摘要
分析试剂的合成与应用研究是现代发光分析方法中的重要内容。本论文以自行合成的四磺基锰酞菁(Maganese-tetrasulfonatop-hthalocyanine,MnTSPc)作为新的过氧化物模拟酶,用荧光及化学发光分析法对环境样品中的过氧化氢及生物样品中的蛋白质进行了分析测定,并对MnTSPc在共振光散射(Resonance Light-Scattering,RLS)领域的应用进行了研究,建立了对生物样品中蛋白质、DNA的高灵敏分析测定新方法。
本论文的主要贡献在于:
1、将MnTSPc作为过氧化物模拟酶在化学发光分析中的应用进行了研究,此工作为国内外首次报道。
2、以邻苯二胺作为底物,建立了MnTSPc催化荧光新方法,实现了环境样品中过氧化氢的含量测定,丰富了底物的选择范围。
3、以MnTSPc为新的染料,用共振光散射法,对蛋白质、DNA进行了分析研究,扩大了RLS法的应用范围。
The development of new generation of analytical reagent used for the molecule luminescence analysis has been an attractive area in the latest decade. In this dissertation, manganese-tetrasulfonatophthalocyanine (MnTSPc) has been synthesized and used as a mimetic peroxidase to the determination of hydrogen peroxide in environment samples and proteins in biological samples based on its catalytic effect on the suitable fluorescent or chemiluminscenst systems, the results are satisfactory. Moreover, MnTSPc could interact with proteins or DNA, and result in the strong enhancing Resonance Light-Scattering signals, so a new RLS method was been established for the determination of proteins or DNA.
As mentioned above, the main contributions of this dissertation are as follows:
1 Application of MnTSPc as a new mimetic peroxidase in the chemiluminescence analysis for the first time.
2 Application of MnTSPc as a mimetic peroxidase in the determination of hydrogen peroxide with 2,3-diaminopHenazine as a substrate.
3 Application of MnTSPc as new dye in the determination of proteins or DNA using Resonance Light-Scattering method.
引文
A1 Robards K, Worsfold P.J. Anal. China. Acta, 1992, 266:147
A2 Kwakman P.J.M., Brinkman U.A.Th. Anal. Chim. Acta, 1992, 266:175
A3 Rongen H.A.H., Hoetelmans R.M.W., Bult A., et al. J. PHarm. Biomed. Anal., 1994, 12:433
A4 Anderson D.J., Guo B, Xu Y., et al. Anal. Chem., 1997, 69:165
A5 Kricka L.J., Stanley P.E.J. Biolumin. Chemilumin., 1992, 7:143
A6 Kricka L.J., Stanley P.E.J. Biolumin. Chemilumin., 1993, 8:133
A7 Kricka L.J., Stanley P.E.J. Biolumin. Chemilumin., 1994, 9:379
A8 Bronstein I, Fortin J., Stanley P.E., et al. Anal. Biochem., 1994, 219:169
A9 Wada M., Nakashima K, et al. J. Chromatogr. B: Biomed. Appl., 1996, 678:129
A10 Imai K, Gohda R, Fukushima T., et al. Biomed. Chromatogr., 1998, 11:73
A11 Wu N.A., Huie C.W.J.Chromatogr., 1993, 634:309
A12 奥西埃 EI. 生物无机化学导论,化学工业出版社出版.1987,24
A13 Tijssen P., In "Laboratory Techniques in Biochemistry and Molecular Biology", Burdon R.H. and Van Knippenberg P.H. eds, Vol 15, Practice and Theory of Enzyme Immunoassays, Elsevier, Amserdam, 1985, p173
A14 Guilbault G.G., Brignac P.J., Juneau M. Anal. Chem., 1968, 40:1256
A15 谢剑伟,鄢远,彭学军,许金钩,陈国珍.高等学校化学学报,1994,15:1770
A16 Mekler V.M. and Bystryak S.M. Anal. Chim. Acta, 1992, 264:359
A17 Thorpe G.H.G, Kricka L.J. In Methods in Enzymology, Deluca M.A, Mcelry W.D. eds., Academic Press, INC., Florid. Vol. 133:331
A18 Eremin S.A., Vlasenko S.B. et al. Anal. Lett., 1989, 22(9): 2037
A19 慈云祥,常文保,帖建科.分析化学,1992,20:1100
A20 Genfa Z., Dasgupta P.K. Anal. Chem., 1992, 64:517
A21 Akimoto K, Shinmen Y, Sumida M., et al. Anal. Biochem., 1990, 189(2): 182
A22 Ci Y.X., Tie J.K., et al. Anal. Chim. Acta., 1993, 277:67
A23 Saito Y, Mifune M, Nakashima S, Odo J, Tanaka Y, Chikuma M, Tanaka N. Anal. Sci., 1987, 3(2): 171
A24 Saito Y, Nakashima S, Mifune M, Odo J, Tanaka Y, Chikuma M, Takaka N. Anal. Chim. Acta, 1985, 172:285
A25 Wang F, Wu X.W, Shang S.S., Ci Y.X. Fresenius'J. Anal. Chem., 1992, 344:556
A26 孙淑声,吴小蔚,汪安,慈云祥.分析测试通报,1992,11(5):28
A27 孙淑声,郑智平.分析化学,1990,18(4):329
A28 孙淑声,王爱民.化学试剂,1990,12(5):259
A29 汪安,吴小蔚,孙淑声,慈云祥.北京大学学报(自然科学版),1992,28(4):399
A30 Ci Y.X., Chen L., Chang W.B. Mickrochem. J., 1992, 45:72
A31 Ci Y.X., Tie J.K., Wang Q.W., Chang W.B. Anal. Chim. Acta, 1992, 269 (1): 109
A32 沈永嘉.酞菁的合成与应用,化学工业出版社出版,2000,p121
A33 Kuder J.E.J. Imag. Sci., 1988, 32:51
A34 Kuder J.E.J. Imag. Tech., 1986, 12:140
A35 Valerian H. J. Appl. PHys., 1993, 73(9): 4370
A36 Xauer F.R. Bull. Mater. Sci., 1995, 18(3): 269
A37 Simon J. Liq. Cryst., 1993, 15(5): 709
A38 Lievre L. Liq. Cryst., 1989, 164(6): 707
A39 Milanesi C. Br. J. Cancer, 1990, 61:846
A40 Chan W.S., Marshall J.F.J. PHotochem. PHotobiol., 1987, 45:757
A41 Devlin R.F., Dandliker W.B. and Hsu. M.L., U.S. patent application, 1992, 856:176
A42 Devlin R., Studcholme R.M., Dandliker W.B., Fahy E., Blumeyer K. and Ghoch S.S., Clin. Chem., 1993, 39:1939
A43 Een J.M. and Paonay G. Anal. Chem., 1991, 63:2934
A44 Casay G.A., Narayanan N., Evans L., Czuppon T. and Patonay G., Talanta, 1996, 43:1997
A45 Li D.H., Zhu Q.Z., Ye D., Fang Y., Xu J.G. Anal. Chim. Acta., 1999, 389:85
A46 Li D. H, Yang H.H., Zheng H., Zhu Q.Z., Fang Y., Xu J.G. Anal. Chim. Acta, 1999, 401:185
A47 李东辉,彭兴跃,叶东,许金钩.荧光各向异性法研究酸度对四磺基铝酞菁与牛血清白蛋白相互作用的影响,高等学校化学学报.1999,20(8):1218
A48 Chen Q.Y., Li D.H., Zhu Q.Z., Zheng H., Xu J.G. Anal. Chim. Acta, 1999, 381:175
A49 Chen Q.Y., Li D.H., Zhu Q.Z., Zheng H., Xu J.G. Anal. Lett., 1999, 32(3): 457
A50 Ci Y.X., Chen L., Wei S. Fresenius'J. Anal. Chem., 1989, 334:36
A51 Ci Y.X., Wang F. Mikrochim. Acta, 1990, 1: 63
A52 Wang F., Wu Y.Z., Qing Y., Ci Y.X. Anal Lett., 1992, 25:1469
A53 Ci Y.X., Wang F. Talanta, 1990, 37(12): 1133
A54 Ci Y.X., Wang F, Fresenius'J. Anal. Chem., 1991, 339:46
A55 慈云祥,陈列.分析化学,1989,17(4):404
A56 Zhu Q.Z., Li Q.G., Lu J.Z., Xu J.G. Anal. Lett., 1996, 29:1729
A57 Genfa Z., Dasgupta P.K. and Sigg A. Anal. Chim. Acta, 1992, 260:57
A58 毛陆原,朱敏,黄雪梅,沈含熙,高等学校化学学报 1997, 18: 1611
A59 Murakami Y, Kikuchi J, Hisaeda Y, Hayashida O. Chem. Rev., 1996, 96: 721
A60 Kricka L.J. Chemiluminescence and Bioluminescence Analysis. In: Ency Mol Biol Mol Med., 1996 ( I ): 322
A61 Ci Y.X., He H.B., Chang W.B., et al. Anal. Chim. Acta, 1990, 237(3) : 497
A62 Ci Y.X., Tie J.K., Chang W.B. the Pittsburgh Conference on Analytical Chemistry and Applied Spectroscopy. 1993, No. 937, (Atlanta, Georgia)
A63 Ci Y.X., Zheng Y.G., et al. Anal. Chim. Acta., 1993,282 (3) : 695
A64 Ikarlyama Y, Suzzuki S, Alzawa M, Anal Chem., 1982, 57 (7) : 1126
A65 Kara T, Tsukagoshi K. Anal. Sci., 1990, 6 (1) : 797
A66 Adam Y, Bernadon J, Meunier B. New J. Chem., 1992,16 (4) : 523
A67 Karatani H. Chem. Lett., 1987, 190 (10) : 1957
A68 Yoshimura F, Suzuki T, et al. Bunseki Kagaku, 1992,41 (4) : 191
A69 Motsenbocker M, lekimori Y, Kondo K. Anal. Chem., 1993, 65 (4) : 397
A70 Miller G.A. J. PHys. Chem., 1978, 82: 616
A71 Anglister J, Steinberg I.Z. Chem. PHys. Lett., 1979, 65: 50
A72 Pasternack R.F., Bustamante C, Collings P.J. et al. J. Am. Chem. Soc., 1993, 115: 393
A73 Arena G., Scolaro L.M., Pasternack R.F. et al. Inorg. Chem., 1995, 34: 2994
A74 Huang C.Z., Li K.A., Tong S.Y. Anal. Chem., 1996, 68 (13) : 2259
A75 Huang C.Z., Li K.A., Tong S.Y. Anal. Chem., 1997, 69: 514
A76 Ma C.Q., Li K.A., Tong S.Y. Anal. Biochem., 1996, 239: 86
A77 Ma C.Q., Li K.A., Tong S.Y. Bull. Chem. Soc. Jpn, 1997, 70: 129
A78 Ma C.Q., Li K.A., Tong S.Y. Fresenius' J. Anal. Chem., 1997, 357
A79 Ma C.Q., Li K.A., Tong S.Y. Anal. Lett., 1997, 30 (4) : 739
A80 Liu S.P., Liu Q., Liu Z.F. et al. Anal. Chim. Acta, 1999, 379: 53
A81 Liu S.P., Liu Z.F, Huang C.Z. Anal. Sci., 1998,14 (4) : 799
A82 Liu S.P., Zhou G.M., Liu Z.F. Fresenius' J. Anal. Chem., 1999, 363 (7) : 651
A83 Liu S.P., Li Z.F. Spectrochim. Acta, Part A., 1995, 51: 1497
A84 Liu S.P., Liu Z.F., Zhou G.M. Anal. Lett., 1998,31 (7) : 1247
B1 Tomaoku K, Murao Y, Akiura K and Ohkura Y. Anal. Chim. Acta., 1982, 136:121
B2 Chen Qiuying, Li Donghui, Zheng Hong, Yang Huanghao, Xu Jingou. Chinese J. Anal. Chem., 1999, 27(9) : 997
B3 Gao Z, Ivaska A, Li P, Lui K, and Yang J. Anal. Chim. Acta., 1992, 259: 211
B4 Zoonan P.V., Kamminga D.A., Gooijer C., Velthorst N.H., and Frei R.W. Anal. Chim. Acta., 1985,167:249
B5 Zhu C.Q., Li D.H., Zheng H., Zhu Q.Z., Chen Q.Y., and Xu J.G. Anal. Sci., 2000,
16:253
B6 Zhu Changqin, Li Donghui, Zheng Hong, Zhu Qingzhi, and Xu Jingou. J. Xiamen University (Natural Science), 2001, 40(1): 68
B7 Weber J., Bush D.H. Inorg. Chem., 1965, 4:469
C1 Tie Jianke(帖建科), Chang Wenbao(常文保), Ci Yunxiang(慈云祥). Chinese J. Anal. Chem.(分析化学), 1994, 22:516
C2 Chen Qiuying(陈秋影), Li Donghui(李东辉), Zheng Hong(郑洪), Yang Huanghao(杨黄浩), Xu Jinggou(许金钩). Chinese J. Anal. Chem.(分析化学), 1999, 27(9): 997
C3 Li Donghui(李东辉), Yang Huanghao(杨黄浩), Zheng Hong(郑洪), Chen Bing(陈宾), Chen Qiuying(陈秋影), Xu Jinggou(许金钩). Chinese J. Anal. Chem.(分析化学), 1999, 27(9): 1018
C4 Zhu C. Q., Li D. H., Zheng H., Zhu Q. Z., Xu J. G. Anal. Sci., 2000, 16:253
C5 Weber J., Bush D. H. Inorg. Chem., 1965, 4:469
D1 Wells K, Cording J.S. Anal. Biochem., 1991, 194:237
D2 Shaopu L, Rui Y, Qin L. Anal. Sci., 2001, 17:243
D3 Soedjak H.S. Anal. Biochem., 1994, 220:142
D4 Nanqiang L, Kean L, Senyang T. Anal. Biochem., 1996, 233:151
D5 Yunxiang C, Lie Ch. Analyst, 1988, 113:679
D6 Tie J.K, Chang W.B., Ci Y.X. Anal. Chim. Acta., 1995, 300:215
D7 Tie Jianke(帖建科), Chang Wenbao(常文保), Ci Yunxiang(慈云祥). Chinese J. Anal. Chem.(分析化学), 1994, 22:516
D8 Ikariyama Y, and Suzuki S. Anal. Chem., 1982, 54:1126
D9 Hara T, Toriyama M, Kitamura K, and Imaki M. Bull. Chem. Soc. Jpn., 1985, 58:2135
D10 Zhu C.Q., Li D.H., Zheng H., Zhu Q.Z., Chen Q.Y., and Xu J.G. Anal. Sci., 2000, 16: 253
D11 Chen Q.Y., Li D.H., Zheng H., Xu J.G. Anal. Chim. Acta., 1999, 381,175
D12 Chen Qiuying(陈秋影), Li Donghui(李东辉), Zheng Hong(郑洪), Yang
Huanghao(杨黄浩), Xu Jingou(许金钩). Chinese J, Anal. Chem.(分析化学), 1999: 997
D13 Li Y.X., Zhu C.Q., Wang L., Li M. G., Gao F., Wang L, Zhu Y.W. Anal. Lett., 2001, 34:1841
D14 Hara T, Toriyama M, Miyoshi H, Syogase S. Bull. Chem. Soc. Jpn., 1984, 57:3009
D15 Weber J, Bush J.H. Inorg. Chem., 1965, 4:469
D16 Wang F, and Ci Y.X. Analyst, 1991, 116:297
D17 Ci Y.X., Tie J.K., Wang Q.W., and Chang W.B. Anal. Chim. Acta., 1992,269: 109
D18 Sugawara K, and Soejima M. "Tampakushitsu No Teiryoho", Gakkai Shuttsupan Center, Tokyo, 1977, pp, 147
D19 Karatani H. Bull. Chem. Soc. Jpn., 1987, 60: 2023
D20 Chen X.L, Li D.H., Zhu Q.Z., Yang H.H., Zheng H., Wang Z.H., Xu J.G. Talanta, 2001,53:1205
E1 Guan Zhengda(管正大). Handbook of Clinical Purpose on Medical Inspection(医 学检验临床意义手册). Beijing(北京): People's Press of Surgeon(人民军医出版 社), 1994:176-177
E2 Cao Qiuer(曹秋娥), Li Zhubi(李祖碧), Wang Jialin(王加林), Li Chonglin(李崇 宁). Chinese J. of Anal. Chem.(分析化学), 2002, 30(2) : 222-226
E3 Ci Y.X., Chen L. Analyst, 1988,113: 679
E4 Li N.Q., Li K.A., Tong S.Y. Anal. Biochem., 1996,233: 151
E5 Liu Shaopu, and Liu Qin. Anal. Sci., 2001,17: 239
E6 Li YanfangO, Huang ChengzhiO, Hu XiaoliO. Chinese J. Anal. Chem.O, 1998, 26(12) : 1508
E7 Ma ChunqiO, Liu YingO, Li KeanO, Tong ShenyangO. Chinese Sci. Bull.O, 1999, 7: 682
E8 Li Y.F., Huang C.Z., Huang X.H., Li M. Anal. Sci., 2000, 16: 1249
E9 Pastemack R.F., Collings P.J. Science, 1995,269: 935
E10 Weber J., Bush D. H. Inorg. Chem., 1965,4:469
E11 Miller G.A. J. PHys. Chem., 1978, 82: 606
E12 Tandler C.J. and Solari A.J. Commun. Biol., 1984,2: 469
E13 Li Z.P., Li K.A., Tong S.Y. Analyst, 1999,124: 907
F1 Huang C Z, Li K A, Tong S Y. Anal. Chim. Acta., 1997,345: 235-242
F2 Zhu Q Z, Yang H H, Li D H. Anal. Chim. Acta., 1999, 394 (2-3) : 177-184
F3 Huang C Z, Li K A, Tong S Y. Anal. Chem., 1996,68 (3) : 2259
F4 Huang C Z, Li K A, Tong S Y. Anal. Chem., 1997,69 (3) : 514
F5 Huang C Z, Li Y F, Liu X D. Anal. Chim. Acta., 1998, 375: 89
F6 Liu Y, Ma C Q, Li K A, Tong S Y. Anal. Chim. Acta., 1999, 379: 39
F7 Huang C Z, Li Y F, Deng S Y, et al Bull. Chem. Soc. Jpn., 1999, 72 (7) : 1501
F8 Huang C Z, Li Y F, Pu Q H, et al. Anal. Lett., 1999, 32 (1) : 2395
F9 Pastemack R F, Collings P J. Science, 1995,269: 935
F10 Liu S P, Hu X L, Luo H Q, Fan L. Science in China (Series B), 2002, 32 (1) : 18
F11 Weber J., Bush D. H. Inorg. Chem., 1965, 4: 469