. M.; Inorg. Chem. 1996, 34, 7229-7231.
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