New approach to incorporation of boron in tumor-seeking molecules

Applied Radiation and Isotopes

Volumn 67, Issue 7-8 SUPPL., 2009, Pages

  Sivaev, I B ^a   Semioshkin, A A ^a   Bregadze, V I ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Biomolecules; Boron neutron capture therapy; Cyclic oxonium derivatives; Functionalization; Polyhedral boron hydrides

Indexed keywords

BORON HYDRIDES; BORON NEUTRON CAPTURE THERAPY; CYCLIC OXONIUM DERIVATIVES; FUNCTIONALIZATION; NEW APPROACHES; OXONIUM; POLYHEDRAL BORON HYDRIDES; STARTING MATERIALS;

BIOMOLECULES; BORON COMPOUNDS; HYDRIDES; NEUTRONS; TUMORS;

BORON;

BORON DERIVATIVE; CYCLIC OXONIUM DERIVATIVE; POLYHEDRAL BORON ANHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER THERAPY; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; NEUTRON CAPTURE THERAPY; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING;

BORON COMPOUNDS; BORON NEUTRON CAPTURE THERAPY; DRUG DESIGN; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS; RADIATION-SENSITIZING AGENTS;

EID: 67649440670     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apradiso.2009.03.022     Document Type: Article

References (33)

1. 2-. J. Organomet. Chem. 689 (2004) 2581-2585
2. Grin M.A., Semioshkin A.A., Titeev R.A., Nizhnik E.A., Grebenyuk J.N., Mironov A.F., and Bregadze V.I. Synthesis of a cycloimide bacteriochlorin p conjugate with the closo-dodecaborate anion. Mendeleev Commun. 17 (2007) 14-15
3. Grin M.A., Titeev R.A., Bakieva O.M., Brittal D.I., Lobanova I.A., Sivaev I.B., Bregadze V.I., and Mironov A.F. A novel boron-containing conjugate on the base of bacteriochlorin p cycloimide. Izv. Akad. Nauk, Ser. Khim. 2190-2192 (2008)
4. Hao E., Jensen T.J., Courtney B.H., and Vicente M.G.H. Synthesis and cellular studies of porphyrin-cobaltacarborane conjugates. Biooconjugate Chem. 16 (2005) 1495-1502
5. Hao E., Sibrian-Vazquez M., Serem W., Garno J.C., Fronczek F.R., and Vicente M.G.H. Synthesis aggregation and cellular investigations of porphyrin-cobaltacarborane conjugates. Chem. Eur. J. 13 (2007) 9035-9047
6. Hao E., Zhang M., E W., Kadish K.M., Fronczek F.R., Courtney B.H., and Vicente M.G.H. Synthesis and spectroelectrochemistry of N-cobaltacarborane porphyrin conjugates. Bioconjugate Chem. 19 (2008) 2171-2181
7. Hawthorne M.F. The role of chemistry in the development of boron neutron capture therapy of cancer. Angew. Chem. Int. Ed. Engl. 32 (1993) 950-984
8. Li H., Fronczek F.R., and Vicente M.G.H. Synthesis and properties of cobaltacarborane-functionalized Zn(II)-phthalocyanines. Tetrahedron Lett. 49 (2008) 4828-4830
9. Li H., Fronczek F.R., and Vicente M.G.H. Cobaltacarborane-phthalocyanine conjugates: syntheses and photophysical properties. J. Organomet. Chem. 694 (2009) 1607-1611
10. Olejniczak A.B., Plešek J., Kŕiz O., and Lesnikowski Z.J. A nucleoside conjugate containing a metallacarborane group and its incorporation into a DNA oligonucleotide. Angew. Chem. Int. Ed. 42 (2003) 5740-5743
11. Olejniczak A.B., Plešek J., and Lesnikowski Z.J. Nucleoside-metallacarborane conjugates for base-specific metal labeling of DNA. Chem. Eur. J. 13 (2007) 311-318
12. Orlova A.V., Kondakov N.N., Zinin A.I., Kimel B.G., Kononov L.O., Sivaev I.B., and Bregadze V.I. A uniform approach to the synthesis of carbohydrate conjugates of polyhedral boron compounds as potential agents for boron neutron capture therapy. Russ. J. Bioorg. Chem. 32 (2006) 568-577
13. Orlova A.V., Kondakov N.N., Kimel B.G., Kononov L.O., Kononova E.G., Sivaev I.B., and Bregadze V.I. Synthesis of novel derivatives of closo-dodecaborate anion with azido group at the terminal position of the spacer. J. Appl. Organomet. Chem. 21 (2007) 98-100
14. Plešek J., Heřmanek S., Franken A., Cisarova I., and Nachtigal C. Dimethyl sulfate induced nucleophilic substitution of the [bis(1,2-dicarbollido)-3-cobalt(1-)]ate ion. Synthesis, properties and structures of its 8,8′-μ-sulfato 8-phenyl and 8-dioxane derivatives. Collect. Czech. Chem. Commun. 62 (1997) 47-56
15. Schaffran T., Lissel F., Samatanga B., Karlsson G., Burghardt A., Edwards K., Winterhalter M., Peschka-Süss R., Schubert R., and Gabel D. Dodecaborate cluster lipids with variable headgroups for boron neutron capture therapy: synthesis, physical-chemical properties and toxicity. J. Organomet. Chem. 694 (2009) 1708-1712
16. 2- groups. J. Porphyrins Phthalocyanines 10 (2006) 1293-1300
17. 12-based ammonium salts and amino acids. J. Organomet. Chem. 692 (2007) 4020-4028
18. Semioshkin A.A., Osipov S.N., Grebenyuk J.N., Nizhnik E.A., Godovikov I.A., Shchetnikov G.T., and Bregadze V.I. An effective approach to 1,2,3-triazole-containing closo-dodecaborates. Collect. Czech. Chem. Commun. 72 (2007) 1717-1724
19. Semioshkin A.A., Sivaev I.B., and Bregadze V.I. Cyclic oxonium derivatives of polyhedral boron hydrides and their synthetic applications. Dalton Trans. (2008) 977-992
20. Semioshkin A., Laskova J., Wojtczak B., Andrusiak A., Godovikov I., Bregadze ., and Lesnikowski Z.J. Synthesis of closo-dodecaborate based nucleoside conjugates. J. Organomet. Chem. 694 (2009) 1375-1379
21. Sibrian-Vazquez M., Hao E., Jensen T.J., and Vicente M.G.H. Enhanced cellular uptake with a cobaltacarborane-porphyrin-HIV-1 Tat 48-60 conjugate. Biooconjugate Chem. 17 (2006) 928-934
22. 2- as a convenient precursor for the synthesis of functional compounds for boron neutron capture therapy. Polyhedron 19 (2000) 627-632
23. Sivaev I.B., Bregadze V.I., and Kuznetsov N.T. Derivatives of the closo-dodecaborate anion in their application in medicine. Russ. Chem. Bull. 51 (2002) 1362-1374
24. - anion. J. Organomet. Chem. 649 (2002) 1-8
25. Sivaev I.B., Kulikova N.Yu., Nizhnik E.A., Vichuzhanin M.V., Starikova Z.A., Semioshkin A.A., and Bregadze V.I. Practical synthesis of 1,4-dioxane derivative of the closo-dodecaborate anion and its ring opening with acetylenic alkoxides. J. Organomet. Chem. 693 (2008) 519-525
26. Soloway A.H., Tjarks W., Barnum B.A., Rong F.-G., Barth R.F., Codogni I.M., and Wilson J.G. The chemistry of neutron capture therapy. Chem. Rev. 98 (1998) 1515-1562
27. Stogniy M.Yu., Abramova E.N., Lobanova I.A., Sivaev I.B., Bragin V.I., Petrovskii P.V., Tsupreva V.N., Sorokina O.V., and Bregadze V.I. Synthesis of functional derivatives of 7,8-dicarba-nido-undecaborate anion by ring-opening of its cyclic oxonium derivatives. Collect. Czech. Chem. Commun. 72 (2007) 1676-1688
28. - in coordination. Generation of the highly uncommon S(thioether)-Na bond. Organometallics 22 (2003) 3414-3423
29. Valliant J.F., Guenther K.J., King A.S., Morel P., Schaffer P., Sogbein O.O., and Stephenson K.A. The medicinal chemistry of carboranes. Coord. chem. Rev. 232 (2002) 173-230
30. Wojtczak B.A., Andrysiak A., Grüner B., and Lesnikowski Z.J. Chemical ligation: a versatile method for nucleoside modification with boron clusters. Chem. Eur. J. 14 (2008) 10675-10682
31. Young D.C., Howe D.V., and Hawthorne M.F. Ligand derivatives of (3)-1,2-dicarbadodecahydro-undecaborate(1-). J. Am. Chem. Soc. 91 (1969) 859-862
32. Zakharkin L.I., Kalinin V.N., and Zhigareva G.G. Oxidation of dicarbadodecahydro-nido-undecaborate anions by mercuric chloride in tetrahydrofuran and pyridine. Russ. Chem. Bull. 28 (1979) 2198-2199
33. 2- with cyclic ethers. Russ J. Inorg. Chem. 49 (2004) 180-189