Preparation of a new carboranyl lactoside for the treatment of cancer by boron neutron capture therapy: Synthesis and toxicity of fluoro carboranyl glycosides for in vivo 19F-NMR spectroscopy

Chemistry - A European Journal

Volumn 6, Issue 5, 2000, Pages 836-842

  Tietze, Lutz F ^a   Bothe, Ulrich ^a   Schuberth, Ingrid ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Antitumor agents; Boron neutron capture therapy; Carboranes; Drug research; Glycosides

Indexed keywords

1 (BETA DEXTRO LACTOPYRANOSYLOXYMETHYL) 2 (6 FLUOROHEXYLOXYMETHYL) 1,2 DICARBA CLOSO DEODECABORANE; 2 FLUOROMETHYL 1 (BETA DEXTRO LACTOPYRANOSYLMETHYL) 1,2 DICARBA CLOSO DODECABORANE; 2 FLUOROMETHYL 1 HYROXYMETHYL 1,2 DICARBA CLOSO DODECABORANE; ANTINEOPLASTIC AGENT; BORON DERIVATIVE; CARBORANE DERIVATIVE; DIAGNOSTIC AGENT; FLUORINATED HYDROCARBON; FLUORINE; GLUCOSIDASE; GLYCOSIDE; LACTOSIDES; UNCLASSIFIED DRUG;

ARTICLE; CANCER THERAPY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CULTURE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CYTOTOXICITY; DRUG EFFECT; HUMAN; HUMAN CELL; METABOLISM; NEOPLASM; NEUTRON CAPTURE THERAPY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BORON COMPOUNDS; BORON NEUTRON CAPTURE THERAPY; CELL SURVIVAL; FLUORINE; GLUCOSIDASES; GLYCOSIDES; HUMANS; HYDROCARBONS, FLUORINATED; NEOPLASMS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0034599015     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000303)6:5<836::AID-CHEM836>3.0.CO;2-8     Document Type: Article

References (39)

1. a) R. F. Brath, A. H. Soloway, R. G. Fairchild, Cancer 1992, 70, 2995-3007;
2. b) M. F. Hawthorne, Angew. Chem. 1993, 105, 997-1033; Angew. Chem. Int. Ed. Engl. 1993, 32, 950-984;
3. b) M. F. Hawthorne, Angew. Chem. 1993, 105, 997-1033; Angew. Chem. Int. Ed. Engl. 1993, 32, 950-984;
4. c) C. Morin, Tetrahedron 1994, 50, 12521-12569;
5. d) D. Gabel, Chem. Unserer Zeit 1997, 31, 235-240;
6. e) A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev. 1998, 98, 1515-1562;
7. f) M. F. Hawthorne, Mol. Med. Today 1998, 4, 174-181.
8. a) J. L. Maurer, A. J. Serino, M. F. Hawthorne, Organometallics 1988, 7, 2519-2524;
9. b) C. Morin, M. Ramburrun in Curr. Top. Chem. Horon. (Ed.: G. W. Kabalka), The Royal Society of Chemistry, Cambridge, UK 1994, pp. 229-231;
10. c) J. L. Maurer, F. Berchier, A. J. Serino, C. B. Knobler, M. F. Hawthorne, J. Org. Chem. 1990, 55, 838-843;
11. d) W. V. Dahlhoff, J. Bruckmann, K. Angermund, C. Krüger, Liebigs Ann. Chem. 1993, 831-835;
12. e) W. Tjarks, A. K. M. Anisuzzaman, L. Liu, A. H. Soloway, R. F. Barth, D. J. Rerkins, D. M. Adams, J. Med. Chem. 1992, 35, 1628-1633;
13. f) W. Tjarks, A. K. M. Anisuzzaman, A. H. Soloway, Nucleosides Nucleotides 1992, 11, 1765-1779;
14. g) R. L. Sneath, Jr., J. E. Wright, A. H. Soloway, S. M. O'Keefe, A. S. Dey, W. D. Smolnycki, J. Med. Chem. 1976, 19, 1290-1294.
15. L. F. Tietze, U. Bothe, Chem. Eur. J. 1998, 4, 1179-1183.
16. a) S. Hakamori, Annu. Rev. Biochem. 1981, 50, 733-764;
17. b) P. O. Livingston, S. Zhang, K. O. Lloyd, Cancer Immunother. 1997, 45, 1-9.
18. a) L. N. Jungheim, T. A. Shepherd, Chem. Rev. 1994, 94, 1553-1556;
19. b) L. F. Tietze, R. Fischer, R. Lögers, M. Beller, Carbohydr. Res. 1989, 194, 155-162;
20. c) L. F. Tietze, M. Neumann, R. Fischer, T. Möllers, K.-H. Glüsenkamp, R. F. Rajewsky, E. Jähde, Cancer Res. 1989, 49, 4179-4184;
21. d) L. F. Tietze, M. Beller, R. Fischer, M. Lögers, E. Jähde, K.-H. Glüsenkamp, M. F. Rajewsky, Angew. Chem. 1990, 102, 812-813; Angew. Chem. Int. Ed. Engl. 1990, 29, 782-783;
22. d) L. F. Tietze, M. Beller, R. Fischer, M. Lögers, E. Jähde, K.-H. Glüsenkamp, M. F. Rajewsky, Angew. Chem. 1990, 102, 812-813; Angew. Chem. Int. Ed. Engl. 1990, 29, 782-783;
23. e) L. F. Tietze, H. Keim, Angew. Chem. 1997, 109, 1704-1706; Angew. Chem. Int. Ed. Engl. 1997, 36, 1615-1617.
24. e) L. F. Tietze, H. Keim, Angew. Chem. 1997, 109, 1704-1706; Angew. Chem. Int. Ed. Engl. 1997, 36, 1615-1617.
25. G. W. Kabalka, C. Tang, P. Bendel, J. Neuro-Oncol. 1997, 33, 153-161.
26. a) P. Bachert, Prog. NMR Spectroscopy 1998, 33, 1-56;
27. b) J. S. Cohen, J. W. Jaroszewski, O. Kaplan, J. Ruiz-Cabello, S.W. Collier, Prog. NMR Spectroscopy 1995, 28, 53-85;
28. c) M. C. Marlet-Martino, R. Martino, Biochimie 1992, 74, 785-800.
29. a) T. L. Heying, J. W. Ager, S. L. Clark, D. J. Mangold, H. L. Goldstein, M. Hillmann, R. J. Polak, J. W. Szymanski, Inorg. Chem. 1963, 2, 1089-1092;
30. b) M. M. Flein, D. Grafstein, J. E. Paustian, J. Bobinski, B. M. Lichstein, N. Mayes, N. N. Schwartz, M. S. Cohen, Inorg. Chem. 1963, 2, 1115-1119.
31. R. R. Schmidt, Angew. Chem. 1986, 98, 213-236; Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
32. R. R. Schmidt, Angew. Chem. 1986, 98, 213-236; Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
33. C. P. Gorst-Allman, S. P. Steyn, J. Chem. Soc. Perkin Trans. 1 1987, 163-168.
34. D. R. Benedict, T. A. Bianchi, L. A. Cate, Synthesis 1979, 428-429.
35. R. Schaeffer, J. Am. Chem. Soc. 1957, 79, 1006-1007.
36. F. Munyemana, A. F.-H. Hesbain, A. Devos, L. Ghosez, Tetrahedron Lett. 1989, 30, 3077-3080.
37. The toxicity tests were performed as described in ref. [3].
38. L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. 1996, 108, 2840-2841; Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2676.
39. L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. 1996, 108, 2840-2841; Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2676.