荧光试剂9-氨基类吖啶衍生物的合成、表征及应用
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摘要
优化合成了三种潜在的抗肿瘤试剂9，9′-乙二胺二吖啶(A_1)、9，9′-丙二胺二吖啶(A_2)和9，9′-三乙烯四胺二吖啶(A_3)；合成了三种新化合物9-苯二胺基吖啶，分别为：9-(2-氨基苯胺基)吖啶(B_1)、9-(3-氨基苯胺基)吖啶(B_2)、9-(4-氨基苯胺基)吖啶(B_3)；两种已知化合物：9-β-羟基乙胺基吖啶(C_1)、9-氨基吖啶(C_2)。通过IR、~1HNMR和元素分析等证实了各化合物的结构。也尝试合成了9-羧甲胺基吖啶(C_3)、9-二乙醇胺吖啶(C_4)和9-三乙醇胺吖啶(C_5)，对结果进行了分析、讨论。另外，采用微波辐射简便快捷的合成了9-甲基吖啶，优化了经典的Bernthsen方法。
9-(2-氨基苯胺基)吖啶(B_1，简称o-APAA)在硫酸介质中，与铬(Ⅵ)作用，产生荧光增敏，建立了测定痕量铬(Ⅵ)的荧光分析法。该方法准确、灵敏、操作简便。o-APAA与牛血清白蛋白(BSA)作用产生荧光增敏，通过实验表明，该方法用于BSA的测定灵敏度高、选择性好。对9-(3-氨基苯胺基)吖啶(B_2，简称m-APAA)与脱氧核糖核酸(DNA)作用的荧光光谱进行了研究，拟定了测定DNA的分析方法，探讨了反应机理，实验了最佳条件、干扰实验。表明该方法简便、快速、灵敏度高。
A novel synthetic method of 9,9' -ethyldiaminodiacridine(AI), 9,9' -propyldiaminodiacridine(A2) and 9,9' -triethylenetraaminodiacridine(A3 ) as potential antitumor was reported; three new reagents: 9-(2-aminoanili o)acridine(B1), 9-(3-aminoanilino)acridine(B2), 9-(4-aminoanilino)acridine (B3), have been synthesized ; and two known compounds: 9- -hydroxyl ethylaminoacridine(Ci), 9-aminoacridine(C2), have also been synthesized. IR, 'HNMR and elemental analysis have characterized compounds. We tried to synthesize 9-carboxymethylaminoacridine(C3), 9-diethanolamino acridine(C4) and 9-triethanolaminoacridine(C5), to discuss and analyze the results. Besides, 9-methylacridine was synthesized by microwave radiation; this method was simple and convenient.
The fluorescent enhancement of 9-(2-aminoanilino)acridine(Bi, o-APAA) by Chromium(VI) in the sulfuric acid medium was studied, so a method of fluoremetry for the determination of trace Chromium(VI) was established. A fluorescence enhancing method based on the studies of interaction of o-APAA and Bovine serum albumin(BSA) for the determination of BSA was studied, the result indicated that this method had the advantages of high sensitivity, good selectivity and simplicity. The fluorescence spectra of 9-(3-aminoanilino)acridine(B2,m-APAA) with Deoxyribonucleic acid(DNA) has been studied, so a fluorescent method for the determination of DNA was established; this method had the advantages of high sensitivity, good selectivity and simplicity.
9-(2-氨基苯胺基)吖啶(B_1，简称o-APAA)在硫酸介质中，与铬(Ⅵ)作用，产生荧光增敏，建立了测定痕量铬(Ⅵ)的荧光分析法。该方法准确、灵敏、操作简便。o-APAA与牛血清白蛋白(BSA)作用产生荧光增敏，通过实验表明，该方法用于BSA的测定灵敏度高、选择性好。对9-(3-氨基苯胺基)吖啶(B_2，简称m-APAA)与脱氧核糖核酸(DNA)作用的荧光光谱进行了研究，拟定了测定DNA的分析方法，探讨了反应机理，实验了最佳条件、干扰实验。表明该方法简便、快速、灵敏度高。
A novel synthetic method of 9,9' -ethyldiaminodiacridine(AI), 9,9' -propyldiaminodiacridine(A2) and 9,9' -triethylenetraaminodiacridine(A3 ) as potential antitumor was reported; three new reagents: 9-(2-aminoanili o)acridine(B1), 9-(3-aminoanilino)acridine(B2), 9-(4-aminoanilino)acridine (B3), have been synthesized ; and two known compounds: 9- -hydroxyl ethylaminoacridine(Ci), 9-aminoacridine(C2), have also been synthesized. IR, 'HNMR and elemental analysis have characterized compounds. We tried to synthesize 9-carboxymethylaminoacridine(C3), 9-diethanolamino acridine(C4) and 9-triethanolaminoacridine(C5), to discuss and analyze the results. Besides, 9-methylacridine was synthesized by microwave radiation; this method was simple and convenient.
The fluorescent enhancement of 9-(2-aminoanilino)acridine(Bi, o-APAA) by Chromium(VI) in the sulfuric acid medium was studied, so a method of fluoremetry for the determination of trace Chromium(VI) was established. A fluorescence enhancing method based on the studies of interaction of o-APAA and Bovine serum albumin(BSA) for the determination of BSA was studied, the result indicated that this method had the advantages of high sensitivity, good selectivity and simplicity. The fluorescence spectra of 9-(3-aminoanilino)acridine(B2,m-APAA) with Deoxyribonucleic acid(DNA) has been studied, so a fluorescent method for the determination of DNA was established; this method had the advantages of high sensitivity, good selectivity and simplicity.
引文
[1]高鸿．分析化学前沿[M]．北京：科学出版社，1990
[2]石影．有机试剂概论[M]．徐州：中国矿业大学出版社，2000
[3]方瑞斌，徐其亨．有机荧光光度试剂的进展．化学试剂1986，8，278
[4]四柳隆夫．用液晶毛细管色谱柱快速分离蒽、菲和咔唑的混合物。分析化学，1984，12，397
[5]袁有宪．金属络合物高效液相色谱-光度分析进展．分析化学，1990，18，87
[6]Hoshino H.,Yotsuyanaki T.. Selective determination of trace lever chromium(Ⅲ) by ion-pare reversed-phase high-performance liquid chromatography based on color formation with 4-(2-pyridylazo) resorcinol in the presence of trithanolamine. Anal. Chem., 1985,57,625
[7]Zhang Xiaosong, Zhu Xiangping, Lin Changshan. Determination of molybdenum, chromium and vanadium by ion-part high-pressure liquid chromatography based on precolumn chelation with 4-(2-pyridylazo) resorcinol. Talanta 1986,33,838
[8]Hangland R.P..Handbook of flourescent probes and reseach chemuals, sixth edition, molecular probes. Inc., Eugene. OR. 1996. 484
[9]陈国珍，黄贤智，许金均，郑朱桦，王尊本．荧光分析法(第二版)[M]．北京：科学出版社，1990，1
[10]Ci Y.X., Li Y.Z.,Liu X.J.. Selective determination of DNA by its enhancement effect on the fluorescence of the Eu~(3+)-tetracycline complex. Anal. Chem., 1997,67,1785
[11]Haugland R. P.. Handbook of fluorescent probes and researth chemicals, sixth edition, molecular probes, Inc. Eugene, CR, 1996,144
[12]Bunth of C.J., Vandenbraak s., Breeuwer P., et al.. Rapid fluorescence assessment of the viability of stressed lactococcus lactis. Applied and Environ. Microbio., 1999,65,3681
[13]丛涛，赵霖．国外医学-临床生物化学与检验学手册．1996，17，32
[14]Morgny J.L., Boutorine A.S., Garestier T.,et al.. Fluorescence energy transfer as a probe for nucleic acid structures and sequences. Nucleic Acids Res., 1994,22,920
[15]靳兰，杨频，李青山．荧光法研究手性金属配合物与DNA的作用机理．高等学校化学学报，1996，17，1345
[16]Li N., Li K. A.,Tong S. Y.. Anal. Biochem., 1996,233,151
[17]Legendre B. L.,Soper S. A.. Applied Spectroscopy, 1996,50,1196
[18]Chen S.,Guillory R. J.. Indentification of the NADH-NAD~+ transhydrogenase peptide of the mitochondrial NADH-CoQ deductase. J. Bio. Chem., 1984,259,5124
[19]杨曼曼，杨频，张立伟．荧光法研究咖啡类药物与白蛋白的作用．科学通报，1994，39，31
[20]董润安，张复实，宋心琦．水溶性四磺酸锌酞菁与牛血清白蛋白结合反应的研究．科学通报，1996，41，1001
[21]北京医学院微生物教研组．实验免疫学[M]．北京：人民卫生出版社，1980，198
[22]Xu Y. Y., Hemmila I. A.,Lovgren T. N. E.. Simultaneous quadruple-label fluoremtric immunoassay of thyiod-stimulating hormone,hydroxyprogesterone, immunoreactive trypsin, and creatine kinase MM isoenzyme in dried blood spots.Analyst, 1992,117,1061
[23]Lopez E., Chypre C.,Alpha B.,et al.. Europium(Ⅲ)tribipyridine cryptata label for time-resolved fluorescence detection of polymerase chain reaction products fixed on a solid support. Clin Chem., 1993,39,1953
[24]Guo X. Q., Castellano F. N., Li L., Labowicz J. R.. Use of a long-lifetime Re(Ⅰ) amplex in fluorescence polarization immunoassays of high-mole cular-weight analytes. Anal. Chem., 1998,70,632
[25]Haugland R. P.. Handbook of fluorescent probes and research chemicals, sixthe edition, moleular probes, Ine., Eugene, OR. 1996,484
[26]Bruchez J.M., Morone M., Gin P., et al.. Sci., 1998,25,2013
[27]王继贵．临床生化检验(第二版)[M]．湖南：湖南科学技术出版社，1996，91
[28]Jin M.L., Masaaki Y.. Chemilumine scent reaction of fluorescent organic compounds with KHSO_5 using cobalt(Ⅱ) as catalyst and its first aplication to mole cular imprinting. Analytical Chemistry, 2000, 72(6): 1148
[29]徐继明，吴斌才．8-氨基喹啉新衍生物的合成及其与铜的荧光反应研究．冶金分析，1999，19(5)：10
[30]吴芳英，黄坚铎，嵇志琴，文翔．新试剂7-(2，4-二羟基-5-羧基苯偶氮)-8-羟基喹啉-5-磺酸与铝的荧光反应性能的研究．分析试验室，1999，18(2)：62
[31]Luster J.,Lioyd T.,Sposito G., et al.. Multi-wavelength molecular fluorescence spectrometry for quantitative characterization of copper(Ⅱ) and aluminum(Ⅲ) complexation by dissolved organic matter. Emironmetal Science of Technology, 1996,30(5):1565
[32]Markku T. M.. Application of NMR spectroscopy to environmental analysis: detection of trace amounts of chemical warfare agents and related compounds in organic extract, water, and sand. Emironmental science & Technology, 1997,31(2):518
[33]Patrick W.A.,Peter M.G.,. James H.I.,et al.. Single molecular fluorescence spectroscopy at ambient temperature. Chem. Rev., 1999,99,2929
[34]Ashor K. K.. Kevin A. B., Ashok K. K. Synthesis, optical absorption, fluorescence quantum efficiency, and electrical conductivity studies of pyridine/pyridinium Dialkynyl organic and pt(Ⅱ)-σ-Acetylide monomers and polymers. Macromeleules, 1996,29(8):2885
[35]Kimber M.C.,Mahadevan I.B.,Lincoln S.F.,et al.. The synthesis and fluorescent properties of analogues of the Zinc(Ⅱ) specific fluorophore zinquin ester. J.Org. Chem.,2000,65 (24):8204-8209
[36]徐其亨，李祖碧，徐幼虹．光度分析．分析实验室，1997，16(4)：88
[37]郑洪，李东辉，吴敏，陈秋影，许金钩．合成的近红外花菁染料测定痕量血清蛋白质．高等学校化学学报，1999，20(4)：555
[38]Qiu-Ying Chem, Dong-Hui Li, Qing-Zhi zhu, Hong Zheng, Jin-Gon Xu. Anal. Chim. Acta, 1999,381,175
[39]林清志，王德雨．1-羟基-4-(对甲苯胺基)蒽醌(HPTA)光度法测定铜合金中微量硼．冶金分析，1998，18(4)：55
[40]崔万苍，史慧明．8-羟基喹啉-5-磺酸-溴化十六烷基三甲铵荧光法测定微量钪的研究．分析化学，1983，11(10)：778
[41]Wilson R.L,Ingle J.D.. Resign and operation of a fluorometric reaction rate instrument. Anal. Chim.Acta, 1977,92(2): 47
[42]于水，王毅．7-碘-8-羟基喹啉-5-磺酸金属络合物荧光特性及其应用．分析化学，1997，25(3)：305
[43]Ito T.,Murata A.. Spectrofluorimetric determination of hafnium with 3-hydroxychromone. Anal. Chim. Acta, 1981,125(1):155
[44]Taketatsu T.,Sato A.. Solvent extraction-spectrophotometric determination of uranium(Ⅵ) with 2, 2'-dihydroxy azobenzene and trioctymethyl ammonium chloride. Anal.Chim. Acta, 1979,108(1):429
[45]慈云祥，宁民柱，阳芳英．铽—乙酰丙酮螯合物的荧光—铽的荧光光度测定分析化学，1981，9(6)：647
[46]马文元，杨景和，葛红梅．荧光光度法同时测定铽、镝和钐．理化检验-化学分册，1997，33(6)：260
[47]Sanz-Medel A.,Gomis D.B.,Alvarez J.R.G.. Ion-pair extraction and fluorcmetric determination of potassium with 18-crown-6 and eosin. Talanta, 1981,28(7):425
[48]Kina K.,Shiraishi K., Ishibashi N.. Ultramicro solvent extraction and fhcorimentry based on the flaw-injection method. Talanta, 1978,25(5):295
[49]Bernthsen A.,Justus L..Ann. Chem., 1878,191,1
[50]Acheson M.,Orgel L. K.. "The Chemistry of Heterocyclic Compounds: The Acridines", Interscience. New York, 1956,362-389
[51] Albert A.. Scientific method in the evolution of new drugs. J.Exp.Pathol., 1942,23,69
[52] David S.B., Robert S.Y., Howard G. W. et al.. Synthesis of acalogs having various aliphatic a-substituents in the side chain. J. Am. Chem., Soc., 1944,66,1922
[53] Burkhatter J.H.,tendick F.H.,Jones E.M.,et al.. Aminoalkylphenols as antimalarials Ⅱ. (Heterocyclic-amino)-a-amino-o-cresols: The synthesis of camoquin. J.Am.Chem.Soc.,1948,70,1363
[54] Samarin A.S.,Vereiskaya T.A.. Synthesis and investigation of certain substituted phenoxyacridines. Perm Politekh, 1965,18,148-150(Russ)
[55] Methta V.K.,Patel S.R.J.India Chem.Soc., 1966,43,235
[56] Dean A.C.R.. Antibacterial action of acridines. Chem.Heterocyel Compounds, 1973,9,789-813
[57] Mishra V.K.,Bahel S.C.. Synthesis of thiazolyl compounds as potential fungicides. J.Indian chem..Soc., 1984,61(10) :9160-918
[58] Ferguson L.R.,Macphee D.G.. Frameshift mutagenesis by acridines in wild-type. uvrB and polA strains of salmonella typhimurium with and without plasmid pKM101． Mutat.Res.,1984,141(2) :83-88
[59] SarkarB.R.,Pathak B.,Dey B.D.,et al.. Synthesis of some substituted anthraquinone and acridine derivatives and their antiamebic activities. J.Indian Chem.Soc.,1984,61(7) :611-613
[60] Demondiaux P.,Laayoun A.,Demeunynck M.,et al.. Synthesis of N-acridinyl and N-quinoliny derivatives of radioprotective amino-thiols. Tetrahedron, 1989,45,6455
[61] Denny W.A.,Turner P.M.,Atwell G.J.. Structure-activity relationship for the mutagehic activity of tricyclic intercalating agents in salmoneua typhimurium. Mutat.Res.,1990,232(2) :233-241
[62] El-Badry O.M.. Synthesis of 3-chloro-7-methoxy-9-substituted acridine derivatives as potential antimicrobial agents. Alexandria J.Pharm.Sci.,1992,6(1) :11-14
[63] Figgitt D.,Denny W.,Chavalit S.P.. Invirto study of anticancer a cridines as potential antitry panosomal and antimollarial agents. Antimicrob.Agents Chemother, 1992,36(8) :1644-1647
[64] Cremieux A.,Chevalier J.. Antimicrobial acticity of 9-ono and 9-thioacridines: Correlation with intercalation into DNA and effects on macromolecular biosynthesis. Res.Microbiol.,1995,146(1) :73-83
[65] Bastianelli C.,Caia N.,Cum G.. Thermal isomerization of photochemically synthesized (z)-9-styrylacridines. An unusually high enthalpy of Z-E conversion for stibene-like compounds. J.Chem.Soc.,Perkin Trans.,1991,679-683
[66] 谢克勤，许建刚，肿瘤化学治疗药物的研究--9-肼(？)啶衍生物的合成，药 学学报，1984,19(6) : 466-470
[67] Jaycox D., Gribble G. W., Hacker. . Potential DNA bis-intercalating agents:synthesis and antitumor activity of novel, conformationacly restricted bis(9-aminoacrdines). J. Heterocycl Chem., 1987,24,1405
[68] Ebeid M. Y, Aly S. M, Eissa A. H.. Synthesis and antitumor potential of isosteres of acridine antineoplastic agents . Egypt J. Pharm. Sci.,1990,31(1-4) :427-436
[69] Dzierzbica K.,Kolodziejczyk A.,Wysocka S. B.. Selectioe synthesis of some acridine muramyl dipetides as potential antitumor agents. Pol.J.Chem.,1991,65(12) :2293-2294
[70] Safwat H. M., El-said M. K., Ragab F. A.,et al.. Synthesis and cytotonic activity of certain new acridine derivatives structurally related to amsacrine. Egypt J.Pharm.Sci.,1992,33(1-2) :253-265
[71] Su tsann-Long, Chou Ting-Chao. 9-substitubed acridine derioatives with long half-life and potent antitumor activity: Synthesis and stnuture-activity relationships. J.Med.Chem.,1995,38(17) :3226-3235
[72] Grenshow J. M., Graves D. E.. Interactions of acridine antitumor agents with DNA: Binding energies and groove preference. Biochemistry, 1995,34(41) :13682-13687
[73] Gamage S. A., Spicer J. A.. A new synthesis of substituted acridine-4-carbonylic acids and the anticanncer drug N-[2-(dimethylamino)-ethyl] acridine-4-carboxamide (DACA). Tetrahedron Lett., 1997,38(4) :399-702
[74] Gimenez A. E., Missoilidis S. . Antitumor polycyclic acridines. Part 4: physicochemical studies on the interactions between DNA and novel tetracyclic acridine derivatives. Anti-Cancer Drug Des., 1998,13(5) :431-451
[75] Haldane A., Finlay G. J.. Celluar uptake of N-[2-(dimethyl amino) ethly]-acridine-4-carbonamine(DACA). Anti-Cancer Drug Des., 1999,14(3) :275-280
[76] 张秀平，时惠麟，颜闵，血吸虫病化学治疗的研究β-(9-(？)啶)丙烯酸及酰胺 类衍生物的合成，医药工业, 1984, (3) : 8-11
[77] Dodigne C.. Chemiluminescence as a diagnostic tool. A reuiew. Talanta 2000, 51,415-459
[78] Littig J. S., Nieman T. Quantiation of acridinium esters using electrogenrated Chemiluminescence and flow injection. Anal. Chem., 1992,64(10) : 1140-1144
[79] Batmanghelich S.,Brown R.C.,Woodhead J.S.,et al.. Preparation of a chemiluminescent imidoester for the non-radio active labelling of proteins. Photochem. Photobiol.B, 1992,12(2) : 193-201
[80] Ruberto M.A.,Grayeski M. L.. Acridinium Chemiluminescence detection with capillary electrophoresis. Anal.Chem.,1992,64(22) :2758-2762
[81] Sliwa W.. The reactivity of acridinium salts and related compounds. Heterocycles 1994,38(4) :897-922
[82] Bostock-smith C. E., Gimenez-Arnau E.. Molecular recognition between a new pentacyclic acridinium satt and DNA sequences investigated by optical spectros copic techniques, proton nuclear magnetic resonance spectroscopy, and molecular modeling. Biochemistry, 1999,38(21) :6723-6731
[83] Achgson R. M, Birtwistle D. H., wyatt P. B.. Synthesis of some 10-phenylacridinium salts and related compounds. J. Chem. Synop., 1986(9) :316
[84] Luo Shineng, Xi Yuefen, Jin jian. Synthesis of a new chemiluminescent immunoassay reagent 4-(2-aminoethyl) phenyl-10-methyl acridinium-9-carboxylate bromide (AEP-MAC). Huaxue Shiji, 1992,14(5) :274-276
[85] Adamczyk M., Chem Y.Y., Maltingly P. G.. Neopentyl 3-triflyonypropane sulfonate A reactive sulfopropylation reagents for the preparation of chemiluminescent labds. J.Org.Chem.,1998,63(16) :5636-5639
[86] Adamczyk M., Chen Y. Y. Modulation of the chemiluminescent signal from N10-(3-sulfopropyl)-N-sulfonly acridinium-9-carboxamides. Tetrahedron, 1999, 55(36) : 10899-10914
[87] Adamczyk M., Mattingly P. G., Moore J. A.. Synthesis of a chemilunescent Acridinium bydroxylamine(AHA) for the direct detection of abastic sites in DNA. Orgt Lett.,1999,1(5) :779-781
[88] 庄惠生，王琼娥，陈国南等，化学发光免疫分析试剂(？)啶酯的合成路线，高等 学校化学学报, 1998, 19(12) : 1933-1936
[89] Balbi A., Sottofattori E.. Synthesis and complementary complen formation properties of oligonucleotides covalently linked to new stabilizing agent. Tetrahedron, 1994,50(13) :4009-4018
[90] tadayuki U., Nobuyasu S.. Hemin binding to DNA with bis-dentate acridine intercalator. Chem. Pharm. Bull., 1994,42(4) :988-990
[91] Tsuneo K., Kazuaki A.. A sensitive fluorometric assay of glutathione reductase activity with N-(9-acridinyl) maleimide. Anal.Sci., 1993,9(6) :867-870
[92] Palmer B.D., Leeh. H., Johnson P.. DNA-directed alkylating agents. 3． Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain. J. Med. Chem.,1990,33(11) :3008-3014
[93] Buchardt O., Eghdm M., Karup G.,NielsenP.E.. 9-(4-Nitrobenzamidopoty methylene) aminoacridines and their photochemical cleavage of DNA. J.Chem.Soc.Chem.Coomun., 1987,22,1696-1697
[94] Li Weimin, Liang Xinqin, Chu Jie, Li Yun. Study on indirect photometric high-performance liquid chromatography of aliphatic al cohols and acids with acridine as the detection reagent. Yaoxue Tongbao,1986,21(5) :270-271
[95] Ferguson L. R., Denny W. A.. The genetic toxicology of acridines. Mutat. Res., 1991,258(2) : 123-160
[96] E1-Badry Ossama M.. Synthesis of 3-Chloro-7-metnony-9-substituted acridine derivatives as potential antimicrobial agents. Alenandria J. Pharm. Sci., 1992,6(1) :11-14
[97] Kimura M.. Acridine derivatives. V. Synthesis and P388 antitumor activity of novel 9-anilino-2． 3-ethylene dioxyacridines. J. Heterocycl. Chem.,
1993,30(4) : 1101-1104
[98] El-Hamouly W. S.. Synthesis of some substituted 9-anilinoacridines and 4-anilinoquinolines with possible antitumor activity. Egypt J. Chem., 1995,3 8(4) :393-402
[99] Cain B. R, Atwell G. J.. Experimental antitumor properties of three congeners of the acridylmethanesulfonanilide(AMSA) series. Eur, J. Cancer, 1974,10,539
[100] Kelly P., Philip O. L., Martin R. F.,et aLInt.J.Pept. Prot. Res., 1985,26,400
[101] Baguely B.C., Holdaway K.M., Fray L. M. Design of DNA intercalators to overcome topoisomerase H-mediated multidrug vesistane. J. Natl. Cancer Inst., 1990,82,1398
[102] Theodorakis E. A., Xiang X., Blom P.. Photochemical cleavage of duplex DNA by N-benzoyloxy-2-thiopyridone linked to 9-aminoacridine. Chem. Commun., 1997,1463
[103] Scarcely M.,Clean S.M., Madden B., Wakelin L.P.G.. Bleomycin minics Design and synthesis of an acridine derivative which cleaves DNA in a sequence-neutral manner. J. Chem. Soc., Perkin Trans., 2, 1997,523-532
[104] rung C. H., wei A., Leibowitz M. J., et al.. An acridine ammo acid derivative for use in Fmoc peptide synthesis. Acad. Sci. USA, 1992,28,7114
[105] Acheson R. M.."Acridines", Ind ed., Wiley, New Your 1973,109
[106] Isaev S. G., Drogovoz S. M., Shulga I. S., et al.. Bioactive nitro derivatives of acridine. Farmzh(Keiv), 1990,2,41-44
[107] Gourdie T.A.,Prakash A.S.,Wakelin L.P.G.. Synthesis and evaluation of DNA-targeted spatially separated bis(aniline mustards) as potential alkytating agents with enhaced DNA cross-linking capability. J.Med.Chem.,1991,34(1) :240-248
[108] Chaganava N.T.,Buyanov V.N.,Ershova Y.A.. Synthesis and antitu mor properties of some N-sulfamyl-5-aminoindolines and 9-indolinylaminoacridines. Khim-Farm-zh., 1991,25(8) :41-43
[109] Belmont P.,Remeunynck M.. Synthesis and study of a new adenine-acridine tanclem, inhibitor of exonuclease Ⅲ. Bioorg. Med. Chem. Len., 2000,10(3) :293-295
[110] Abdellatif F., Martine D.. A new class of artificial nucleases that recognize and cleave aparinic sites in DNA with great selectivity and efficiency. J. Am. Chem. Soc, 1993,115,22,9952-9959
[111] Sarah R.K.,NathanW.L.,Yitzhak T. Designed signaling aptamers that transduce molecular recognition to changes in fluorescence intensity. J. Am. Chem. Soc., 2000,122,980-981
[112] Johannes R.,Gumaherath G.M.,Kanal B.. Acetylene chemistry. Part 29． A convenient synthesis of 9-(N-alkynly) acridinamines via a nucleophilic displacement reaction between 9-chloracridine and N-alkynylamines. J.Heterocycl.,Chem., 1993,30(6) :1677-1678
[113] Takenaka S., Ivoamasa K.. Synthesis of a 9-acridinly nonapeptide containing the
DNA recognizing region of 434 phage represser protein. J. Heterocycl. Chem., 1996,33(6) :2043-2046
[114] Fkyerat A.,Demeunynck M.,Constant I.F.,et al.. Synthesis of purine-acridine hybrid molecules related to artificial endonucleases. Tetrahedron, 1993,49(48) :11237-11251
[115] Kimara M., Kato A., Okabayashi I.. Acridine derivatives Ⅳ. Synthesis, molecular structive, and antitumor activity of the novel 9-anilino-2． 3-methylene-dionyacridines. J. Heterocycl. Chem., 1992,29,73-80
[116] Drozdov N.S., Chemtzov M. O..J.Gen.Chem.,1935,5,1576
[117] Ledochowski A., Skonieczony S.. New interpretation of the mechanism of nucleophilic substitubion in 9-phenoxyacridine in phenol. Roczniki Chem., 1973,47(9) : 1577
[118] Peck R. M.. J. Med. Chem., 1968,11,315
[119] Baguley B. C.. Baguley B.C., Nash R. Antitumor activity of substitated 9-anilinoacridines comparison of in vivo and invitro testing systems. Ibid, 1981,24,170
[120] Furlong N. B., Sato J., Brown t, et al.. Induction of limited DNA damage by the antitumor agent cain's avridine. Cancer Res., 1978,38,1329
[121] Legha S.S.,Gutterman J.U.,Hall S.W.,et al.. Surface. Immunoglobulins and protease inhibitors of human acute leukemia blasts. Cancer Res., 1978,38,3712
[122] Can B.F., Baguley B.C., Denny W.A.. Potential antitumor agents, 28． Deoxyribonu cleic acid polyintercalating agents. Ibid, 1978,18,1110
[123] 张葆(？)，肿瘤化学治疗药物的研究胺基(？)啶类化合物的合成，药学学报， 1980, 15, 40
[124] Courseille P. C., Busetta B., Hospital M.. 7-chloro-4-(4-diahylamino-l-rnethybutyl amino) quinoline. Crystal and mdeeular structural of quinacrine. Acta Cryst., 1973,629,2349
[125] Sakore T. D.,Reddy B.S.,Sobdl H.M.. Visualization of drug-nucleic acid interactions at atomic resolation. IV. Stnuture of an aminocecrine 1 dinucleoside monophosphate crystalline comples. 9-amino acridine: 5-iodocytid-ylyl(3'-5') guanosine. J. Mol. Biol.,1979,135,763
[126] Peddy B.S.,Seshadri T.P.,Sakore T.D.,et al.. Visualization of drug-nucleic acid interactions at atomic resolution. V. Structure of two amino acridine/ dinucleoside monophosphate crystalline complexes, proflavine: 5-iodocytidylyl-(3'-5') gguanosine and acridine oronge: 5-iodocytidylyl (3'-5') quanosine. J.Mol.Biol., 1979,135,787
[127] Constant J.F.,Carden B.M.,Lhomme J.. Synthetic models related to DNA intercalating molecules: preparation of 9-aminoacridines linked to the nucleotide Bases Adenine, Guanine and Thymine. J.Heterocycl.Chem., 1985,22,1035
[128]Bhattacharya S.,Thomas M.. DNA binding properties of some cationic acridine derivatioes. J.Indina Chem. Soc., 1998,75,716-724
[129]张孙玮，汤福隆，张秦等．现代化学试剂手册[M]．第二分册．北京：北京化学工业出版社
[130]樊能廷．有机合成事典[M]，北京：北京理工大学出版社，1992，857
[131]Robert C. E.. Hetercyclic Compounds[M]. Volume 4, 1852,511
[132]Hall D.M.,Tumer E.E.. Structre and antimalarial activity part 1. some acridine derivatives. J.Chem. Soc.,1945,694-699
[133]Luigi M.S.,Giuseppe A.,Raffuello R.,et al.. Synthesis, absorption spectra, and luminescence properties of platinum(Ⅱ) complexes with aminoquinoline and aminoacridine ligands. Inorg. Chem., 1992,31,2074-2078
[134]Wesley I.S.,Daniel P.B.,Stephen J.L.. Synthesis, characterization, and biological activity of cis-diammineplatinum(Ⅱ) complexes of the DNA intercalators 9-aminoacridine and chloroquine. J.Am. Chem. Soc.,1990,112(4): 1590-1596
[135]Dupre D.J.,Robinsoc EA.. N-Substituted 5-aminoacridines. J.Chem. Soc., 1945,549-551
[136]张正行．有机光谱分析[M]．北京：人民卫生出版社，1996，139
[137]洪山海．光谱解析在有机化学中的应用[M]．北京：科学出版社，1980
[138]Santanu B.,Mini T.. DNA binding properties of some cationic acridine derivatives. J.Indian Chem. Soc., 1998,75,716-724
[139]花文廷．杂环化合物[M]．北京：北京大学出版社，1990，373
[140]Watter S.,Trahanovsky S.L.. A novel flash vaccum pyrolysis route to acridine. Synthesis, 1996,9:1085-1086
[141]Frank D.P.. J.Org. Chem., Polyphosphoric acid in bernthen reaction. 1962,27:2658-2659
[142]邵明望，张文敏．微波化学与工程[M]．合肥：安徽大学出版社，1999，46-112
[143]Jie Nianqin,Zhang Qiang,Yang Jinghe,et al.. Retermination of cbromium in waste-water and cast iron samples by fluorescence quenching of rhodamine 6 G. Talanta, 1998,46(1):215-219
[144]冯素玲，唐安娜，樊静．荧光分析法测定痕量铬(Ⅵ)．分析化学，2001，29(5)：558-560
[145]杨睿，刘绍璞．某些分子光谱分析法测定蛋白质的进展．分析化学，2001，29(2)：232-241
[146]Ma Chunqi,Li Kean,Tong Shenyang. Determination of proteins by flucrescence quecehing of erythrosing. Anal. Acta, 1996,333:83
[147]覃文武，包永军，龚国权等．茜素红S荧光熄灭法测定蛋白质．分析化学，2000，28，526
[148]魏晓芳，刘会洲．Trinton X—100与牛血清白蛋白的相互作用。分析化学，2000，28，699-701
[149]卢继新，张贵珠，王月梅．金属离子存在下5-氟尿嘧啶与脱氧核糖核酸、血清白蛋白的相互作用．分析化学，2001，29，192-194
[150]刘绍璞，龙秀芬．某些分子光谱分析法测定核酸的进展．理化检验(化学分册)，2002，38(2)：101-107
[151]Li Wenyou,Xu Jingou,Guo Xiangqun. Anal.Lett., 1997,30(2):245
[152]Kumar C.V.,Asuncion E.H.. Sequence dependent energy transfer from DNA to, a simple aromatic cbromophere. J.Chem. Soc. Chem. Commun.,1992,6,470
[153]Kumar C.V.,Turner R.S.,Asuncion E.H.. Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect. J.Photochem. Photobiol. A: Chem., 1993,74,231
[154]Pasternack R.F.,Brigandi R.A.,Abrams M.J.,et al.. Interactions of porphyrins and metalloporphyrins with single-stranded poly(dA). Inorg. Chem., 1990,29,4483
[2]石影．有机试剂概论[M]．徐州：中国矿业大学出版社，2000
[3]方瑞斌，徐其亨．有机荧光光度试剂的进展．化学试剂1986，8，278
[4]四柳隆夫．用液晶毛细管色谱柱快速分离蒽、菲和咔唑的混合物。分析化学，1984，12，397
[5]袁有宪．金属络合物高效液相色谱-光度分析进展．分析化学，1990，18，87
[6]Hoshino H.,Yotsuyanaki T.. Selective determination of trace lever chromium(Ⅲ) by ion-pare reversed-phase high-performance liquid chromatography based on color formation with 4-(2-pyridylazo) resorcinol in the presence of trithanolamine. Anal. Chem., 1985,57,625
[7]Zhang Xiaosong, Zhu Xiangping, Lin Changshan. Determination of molybdenum, chromium and vanadium by ion-part high-pressure liquid chromatography based on precolumn chelation with 4-(2-pyridylazo) resorcinol. Talanta 1986,33,838
[8]Hangland R.P..Handbook of flourescent probes and reseach chemuals, sixth edition, molecular probes. Inc., Eugene. OR. 1996. 484
[9]陈国珍，黄贤智，许金均，郑朱桦，王尊本．荧光分析法(第二版)[M]．北京：科学出版社，1990，1
[10]Ci Y.X., Li Y.Z.,Liu X.J.. Selective determination of DNA by its enhancement effect on the fluorescence of the Eu~(3+)-tetracycline complex. Anal. Chem., 1997,67,1785
[11]Haugland R. P.. Handbook of fluorescent probes and researth chemicals, sixth edition, molecular probes, Inc. Eugene, CR, 1996,144
[12]Bunth of C.J., Vandenbraak s., Breeuwer P., et al.. Rapid fluorescence assessment of the viability of stressed lactococcus lactis. Applied and Environ. Microbio., 1999,65,3681
[13]丛涛，赵霖．国外医学-临床生物化学与检验学手册．1996，17，32
[14]Morgny J.L., Boutorine A.S., Garestier T.,et al.. Fluorescence energy transfer as a probe for nucleic acid structures and sequences. Nucleic Acids Res., 1994,22,920
[15]靳兰，杨频，李青山．荧光法研究手性金属配合物与DNA的作用机理．高等学校化学学报，1996，17，1345
[16]Li N., Li K. A.,Tong S. Y.. Anal. Biochem., 1996,233,151
[17]Legendre B. L.,Soper S. A.. Applied Spectroscopy, 1996,50,1196
[18]Chen S.,Guillory R. J.. Indentification of the NADH-NAD~+ transhydrogenase peptide of the mitochondrial NADH-CoQ deductase. J. Bio. Chem., 1984,259,5124
[19]杨曼曼，杨频，张立伟．荧光法研究咖啡类药物与白蛋白的作用．科学通报，1994，39，31
[20]董润安，张复实，宋心琦．水溶性四磺酸锌酞菁与牛血清白蛋白结合反应的研究．科学通报，1996，41，1001
[21]北京医学院微生物教研组．实验免疫学[M]．北京：人民卫生出版社，1980，198
[22]Xu Y. Y., Hemmila I. A.,Lovgren T. N. E.. Simultaneous quadruple-label fluoremtric immunoassay of thyiod-stimulating hormone,hydroxyprogesterone, immunoreactive trypsin, and creatine kinase MM isoenzyme in dried blood spots.Analyst, 1992,117,1061
[23]Lopez E., Chypre C.,Alpha B.,et al.. Europium(Ⅲ)tribipyridine cryptata label for time-resolved fluorescence detection of polymerase chain reaction products fixed on a solid support. Clin Chem., 1993,39,1953
[24]Guo X. Q., Castellano F. N., Li L., Labowicz J. R.. Use of a long-lifetime Re(Ⅰ) amplex in fluorescence polarization immunoassays of high-mole cular-weight analytes. Anal. Chem., 1998,70,632
[25]Haugland R. P.. Handbook of fluorescent probes and research chemicals, sixthe edition, moleular probes, Ine., Eugene, OR. 1996,484
[26]Bruchez J.M., Morone M., Gin P., et al.. Sci., 1998,25,2013
[27]王继贵．临床生化检验(第二版)[M]．湖南：湖南科学技术出版社，1996，91
[28]Jin M.L., Masaaki Y.. Chemilumine scent reaction of fluorescent organic compounds with KHSO_5 using cobalt(Ⅱ) as catalyst and its first aplication to mole cular imprinting. Analytical Chemistry, 2000, 72(6): 1148
[29]徐继明，吴斌才．8-氨基喹啉新衍生物的合成及其与铜的荧光反应研究．冶金分析，1999，19(5)：10
[30]吴芳英，黄坚铎，嵇志琴，文翔．新试剂7-(2，4-二羟基-5-羧基苯偶氮)-8-羟基喹啉-5-磺酸与铝的荧光反应性能的研究．分析试验室，1999，18(2)：62
[31]Luster J.,Lioyd T.,Sposito G., et al.. Multi-wavelength molecular fluorescence spectrometry for quantitative characterization of copper(Ⅱ) and aluminum(Ⅲ) complexation by dissolved organic matter. Emironmetal Science of Technology, 1996,30(5):1565
[32]Markku T. M.. Application of NMR spectroscopy to environmental analysis: detection of trace amounts of chemical warfare agents and related compounds in organic extract, water, and sand. Emironmental science & Technology, 1997,31(2):518
[33]Patrick W.A.,Peter M.G.,. James H.I.,et al.. Single molecular fluorescence spectroscopy at ambient temperature. Chem. Rev., 1999,99,2929
[34]Ashor K. K.. Kevin A. B., Ashok K. K. Synthesis, optical absorption, fluorescence quantum efficiency, and electrical conductivity studies of pyridine/pyridinium Dialkynyl organic and pt(Ⅱ)-σ-Acetylide monomers and polymers. Macromeleules, 1996,29(8):2885
[35]Kimber M.C.,Mahadevan I.B.,Lincoln S.F.,et al.. The synthesis and fluorescent properties of analogues of the Zinc(Ⅱ) specific fluorophore zinquin ester. J.Org. Chem.,2000,65 (24):8204-8209
[36]徐其亨，李祖碧，徐幼虹．光度分析．分析实验室，1997，16(4)：88
[37]郑洪，李东辉，吴敏，陈秋影，许金钩．合成的近红外花菁染料测定痕量血清蛋白质．高等学校化学学报，1999，20(4)：555
[38]Qiu-Ying Chem, Dong-Hui Li, Qing-Zhi zhu, Hong Zheng, Jin-Gon Xu. Anal. Chim. Acta, 1999,381,175
[39]林清志，王德雨．1-羟基-4-(对甲苯胺基)蒽醌(HPTA)光度法测定铜合金中微量硼．冶金分析，1998，18(4)：55
[40]崔万苍，史慧明．8-羟基喹啉-5-磺酸-溴化十六烷基三甲铵荧光法测定微量钪的研究．分析化学，1983，11(10)：778
[41]Wilson R.L,Ingle J.D.. Resign and operation of a fluorometric reaction rate instrument. Anal. Chim.Acta, 1977,92(2): 47
[42]于水，王毅．7-碘-8-羟基喹啉-5-磺酸金属络合物荧光特性及其应用．分析化学，1997，25(3)：305
[43]Ito T.,Murata A.. Spectrofluorimetric determination of hafnium with 3-hydroxychromone. Anal. Chim. Acta, 1981,125(1):155
[44]Taketatsu T.,Sato A.. Solvent extraction-spectrophotometric determination of uranium(Ⅵ) with 2, 2'-dihydroxy azobenzene and trioctymethyl ammonium chloride. Anal.Chim. Acta, 1979,108(1):429
[45]慈云祥，宁民柱，阳芳英．铽—乙酰丙酮螯合物的荧光—铽的荧光光度测定分析化学，1981，9(6)：647
[46]马文元，杨景和，葛红梅．荧光光度法同时测定铽、镝和钐．理化检验-化学分册，1997，33(6)：260
[47]Sanz-Medel A.,Gomis D.B.,Alvarez J.R.G.. Ion-pair extraction and fluorcmetric determination of potassium with 18-crown-6 and eosin. Talanta, 1981,28(7):425
[48]Kina K.,Shiraishi K., Ishibashi N.. Ultramicro solvent extraction and fhcorimentry based on the flaw-injection method. Talanta, 1978,25(5):295
[49]Bernthsen A.,Justus L..Ann. Chem., 1878,191,1
[50]Acheson M.,Orgel L. K.. "The Chemistry of Heterocyclic Compounds: The Acridines", Interscience. New York, 1956,362-389
[51] Albert A.. Scientific method in the evolution of new drugs. J.Exp.Pathol., 1942,23,69
[52] David S.B., Robert S.Y., Howard G. W. et al.. Synthesis of acalogs having various aliphatic a-substituents in the side chain. J. Am. Chem., Soc., 1944,66,1922
[53] Burkhatter J.H.,tendick F.H.,Jones E.M.,et al.. Aminoalkylphenols as antimalarials Ⅱ. (Heterocyclic-amino)-a-amino-o-cresols: The synthesis of camoquin. J.Am.Chem.Soc.,1948,70,1363
[54] Samarin A.S.,Vereiskaya T.A.. Synthesis and investigation of certain substituted phenoxyacridines. Perm Politekh, 1965,18,148-150(Russ)
[55] Methta V.K.,Patel S.R.J.India Chem.Soc., 1966,43,235
[56] Dean A.C.R.. Antibacterial action of acridines. Chem.Heterocyel Compounds, 1973,9,789-813
[57] Mishra V.K.,Bahel S.C.. Synthesis of thiazolyl compounds as potential fungicides. J.Indian chem..Soc., 1984,61(10) :9160-918
[58] Ferguson L.R.,Macphee D.G.. Frameshift mutagenesis by acridines in wild-type. uvrB and polA strains of salmonella typhimurium with and without plasmid pKM101． Mutat.Res.,1984,141(2) :83-88
[59] SarkarB.R.,Pathak B.,Dey B.D.,et al.. Synthesis of some substituted anthraquinone and acridine derivatives and their antiamebic activities. J.Indian Chem.Soc.,1984,61(7) :611-613
[60] Demondiaux P.,Laayoun A.,Demeunynck M.,et al.. Synthesis of N-acridinyl and N-quinoliny derivatives of radioprotective amino-thiols. Tetrahedron, 1989,45,6455
[61] Denny W.A.,Turner P.M.,Atwell G.J.. Structure-activity relationship for the mutagehic activity of tricyclic intercalating agents in salmoneua typhimurium. Mutat.Res.,1990,232(2) :233-241
[62] El-Badry O.M.. Synthesis of 3-chloro-7-methoxy-9-substituted acridine derivatives as potential antimicrobial agents. Alexandria J.Pharm.Sci.,1992,6(1) :11-14
[63] Figgitt D.,Denny W.,Chavalit S.P.. Invirto study of anticancer a cridines as potential antitry panosomal and antimollarial agents. Antimicrob.Agents Chemother, 1992,36(8) :1644-1647
[64] Cremieux A.,Chevalier J.. Antimicrobial acticity of 9-ono and 9-thioacridines: Correlation with intercalation into DNA and effects on macromolecular biosynthesis. Res.Microbiol.,1995,146(1) :73-83
[65] Bastianelli C.,Caia N.,Cum G.. Thermal isomerization of photochemically synthesized (z)-9-styrylacridines. An unusually high enthalpy of Z-E conversion for stibene-like compounds. J.Chem.Soc.,Perkin Trans.,1991,679-683
[66] 谢克勤，许建刚，肿瘤化学治疗药物的研究--9-肼(？)啶衍生物的合成，药 学学报，1984,19(6) : 466-470
[67] Jaycox D., Gribble G. W., Hacker. . Potential DNA bis-intercalating agents:synthesis and antitumor activity of novel, conformationacly restricted bis(9-aminoacrdines). J. Heterocycl Chem., 1987,24,1405
[68] Ebeid M. Y, Aly S. M, Eissa A. H.. Synthesis and antitumor potential of isosteres of acridine antineoplastic agents . Egypt J. Pharm. Sci.,1990,31(1-4) :427-436
[69] Dzierzbica K.,Kolodziejczyk A.,Wysocka S. B.. Selectioe synthesis of some acridine muramyl dipetides as potential antitumor agents. Pol.J.Chem.,1991,65(12) :2293-2294
[70] Safwat H. M., El-said M. K., Ragab F. A.,et al.. Synthesis and cytotonic activity of certain new acridine derivatives structurally related to amsacrine. Egypt J.Pharm.Sci.,1992,33(1-2) :253-265
[71] Su tsann-Long, Chou Ting-Chao. 9-substitubed acridine derioatives with long half-life and potent antitumor activity: Synthesis and stnuture-activity relationships. J.Med.Chem.,1995,38(17) :3226-3235
[72] Grenshow J. M., Graves D. E.. Interactions of acridine antitumor agents with DNA: Binding energies and groove preference. Biochemistry, 1995,34(41) :13682-13687
[73] Gamage S. A., Spicer J. A.. A new synthesis of substituted acridine-4-carbonylic acids and the anticanncer drug N-[2-(dimethylamino)-ethyl] acridine-4-carboxamide (DACA). Tetrahedron Lett., 1997,38(4) :399-702
[74] Gimenez A. E., Missoilidis S. . Antitumor polycyclic acridines. Part 4: physicochemical studies on the interactions between DNA and novel tetracyclic acridine derivatives. Anti-Cancer Drug Des., 1998,13(5) :431-451
[75] Haldane A., Finlay G. J.. Celluar uptake of N-[2-(dimethyl amino) ethly]-acridine-4-carbonamine(DACA). Anti-Cancer Drug Des., 1999,14(3) :275-280
[76] 张秀平，时惠麟，颜闵，血吸虫病化学治疗的研究β-(9-(？)啶)丙烯酸及酰胺 类衍生物的合成，医药工业, 1984, (3) : 8-11
[77] Dodigne C.. Chemiluminescence as a diagnostic tool. A reuiew. Talanta 2000, 51,415-459
[78] Littig J. S., Nieman T. Quantiation of acridinium esters using electrogenrated Chemiluminescence and flow injection. Anal. Chem., 1992,64(10) : 1140-1144
[79] Batmanghelich S.,Brown R.C.,Woodhead J.S.,et al.. Preparation of a chemiluminescent imidoester for the non-radio active labelling of proteins. Photochem. Photobiol.B, 1992,12(2) : 193-201
[80] Ruberto M.A.,Grayeski M. L.. Acridinium Chemiluminescence detection with capillary electrophoresis. Anal.Chem.,1992,64(22) :2758-2762
[81] Sliwa W.. The reactivity of acridinium salts and related compounds. Heterocycles 1994,38(4) :897-922
[82] Bostock-smith C. E., Gimenez-Arnau E.. Molecular recognition between a new pentacyclic acridinium satt and DNA sequences investigated by optical spectros copic techniques, proton nuclear magnetic resonance spectroscopy, and molecular modeling. Biochemistry, 1999,38(21) :6723-6731
[83] Achgson R. M, Birtwistle D. H., wyatt P. B.. Synthesis of some 10-phenylacridinium salts and related compounds. J. Chem. Synop., 1986(9) :316
[84] Luo Shineng, Xi Yuefen, Jin jian. Synthesis of a new chemiluminescent immunoassay reagent 4-(2-aminoethyl) phenyl-10-methyl acridinium-9-carboxylate bromide (AEP-MAC). Huaxue Shiji, 1992,14(5) :274-276
[85] Adamczyk M., Chem Y.Y., Maltingly P. G.. Neopentyl 3-triflyonypropane sulfonate A reactive sulfopropylation reagents for the preparation of chemiluminescent labds. J.Org.Chem.,1998,63(16) :5636-5639
[86] Adamczyk M., Chen Y. Y. Modulation of the chemiluminescent signal from N10-(3-sulfopropyl)-N-sulfonly acridinium-9-carboxamides. Tetrahedron, 1999, 55(36) : 10899-10914
[87] Adamczyk M., Mattingly P. G., Moore J. A.. Synthesis of a chemilunescent Acridinium bydroxylamine(AHA) for the direct detection of abastic sites in DNA. Orgt Lett.,1999,1(5) :779-781
[88] 庄惠生，王琼娥，陈国南等，化学发光免疫分析试剂(？)啶酯的合成路线，高等 学校化学学报, 1998, 19(12) : 1933-1936
[89] Balbi A., Sottofattori E.. Synthesis and complementary complen formation properties of oligonucleotides covalently linked to new stabilizing agent. Tetrahedron, 1994,50(13) :4009-4018
[90] tadayuki U., Nobuyasu S.. Hemin binding to DNA with bis-dentate acridine intercalator. Chem. Pharm. Bull., 1994,42(4) :988-990
[91] Tsuneo K., Kazuaki A.. A sensitive fluorometric assay of glutathione reductase activity with N-(9-acridinyl) maleimide. Anal.Sci., 1993,9(6) :867-870
[92] Palmer B.D., Leeh. H., Johnson P.. DNA-directed alkylating agents. 3． Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain. J. Med. Chem.,1990,33(11) :3008-3014
[93] Buchardt O., Eghdm M., Karup G.,NielsenP.E.. 9-(4-Nitrobenzamidopoty methylene) aminoacridines and their photochemical cleavage of DNA. J.Chem.Soc.Chem.Coomun., 1987,22,1696-1697
[94] Li Weimin, Liang Xinqin, Chu Jie, Li Yun. Study on indirect photometric high-performance liquid chromatography of aliphatic al cohols and acids with acridine as the detection reagent. Yaoxue Tongbao,1986,21(5) :270-271
[95] Ferguson L. R., Denny W. A.. The genetic toxicology of acridines. Mutat. Res., 1991,258(2) : 123-160
[96] E1-Badry Ossama M.. Synthesis of 3-Chloro-7-metnony-9-substituted acridine derivatives as potential antimicrobial agents. Alenandria J. Pharm. Sci., 1992,6(1) :11-14
[97] Kimura M.. Acridine derivatives. V. Synthesis and P388 antitumor activity of novel 9-anilino-2． 3-ethylene dioxyacridines. J. Heterocycl. Chem.,
1993,30(4) : 1101-1104
[98] El-Hamouly W. S.. Synthesis of some substituted 9-anilinoacridines and 4-anilinoquinolines with possible antitumor activity. Egypt J. Chem., 1995,3 8(4) :393-402
[99] Cain B. R, Atwell G. J.. Experimental antitumor properties of three congeners of the acridylmethanesulfonanilide(AMSA) series. Eur, J. Cancer, 1974,10,539
[100] Kelly P., Philip O. L., Martin R. F.,et aLInt.J.Pept. Prot. Res., 1985,26,400
[101] Baguely B.C., Holdaway K.M., Fray L. M. Design of DNA intercalators to overcome topoisomerase H-mediated multidrug vesistane. J. Natl. Cancer Inst., 1990,82,1398
[102] Theodorakis E. A., Xiang X., Blom P.. Photochemical cleavage of duplex DNA by N-benzoyloxy-2-thiopyridone linked to 9-aminoacridine. Chem. Commun., 1997,1463
[103] Scarcely M.,Clean S.M., Madden B., Wakelin L.P.G.. Bleomycin minics Design and synthesis of an acridine derivative which cleaves DNA in a sequence-neutral manner. J. Chem. Soc., Perkin Trans., 2, 1997,523-532
[104] rung C. H., wei A., Leibowitz M. J., et al.. An acridine ammo acid derivative for use in Fmoc peptide synthesis. Acad. Sci. USA, 1992,28,7114
[105] Acheson R. M.."Acridines", Ind ed., Wiley, New Your 1973,109
[106] Isaev S. G., Drogovoz S. M., Shulga I. S., et al.. Bioactive nitro derivatives of acridine. Farmzh(Keiv), 1990,2,41-44
[107] Gourdie T.A.,Prakash A.S.,Wakelin L.P.G.. Synthesis and evaluation of DNA-targeted spatially separated bis(aniline mustards) as potential alkytating agents with enhaced DNA cross-linking capability. J.Med.Chem.,1991,34(1) :240-248
[108] Chaganava N.T.,Buyanov V.N.,Ershova Y.A.. Synthesis and antitu mor properties of some N-sulfamyl-5-aminoindolines and 9-indolinylaminoacridines. Khim-Farm-zh., 1991,25(8) :41-43
[109] Belmont P.,Remeunynck M.. Synthesis and study of a new adenine-acridine tanclem, inhibitor of exonuclease Ⅲ. Bioorg. Med. Chem. Len., 2000,10(3) :293-295
[110] Abdellatif F., Martine D.. A new class of artificial nucleases that recognize and cleave aparinic sites in DNA with great selectivity and efficiency. J. Am. Chem. Soc, 1993,115,22,9952-9959
[111] Sarah R.K.,NathanW.L.,Yitzhak T. Designed signaling aptamers that transduce molecular recognition to changes in fluorescence intensity. J. Am. Chem. Soc., 2000,122,980-981
[112] Johannes R.,Gumaherath G.M.,Kanal B.. Acetylene chemistry. Part 29． A convenient synthesis of 9-(N-alkynly) acridinamines via a nucleophilic displacement reaction between 9-chloracridine and N-alkynylamines. J.Heterocycl.,Chem., 1993,30(6) :1677-1678
[113] Takenaka S., Ivoamasa K.. Synthesis of a 9-acridinly nonapeptide containing the
DNA recognizing region of 434 phage represser protein. J. Heterocycl. Chem., 1996,33(6) :2043-2046
[114] Fkyerat A.,Demeunynck M.,Constant I.F.,et al.. Synthesis of purine-acridine hybrid molecules related to artificial endonucleases. Tetrahedron, 1993,49(48) :11237-11251
[115] Kimara M., Kato A., Okabayashi I.. Acridine derivatives Ⅳ. Synthesis, molecular structive, and antitumor activity of the novel 9-anilino-2． 3-methylene-dionyacridines. J. Heterocycl. Chem., 1992,29,73-80
[116] Drozdov N.S., Chemtzov M. O..J.Gen.Chem.,1935,5,1576
[117] Ledochowski A., Skonieczony S.. New interpretation of the mechanism of nucleophilic substitubion in 9-phenoxyacridine in phenol. Roczniki Chem., 1973,47(9) : 1577
[118] Peck R. M.. J. Med. Chem., 1968,11,315
[119] Baguley B. C.. Baguley B.C., Nash R. Antitumor activity of substitated 9-anilinoacridines comparison of in vivo and invitro testing systems. Ibid, 1981,24,170
[120] Furlong N. B., Sato J., Brown t, et al.. Induction of limited DNA damage by the antitumor agent cain's avridine. Cancer Res., 1978,38,1329
[121] Legha S.S.,Gutterman J.U.,Hall S.W.,et al.. Surface. Immunoglobulins and protease inhibitors of human acute leukemia blasts. Cancer Res., 1978,38,3712
[122] Can B.F., Baguley B.C., Denny W.A.. Potential antitumor agents, 28． Deoxyribonu cleic acid polyintercalating agents. Ibid, 1978,18,1110
[123] 张葆(？)，肿瘤化学治疗药物的研究胺基(？)啶类化合物的合成，药学学报， 1980, 15, 40
[124] Courseille P. C., Busetta B., Hospital M.. 7-chloro-4-(4-diahylamino-l-rnethybutyl amino) quinoline. Crystal and mdeeular structural of quinacrine. Acta Cryst., 1973,629,2349
[125] Sakore T. D.,Reddy B.S.,Sobdl H.M.. Visualization of drug-nucleic acid interactions at atomic resolation. IV. Stnuture of an aminocecrine 1 dinucleoside monophosphate crystalline comples. 9-amino acridine: 5-iodocytid-ylyl(3'-5') guanosine. J. Mol. Biol.,1979,135,763
[126] Peddy B.S.,Seshadri T.P.,Sakore T.D.,et al.. Visualization of drug-nucleic acid interactions at atomic resolution. V. Structure of two amino acridine/ dinucleoside monophosphate crystalline complexes, proflavine: 5-iodocytidylyl-(3'-5') gguanosine and acridine oronge: 5-iodocytidylyl (3'-5') quanosine. J.Mol.Biol., 1979,135,787
[127] Constant J.F.,Carden B.M.,Lhomme J.. Synthetic models related to DNA intercalating molecules: preparation of 9-aminoacridines linked to the nucleotide Bases Adenine, Guanine and Thymine. J.Heterocycl.Chem., 1985,22,1035
[128]Bhattacharya S.,Thomas M.. DNA binding properties of some cationic acridine derivatioes. J.Indina Chem. Soc., 1998,75,716-724
[129]张孙玮，汤福隆，张秦等．现代化学试剂手册[M]．第二分册．北京：北京化学工业出版社
[130]樊能廷．有机合成事典[M]，北京：北京理工大学出版社，1992，857
[131]Robert C. E.. Hetercyclic Compounds[M]. Volume 4, 1852,511
[132]Hall D.M.,Tumer E.E.. Structre and antimalarial activity part 1. some acridine derivatives. J.Chem. Soc.,1945,694-699
[133]Luigi M.S.,Giuseppe A.,Raffuello R.,et al.. Synthesis, absorption spectra, and luminescence properties of platinum(Ⅱ) complexes with aminoquinoline and aminoacridine ligands. Inorg. Chem., 1992,31,2074-2078
[134]Wesley I.S.,Daniel P.B.,Stephen J.L.. Synthesis, characterization, and biological activity of cis-diammineplatinum(Ⅱ) complexes of the DNA intercalators 9-aminoacridine and chloroquine. J.Am. Chem. Soc.,1990,112(4): 1590-1596
[135]Dupre D.J.,Robinsoc EA.. N-Substituted 5-aminoacridines. J.Chem. Soc., 1945,549-551
[136]张正行．有机光谱分析[M]．北京：人民卫生出版社，1996，139
[137]洪山海．光谱解析在有机化学中的应用[M]．北京：科学出版社，1980
[138]Santanu B.,Mini T.. DNA binding properties of some cationic acridine derivatives. J.Indian Chem. Soc., 1998,75,716-724
[139]花文廷．杂环化合物[M]．北京：北京大学出版社，1990，373
[140]Watter S.,Trahanovsky S.L.. A novel flash vaccum pyrolysis route to acridine. Synthesis, 1996,9:1085-1086
[141]Frank D.P.. J.Org. Chem., Polyphosphoric acid in bernthen reaction. 1962,27:2658-2659
[142]邵明望，张文敏．微波化学与工程[M]．合肥：安徽大学出版社，1999，46-112
[143]Jie Nianqin,Zhang Qiang,Yang Jinghe,et al.. Retermination of cbromium in waste-water and cast iron samples by fluorescence quenching of rhodamine 6 G. Talanta, 1998,46(1):215-219
[144]冯素玲，唐安娜，樊静．荧光分析法测定痕量铬(Ⅵ)．分析化学，2001，29(5)：558-560
[145]杨睿，刘绍璞．某些分子光谱分析法测定蛋白质的进展．分析化学，2001，29(2)：232-241
[146]Ma Chunqi,Li Kean,Tong Shenyang. Determination of proteins by flucrescence quecehing of erythrosing. Anal. Acta, 1996,333:83
[147]覃文武，包永军，龚国权等．茜素红S荧光熄灭法测定蛋白质．分析化学，2000，28，526
[148]魏晓芳，刘会洲．Trinton X—100与牛血清白蛋白的相互作用。分析化学，2000，28，699-701
[149]卢继新，张贵珠，王月梅．金属离子存在下5-氟尿嘧啶与脱氧核糖核酸、血清白蛋白的相互作用．分析化学，2001，29，192-194
[150]刘绍璞，龙秀芬．某些分子光谱分析法测定核酸的进展．理化检验(化学分册)，2002，38(2)：101-107
[151]Li Wenyou,Xu Jingou,Guo Xiangqun. Anal.Lett., 1997,30(2):245
[152]Kumar C.V.,Asuncion E.H.. Sequence dependent energy transfer from DNA to, a simple aromatic cbromophere. J.Chem. Soc. Chem. Commun.,1992,6,470
[153]Kumar C.V.,Turner R.S.,Asuncion E.H.. Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect. J.Photochem. Photobiol. A: Chem., 1993,74,231
[154]Pasternack R.F.,Brigandi R.A.,Abrams M.J.,et al.. Interactions of porphyrins and metalloporphyrins with single-stranded poly(dA). Inorg. Chem., 1990,29,4483
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