Синтез новых производных клозо-додекаборатного аниона для потенциального использования в бор-нейтронозахватной терапии рака
Диссертация
Молекула" «характеризуется высокой симметрией борного остова, близкой к сферической, что обуславливает его основные достоинства и недостатки. Так, благодаря делокализации валентных электронов, /слозо-додекаборатный анион стабилизирован и проявляет свойства, характерные для ароматических систем, что определяет его устойчивость к действию различных окислителей и растворам сильных кислот. С другой… Читать ещё >
Список литературы
- Hawthorne M.F. The Role of Chemistry in the Development of Boron Neutron Capture Therapy of Cancer// Angew. Chem. Int. Ed. 1993. — V. 32. — P. 950 984.
- Soloway A. H, Tjarks W, Barnum B. A, Rong F.-G., Barth R.F., Codogni I. M,
- Wilson J.G. The Chemistry of Neutron Capture Therapy // Chem. Rev. 1998. -V. 98. — P. 1515−1562.
- Farr L. E, Sweet W.H., Robertson J. S, Foster C. G, Locksley H.B., Sutherland D. L, Mendelsohn M. L, Stickley E.E. Neutron capture therapy withboron in the treatment of glioblastoma multiforme // AJR. 1954. — V. 71. — P. 279−293.
- Barth R. F. A critical assessment of boron neutron capture therapy: an overview //lournal of Neuro-Oncology. 2003. — V. 62. — P. 1−5.
- Kabalka G. W, Yao Min-Liang. The Synthesis and Use of Boronated Amino Acids for Boron Neutron Capture Therapy // Anti Cane. Agents Med. Chem. -2006. V. 6 — № 2 — P. 111−125.
- Wang F, Wang Y., Wang X, Huaxue Yingyong. 1998,15(5), 111
- Gu Weixing, Ozerov O.V. Exhaustive Chlorination of Bi2Hi2.2- without Chlorine Gas and the Use of [B12Cli2]2″ as a Supporting Anion in Catalytic
- Hydrodefluorination of Aliphatic C~F Bonds // Inorg.Chem. 2011. — V. 50. -P. 2726−2728.t л ^
- Dudenkov L.V., Zhizhin K.Yu., Chernyavskii A.S., Katser S.B. at al. Synthesis and Crystal Structure of l, 7-(NH3)2Bi2HI0 • 0.5H20 // Russ. J. Inorg. Chem. -2000.- V. 45.-P. 1864−1869.
- Peymann Т., Lork E., Schmidt M., Noth H. and Gabel D. N-Alkylation of Ammine—Undecahydro-C7aso-dodecaborate (l-) // Chem. Ber. 1997. — V. 130. — P. 795−799.
- El-Zaria M.E., Genady A.R. and Nakamura H. Synthesis of triazolyl methyl-substituted amino- and oxy-undecahydrododecaborates for potential application in boronneutron capture therapy // New J.Chem. 2010. — V. 34. — P. 16 121 622.
- Kolb H.C., Finn M.G. and Sharpless K.B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions // Angew. Chem., Int. Ed. 2001. — V. 40.- P. 2004−2021.
- Nakagawa Т., Aono K. Syntheses of Chlorpromazine Undecahydrododecaborate and Nonahydro-decaborate-Promising Agents for Neutron Capture Therapy of Malignant Melanoma // Chem. Pharm.Bull. 1976. — V. 24. — P. 778−781.
- Hoffmann S., Justus E., Ratajski M., Lork E., Gabel D. B12Hn-containing guanidinium derivatives by reaction of carbodiimides with H3N-Bi2Hn (l-). A new method for connecting boron clusters to organic compounds // J.Organomet.Chem. 2005. — P. 2757−2760.
- Sivaev LB., Bruskin A.B., Nesterov V.V., Antipin M.Yu., Bregadze V.l. and Sjoberg S. Synthesis of Schiff Bases Derived from the Ammoniaundecahydro-closo-dodecaborate (l-) Anion, Bi2HnNHCHR.-, and Their Reduction into
- Monosubstituted Amines B12H11NH2CH2R.-: A New Route to Water Soluble
- Agents for BNCT // J. Inorg. Chem. 1999. — V. 38. — P. 5887−5893.
- Bregadze V.l., Sivaev I.B., Bruskin A.B., Sjoberg S., Nesterov V.V. Synthesis of schiff bases and monoalkylamino derivatives of closo-dodecaborate (2-) anion // Contemporary Boron Chemistry (M. Davidson). 2000. — P. 162.
- Orlova A., Bruskin A., Sivaev I., Sjoberg S., Lundqvist H., Tolmachev V.1
- Radio-iodination of monoclonal antibody using potassium ~ I.-(4-isothiocyanatobenzylammonio)-iodo-decahydro-closo-dodecaborate (iodo-DABI) // Anticancer Res. 2006. — P. 1217−23.1
- Genady A.R., El-Zaria M.E., Gabel D. Non-covalent assemblies of negatively charged boronated porphyrins with different cationic moieties // l.Organomet.Chem. 2004. — P. 3242−3250.
- Koo M., Ozawa T., Santos R. A., Lamborn K. R., Bollen A. W., Deen D. F., Kahl S. B. Synthesis and Comparative Toxicology of a Series of Polyhedral Borane Anion-Substituted Tetraphenyl Porphyrins // J. Med. Chem. 2007. — V. 50.-P. 820−827.
- Ozawa T., Santos R. A., Lamborn K. R., Bauer W. F., Koo M.-S., Kahl S. B., Deen D. F. In Vivo Evaluation of the Boronated Porphyrin TABP-1 in U-87 MG Intracerebral Human Glioblastoma Xenografts // Molecular Pharm. 2004. — V. 1.-issue5.-P. 368−374.1. OA
- Barth R.F., Coderre J.A., Graga M., Vicente H., Blue T.E. Boron Neutron Capture Therapy of Cancer: Current Status and Future Prospects // Clin. Cancer Res. 2005. — V. 11. — P. 3987−4002.
- Knoth W. H., Sauer J. C., England D. C., Hertler W. R., Muetterties E. L. Chemistry of Boranes. XIX.1 Derivative Chemistry of B10Hjo."2 and [Bi2Hi2]~2// J. Am. Chem. Soc. 1964. — V. 86. — P. 3973−3983.
- Tolpin E.I., Wellum G.R., Berley S.A. Synthesis and Chemistry of Mercaptoundecahydro-closo-dodecaborate2(-) // J. Inorg. Chem. 1978. — V. 17. — P.2867−2873.
- Gabel D., Moller D., Harfst S., Roesler J., Ketz H. Synthesis of S-alkyl and S-acyl derivatives of mercaptoundecahydrododecaborate, a possible boron carrier for neutron capture therapy // J. Inorg. Chem. 1993. — V. 32. — P. 2276−2278.1. OQ
- Boronated Liposomes for Neutron Capture Therapy // Org. Lett. 2007. — V. 9. — P. 323−326.
- Nakamura H., Lee Jong-Dae, Ueno M., Miyajima Y., Ban H. S. Synthesis of cIoso-Dodecaboryl Lipids and their Liposomal Formation for Boron Neutron Capture Therapy // NanoBioTechnology. 2007. — V. 3. — P. 135−145.
- Nakamura H., Ueno M., Ban H. S., Nakai K., Tsuruta K., Kaneda Y., Matsumura A. Development of boron nanocapsules for neutron capture therapy // Appl Radiat Isot. 2009. — V. 67. — P.84−87.
- Ueno M., Ban H.S., Nakai K., Inomata R., Kaneda Y. Dodecaborate lipid liposomes as new vehicles for boron delivery system of neutron capture therapy // Bioorg.Med.Chem. 2010. — V. 18. — P. 3059−3065.
- Kusaka S., Hattori Y., Uehara K., Asano T., Tanimori S., Kirihata M. Synthesis of optically active dodecaborate-containing 1-amino acids for BNCT // Appl.Radiat.Isotopes. 2011. — V. 69(12). — P. 1768−1770.
- Hattori Y., Kusaka S., Mukumoto M., Uehara K., Asano T., Suzuki M., Masunaga S., Ono K., Tanimori S., Kirihata M. Biological Evaluation of
- Dodecaborate-Containing L-Amino Acids for Boron Neutron Capture Therapy // J.Med.Chem. 2012. — V. 55. — P. 6980−6984.
- Lechtenberg B., Gabel D. Synthesis of a (Bi2HnS)2- containing glucuronoside as potential prodrug for BNCT // l.Organomet.Chem. 2005. — V. 690. — P. 27 802 782.1. AO
- Fabris C., lori G., Giuntini F., Roncucci G. Photosensitizing properties of a boronated phthalocyanine: studies at the molecular and cellular level // 1. Photochem. Photobiol. B. 2001. — V. 64. -1.1. — P. 1−7.
- Sivaev I. B., Bregadze V. I., Sjoberg S. Chemistry of closo-Dodecaborate Anion B12H12.2″: A Review // Collect. Czech. Chem. Commun. 2002. — V. 67. — P. 687−703.
- Peymann T., Knobler C. B. and Hawthorne M. F. A Study of the Sequential Acid-Catalyzed Hydroxylation of Dodecahydro-closo-dodecaborate (2-) // Inorg. Chem. 2000. — V. 39. — P. 1163−1170.
- Maderna A., Knobler C. B., Hawthorne M. F. Twelve fold Functionalization ofOan Icosahedral Surface by Total Esterification of B12(OH)i2.~~: 12(12)-Closomers // Angew. Chem. Int. Ed. 2001. — V. 40. — № 9. — P. 1661−1664.
- Bayer M.I., Hawthorne M. F. An Improved Method for the Synthesis of closo-BI2(OH)I2."2 // Inorg. Chem. 2004. — V. 43. — P. 2018−2020.
- Bondarev O., Hawthorne M. F. Catalytic hydroxylation of Closo-B12H12.2" — adaptation of the Periana reaction to a polyhedral borane // Chem.Com. 2011. -V. 47. — P. 6978−6980.
- Семиошкин А.А., Петровский П.В, Сиваев И. Б, Баландина Э. Г., Брегадзе В. И. Синтез и изучение методом ЯМР гидроксиундекагидро-клозо-додекаборатдианиона B12Hi2OH.2″ и продуктов его ацилирования // Изв.Акад.Наук- 1996. № 3. — стр. 722−725.
- Semioshkin A, Sivaev I., Bregadze V. Cyclic oxonium derivatives of polyhedral boron hydrides and their synthetic applications // Dalton Trans. 2008. — P. 977−992.
- Semioshkin A, Nizhnik E, Godovikov I, Starikova Z, Bregadze V. Reactions of oxonium derivatives of B12H12.~ with amines: Synthesis and structure of novel B12-based ammonium salts and amino acids // J Organomet. Chem. -2007. V. 692. — P. 4020−4028.
- Schaffran T, Lissel F, Samatanga B, Gabel D. Dodecaborate cluster lipids with variable headgroups for boron neutron capture therapy: Synthesis, physical-chemical properties and toxicity // J Organomet. Chem. 2009. — V. 694. — P. 1708−1712.
- RejmanJ., WagenarA., EngbertsJ.B., HoekstraD. Characterization and transfection properties of lipoplexes stabilized with novel exchangeable polyethylene glycol-lipid conjugates // Biochim. Biophys. Acta. 2004. — V. 1660. — P. 41−52.
- Romanova N.N., Gravis A.G., Kudan P.V., Bundel Y.G. Solvent-free stereoselective synthesis of P-aryl-f3-amino acid esters by the Rodionov reaction using microwave irradiation // Mendeleev Comm. 2001. — V. 11. — 1. 1. — P. 26−27.
- Grayson J.I., Roos J., Osswald S. Development of a Commercial Process for (S)-(3-Phenylalanine // Org. Process Res. Dev. 2011. — V. 15. — P. 1201−1206.
- Taurog A., Abraham S., Chaikoff I. L. Synthesis of Some O-Glucuronides and O-Glucosides of Phenolic Amino Acids // J. Am. Chem. Soc. 1953. V. 75 (14). — P. 3473−3477.
- 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 afused N-aminoimide ring, J. Porphyrins Phthalocyanines 2003. — V. 7. — I. 11.- P. 725−730.
- Mironov A.F., Grin M.A., Tsyprovskiy A.G., Titeev R.A., Nizhnik E.A., Lonin I.S. Synthesis of cationic bacteriochlorins // Mendeleev Comm. 2004. — № 5. -P. 204−207.
- Грин M.A., Титеев P.A., Бакиева O.M., Бриттал Д. И., Лобанова И. А., Сиваев И. Б., Брегадзе В. И., Миронов А. Ф. Новый борсодержащий коньюгат на основе циклоимида бактериохлорина р // Изв. АН, Сер.Хим. -2008. № 10, Р. 2188−2190.
- Grin М.А., 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 Comm. 2008. — № 18. — P. 135−137.
- Schinazi R.F., Prusoff W.H. Synthesis of 5-(dihydroxyboryl)-2'-deoxyuridine and related boron-containing pyrimidines // J. Org. Chem. 1985. — V. 50. — P. 841−845.
- Olejniczak A.B., Plesek J., Lesnikowski Z. J. Nucleoside-Metallacarborane Conjugates for Base-Specific Metal Labeling of DNA // Chem- Eur. J. 2007. -V. 13.-P. 311−318.
- Wojtczak B. A., Andrysiak A., Gruner B., Lesnikowski Z. J. «Chemical Ligation»: A Versatile Method for Nucleoside Modification with Boron Clusters // Chem-Eur. J. 2008. — V. 14. -1. 34. — P. 10 675−10 682.
- Holmes R.E., Robins R.K. Purine Nucleosides. VII. Direct Bromination of Adenosine, Deoxyadenosine, Guanosine, and Related Purine Nucleosides // 1. Am. Chem. Soc. 1964. — V. 86 (6). — P. 1242−1245.
- Sheu C., Foote C.S. Reactivity toward Singlet Oxygen of a 7,8-Dihydro-8-oxoguanosine («8-Hydroxyguanosine») Formed by Photooxidation of a Guanosine Derivative // 1. Am. Chem. Soc. 1995. — V. 117 (24). — P. 64 396 442.73
- Farras P., Teixidor F., Sillanpaa R., Vinas C. A convenient synthetic route to useful monobranched polyethoxylated halogen terminated 3,3-Co (l, 2-C2B9Hn)2.~ synthons // Dalton Trans. 2010. — V. 39. — P. 1716−1718.
- Crossley E.L., Rendina L.M. // RACI Inorganic Conference, Habart (Tasmania), February 2007.
- Knoth W. H ., Miller H.C., Sauer I.C., Balthis J.H., Chia Y.T., Mueterties E.L. Chemistry of Boranes. IX. Halogenation of B10Hi0~" and Bi2H.2~" // Inorg. Chem. 1964. — V. 3. — P. 159−167.
- Bernard R., Cornu D., Gruner B., Dozol J.F., Miele P., Bonnetot B. Synthesis of B12H12 based extractants and their application for the treatment of nuclear wastes // J. Organomet. Chem. 2002. — V. 657. — № 1−2. — P. 83−90.79
- Peymann T., Knobler C.B., Hawthorne M.F. Synthesis of Alkyl and Aryl Derivatives of closo-Bi2Hi22″ by the Palladium-Catalyzed Coupling of closo-Bi2HnI2″ with Grignard Reagents // Inorg. Chem. 1998. — 37 (7). — P. 15 441 548.80
- Himmelspach A., Finze M., Voge A., Gabel D., Cesium and Tetrabutylammonium Salt of the Ethynyl-closo-dodecaborate Dianion // ZAAC. 2012. — V. 638 (3−4). — P. 512−519.
- Sheldrick G.M., A short history of SHELX // Acta Cryst. A. 2008. — V. 64. -P. 112−122.