Синтез модифицированных природных хлорофиллов и изучение их свойств для бинарных методов терапии в онкологии
![Диссертация: Синтез модифицированных природных хлорофиллов и изучение их свойств для бинарных методов терапии в онкологии](https://westud.ru/work/2514871/cover.png)
Диссертация
В настоящее время применяются в клинике или находятся на разных стадиях клинических испытаний фотосенсибилизаторы различных классов (хлорины, пурпурины, производное бензопорфирина, фталоцианины). Соединения с интенсивным поглощением в ближней* ИК-области спектра привлекают особое внимание в качестве потенциальных ФС, так как их поглощение в диапазоне 650 — 850 нм открывает новые возможности для… Читать ещё >
Содержание
- ЛИТЕРАТУРНЫЙ ОБЗОР
- 1. Основные требования, предъявляемые к фотосенсибилизаторам
- 1. 1. Интенсивное поглощение в дальней красной и ближней инфракрасной областях спектра
- 1. 2. Амфифильность ФС и высокая растворимость в полярных растворителях и воде
- 1. 3. Высокий квантовый выход синглетного кислорода и других реакци-онноспособных форм кислорода
- 1. 4. Высокая селективность накопления ФС в опухоли
- 1. 5. Низкая темновая токсичность
- 1. 6. Быстрое выведение ФС из организма
- 2. Хлорофилл, а и его производные
- 2. 1. Хлорофиллид, а и его производные
- 2. 2. Феофорбид и его производные
- 2. 2. 1. Алломеризация циклопентанонового фрагмента
- 2. 2. 2. Нуклеофильное раскрытие экзоцикла Е
- 2. 3. Пирофеофорбид и его производные
- 2. 4. Бифункциональные агенты для диагностики и фотодинамической терапии опухолей на основе НРРН
- 2. 5. Вердинохлорины — новый класс ИК-фотосенсибилизаторов в ряду хлорофилла а
- 2. 6. Новые хлорины с конденсированными хиноксалиновым и бенз-имидазольным циклами
- 2. 7. Пути модификации винильной группы пирофеофорбида а
- 2. 8. Пурпурин 18 и циклические имиды
- 2. 8. 1. Восстановление ангидридного цикла
- 2. 8. 2. Синтез хлоринов с циклоимидным фрагментом
- 2. 8. 3. Фторсодержащие пурпуринимиды и их биологическая активность
- 2. 8. 4. Пурпуринимиды, содержащие ковалентно связанные остатки Сахаров
- 2. 8. 5. Конъюгаты пурпуринимидов с фуллеренами
- 2. 8. 6. тУ-Гидроксипурпуринимиды и их производные
- 2. 9. Фотосенсибилизаторы хлоринового ряда для ФДТ рака
- 3. Природные бактериохлорины и их химические модификации
- 3. 1. Амфифильные и водорастворимые производные бактериохлорофилла а
- 3. 2. Производные бактериопирофеофорбида а, содержащие различные заместители в пирроле А
- 3. 3. Бактериопурпурин — ключевое соединение в синтезе новых ФС бактериохлоринового ряда
- 3. 4. Циклические имиды в ряду бактериохлорофилла а.93 ¦
- 3. 5. Структурно-функциональные исследования производных бактериохлорофилла а
- 3. 6. Бактериопурпуринимиды с фторсодержащими заместителями и их биологическая активность
Список литературы
- Gross S., Gilead A., Scherz A., Neeman M., Salomon Y. Monitoring photodynamic therapy of solid tumors online by BOLD-contrast MR // Nature Medicine.-2003.-Vol. 9.-P. 1327−1331.
- Oseroff A., Shieh S., Frawley N., Blumenson L., Parsons J., Potter E., Graham A., Henderson B.W., Dougherty T.J. PDT for skin cancer: What do we know about how to go // 29th Annu, Meeting Am. Soc. Photobiol. Abstract. 2001. — P. 146.
- Henderson B.W., Gollnick S.O. Mechanistic principles of photodynamic therapy // In: Biomedical Photonics Handbook, Editor T. Vo-Dinh, Boca Raton: CRC Press. 2002.
- Keefe K.A., Tadir Y., Tromberg B., Berns M., Osann K., Hashad R., Monk B.J. Photodynamic therapy of high-grade cervical intraepithelial neoplasia with 5-aminolevulinic acid // Lasers Surg. Med. 2002. — Vol. 31. — P. 289−293.
- Gronlund-Pakkanen S., Pakkanen T.M., Koski E., Talja M., Ala-Opas M., Alhava E. Effect of photodynamic therapy on urinary bladder function: an experimental study with rats // Urol. Res. 2001. — Vol. 29. — P. 205−209.
- Wilson B.C., Jeeves W.P., Lowe D.M., Adam G. Light propagation in animal tissues in the wavelength range 375−825 nanometers // Prog.Clin. Biol. Res. -1984.-Vol. 170.-P. 115−132.
- Karmakova T., Feofanov A., Pankratov A., Kazachkina N., Nazarova A., Yakubovskaya R., Lebedeva V., Ruziyev R., Mironov A., Maurizot J.-C., Vigny
- P. Tissue distribution and in vivo photosensitizing activity of 13,15-N-(3-hydroxypropyl)cycloimide chlorin p6 and 13,15-N-methoxycycloimide chlorin p6 methyl ester // Photochem. Photobiol. B: Biology. 2006. — Vol. 82. — P. 28−36.
- Wainwright M. Photodynamic antimicrobial chemotherapy (PACT) // J. Antimicrob. Chemother. 1998. — Vol. 42. — P. 13−28.
- Krasnovsky A.A. Primary mechanisms of photoactivation of molecular oxygen. History of development and the modern status of research // Biochemistry. 2007. — Vol. 72. — P. 1065−1080.
- Crestini C., D’Auria M. Photodegradation of lignin: the role of singlet oxygen // J. Photochem. and Photobiol. A. 1996. — Vol. 101. — P. 69−73.
- Seen H., Spikes J., Kopecek P. Photodynamic crosslinking of proteins. I. Model studies using histidine- and lysine-containing N-(2-hydroxypropyl) methacrylamide copolymers // J. Photochem. and Photobiol. B. 1996. — Vol. 34. -P. 203−210.
- Girotti A.W. Photodynamic lipid peroxidation in biological systems // J. Photochem. and Photobiol. 1990. — Vol. 51. — P. 497−509.
- Piette J. New trends in photobiology: Biological consequences associated with DNA oxidation mediated by singlet oxygen // J. Photochem. and Photobiol. B. -1991.-Vol. 11.-P. 241−260.
- Baker A., Kanofsky J. Quenching of singlet oxygen by biomolecules from L1210 leukemia cells // J. Photochem. and Photobiol. 1992. — Vol. 55. — P.523−528.
- Moan J. On the diffusion length of singlet oxygen in cells and tissues // J. Photochem. and Photobiol. B. 1990. — Vol. 6. — P. 343−344.
- Daziano J., Steenken S., Chabannon C., Mannoni P., Chanon M., Julliard M. Photophysical and Redox Properties of a Series of Phthalocyanines: Relation with
- Their Photodynamic Activities on TF-1 and Daudi Leukemic Cells // Photochem. and Photobiol. 1996. — Vol. 64. — P. 712−719.
- Takemura Т., Ohta N., Nakajima S., Sakata I. Critical importance of the triplet lifetime of photosensitizer in photodynamic therapy of tumor. // Photochem. and Photobiol. 1989. — Vol. 50. — P. 339−344.
- Spiller W., Kliesch H., Wohrle D., Hackbarth S., Roder В., Schnurpfeil G. Singlet oxygen quantum yields of different photosensitizers in polar solvents and micellar solutions // Porphyrins and Phthalocyanines. 1998. — Vol. 2. — P. 145 158.
- Goff B.A., Bamberg M., Hasan T. Photoimmunotherapy of human ovarian carcinoma cells ex vivo // Cancer Res. 1991. — Vol. 51. — P. 4762−4767.
- Reddi E. Role of delivery vehicles for photosensitizers in the photodynamic therapy of tumours // J. Photochem. and Photobiol. B. 1997. — Vol. 37. — P. 189 195.
- Sears P., Wong C.H. Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition // Angew. Chem., Int. Ed. 1999. — Vol. 38. — P. 2301−2324.
- Krasnovsky A.A., Neverov K.V., Egorov S.Yu., Roder B., Lewald W. Photophysical studies of pheophorbide a and pheophytin a phosphorescence and photosensitized singlet oxygen luminescence // J. Photochem. Photobiol. B-Biol. -1990i — Vol. 5. — P. 245−254.
- Hynninen P.H. Multiple liquid-liquid partition: II. Theory of Martin-Synge distribution (MSD) // Acta Chem. Scand. 1973. — Vol. 27. — P. 1771−1780i
- Hynninen P.H., Wasielewski M.R., Katz J.J. Chlorophylls VI. Epimerization and enolization of chlorophyll’a and its magnesium free derivatives // Acta Chem. Scand. B. 1979. — Vol. 33. — P. 637−648.
- Gaffar R., Kermasha S., Bisakowski B. Biocatalysis of immobilized chlorophyllase in a ternary micellar system // J. Biotechnology. 1999. — Vol. 75. — P. 45−55.
- Scherz A., Salomon Y., Fiedor L. Preparation of chlorophyll" and bacteriochlorophyll conjugates and their applications as photosensitizers in photodynamic therapy and general diagnostics // 1994, EP Appl 584 552.
- Weller A., Livingston R. The reaction of chlorophyll in amines // J. Am. Chem. Soc. 1954. — Vol. 76. — P. 1575−1578.
- Willstater R., Stoll A. Untersuchungen uber chlorophyll // In Chlorophyll- Springer: Berlin. 1913.
- Hynninen P. H. Mechanism of the allomerization of chlorophyll: the inhibition of the allomerization by carotenoids pigments // Z. Naturforsch. 1981. — Vol. 36b.-P. 1010−1016.
- Seely G.R. The structure and chemistry of functional groups. // In «The Chlorophylls» L.P. Vernon, G.R. Seely. Academic Press. New York, London. -1966.-P. 67−109.
- Hynninen P.H. Chemistry of chlorophylls: modifications // In: Chlorophylls, Ed. H. Scheer, CRC Press, Boca Raton AnnArbor. Boston, London. 1991. — P. 145−209.
- Lotjonen S., Hynninen P.H. A convenient method for the preparation of chlorin and rhodin g7 trimethyl esters // Synthesis. 1980. — P. 541−543.
- Миронов А.Ф. Разработка сенсибилизаторов второго поколения, на основе природных хлорофиллов // Российский хим. журнал. 1998. — С. 2326.
- Belykh D.V., Karmanova L.P., Spirikhin L.V., Kuchin A.V. Synthesis of amide derivatives of chlorin e6 // Russ. J. Org. Chem. 2007. — Vol. 43. — P. 126 134.
- Sternberg E.D., Dolphin D., Bruckner С. Porphyrin-based photosensitizers for use in photodynamic therapy // Tetrahedron. 1998. — Vol. 54. — P. 4151−4202.
- Mody T.D. Pharmaceutical development and medical applications of porphyrin-type macrocycles // J. Porphyrins and Phthalocyanines. 2000. — Vol. 4.-P. 362−367.
- Pandey R.K. Recent advances in photodynamic therapy // J. Porphyrins and Phthalocyanines. 2000. — Vol. 4. — P. 368−373.
- MacDonald I., Dougherty T.J. Basic principles of photodynamic therapy // J. Porphyrins and Phthalocyanines. 2001. — Vol. 5. — P. 105−129.
- Taber S.W., Fingar V.H., Coots C.T., Wieman T.J. Photodynamic therapy using mono-L-aspartyl chlorine // Clin. Cancer. Res. 1998. — Vol. 4. — P. 27 412 746.
- Spikes J.D., Boomer J.C. Chlorophyll and related pigments as photosensitizers in biology and medicine // In: Chlorophylls, Scheer H. Ed. CRC Press: Boston. -1996. -P. 1182−1204.
- Bommer J., Ogden B. F. Tetrapyrrole therapeutic agents // U. S. Patent 4,693,885, Sept 15, 1987.
- Gomi S., Nishizuka T., Ushiroda O., Takahashi H., Sumi S. The structures of mono-L- aspartyl chlorin e6 and its related compounds // Heterocycles. 1998. -Vol. 48.-P. 2231−2243.
- A Thesis of J.A. Hargus. Naturally-derives porphyrin and chlorine photosensitizers for photodynamic therapy // Louisiana State University, December 2005.
- Belykh D.V., Tarabukina, Gruzdev I.V., Kodess M.I., Kuchin A.V. Aminomethylation of chlorophyll a derivatives using bis (N, N-dimethylamino) methane // J. Porphyrins and Phthalocyanines. 2009. — Vol. 13. — P. 949−956.
- Kuchin A.V., Ol’shevskaya V.A., Mal’shakova M.V., Belykh D.V., Petrovskii P.V., Ivanov O.G., Shtil A.A., Kalinin V.N. New carborane derivatives of chlorin e6 // Doklady Chemistry. 2006. — Vol. 409. — P. 135−138.
- Pandey R.K., Bellnier D.A., Smith K.M., Dougherty T.J. Chlorin and porphyrin derivatives as potential photosensitizers in photodynamic therapy // Photochem. Photobiol. 1991. — Vol. 53. — P. 65−72.
- Bellnier D.A., Henderson B.W., Pandey R.K., Potter W.R., Dougherty T.J. Murine pharmacokinetics and anti- tumor efficacy of the photodynamic sensitizers // J. Photochem. Photobiol. 1993. — Vol. 20. — P. 55−61.
- Kenner G.W., McCombie S.W., Smith K.M. Separation and oxidative degradation of chlorophyll derivatives // J. Chem. Soc., Perkin Trans. 1. 1973. -P. 2517−2523.
- Kozyrev A.N., Dougherty T.J., Pandey R.K. LiOH protonated allomerization of pyropheophorbide a. A convenient synthesis of 132-oxopyropheophorbide a and its unusual enolization // Chem. Commun. 1998. — P. 481−482.
- Pandey R.K., Goswami L.N., Chen Y., Gryshuk A., Missert J.R., Oseroff A., Dougherty T.J. Tumor-imaging and photodynamic therapy // Lasers in Surgery and Medicine. 2006. — Vol. 38. — P. 445−467:
- Profio A.E. Review of Fluorescence Diagnosis Using Porphyrins // Proc. SPIE. 1988. — Vol. 907. — P. 150−156.
- Monnier Ph., Savary M., Fontolliet C.H. Photodetection and photodynamic therapy of 'early' squamous cell carcinomas of the pharynx, oesophagus and tracheo-bronchial tree // Lasers in Med. Science. 1990. — Vol. 5. — P. 149−169.
- Scherz A., Brandis A., Mazor O., Salomon Y., Scheer H. Water-soluble bacteriochlorophyll derivatives and their pharmaceutical uses // PCT/IL Appl 152 900.-2002.
- Scherz A., Salomon Y., Fiedor L. Chlorophyll and bacteriochlorophyll derivatives, their preparation and pharmacological compositions comprising them //US Pat 5,650,292.- 1997.
- Kozyrev A.N., Alderfer J.L., Dougherty T.J., Pandey R.K. Synthesis of verdinochlorins: A new class of long-wavelength absorbing photosensitizers // Chem. Commun. 1998. — P. 1083−1084.
- Fuhrhop J.H. Irreversible reactions on the porphyrin periphery (excuding oxidations, reductions and photochemical reactions) // In: The Porphyrins, ed. D. Dolphin, Elsevier. 1978. — P. 131−159.
- Fischer H., Ebersberger J. Uber Mesorhodin und seinen Ubergang zu Chlorophyll porphyrinen, sowie Oxydation des Phylloerythrins // Justus Liebigs Ann. Chem. 1934. — Vol. 509. — P. 19−37.
- Morgan A.R., Rampersaud A., Keck R.W., Selmam S.H. Verdins: new photosensitizers for photodynamic therapy // Photochem. Photobiol. 1987. -Vol. 46.-P. 441−444.
- Sakata G., Makino K. Recent progress in the quinoxaline chemistry synthesis and biological activity // Heterocycles. — 1988. — Vol. 27. — P. 2481−2515.
- Sessler J.L., Hemmi G., Mody T.D., Murai T., Burrel A., Young S.W. Texaphyrins: synthesis and applications // Ass. Chem. Res. 1994. — P. 43−50.
- Smith K.M., Goff D.A., Simpson D.J. Meso- substitution of chlorophyll derivatives: direct route for transformation of bacteriopheophorbides d into bacteriopheophorbides c // J. Am. Chem. Soc. 1985. — Vol. 107. — P. 4946−4954.
- Sasaki S., Mizutani K., Kunieda M., Tamiaki H. Synthesis, modification and optical properties of C3-ethynylated chlorophyll derivatives // Tetrahedron Letters. 2008. — Vol. 49. — P. 4113−4115.
- Kolb H.C., Sharpless B. The growing impact of click chemistry on drug discovery // Drug Discovery Today (DDT). 2008. — Vol. 24. — P. 1128−1137.
- Kozyrev A.N., Alderfer J.L., Robinson В. Pirazolinyl and' cyclopropyl' derivatives of protoporphyrin IX and, chlorins related to chlorophyll a // Tetrahedron. 2003. — Vol. 59. — P. 499−504.
- Vicente M.G.H. Reactivity and functionalization of ?-substituted porphyrins and chlorins // The Porphyrin Handbook: Kadish K.M., Smith K. Ml, Guilard R. Eds.'.Academic. New York. 2000. — Vol. 1. — P. 149−199i
- Chatterjee A.K., Morgan J.P., Scholl M., Grubbs R.H. Synthesis of functionalized olefins by cross and ring-closing metatheses // J. Am. Chem. Soc. -2000. Vol. 122. — P. 3783−3784.
- Lin X., Sternberg E., Dolphin D. Cross-metathesis reactions of vinyl- chlorins* and porphyrins catalyzed by a «second generation» Grubbs1 catalyst // Chem. Commun. 2004. — P. 852−853.
- Fischer H., Stern A. Die chemie des pyrrols // Academ. Verlags.: Leipzig. -1940.-Vol. 2. P. 108'.
- Kenner G.V., McCombie S.W., Smith K.M. Pyrroles and related compounds // J. Chem. Soc., Perkin Trans 1. 1973. — P. 2517−2523.
- Lee S-J. H., Jagerovic N., Smith K.M. Use of the chlorophyll derivative, purpurin-18 for syntheses of sensitizers for use in photodynamic therapy // J. Chem. Soc., Perkin Trans 1. 1993. — P. 2369−2377.
- Mironov A.F., Kozyrev A.N., Brandis A.S. Sensitizers of second generation for photodynamic therapy of cancer based on chlorophyll' and bacteriochlorophyll derivatives // Proc. SPIE. 1993. — Vol. 1922. — P. 204−208.
- Zenkevich E., Sagun E., Knyukshto V., Shulga A., Mironov A., Efremova O., Bonnett R., Pinda Songca S., Kassem M. New fluorinated photosensitizers based on tetrakis (hydroxyphenyl) porphyrins // J. Photochem. Photobiol. B. 1996. -Vol. 33.-P. 171−180.
- Физер M., Физер Л. Реагенты для органического синтеза // М.: Мир. -1975.-Т. 6.-С. 186.
- Mironov A.F., Efremov A.V., Efremova O.A., Bonnett R., Martinez G. Chlorins with an exocyclic 8-lactone ring and their derivatives // J. Chem. Soc., Perkin Trans 1. 1998. — P. 3601−3608.
- Pandey R.K., Shiau F.-Y., Sumlin A. B, Dougherty T. J., Smith K. M. Syntheses of new bacteriochlorins and their antitumor activity // Bioorg. Med. Chem. Lett. 1994. — Vol. 4. — P. 1263−1267.
- Kozyrev A.N., Zheng G., Zhu C.F. Synthesis of stable bacteriochlorophyll a derivatives as potential photosensitizers for photodynamic therapy // Tetrahedron Letters. 1996. — Vol. 37. — P. 6431−6434.
- Mironov A.F., Lebedeva V.S., Efremova O.A. Int. Simp. «Problems and Trends of Photobiochemistry». Moscow. — 1997. — P. 47.
- Mironov A.F., Lebedeva V.S., Yakubovskaya R.I. Abstract Book of the «BIOS Europe-98». 1998. — P. 37.
- Prakash S, Yudin A.K. Perfluoroalkylation with organosilicon reagents // Chem. Rev. 1997. — Vol. 97. — P. 757−786.
- Banks R.E., Smart B.E., Tatlow J.C. Fluorinated inhalation anesthetics // Organofluorine chemistry principles and commercial applications. Plenum Press: — New York. — 1994.
- Gryshuk A.L., Graham A., Pandey S.K., Potter W.R., Missert J.R., Oseroff A., Dougherty T.J., Pandey R.K. Nonfluorinated photosensitizers for photodynamic therapy // Photochem. and Photobiology. 2002. — Vol. 76. — No. 5. — P. 555−559.
- Barondes S. H., Castronovo V., Cooper D.N.W., Cummings R. D., Drickamer K., Feizi T., Gitt M. A., Hirabayashi J., Hughes C., Kasai K., Leffler H., Liu F., Lotan R., Mercurio A. M., Monsigny M., Pillai S., Poirer F., Raz A., Rigby
- P.W.J., RiniJ. M., Wang J.L. Galectins: a family of animal f3-galactoside-binding lectins // Cell. 1994. — Vol. 76. — P.1 597−598.
- Zheng G., Dougherty T. J., Pandey R. K. Novel chlorin-diene building block by enyne metathesis: synthesis of chlorin-fullerene dyads // Chem. Commun. -1999. P. 2469−2470.
- Mironov A.F., Lebedeva V.S., Yakubovskaya R. I, Kazachkina Nil., Fomina G.I. Chlorins withsix-membered imide ring as prospective sensitizers for cancer PDT // Proc SPIE. 1999. — Vol. 3563. — P. 59−67.
- Feofanov A.V., Grichine A., Karmakova T., Pljutinskaya T., Lebedeva V., i
- Lebedeva V.S., Ruziev R.D., Popov A.V., Sebyakin Y.L., Mironov A.F. Synthesis of glycoconjugated chlorin p6 cycloimide // Mendeleev Commun. -2007.-Vol. 17.-P. 212−213.
- Pandey R.K., Zheng G. Porphyrins as Photosensitizers in Photodynamic Therapy // Edited by Karl M. Kadish- Kevin M. Smith and Roger Guilard. The Porphyrin Handbook. 2000. — P. 157−230.
- Eisner U. Some novel hydroporphyrins // 'J.Chem. Soc. 1957. — P. 3461 -3469.
- Scheer H. Chlorophylls // CRC Press, Boca Raton Ann Arbor. Boston London. — 1991.
- Миронов А.Ф., Ефремов A.B. Патент РФ «Способ получения бактериохлорофилла а» № 2,144.085 12.07. 1996.
- Tsygankov A.A., Laurinavichene T.V., Gogotov I.N. Laboratory scale photobioreactor // Biotechnol. Tech. 1994. — Vol. 8 — P. 575−578.
- Tsygankov A.A., Laurinavichene T.V., Bukatin V.E., Gogotov I.N., Hall D.O. Biomass production by continuous cultures of Rhodobacter capsulatus grown in various bioreactors // Biochem. Microbiol. 1997. — Vol. 33. — P. 485 490.
- Bonnett R. Chemical Aspects of Photodynamic Therapy // Gordon and Breach Science Publishers. UK. — 2000.
- Fiedor L., Rosenbach-Belkin V., Sai M., Scherz A. Preparation of tetrapyrrole-amino acid covalent complexes // Plan. Physiol. Biochem. 1996. -Vol. 34. — P. 393−398.
- Scherz A., Salomon Y., Brandis A., Scheer H. Palladium-substituted bacteriochlorophyll derivatives and use there of// PCT Pat WOOO/33 833. 2000.
- Henderson B.W., Sumlin A.B., Owcharczak B.L., Dougherty T.J. Bacteriochlorophyll a as photosensitiser for photodynamic treatment of transplantable murine tumors // Photochem. Photobiol. B-Biol. 1991. — Vol. 10. -P. 303−313.
- Vakrat-Haglili Y., Weiner L., Brumfeld V., Brandis A., Salomon Y., Mcllroy B., Wilson B.C., Pawlak A., Rozanowska M., Sarna T., Scherz A. // J. Am. Chem. Soc. 2005. — Vol. 127. — P. 6487−6497.
- Sasaki S., Tamiaki H. Synthesis and optical properties of bacteriochlorophyll-a derivatives having various C3-substituents on the bacteriochlorin 7i-system // J. Org. Chem. 2006. — Vol. 71. — No. 7. — P. 26 482 654.
- Mironov A.F., Kozyrev A.N., Brandis A.S. Sensitizers of second generation for photodynamic therapy of cancer based on chlorophyll and bacteriochlorophyll derivatives// Proc. SPIE. 1992. — Vol. 1922. — P. 204−208.
- Fischer, H., Lambrecht R., Mittenzwei H. Z. Physiol. Chem. — 1939. — Vol. l.-P. 253.
- Hartwich G., Fiedor L., Simonin I.,.Cmiel E., Schafer W., Noy D., Scherz A., ScheerH1. Metal-substituted bacteriochlorophylls. 1. Preparation and influence of metal and’coordination on, spectra // J. Am. Chem. Soc. 1998. — Vol. 120. — P. 3675−3683.
- Waielewski M.R., Svec W.A. Synthesis of covalently linked dimeric derivatives of chlorophyll a, pyrochlorophyll a1, chlorophyll b, and bacteriochlorophyll a // J. Org. Chem. 1980. — Vol: 45. — P. 1969−1974.
- Gryshuk A.L., Chen Y., Potter W., Ohulchansky T., Oseroff A., Pandey R.K. In vivo stability and photoidynamic efficacy of fluorinated bacteriopurpurinimides derived from* bacteriochlorophyll-a // J. Med. Chem. -2006.-Vol. 49.-P. 1874−1881.
- Kessel D, Luo Y., Deng Y., Chang C. K. The role of subcelular localization in initiation of apoptosis by photodynamic therapy // Photochem. Photobiol. -1997. Vol. 65. — No. 3. — P. 422−426.
- Almeida R. D., Manadas B. J., Carvalho A. P., Duarte С. B. Intracellular signaling mechanisms in photodynamic therapy // Biochim. Biophys. Acta. -2004. P. 59−86.
- Mironov A.F., Grin M.A., Nochovny S.A., Toukach F.V. Novel cycloimides in the chlorophyll a series // Mendeleev Commun. 2003. — Vol. 13. — No. 4. — P. 156−158.
- Mironov A.F., Grin M.A., Tsiprovskiy A.G., Kachala V.V., Karmakova T.A., Plyutinskaya A.D., Yakubovskaya R.I. New bacteriochlorin derivatives with a fused N-aminoimide ring // J. Porphyrins Phthalocyanines. 2003. — Vol. 7. — P. 725−730.
- Remy D.E., Whitfield R.E., Needles H.L. Study of the decomposition rates of aqueous peroxydisulphate in the presence of selected amides and N-acetylamino-acids // J. Chem. Soc., Chem. Commun. 1967. — P. 681−695.
- McCarthy A.R., Ollis W.D., Barnes A.N. Cyclic meso-ionic compounds. Part VI. Synthesis, spectroscopic properties, and dipole moments of the isosydnones // J. Chem. Soc. (B). 1969. — P. 1185−1193.
- Belnaik K., Domagaliva E., Nopkala H. Cyclic hydrazides of dicarboxylic aromatic and heterocyclic acids. VI. Sulfamide and sulfhydrazide derivatives of the phthalazine series // Roczniki Chem. 1967. — Vol. 41. — P. 831−843.
- Миронов А.Ф., Грин M.A., Ципровский А. Г., Дзарданов Д. В., Головин К. В., Феофанов А. В., Якубовская Р. И. Гидразиды в ряду бактериохлорофилла а, обладающие фотодинамической активностью, и способ их получения. Патент РФ № 2 223 274. — 2004 г.
- Yoshikawa Т.Т. Antimicrobial resistance and aging: beginning of the end of the antibiotic era// Am. Geriatr. Soc. 2002. — Vol. 50 (7 Suppl). — P. 226−229.
- Sanglard D. Resistance of human fungal pathogens to antifungal drugs // Curr. Opin. Microbiol. 2002. — Vol. 5. — No. 4. — P. 379−385.
- Malik Z., Hanania J., Nitzan Y. Bactericidal effects of antimicrobial drugs // J. Photochem. Photobiol. B: Biol. 1990. — Vol. 5. — P. 281−293.
- Hawthorne M.. F. The Role of Chemistry in the Development of Boron Neutron Capture Therapy of Cancer // Angew. Chem. Int. Ed. Engl. 1993. — Vol. 32. — P. 950−984. ' 1
- Soloway A. I-I., Tjarks W., Barnum B. A., Rong F.-G., Barth R. F., Codogni I: Mi, Wilson J, G- The chemistry of neutron capture therapy // Chem. Rev. -1998.-Vol. 98.-P. 1515−1562.
- Bregadze V. I., Sivaev I. B, Glazun S. A. Polyhedral boron compounds as potential diagnostic and therapeutic antitumor agents // Anti-Cancer Agents in Medicinal Chemistry. 2006. — Vol. 6. — P. 75−109.
- Bregadze V. I., Sivaev I. B., Gabel D., Wohrle D. Polyhedral boron derivatives of porphyrins and phthalocyanines // J. Porphyrins and Phthalocyanines. 2001. — Vol. 5. — P. 767−781.
- Renner M. W., Miura M., Easson M. W., Vicente M. G. H. Recent Progress in the Syntheses and Biological Evaluation of Boronated Porphyrins for Boron Neutron-Capture Therapy // Anti-Cancer Agents in Medicinal Chemistry. 2006. -Vol. 6.-P. 145−157.
- Fabris C., Jori G., Giuntini F., Roncucci G. Photosensitizing properties of a boronated phthalocyanine: studies at the molecular and cellular level // Photochem. Photobiol. 2001. — Vol. 64. — P. 1−7.
- Tsaiyova O., Semioshkin A., Wohrle D., Bregadze V. Novel Polyhedral Boron Derivatives of Phthalocyanines // Porphyrins Phtalocyanines. 2005. -Vol. 9. — P. 268−274.
- Grin M.A., Semioshkin A.A., Titeev R.A., Nizhnik E.A., Grebenyuk J.N., Mironov A.F., Bregadze V.I. Synthesis of a cycloimide bacteriochlorin p conjugate with the closo-dodecaborate anion // Mendeleev Commun. 2007. -Vol. 17.-No. l.-P. 14−15.
- Sivaev I. B., Bregadze V.I. Chemistry of cobalt bis (dicarbollides).A review // Collect. Czech. Chem. Commun. 1999. — Vol. 64. — P. 783−805.
- Sivaev I. B., Starikova Z. A., Sjoberg S., Bregadze V. I. Synthesis of functional derivatives of 3,3'-Co (l, 2-C2B9Hn)2. anion // J. Organomet. Chem. — 2002.-Vol. 649. — P. 1−8.
- Olejniczak A. B., Plesek J., Kriz O., Lesnikowski Z. A Nucleoside Conjugate Containing a Metallacarborane Group and Its Incorporation into a DNA Oligonucleotide // J. Angew. Chem. Int. Ed. 2003. — Vol. 42. — P. 5740−5743.
- Olejniczak А. В., Plesek J., Lesnikowski Z. Nucleoside conjugate containing metallacarborane group and its incorporation into DNA-oligonucleotide // Chem. Eur. J. 2007.-Vol. 13.-P. 311−318.
- Hao E., Vicente M. G. H. Expeditious synthesys of porphyrin-cobaltocarborane conjugates // Chem. Commun. 2005. — P. 1306.
- Hao E., Jensen T. J., Courtney В. H., Vicente M. G. H. Synthesis and Cellular Studies of Porphyrin-Cobaltacarborane Conjugates // Bioconjugate Chem. 2005. — Vol. 16. — P. 1495−1502.
- Hao E., Sibrian-Vazquez M., Serem W., Garno J. C., Fronczek F. R."Vicente M. G. H. Enhanced cellular uptake with a cobaltacarborane-porphyrin-HIV-1 Tat 48−60 conjugate // Chem. Eur. J. 2007. — Vol. 13. — P: 9035−9039.
- Mironov A.F., Grin M.A., Tsiprovskiy A.G. Synthesis of the first N-hydroxycycloimide in bacteriochlorophyll a series // J. Porphyrins Phthalocyanines. 2002. — Vol. 6. — No. 5. — P. 358−361.
- Лебедева B.C. Синтез сенсибилизаторов второго поколения с функциональными группами для получения конъюгатов направленногодействия к злокачественным опухолям // Диссертация на соиск. уч. степени канд. хим. наук. Москва. — 1999.
- Меерович И.Г., Грин М. А., Меерович Г. А., Ципровский А.Г., МассI
- Mironov A.F., Grin М.А., Dzardanov D.V., Golovin K.V., Shim Y.K. Synthesis of a vinyl-containing analogue of bacteriochlorophyll a // Mendeleev Commun. 2001. — Vol. 11. — No. 6. — P. 205−206.
- Grin M.A., Mironov A.F., Shtil A.A. Bacteriochlorophyll a and Its Derivatives: Chemistry and Perspectives for Cancer Therapy // Anti-Cancer Agents in Medicinal Chemistry. 2008. — Vol. 8. — No. 6. — P. 683−697.
- Mironov A.F., Grin M.A. Synthesis of Chlorin and Bacteriochlorin Conjugates for Photodynamic and Boron Neutron Capture Therapy // J. Porphyrins Phthalocyanines. 2008. — Vol. 12. — P. 1163−1172.
- Wang Q., Chan T.R., Hilgraf R., Fokin V.V., Sharpless K.B., Finn M.G. Bioconjugation by copper (I)-catalyzed azide-alkyne 3+2. cycloaddition // JACS.- 2003.-Vol. 125.-P. 3192−3193.
- Chen Q., Yang F., Du Y. Synthesis of a C3-symmetric (l-6)-N-acetyl-|3-D-glucosamine octadecasaccharide using click chemistry // Carbohydrate Research.- 2005. Vol. 340. — P. 2476 — 2482.
- Link A.J., Tirrell D.A. Cell Surface Labeling of Escherichia coli via copper (I)-catalyzed 3+2. cycloaddition// JACS. 2003. — Vol. 125. — P. 1 116 411 165.
- Silva A.M.G., Tome A.C., Neves M.G.P.M.S., Cavaleiro J.A.S., Perrone D., Dondoni A. Porphyrins in 1,3-Dipolar Cycloadditions with Sugar Azomethine Ylides. Synthesis of Pyrrolidinoporphyrin Glycoconjugates. // Synlett. 2005. — P. 857−859.
- Bock V.D., Hiemstra H., Maarseveen J.H. Cul-catalyzed alkyne-azide «click» cycloadditions from a mechanistic and synthetic perspective // Eur. J. Org. Chem. 2006.-P. 151−167.
- Grin M.A., Lonin I. S., Makarov A.I., Lakhina A.A., Toukach F.V., Kachala V.V., Orlova A.V., Mironov A.F. Synthesis of chlorin-carbohydrate conjugates by «click chemistry // Mendeleev Commun. 2008. — Vol. 18. — No. 3. — P. 135−137.
- Dieck H.A., Heck F.R. Palladium Reagents in Synthesis // J. Organomet. Chem. 1975. — Vol. 93. — P. 259−263.
- Cassar L. Synthesis of aryl- and’vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes // J. Organomet. Chem. 1975. — Vol. 93. — P. 253−257.
- Sonogashira K., Tohda Y., HagiharaN. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and-bromopyridines // Tetrahedron Lett. 1975. — Vol. 16. — P. 4467−4470.
- Sonogashira K., Pd-catalyzed cross-coupling reaction // In: Metal-catalyzed cross-coupling reactions Eds: F. Diederich, P.J. Stang, Eds Wiley-VCH. -Weinheim, Germany. 1998. — P. 203−229.
- Marsden J.A., Haley M.M. Cross-coupling reactions to sp carbon atoms // In: Metal-catalyzed cross-coupling reactions. A. de Meijere, F. Diederich, Eds: Wiley-VCH. Weinheim, Germany. — 2004. — P. 319−345.
- Wagner R.W., Ciringh Y., Clausen C., Lindsey J.S. Investigation and Refinement of Palladium-Coupling Conditions for the Synthesis of Diarylethyne-Linked Multiporphyrin Arrays // Chem. Mater. 1999. — Vol. 11. — P. 2974−2983.
- Chaignon F., Torroba J., Blart E., Borgstrom M., Hammarstrom L., Odobel F. Distance-independent photoinduced energy transfer over 1.1 to 2.3 nm in ruthenium trisbipyridine-fullerene assemblies // New J. Chem. 2005. — Vol. 29. -P. 1272−1284.
- Etheve-Quelquejeu M., Tranchier J.-P., Rose-Munch F., Rose E., Naesens L., Clereq E.D. n6-(Arene)tricarbonylchromium and Manganese Complexes Linked to 2'-Deoxyuridine // Organometallics. 2007. — Vol. 26. — P. 5727−5730.
- Sasaki Т., Morin J.-F., Lu M. Synthesis of a Single-Molecule Nanotruck // J. M. Tour. Tetrahedron Letters. 2007. — Vol. 48. — P. 5817−5820.
- Bregadze V.I., Sivaev I.B., Lobanova I.A., Titeev R.A., Brittal D.I., Grin M.A., Mironov A.F. Conjugates of boron clusters with derivatives of natural chlorin and bacteriochlorin // Applied Radiation and Isotopes. 2009. — Vol. 67 -P. 101−104.
- Gottlieb H.E., Kotlyar V., Nudelman A. NMR chemical shifts of common laboratory solvents as trace impurities // J. Org. Chem. 1997. — Vol. 62. — P. 7512−7515.