Получение и физико-химические свойства липосомальных форм ДОФА, дофамина и их боратных производных
Диссертация
116 Приложение 117−126Список сокращений2-АЭ 2-АминоэтанолГЭБ Гемато-энцефалический барьерДА 3,4 -Дигидроксифенилэтиламин (дофамин)ДОФА Ь-З, 4-дигидроксифенилаланинДПФХ ДипальмитоилфосфатидилхолинДСФХ ДистеароилфосфатидилхолинДХН Дезоксихолат натрияКхх КатехолыкР Коэффициент распределенияЛс Липосомы2-МП К N — м ети л п ир и ди ния -2 -кар б ал ьдокси мОВС Окислительно-восстановительные системыПОЛ… Читать ещё >
Список литературы
- Robinson D.H., Mauger J.W. Drug delivery systems//Amer. J. hosp. pharm. 1991. V.48. Suppl. 1. Pp. 14−23.
- Биополимеры. Под ред. Иманиси Ю. М: Мир. 1988. Сс. 518−535.
- Ganderton D. Current innovations in drug delivery//Drug des. deliv. 1987. N2. Pp. 1−7.
- Pimlott S., Addy M. A study into mucosal absorption of isosorbide dinitrate at different intraoral sites//Oral surg. Oral med. Oral pathol. 1985. N59. Pp. 145−148.
- Kreuter J. Peroral administration of nanoparticles//Adv.Drug Del. Rev. 1991. V.7. N1. Pp. 71−86.
- Speiser P.P. Nanoparticles and liposomes: a state of the art//Methods find. exp. clin. Pharmacol. 1991. V. 13. N5. Pp. 337−342.
- Leuroux J.C., Allemann E., Dejaeghere F., Doelker E. Biodegradable nanoparticles from sustained release formulations to improve site specific drug delivery//J.control, release. 1996. V. 39. N2−3. Pp. 339−350.
- Sjostrom В., Bergenstahl В. Preparation of submicron drug particles in lecithin-stabilized o/w emulsions. 1. Model studies of the precipitation of cholesteryl acetate//lnter.J.Pharm. 1992. V.84. N2. Pp. 107−116.
- Bohlinder К., Olsson В., Ragnarsson G., Singh S.K., Ohman G.S., Wadsten Т., Carlsson A., Herslof B. Use and characteristics of a novel lipid particle-forming matrix as a drug-carrier system//Europ. J. pharm.sei. 1994. V. 2. N4. Pp. 271−279.
- Erlich P. Uber die Beziehungen von chemische Constitution, Verteilung und pharmakologisher Wirkung//New York.: Wiley. 1906. Pp. 567−595.
- Goldmann E.E. Vitalfarbung am Zentralnervensystem//Abh. Preuss Akad. Wiss. Phys-Math. 1913. N1. Pp. 1−60.
- Brightman M.W., Reese T.S. Junctions between intimately apposed cell membranes in the vertebral brainZZJ. cell biol. 1969. N40. Pp. 648−677.
- Maher F., Vannucci S.J., Simpson I.A. Glucose transporter proteins in brain//FASEB J. 1994. V.8. N13. Pp. 1003−1011.
- Van-Bree J.В., De-Boer A.G., Danhof M., Breimer D.D. Drug transport across the blood-brain barrier. III. Mechanisms and methods to improve drug delivery to the central nervous systemZZPharm. world sci. 1993. V.15. N1. Pp. 2−9.
- Partridge W.M. Blood-brain barrier transport of glucose, free fatty acids and ketone bodiesZZAdv.exp.biol.med. 1991. V.291. Pp. 43−53.
- Луцевич A.H., Бендер К. И., Купчиков В. В. Белки плазмы крови и транспорт лекарственных веществ через гемато-энцефалический барьер/УФармак. токсикол. 1991. Т.54. N1. Сс. 70−76.
- Smith Q.R. The blood-brain barrier and the regulation of amino acids uptake and availability to brain//Adv. exp. med. biol. 1991. V.291. Pp. 55−71.
- Begley D.J. Peptides and the blood-brain barrier: the status of our understandingZZAnn. NY Acad. sci. 1994. V.739. Pp. 89−100.
- Banks W.A., Kastin A.J., Barrera C.M. Delivering peptides to the central nervous system: dilemmas and strategiesZZPharm. res. 1991. V.8. N11. Pp. 1345−1350.
- Banks W.A., Kastin A.J. Peptide transport for opiates across the blood-brain barrierZZAm. J. physiol. 1990. V.259. N1. Pt.1. Pp. E1−10.
- Plata-Salaman C.R. Insulin in the cerebrospinal fluidZZNeurosci. biobehav. rev. 1991. V.15. N2. Pp. 243−358.
- Spector R. Drug transport in the central nervous system: role of carriersZZPharmacology. 1990. V.40. N1. Pp. 1−7.
- Betz A.L. An overview of the multiple functions of the blood-brain barrierZZNIDA Res. monogr. 1992. V.120. Pp. 54−72.
- Fenstermacher J.D. The blood-brain barrier is not a «barrier» for many drugsZZNIDA Res. monogr. 1992. V.120. Pp. 108−120.
- Brust P. Blood-brain barrier transport under different physiological and pathophysiological circumstances including ischemiaZZExp. pathol. 1991. V. 42. N4. Pp. 213−219.
- Greenwood J. Mechanisms of blood-brain barrier breakdown//Neuroradiology. 1991. V.33. N2. Pp. 95−100.
- Joo F. Insight into the regulation by second messenger molecules of the permeability of the blood-brain barrier//Microsc. res. tech. 1994. V.27. N6. Pp. 507−515.
- Pardridge W.M., Boado R.J., Black K.L., Cancilla P.A. Blood-brain barrier and new approaches to brain drug delivery//West. J. med. 1992. V.156. N3. Pp. 281−286.
- Pardridge W.M. Recent development in peptide drug delivery to the brain//Pharmacol. Toxicol. 1992. V.71. N.1. Pp. 3−10.
- Bodor N. Novel approaches for the design of membrane transport properties of drugs//Design of biopharmaceutical properties through prodrugs and analogs. Washington: D.C. 1976. Pp. 98−135.
- Woodard P.A., Winwood D., Brewster M.E., Estes K.S., Bodor N. Improved delivery through biological membranes. XXI. Brain-targeted anticonvulsive agents//Drug design and del. 1990. N.6. Pp. 15−28.
- Bodor N. Brain-specific drug delivery/ZScience. 1981. V.214. Pp. 13 701 372.
- Bodor N. Brain-specific delivery// US Pat. 4,824,850 (CI 514−270, A61 K31/515). 1989.
- Bodor N. Brain-specific dopaminergic activity involving dopamine conjugates of dihydropyridine carboxamides, dihydroquinoline and dihydroisoquinoline carboxamides// US Pat. 4,727,079 (CI 514−307. A 61 K31/44).1988.
- Bodor N. Pharmaceutical formulations for parenteral use containing cyclodextrins and dihydropyridine redox systems//Eur.Pat. 335,545 (CI A61 K9/08).1989.
- Szejtly N. Cyclodexrins and their inclusion complexes. Budapest: Acad. Kiado. 1982. Pp.234−240.
- Кулаков B.H. Фармакокинетическое изучение конъюгатов декстрана с катехоламинами, обладающими гипотензивной активностью//Фармак. и токсикол. 1988. Т.51. N2. Сс.99−101.
- Rozenkranz R.P. An historical perspective of dopamine and it’s analogs//Proc. West. Pharmacol, soc. 1990. V.33. Pp.15−19.
- Mc Geer, Searl K. Chemical specifity of dopamine transport in the nigroneostriatal projection/^. neurochem. 1975. V. 24. N2. Pp. 283−288.
- Barbeau A. L-DOPA therapy in Parkinson’s disease: a critical review of nine years experience//Can. med. ass.j. 1969. V.101. Pp. 791−800.
- Cotzias G.C. Levodopa in the treatment of Parkinsonism//JAmer. med. ass. 1971. V. 218. N13. Pp. 1903−1908.
- Сэндпер M. Биохимические основы болезни Паркинсона и лечение ее 1.-ДОФА//ЖВХО им. Менделеева Д. И. 1976. N2. Сс. 190−196.
- Friis М., Paulson О. Blood-brain barrier permeability of L-DOPA in man//Eur. J. clin. invest. 1981. V.11. N3. Pp. 231−234.
- Машковский М.Д. Лекарственные средства. М.Медицина. 1988. Т.1. С. 163.
- Repta N. Rectally absorbable form of L-DOPA//US Pat. 4,663,349 (CI 514−535). 1987.
- В odor N., Kenneth В., Sloan K. Improved delivery through biological membranes. 4. Prodrugs of L-DOPA//J.med.chem. 1977. V.20. N11. Pp. 1435−1445.
- Agarval J., Nath C. Antiparkinsonian and anticonvulsant activity of some silyl substituted dopamine derivatives//Pharm. res. commun. 1981. V. 13. N10. Pp. 937−947.
- Cooper D.R., Marrel C. L-DOPA methyl ester a candidate for chronic system delivery of L-DOPA in Parkinson’s disease//Clin. neurophamacol. 1984. V.7. N1. Pp. 89−98.
- Cooper D.R. L-DOPA esters as potential prodrugs: behavioral activity in experimental models of Parkinson’s disease//J. Pharm. Pharmacol. 1987. V.39. N8. Pp. 627−635.
- Ibrecht R. Dopamine derivatives//Ger.Offen. 3,430,310 (CI C07D231/54). 1986.
- Sakami T.G. The investigation of amino acid reactions by methods of non-aqueous titrimetry//J.biol.chem. 1942. V.144. N1. Pp. 90−107.
- Bretschneider H., Biemann K. Uber o-acylderivate einiger biogener oxyaminoverbindungen mit primaren Aminogruppen. Monatshefte fur Chemie. 1950. B. 51. H.5. Pp. 57−65.
- Holding Wh. ?-(3,4-Dialkyloxyphenyl)-a-alanine// Ger. Offen. 2,330,653 (CI C0763/100). 1972.
- Winner Thr., Lannach K. Phenylalaninderivate//Ger. Offen. 2,263,814 (CI C07C103/52). 1972.
- Watanabe T., Kono K., Tsukamoto G. p-(3,4-Diacyloxyphenyl)alanines//Jpn. Pat. 7,231, 949 (C116 i64). 1972.
- Watanabe T" Kono K., Tsukamoto G.// Jpn. Pat. 7,231,950 (CI 16C 64). 1971.
- Porteiii M., Renzi G. ?-(3,4-Diacetoxyphenyl)-L-alanine//Ger.Offen 2,330,653 (CI C07C/A61 K). 1974.
- Wimmer Th. a-?-3,4-Bis (acyloxy)phenyl-L-alanine derivatives//Ger.Offen. 2,263,814 (CI C 07C, A 61 K). 1973.
- Shih Ch. The chemistry of potential prodrugs of dopamine//Diss.abstr.lnt.B. 1980. V.41. N5. Pp. 1744−1745.
- Ihara M., Nakajima S. Hydrolysis and acyl migration of a catechol monoester of L-DOPA//J.pharm, sei: 1990. V.79. N8. Pp. 703−708.
- Bodor N., Sloan K. Novel DOPA/dopamine prodrugs// US Pat. 4,311,706 (CI 514−513). 1982.
- Ihara M., Tsuchiya Y., Sawasaki Yo. A new potential prodrug to improve the duration of L-DOPA//J.pharm.sci. 1989. V. 78. N7. Pp. 525−529.
- Hiemke Chr., Kauert G., Kalbhen D. Gas-liquid chromatographic properties of catecholamines, phenylethylamines and indolalkylamines as their propionyl derivatives//J.chrom. 1978. V.153. N2. Pp. 451−460.
- Hoffman F. Verfahren zur Herstellung von Phenylalaninderivate// Swiss Pat. 562,202. 1975.
- Sinda J.F. Investigation of some methylated products obtained by reaction of ?-3−4-dihydroxyphenylalanine with diazomethane in methanol-ether//J.org.chem. 1975. V.40. N24. Pp. 3611−3614.
- Ginos J.Z., Catzias G.C. New dopaminergic and potential anti-parkinson compounds N, N -substituted-?-(3,4-dihydroxyphenylethylamines//J. med. chem. 1978. V.21. N2. Pp. 160−165.
- Bodor N. Novel transient prodrug forms of L-DOPA// US Pat. 3,998,799 (CI 260−112.5R, C 07C103/52). 1976.
- Shashona V. Fatty acid-drug conjugate for delivery of the drug across the blood-brain barrier//W0 8907,938 (CI A61 K31/16). 1989.
- Fuller W., Verlander M. DOPA-containing polypeptides. I. Improved synthesis of high-molecular weight-poly-(L-DOPA) and water soluble copolypeptides//Biopolymers. 1978. V.17. N12. Pp. 2939−2943.
- Goodmann M., Verlander M. Polypeptides containing 3,4-dihydroxyphenylalaine/AJS Pat. 4,125,519 (CI 528−363, C08669/10). 1978.
- Yanaihora N., Igarashi T., Kuni T. Dopamine derivatives//Ger.Offen. 2,637,600 (CI C07 C103/52). 1977.
- Prokai L. Chemical delivery system to transport a pyroglutamyl peptide amide to the central nervous system//J.Am.chem.soc. 1994. V.116. Pp. 2643−2644.
- Felix A., Winter D. Synthesis and antireserpine activity of L-DOPA//J.med.chem. 1974. V.17. N4. Pp. 422−426.
- Losse G., Barth A. Natiz uber die synthese von N-terminalen Peptiden des 3,4-Dihydroxyphenylalanine//J.praktisch. chem. 1963. V. 21. N.4. H.1−2. Pp. 32−35.
- O’Neill J.J., Veitch F.P., Vagner-Jauregg T. The preparation of phthalyl glycyl DL-?-(3,4-dihydroxyphenyl)alanine methyl ester//J.org.chem. 1956. V.21. N3. Pp. 13−16.
- Weinhold P. Prodrugs of dopamine//EP 8,911,401.21 (CI C07 C237/22).1987.
- Bodor N., Sloan K., Kaminski J.J., Shih Ch. A convenient synthesis of (acyloxy)alkyl a-ethers of phenols//J.org.chem. 1983. V.48. N26. Pp. 5280−5284.
- Gregoriadis G. Engineering liposomes for drug delivery: Progress and problems//Trends in Biotechnology. 1995. V. 13. N12. Pp. 527−537.
- Oku N. Basic study and application of functional liposomes//J.Pharm. soc.Japan. 1995. V. 115. N7. Pp. 483−498.
- Липосомы в медицине. Серия статей из Вестника АМН СССР. 1990.1. N6.
- Ceve G., Blume G., Zellmer S. Rational liposome design and application optimization based on the simultaneous consideration of the lipid and drug propertiesZ/Liposome in drug delivery 21 years on/Ed. Gregoriadis G. et al. 1990.
- Yagi K., Naoi M., Sakai H., Abe H., Konishi H., Arichi Sh. Incorporation of ensyme into the brain by means of liposomes of novel composition//J. appl. biochem. 1982. N4. Pp. 121−125.
- Micklus M.J., Greig N.H., Tung J., RapoportS.I. Organ distribution of liposomal formulations following intracarotid infusion in rats//Bioch. biophis. acta. 1992. V.1124. N.1. Pp. 7−12.
- Umezawa F., Eto Y. Liposome targeting to mouse brain: mannose as a recognition marker//Biochem. Biophys. Res. Commun. 1988. V. 153. Pp. 1038−1044.
- Gomes I., Sharma S.K. Effect of hyperosmolar mannitol on the delivery of high molecular weight substances entrapped in liposomes to the brain and cultured C6 glioma cells//J. Clin. Biochem. Nutrit. 1995. V.18. N3. Pp. 133−144.
- Sakamoto A., Ido T. Liposome targeting to rat brain effect of osmotic opening of the blood brain barrier/ZBrain Res. 1993. V. 629. N1. Pp. 171−175.
- Gennuso R., Spigelman M.K., Chinol M., Zappulla RA Effect of BBB and blood-tumor barrier modification on central nervous system liposomal uptake//Cancer invest. 1993. V.11. N2. Pp. 118−128.
- Weinstein J.N., Magin R.L., Cysyk R., Treatment of solid L1210 murine tumors with local hypertermia and temperature-sensitive liposomes containing methotrexate//Cancer Res. 1980. V. 40. Pp. 1388−1395.
- Lin J.C., Lin M.F. Microwave hypertermia-induced BBB alterations//Radiat. Res. 1982. V. 89. Pp. 77−87.
- Iga K., Hamaguchi N. Enhanced antitumor activity in mice after administration of thermosensitive liposomes encapsulating cisplatin with hyperthermia//J.Pharmacol.Exp. Ther. 1991. N257. Pp. 1203−1207.
- Kakimuna K., Tanaka R., Takahashi H., Watanabe M., Nakagawa T., Kuroki M. Targeting chemotherapy for malignant brain timor using thermosensitive liposomes and localized hypertermia//J.neurosurg. 1996. V.84. Pp.180−184.
- Huwyler J., Wu D.F., Pardridge W.M. Brain drug delivery of small molecules using immunoliposomes//Proc.Nat.Acad.sci. USA. 1996. V. 93. N24. Pp. 14 164−14 169.
- Wang J.V., Xu Y.R., Huang K., Sun L.Y. Proliposome targeting to rabbit brain tissue//J.Pharm.Pharmacol. 1995. V. 47. N12A. Pp. 1053−1054.
- Mehta S.C., Lu D.R. Targeted drug delivery for boron neutron therapy//Pharm.res. 1996. V. 13. N3. Pp. 344−351.
- Wang J.-Y., Xu Yu-Ru, Huang K., Sun L.-U. Proliposome targeting to rabbit brain tissue//J. pharm. Pharmacol. 1995. V.47. Pp. 1053−1054.
- Kobayashi K., Han M., Watarai Sh., Yasuda T. Availavility of liposomes as drug carriers to the brain//Acta med. Okayama. 1996. V.50. N2. Pp. 67−72.
- LeWitt PA. The pharmacology of Levodopa in treatment of Parkinson’s disease. An uptake//Handbook of experimental pharmacology/Ed.Calne D.B. 1989. V.88. Pp. 325−384.
- Lloyd K.G., Daidson L., Hornykiewicz O. The neurochemisfry of Parkinson’s disease: effect of L-DOPA therapy//J. pharmac. exp. ther. 1975. N195. Pp. 453−464.
- Miranda M., Amicarelli F., Volpe A.R., Poma A., Masciocco L., Carmignani M. Specific increase of L-DOPA levels in plasma upon infusion of tyrosinase containing liposomes//Gen. pharmca. 1993. V.24. N6. Pp.1319−1322.
- Miranda M., Amikarelli F., Poma A., Ragnelli A.M., Arcadi A. Liposomes as a tool for enzyme therapy: models of employment in catecholamine related disorders//Chim. oggl. 1989. N7. Pp. 9−12.
- Cederbaun J.M., Breck L., Kutt H., McDowell F.H. Contolled-release levodopa/carbidopa. 1. Sinemet CR3 treatment of response fluctuations in Parkinson’s disease//Neuroloy. 1987. V.37. Pp. 233−241.
- During M.J., Freese A., Sabel B.A. et al. Controlled release of dopamine from a polymeric brain implant: in vivo characterization//Ann. neurol. 1989. V.25. Pp. 351−356.
- Freese A., Sabel BA, Saltzman W.M., et al. Controlled release of dopamine from a polymeric brain implant: in vitro characterization//Exp. neurol. 1989. V.103. Pp. 234−238.
- McRae-Degueurce A., Hjorth S., Dillon D.L., et. al. Implantable microencapsulated dopamine (DA): A new method for slow-release DA delivery into brain tissue//Neurosci. lett. 1988. N92. Pp. 303−309.
- Puglisi G., Fresta M., C. La Rosa, Ventura C.A., Panico A.M., Mazzone G. Liposomes as a potential drug carrier for citicoline (CDP-choline) and the effect of formulation conditions on encapsulation efficiency/VPharmazie. 1992. V. 47. H.3. Pp. 211−215.
- Марголис Л.Б., Бергельсон Л. Д. Липосомы и их взаимодействие с клетками. М.: Наука. 1986. С. 45.
- Досон Р., Элиотт Д., Элиотт У., Джонс К. Справочник биохимика. М.: Мир. 1991. С. 23.
- Kirby Ch., Clarke J., Gregoriadis G. Effect of the cholesterol content of small unilamellar liposomes on their stability in vivo and in vitro//Biochem. J. 1980. V.186. N2. Pp. 591−598.
- Gregoriadis G. Liposomes in therapeutic and preventive medicine: The development of the drug-carrier consept//Ann. N.Y. Acad. sci. 1978. V.308. Pp. 343−370.
- Palmeira C.M., Oliveira C.R. Partitioning and membrane disordering effects of dopamine antagonists: influence of lipid peroxidation, temperature and drug concentration/Archives biochem. biophys. 1992. V.295. N1. Pp. 161−171.
- Custodio J.B.A., Almeida L.M., Madeira V.M.C. A reliable and rapid procedure to estimate drug partitioning in biomembranes//Biochem. biophys. res. comm. 1991. V.176. N3. Pp. 1079−1085.
- Connors К A. Textbook of Pharmaceutical analysis//John Wiley and Sons, Inc. 1967. Pp. 277−294.
- Руднев Д.Н. Исследование некоторых механизмов действия КА, стероидов и их сочетания на биомембраны. М.: Дисс. на звание канд. мед. наук. 1978. Сс. 118−121.
- Drechsler М., Banchmann D., Brandl М.//Abstracts of Fourth Liposome Reseach flays Conference (Freiburg, Germany). 1995. P.80.
- Lasic D.D., Ceh В., Stuart M.C.A., Guo L., Frederik P.M., Barenholz Y. Transmembrane gradient driven phase transitions within vesicles: Lessons for drug delivery//Biochim.biophys. acta-biomemb. 1995. V.1239. N2. Pp. 145−156.
- Sotomatsu A., Nakano M., Hirai Sh. Phospholipid peroxidation induced by the catechol-Fe 3+ (Cu 2+) complex: a possible mechanism of nigrostriatal cell damage/ZArch. biochem.biophys. 1990. V.283. N2. Pp. 334−341.
- Гуляева H.B., Лузина Н. Л., Левшина И. П., Крыжановский Г. Н. Стадия ингибирования ПОЛ при стрессе//Бюл. эксперим. биол.мед. 1988. N12. Сс. 660−663.
- Сергеев Т.В., Сейфулла Р. Д., Дунаев В. Г., Руднев Ю.К.Эффект радиозащитных биогенных аминов на перекисное окисление липидов//Бюл. экспер. биол. мед. 1976. Т.81. N2. Сс. 169−171.
- Кучеряну В.Г., Атаджанов М. А., Никушкин Е. В., Загоревский В. А., Шаркова Л. М. Перекисное окисление липидов в хвостатых ядрах при экспериментальном паркинсоническом синдроме//Бюлл.эксперим.биол.мед. 1989. N1. Сс.39−41.
- Владимиров Ю.А., Арчаков А. И. Перекисное окисление липидов в биологических мембранах. М.:Наука. 1972. Сс.136−140.
- Кулинский В.И. Механизм действия катехоламинов на окислительно-восстановительные процессы/ЛГезисы конференции «Механизм действия гормонов», Ташкент. 1976. Сс. 56−62.
- Pelizzetti E., Mentasti Ed., Pramauro Ed. Kinetics and mechanism of oxidation pathways of some catecholamines with periodic acid//J.chem. soc. Perkin. Trans. II. 1976. N14. Pp/ 1651−1655.
- Fukuzawa K., Seko Т., Minami K., Terao J. Dynamics of iron-ascorbate-induced lipid peroxidation in charged and uncharged phospholipid vesicles//Lipids. 1993. V.28. N6. Pp. 497−503.
- Tse D.C.S., McCreery R.L., Adams R.N. Potential oxidative pathways of brain catecholamines//J.med.chem. 1976. V.19. N1. Pp. 37−40.
- Maiorino M., Zamburlini A., Roveri A., Ursini F. Copper-induced lipid peroxidation in liposomes, micelles, and LDL: which is the role of vitamin E?//Free radical biol.med. 1995. V.18. N1. Pp. 67−74.
- Trautner E.M., Messer M. Inhibition of adrenaline oxidation by borate//Nature. 1952. V.169. Pp. 31−32.
- Antikainen P.J., Terauen K. Chelation of adrenaline with boric acid in aqueous solutions//Suom.Kem. 1966. V.39. N12. Pp. 285−288.
- Soloway A.H. Stability and synthesis of phenylboronic acids//J.Amer.chem.soc. 1959. V.81. Pp. 3017−3019.
- Soloway A.H. Penetration of brain and brain tumor by aromatic aompounds as a function bo molecular sustituents//J.pharmacol.exptl.therap.1960. V.129. Pp. 310−314.
- Soloway A.H. Evaluation of boron compounds for use in neutron-capture therapy of brain tumors. I. Animal investigations//J.Pharmacol.exptl.therap.1961. V.134. Pp. 117−122.
- Soloway A.H. Penetration of brain and brain tumor by aromatic aompounds as a function fo molecular sustituents//J.med.pharm, ehem. 1962. N5. Pp. 191−196.
- Yoshino K., Okamoto M., Kakihana H., Yoshihiro M. Chemical assay of boron and its distribution in melanoma-bearing subjects//Neutron capture therapy. Proc. 2nd Int.Symp. 1986. Pp. 291−302.
- Yoshino K., Takahashi H., Toriis S., Kakihana H. Complex formation of p-borophenylalanine with L-DOPA (a precursor of melanine metabolism) and oxidation reaction of the analogs/ZKyoto Daigaku Genshiro Jikkensho. 1993. KURRI-TR-382. Pp. 33−38.
- Baraldi E., Cavani L., Seghedoni S., Chiossi KTX., Roli L., Scacchetti A.T., Baraghini KTX.F. Assay of urinary free Ktx: routine use in a clinical chemistry laboratory//Chromatographia. 1987. V. 24. Pp. 407−410.
- Andrew R., Watson D. The determination of hydroxydopamines and other trace amines in the urine of Parkinsonian patients and normal controls//Neurochem. res. 1993. V.18. N11. Pp. 1175−1177.
- Betto P.KTX. HPLC monitoring of plasma catechol levels in the characterization of Parkinson’s disease//!tal.chim.clin. 1992. V.17. N6. Pp.441−453.
- Imai Y., I to S., Maruta K., Fujita K. Simultaneous determination of CA and serotonin by liquid-chromatography after treatment with boric-acid gel//Clin.chem. 1988. V.34. iss.3. Pp.528−530
- Tanaka S., Kaneta T., Yoshida H. Isotachoforetic separation and behavior of catechol derivatives//J. Chrom. 1990. V.498. N1. Pp. 205−211.
- Tanaka S., Kaneta T., Yoshida H. Capillary isotachophoretic separation of catechol and its derivatives using the reaction with terminating ion//Anal. Sei. 1989. V. 5. N2. Pp. 217−218.
- Schafer H. Uber die Gleichgewichte zwischen Borationen, Brenzkatechin und Brenzkatechin-borationen in wassriger Losung und uber die Darstellung von Monobrenzkatechinboraten/ZZ.fur anorg.allg.chem. 1942. Bd. 250. H.2. Pp. 127−143.
- Schafer H. Borsaure Komplexverbindungen//Allg.chem. A. 1948. N1. Pp. 73−76.
- Schafer H. Borsaure und Oxyverbindungen. IY. Neue Salze der Dibrenzkatechinborsaure//Z. fur Anorg. Chem. 1949. V.259. Pp. 86−91.
- Камянов И.М., Полис Я. Ю., Купнек А. Г. Мидантан и его применение в терапии и профилактике//М.Медицина. 1987. Сс. 3−10.
- Gorin PAJ., Mazurek М. 13С magnetic resonance spectroscopic evidence for formation of borate complexes of polyhydroxy compounds // Carbohydrate Res. 1973. N 27. Pp. 325−329.
- Kennedy G.R., How M.J. The interaction of sugars with borate: an N.M.R. spectroscopic study// Carbohydrate Res. 1973. N28. Pp. 13−19.
- Жунке А. Ядерный магнитный резонанс в органической химии. М.: Мир. 1974. С. 44.
- Heller G., Seeger К. Mixed esters of boric acid with aminoalcohols and dilols Hl.Naturforsch. В: Chem.Sci. 1988. V.43. N5. Pp. 547−556.
- Robert K.M., Nachtrieb N.H., Nuclear magnetic resonance study of borate-polyborate equilubrium in aqueous solution//!norg.chem. 1967. V.6. N6. Pp. 1189−1192.
- Yoshino K., Kotaka M., Okamoto M., Kakihana H. 11 B-NMR study of the complex formation of borate with catechol and L-DOPA//Bull.chem.soc.Jap. 1979. V.52. N10. Pp. 3005−3009.
- Mohr S., Heller G., Timper U., Woller K-H. Neue Untersuchungen an borsaureestern von Brenzcatechin und einiger Catecholamine in wassriger Losung und an Feststoffen // Z. fur Naturforschung. В: Chem. Sei. 1990. V. 45 N3. Pp.308−322.
- Carter J.E. Johnson J.H., Baaske D.M. Dopamine hydrochloride//Anal.profile of drug substances. 1982. V.11. Pp.34−47.
- Gomez R., Hagel R.B. Levodopa/ZAnal. profile of drug substances. 1976. V.5. Pp. 131−145.
- Pistorins C.W.F. IR and Raman potential function of boric acid // J.Chem. Phys, 1959. V.31. N6. Pp. 127−135.
- Желиговская H.H., Черняев И. И. Химия комплексных соединений. М: Высшая школа. 1966. Сс. 356−363.
- Foil A., Wilkins M., Wilkins Ch. H. Infraread spectra and charecteristic frequencies of inorganic ions//Anal. Chem. 1952. V.24. N8. P. 1253.
- Алекперов Э.Р., Резник A.M. Комплексообразование бора с азот и кислородосодержащими лигандами//Журнал координ. химии. 1993. N1. Сс. 5−14.
- Rajan K.S., Skripkus A., Marks G.E., Davis J.M. Coordination of biogenic amines with synaptosomal and vesicular metal ions: equilibrium and spectral studies in model systems// Bioinorg. chem. 1976. N6. Pp. 93−117.
- Sundqvist B.U.R. // Biological mass spectrometry. Eds. A.L.Burlingame. JAMcCloskey. Amsterdam: Elsevier. 1990. P. 37.
- Antikainen P.J., Witikainen U. The oxyanion chelates of o-diphenols. Part III. The chelation of boric acid with dopamine//Finn. Chem. Lett. 1974. N4. Pp. 156−158.
- Albert A. Quantitative studies of the avidity of naturally occuring substances for trace metals//Biochem.J. 1950. V. 47. N4. Pp. 531−537.
- Antikainen P.J., Witikainen U. A comparative study on the ionization of catechol amines in aqueous solutions//Acta Chem. Scand. 1973. V. 27. N6. Pp.2075−2082.
- Yasunobu K.T., Norris E.R. Mechanism of borate inhibition of diphenol oxidation by tyrosinase//^ of biol. chem. 1957. V. 227. N1. Pp. 473−482.
- Yoshino K., Kakihana H., Okamoto M., Yoshihiro M. Chemical behavior of dopaborate and 10B-p-borophenylalanine//Proc. 2nd Int. Symp. on Neutron capture therapy. 1985. Pp. 55−60.
- Pizer R., Babcock L. Mechanism of the complexation of boron acids with catechol and substituted catechols//lnorg. chem. 1977. V. 16. N7. Pp. 52−56.
- Васильева М.Г., Лапыкина B.M., Махарашвили H.A., Соколова А. Л., Сойфер В. М., Цкирия Н.Г.//Анализ бора и его неорганических соединений. М.Агомиздат. 1965. С. 5.
- Краткий справочник физико-химических величин. Под ред. А. А. Равделя и А. М. Пономаревой. Л.Химия. 1983. С. 123.
- Pettit L.D. Critical evaluation of equilibrium constants in solution. Part A. Stability constants of metal complexes//Pure and appl. chem. 1984. V. 56. N2. Pp. 247−292.
- Rajan K.S., Davis J.M. Interactions of iron with biogenic amines and ATP//J. inorg. nucl. chem. 1976. V.38. Pp. 897−905.
- Rajan K.S., Mainer S. Formation and stabilities of the ternary metal chelates of L-3,4-dihydroxyphenyl alanine (l-DOPA) with a number of secondary ligands//J. inorg. nucl. chem. 1978. V. 40. Pp. 2089−3099.
- Rajan K.S., Mainer S. Studies on chelation of L-DOPA with metal ions and metal ATP systems//Bioinorg. chem. 1978. V.9. Pp. 187−203.
- Rajan K.S., Skipkus A., Marks G.E., Davis J.M. Coordination of biogenic amines with synaptosomal and vesicular metal ions: equilibrium and spectral studies in model systems/ZBioinorg. chem. 1976. N6. Pp. 93−117.