Биологически активные фосфоаналоги аминокислот обмена метионина
Диссертация
В 1-аминоалкилфосфонатах 2 двухосновная фосфонатная группа Р (0)(0Н)2 значительно отличается размерами, геометрией и кислотностью от карбоксильной группы аминокислоты, что делает представления о прямом структурном подобии фосфонатов 2 аминокислотам достаточно формальными. Вместе с тем, строение фосфонатов 2 позволяет рассматривать их как стабильные аналоги лабильных переходных состояний или… Читать ещё >
Список литературы
- Kafarski P., Lejczak В. Biological activity of aminophosphonic acids, Phosphorus, Sulfur and Silicon, 1991, 63, 193 — 215.
- Хомутов P.M. О путях создания пиридоксаль-5'-фосфат зависимых каталитических антител, Биохимия, 2002, 67:1312−1316.
- Dingwall J. G. Phosphorus containing amino acids biologically active natural and unnatural products, in Proc. Ill Int. Conf. Chem. and Biotech. Biol. Active Comps. Bulgaria, Sofia, 1985, V. 1, p. 87 — 103.
- Хомутов P. M, Жуков Ю. Н., Хомутов A.P., Хурс E.H., Крамер Д. Л., Миллер Дж.Т., Портер К. В. Фосфиновый аналог метионина тормозит рост лейкозных клеток L1210 и превращается в фосфиновый аналог S-аденозилметионина, Биоорганическая химия, 2000, 26,735−737.
- Жуков Ю.Н., Вавилова Н. А., Воинова Т. М., Хурс Е. Н., Джавахия В. Г., Хомутов P.M. Фунгицидная активность фосфиновых аналогов аминокислот обмена метионина, Доклады Академии наук, 2004. Т. 397. № 1.С. 1−3.
- Walker J., Barrett J. Parasite Sulfur Amino Acid Metabolism, Int. J. for Parasitology, 1997, V. 27, No. 8, p. 883 897.
- Soda K. Microbial Sulfur Amino Acids, Methods in enzymology, 1987, V. 143,453−456.
- Ингрем В., Биосинтез макромолекул, 1975, Москва, «Мир»
- Stock J., Stock A. What is the role of receptor methylation in bacterial Chemotaxis? Trends Biochem. Sei., 1987,12, 371 375.
- Noort Van J.M., Krall B., Sinjorgo K.M., Persoon N.L.M., Johanns E.S.D., Bosch L. Methylation in vivo of elongation factor EF-Tu at lysine-56 decreases the rate of tRNA-dependent GTP hydrolisis, Eur. J. Biochem., 1986, 160, 557−561.
- Brown P.T.H. DNA methylation in plants and its role in tissue culture, Genome, 1989,31,717−729.
- Selker E.U., Fritz D.Y., Singer M.J. Dense nonsymmetrical DNA methylation resulting from repeat-induced point mutation in Neurospora, Science, 1993, 262, 1724 1728.
- Weissbach A., Ward C., Bolden A. Eukaryotic DNA methylation and gene expression, Curr. Topics Cell Regul., 1989, 30, 1−21.
- Macnab J.C., Adams R.L., Rinaldi A., Orr A., Clark L. Hypomethylation of host cell DNA synthesized after infection or transformation of cells by herpes simplex virus, Mol. Cell Biol, 1988, 8, 1443 1448.
- Wu J, Issa J.-P, Herman J, Basset D.E., Nelkin B.D., Baylin S.B. Expression of an exogenous eukaryotic DNA methyltransferase gene induces transformation ofNIH 3T3 cells, Proc. Natl. Acad. Sei. USA, 1993, 90, 8891 8895.
- Doerfler W. Abortive infection and malignant transformation by adenoviruses: integration of viral DNA and control of viral gene expression by specific patterns of DNA methylation, Adv. Virus. Res., 1991, 39, 89 -128.
- Rosl F., Arab A., Klevenz В., zur Hasen H. The effect of DNA methylation on gene regulation of human papillomaviruses, J. Gen. Virol., 1993, 74, 791 -801.
- Alix J.-H. Relationship between methylation and maturation of ribosomal RNA in prokaryotic and eukaryotic cells, N.Y.: The Humana Press, 1986, 175- 187.
- Moss В., Barbosa E., Keith J.N. Specificity of mRNA methyltransferases. -In: Transmethylation N.Y.: Elsevier, 1979, 373 380.
- Киселев О.И., Пиотровский JI.Б. Структура, биосинтез и функции 5'-концевых групп (кэпов) мРНК.- В сб.: Итоги науки и техники, серия Молекулярная биология, М: 1979, т.16, 139−195.
- Banerjee A.K. 5'-Terminal cap structure in eukaryotic messenger ribonucleic acids, Microbiol. Rev., 1980, 44, 175 205.
- Reddy R., Singh R., Shimba S. Methylated cap structures in eukaryotic RNAs: structure, synthesis and functions, Pharmacol. Ther., 1992, 54, 249 267.
- Salvatore F., Isso P., Colonha A., Traboni C., Cinino F. Transfer RNA methyltransferases: Properties and role in the maturation of tRNA, In: Transmethylation. N.Y.: Elsevier, 1979, 449−456.
- Hau F. The methylation of tRNA, Biochimia, 1976, 58, № 6, 629−645.
- Kim S.H., Sussman J.L. Transfer RNA: Structure-function correlation, Horiz. Biochem. Biophys., 1977,4,159−200.
- Borek E., Gehrke, Waalkes T.P. Aberrant methylation of tRNA in tumor tissue. In: Transmethylation. N.Y.: Elsevier, 1979,457−463.
- Lombardini J.B., Talalay P. Effect of inhibitors of adenosine triphosphate: L-methionine S-adenosyltransferase on levels of S-Adenosylmethionine and L-methionine in normal and malignant mammalian tissues, Mol. Pharmacol., 1973, 9, № 4, 542−560.
- Baldessarini R.J., Carbone P.P. Adenosylmethionine elevation in leukemic white blood cell, Scince, 1965, 149, № 3684, 644.
- Орлов H.H. Сравнительное содержание SAM и SAH в тканях некоторых экспериментальных опухолей в процессе их роста, Вопр. мед. химии, 1980, т. 26, в. 5, 699−704.
- Робер-Жеро М., Ледерер Э. Антивирусное, антимитогенное и антималярийное действие синтетических аналогов S-аденозилгомоцистеина, В кн.: Итоги и перспективы развития биоорганической химии и молекулярной биологии., М.: Наука, 1978, 111−127.
- Coward J.K., Bussolotti D.L., Chang C.D. Analogs of S-adenosylhomocysteine as potential inhibitors of biological transmethylation. Inhibition of several methylases by S-tubercidinylhomocysteine, J. Med. Chem, 1974, v. 17, N 12, 1286−1289.
- Raies A., Lawrence F., Robert-Gero M., Loche M., Cramer R. Effect of 5-•A deoxy-5-S-isobutyl adenosine on polyoma virus replication, FEBS Lett., 1976, 72, № 1,48−52.
- Pugh C.S.G., Borchardt R.T. Effects of S-adenosylhomocysteine analogues on Vaccinia viral messenger ribonucleic acid synthesis and methylation, Biochemistry, 1982, 21, № 7, 1535−1541.
- Borchardt R.T., Kuonen D., Huber J.A., Moorman A. Inhibition of calf thymus and rat hypothalmic synaptosomal protein carboxymethyltransferase by analogues of S-adenosylhomocysteine, Mol. Pharmacol., 1981, 21, 181 186.
- Borchardt R.T. N- and O-methylation, In Enzymatic basis of detoxification, Academic press, New York, 1980, V. 2,43 62.
- Borchardt R.T., Keller B.T., Patel-Thombre U. Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus replication in mouse L929 cells, J. Biol. Chem., 1984,259,4353 4358.
- Tabor C.W., Tabor H. 1,4-Diaminobutane (putrescine), spermidine and spermine, Annual Rev. Biochem., 1976, 45, 285 306.
- Pegg A.E., McCann P. S-Adenosylmethionine decarboxylase as an enzyme target for therapy, Pharmacol. Ther., 1992, 56, 359−377.
- Shapiro S.K., Hather A.N. The enzymatic decomposition of S-adenosyl-L-methionine, J. Biol. Chem., 1958, 233, № 3, 631−633.
- Swiatck K.R., Simon L.N., Chao K.-L. Nicotinamide Methytransferase and S-adenosylmethionine: 5'-methylthioadenosine hydrolase. Control of transfer ribonucleic acid methylation, Biochemistry, 1973, V. 12, № 4, 1273−1280.
- Riscoe M.K., Ferro A.J., Fitchen J.H. Methionine recycling as a target for antiprotozoan drug development, Parasitology today, 1989, 5, 330−333.
- Riscoe M.K., Tower P.A., Peyton D.H., Ferro A.J., Fitchen J.H. Methionine recycling as a target for antiprotozoan drug development, in Biochemical protozoology, Taylor and Francis, London, 1991, 450−457.
- Toohey J.I. Methylthio group cleavage from methylthioadenosine. Description of an enzyme and its relationship to the methylthio requirement of certain cells in culture, Biochem. Biophys. Res. Com., 1977, 78, № 4, 1273−1280.
- Mudd S.H., Mann J.D. Activation of methionine for transmethylation VII. Some energetic and kinetic aspects of reaction catalysed by the methionine-activating enzyme of bakers yeast, J. Biol. Chem., 1963, 238, № 6, 21 642 170.
- Khappe J., Schmitt T. A novel reaction of S-Adenosyl-L-methionine correlated with the activation of pyruvate formiate-lyase, Biochem. Biophys. Res. Com., 1972,48, № 1, 58−64.
- Zappia V., Ayala F. Studies on the activation of lysine-2,3-aminomutase by 7-i (-)-S-adenosyl-L-methionine, Biochem. Biophys. Acta, 1972, 268, № 2, 573 580.
- Plantavid M., Maget-Dana R., Douste-Blazy L. Inhibition of phosphatidylethanolamine biosynthesis by 5-adenosylmethionine, FEBS Lett., 1976, 72, № 1,169−172.
- Theologis A. One rotten apple spoils the whole bushel: the role of ethylene in fruit ripening, Cell, 1992, 70, 181−184.
- Bottiglieri Т., Hyland K. S-Adenosylmethionine levels in psychiatric and neurological disorders: a review, Acta Neurol. Scand., 1994, 154, 19−26.
- Williams J.H., Jasik A.D. A markedly anti-lipotropic action of methionine, Nature, 1963, 200, N2,472.
- Shapiro S.K. Biosynthesis of methionine from homocysteine and s-methylmethionine in bacteria, J. Bacterid., 1956, 72, 730−735.
- Sato C.S., Byerrum R.U., Albersheim P., Booner J. Metabolism of y-t methionine and pectin esterification in a plant tissue, J. Biol. Chem., 1958,233,128−131.
- Букин B.H., Хучуа Г.Н. S-метилметионин витамин U, В кн.: Витамин U (S-метилметионин): природа, свойства, применение, Москва, Наука, 1973, 7−22.
- Cooper A. J. L. Biochemistry of sulfur-containing amino acids, Annual Review of Biochemistry, 1983,52, 187−222.
- Barret J. Amino acid methabolism in helmints, Advances in Parasitology, 1991,30,39−105.
- Biryukov A.I., Osipova T.I., Khomutov R.M. a-Aminophosphonous acids: the substrates of ATP-PPj exchange reaction, catalysed by aninoacyl-tRNA synthetases, FEBS Lett., 1978, 91, 246 248.
- Сырку В.И., Завалова JI.JI., Хомутов P.M. Химическое регулирование «Л S-аденозилметионин зависимых ферментативных реакцийфосфорорганическими аналогами S-аденозилметионина и S-аденозилгомоцистеина, Биоорганическая химия, 1986, 12, № 6, 839−841.
- Steere J.A., Sampson Р.В., Honek J.F. Synthesis of an a-Aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase, Bioorg.&Med. chem. left., 2002, 12, 3, 457−460.
- Щипанова А. И, Жуков Ю. Н., Осипова Т. И., Хурс E.H., Хомутов P.M. Тез. докл. 7 съезд офтальмологов России. 16−20 мф. МЗ РФ, Об-во офтальмологов. М., 2000, 168−169.
- Tanaka Н., Esaki N., Soda К. Properties of L-methionine-y-lyase from Pseudomonas ovalis, Biochemistry, 1977, 16, 100−106.
- Ito S., Nakamura Т., Eguchi Y. Purification and characterization of methioninase from Pseudomonas putida, J. Biochem., 1976, 79,1263−1272.
- Фалеев Н.Г., Троицкая M.B., Ивойлов B.C., Карпова B.B., Беликов В. М. Метионин-у-лиаза в клетках Citrobacter intermedius. Синтез S-бутил-Ь-гомоцистеина и 8-бутил-Ь-цистеина, Прикл. биохимия и микробиол., 1994,30,3,458−463.
- Nakayama Т., Esaki N., Lee W.-J., Tanaka I., Tanaka H., Soda K. Purification and properties of L-methionine-y-lyase from Aeromonas sporogenes, Agric. Biol. Chem., 1984,48, 2367−2369.
- Lockwood B.C., Coombs G.H. Purification and characterization of L-methionine-y-lyase from Trichomonas vaginalis, Biochem. J., 1991, 279, 675−682.
- Inoue H., Inagaki K., Eriguchi S., Tamura Т., Esaki N., Soda K., Tanaka H. Molecular characterization of the mde operon involved in L-methionine catabolism of Pseudomonas putida, J. Bacteriol., 1997, 179, № 12, 39 563 962.
- Dias В., Weimer В. Purification and characterization of L-methionine-y-1 lyase from Brevibacterium linens BL2, Appl. Environ. Microbiol., 1998, 64,3327−3331.
- Coombs G.H., Mottram J.C. Trifluoromethionine, a prodrug designed against methionine-y-lyase-containing pathogens, has efficacy in vitro and in vivo against Trichomonas vaginalis, Antimicrobial agents and chemotherapy, 2001,45,6, 1743−1745.
- Esaki N., Nakayama Т., Sawada S., Tanaka H., Soda K. NMR Studies of substrate hydrogen exchange reactions catalysed by L-methionine-y-lyase, Biochemistry, 1985, 24, 3857−3862.
- Inoue Н., Inagaki К., Adachi N., Tamura Т., Esaki N., Soda K., Tanaka H. Role of tyrosine 114 of L-methionine-y-lyase lyase from Pseudomonas putida, Biosci. Biotechnol. Biochem., 2000, 64(11), 2336−2343.
- Alexander F.W., Sandmeier E., Metha P.K., Christen P. Evolutionary relationships among pyridoxal 5'-phosphate dependent enzymes. Regio-specific a, (3 and у families, Eur. J. Biochem., 1994, 219, 953−960.
- Кухарь В.П., Солоденко B.A. Фосфорные аналоги аминокарбоновых кислот, Успехи химии, 1987, 51(9), 1504−1532.
- Петров К.А., Чаузов В. А., Ерохина Т. С. Аминоалкильные фосфорорганические соединения, Успехи химии, 1974, 43(11), 20 452 087.
- Baylis Е.К., Campbell C.D., Dingwall J.G. 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids, J. Chem. Soc. Perkin Trans, 1984, 1, № 12, 2845−2853.
- Chalmers M.E., Kosolapoff G. N. The Synthesis of Amino-substituted Phosphonic Acids. Ill, J. Amer.Chem. Soc., 1953, 75, № 21, 5278−5280.
- Grobelny D. A New Synthetic Route to 1-Aminoalkylphosphonous Acids, Synthesis, 1987, 942−943.
- Maier L., Diel P.J. Organic phosphorus compounds. Preparation, physical and biological properties of aminoarylmethylphosphonic and -phosphonous acids, Phosphorus, Sulfur & Silicon, 1991, 57, 57−64.
- Jiao X., Verbruggen C., Borloo M., Bollaert W., Groot A., Dommisse R., Haemers A. A novel synthetic route to 1-aminoalkylphosphinic acids, Synthesis, 1994, 23−24.
- McCleery P.P., Tuck B. Synthesis of 1-aminoalkylphosphinic acids. Part 2. An alkylation approach, J. Chem. Soc. Perkin Trans 1,1989, 1319−1329.
- Хомутов P.M., Осипова Т. И. Новый метод синтеза а-аминофосфонистых и а-аминофосфоновых кислот, Изв. Академии Наук, Сер. хим., 1978, 8, 1954.
- Жуков Ю.Н., Хомутов А. Р., Осипова Т. И., Хомутов P.M. Синтез фосфиновых аналогов серосодержащих аминокислот, Изв. Академии Наук. Сер. хим., 1999, № 7, 1360−1363.
- Hoffman J.L. Chromatographic analysis of the chiral and covalent instability of S-adenosylmethionine, Biochemistry, 1986, 25, 4444−4449.
- Пурдела Д., Вылчану P. Химия органических соединений фосфора, М.: Химия, 1972, 630−631.
- Арбузов Б.А., Ярмухаметова Д. Х. Синтез гетероциклических соединений с фосфором в кольце. Сообщение 1. Синтез производных окса- и диоксаоксидофосфорина, Изв. АН СССР, ОХН, 1960, 8, 17 671 771.
- Кухарь В.П., Свистунова Н. Ю., Солоденко В. А., Солошонок В. А. Ассиметрический синтез фтор- и фосфорсодержащих аналогов аминокислот, Успехи химии, 1993, 62(3), 284−302.
- Brand L.M., Lowenstein J.M. Inhibition of adenylato succinase by adenylato phosphopropionate and related compounds, Biochemistry, 1978, 17, 1365−1370.
- Sosnovsky G., Lukszo J., Gravela E., Zuretti F. In search of new anticancer drugs. 13. Phosphinic and phosphonic analogs of ornithine, J. Med. Chem., 1985,28, 1350−1354.
- Хомутов P.M., Хурс E.H., Джавахия В. Г., Воинова T.M., Ермолинский Б. С. Ингибирование биосинтеза поликетидов 1-аминоэтилфосфонистой кислотой, Биоорг. химия, 1987,13, 1422−1424.
- Хурс Е.Н., Осипова Т. И., Хомутов P.M. Ферментативное переаминирование фосфорорганических аналогов аспартата и глутамата, Биоорг. химия, 1989,15, 552−555.
- Metzger Н., in Methoden der Organischen Chemie (Houben-Weyl), Thieme Verlag, Stuttgart, 1971, 10, № 4.
- Kikugawa K., Ichino M. Direct halogenation of sugar moiety of nucleosides, Tetrahedron Lett., 1971, 2, 87−90.
- Букин B.H., Хучуа Г. Н., Рубцов И. А. Синтез S-метилметионина, В кн.: Витамин U (S-метилметионин): природа, свойства, применение, Москва, Наука, 1973, 146−150.
- Fitch P.J. Synthesis of hypophosphite esters from orthocarbonyl compounds, J. Am. Chem. Soc., 1964, 86(1), 61−64.
- Cleland W.W. Statistical analysis of enzyme kinetic data, Methods Enzymol., 1979, 63, 103.
- Friedmann T.E., Haugen G.E. Pyruvic acid, the determination of keto acids in blood and urine, J. Biol. Chem., 1943, 147, 415−443.