Total syntheses of three copper (II) tetracarboranylphenylporphyrins containing 40 or 80 boron atoms and their biological properties in EMT-6 tumor-bearing mice

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 15, 2006, Pages 5083-5092

  Wu, Haitao ^a   Micca, Peggy L ^a   Makar, Michael S ^a   Miura, Michiko ^a  

^a BROOKHAVEN NATIONAL LABORATORY   (United States)

Author keywords

BNCT; EMT 6 tumors; Mice; Porphyrins

Indexed keywords

BORON 10; BORON DERIVATIVE; COPPER 5,10,15,20 TETRAKIS[3 (3,5 DI 2 CARBORANYLMETHOXYBENZYLOXY)PHENYL] PORPHYRIN; COPPER 5,10,15,20 TETRAKIS[3 HYDROXY 4 (2 CARBORANYLMETHOXY)PHENYL] PORPHYRIN; COPPER 5,10,15,20 TETRAKIS[3 METHOXY 4 (2 CARBORANYLMETHOXY)PHENYL] PORPHYRIN; CUPRIC ION; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ATOMIC PARTICLE; BREAST TUMOR; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG UPTAKE; LEUKOCYTOSIS; MOUSE; MOUSE STRAIN; NEUTRON CAPTURE THERAPY; NONHUMAN; STRUCTURE ANALYSIS; THROMBOCYTOPENIA; TOXICITY TESTING;

ANIMALS; ANTINEOPLASTIC AGENTS; BORON COMPOUNDS; CELL LINE, TUMOR; COPPER; DISEASE MODELS, ANIMAL; DRUG SCREENING ASSAYS, ANTITUMOR; MAMMARY NEOPLASMS, EXPERIMENTAL; METALLOPORPHYRINS; MICE; MICE, INBRED BALB C; MOLECULAR STRUCTURE; STEREOISOMERISM; TISSUE DISTRIBUTION; TRANSPLANTATION, HETEROLOGOUS;

EID: 33745167732     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.04.010     Document Type: Article

References (38)

1. Hatanaka H. In: Hatanaka H. (Ed). Boron-Neutron Capture Therapy for Tumours (1986), Nishimura, Niigata, Japan 349
2. Slatkin D.N. Brain 114 (1991) 1609
3. Diaz A.Z., Coderre J.A., Chanana A.D., and Ma R.M. Ann. Med. 32 (2000) 81
4. Obayashi S., Kato I., Ono K., Masunaga S.-I., Suzuki M., Nagata K., Sakurai Y., and Yura Y. Oral Oncol. 40 (2004) 474-482
5. Kageji T., Nakagawa Y., Kitamura K., Matsumoto K., and Hatanaka H.. J. Neurooncol. 33 (1997) 117
6. Gabel D., Preusse D., Haritz D., Grochulla F., Haselsberger K., Fankhauser H., Ceberg C., Peters H.-D., and Klotz U. Acta Neurochir. 139 (1997) 606
7. Chanana A.D., Capala J., Chadha M., Coderre J.A., Diaz A.Z., Elowitz E.H., Iwai J., Joel D.D., Liu H.B., Pendzick N., Peress N.S., Shady M.S., Slatkin D.N., Tyson G.W., and Wielopolski L. Neurosurgery 44 (1999) 1182
8. Pignol J.-P., Oudart H., Chauvel P., Sauerwein W., Gabel D., and Prevot G. Br. J. Radiol. 71 (1998) 320
9. Fairchild R.G., and Bond V.P. Int. J. Radiat. Oncol. Biol. Phys. 11 (1985) 831
10. Gabel D., Foster S., and Fairchild R.G. Radiat. Res. 111 (1987) 14
11. Hawthorne M.F. Angew. Chem., Int. Ed. Engl. 32 (1993) 950
12. Barth R.F., Soloway A.H., Goodman J.H., Gahbauer R.A., Gupta N., Blue T.E., Yang W., and Tjarks W. Neurosurgery 44 (1999) 433
13. Soloway A.H., Tjarks W., Barnum B.A., Rong F.G., Barth R.F., Codogni I.M., and Wilson J.G. Chem. Rev. 98 (1998) 1515
14. Yinghuai Z., Peng A.T., Carpenter K., Maguire J.A., Hosmane N.S., and Takagaki M. J. Am. Chem. Soc. 127 (2005) 9875
15. Miura M., Micca P.L., Fisher C.D., Heinrichs J.C., Donaldson J.A., Finkel G.C., and Slatkin D.N. Int. J. Cancer 68 (1996) 114
16. Miura M., Micca P.L., Fisher C.D., Gordon C.R., Heinrichs J.C., and Slatkin D.N. Br. J. Radiol. 71 (1998) 773
17. Miura M., Morris G.M., Micca P.L., Lombardo D.T., Youngs K.M., Kalef-Ezra J.A., Hoch D., Slatkin D.N., Ma R., and Coderre J.A. Radiat. Res. 155 (2001) 603
18. Vicente M.G.H. Anticancer Agents Med. Chem. 1 (2001) 175
19. Vicente M.G.H., Shetty S., Wickramasinghe A., and Smith K.M. Tetrahedron Lett. 41 (2000) 7623
20. Renner M.W., Miura M., Easson M.W., and Vicente M.G.H. Anticancer Agents Med. Chem. 6 (2006) 145
21. Lee J., Park S., Kim Y., and Kang H.C. Bull. Korean Chem. Soc. 20 (1999) 1371
22. Miura M., Gabel D., Oenbrink G., and Fairchild R.G. Tetrahedron Lett. 31 (1990) 2247
23. Becker H.-D., Björk A., and Adler E. J. Org. Chem. 45 (1980) 1596
24. Kopcho J.J., and Schaeffer J.C. J. Org. Chem. 51 (1986) 1620
25. McOmie J.F.W., Watts M.L., and West D.E. Tetrahedron 24 (1968) 2289
26. Hawker C.J., and Fréchet J.M.J. J. Am. Chem. Soc. 112 (1990) 7638
27. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., and Marguerettaz A.M. J. Org. Chem. 52 (1987) 827
28. Miura M., Morris G.M., Micca P.L., Nawrocky M.M., Makar M.S., Cook S.P., and Slatkin D.N. Br. J. Radiol. 77 (2004) 573
29. Zuk M.M., Rihter B.D., Kenney M.E., Rodgers M.A.J., and Kreimer-Birnbaum M. Photochem. Photobiol. 59 (1994) 66
30. Wu G., Barth R.F., Yang W., Chatterjee J., Tjarks W., Ciesilski M.J., and Fenstermaker R.A. Bioconjugate Chem. 15 (2004) 185
31. Ozawa T., Santos R.A., Lamborn K.R., Bauer W.F., Koo M.-S., Kahl S.B., and Deen D.F. Mol. Pharmacol. 1 (2004) 368
32. Coderre J.A., Button T.M., Micca P.L., Fisher C.D., Nawrocky M.M., and Liu H.B. Int. J. Radiat. Oncol. Biol. Phys. 30 (1994) 643
33. Miura M., Micca P.L., Heinrichs J.C., Gabel D., Fairchild R.G., and Slatkin D.N. Biochem. Pharmacol. 43 (1992) 467
34. Vicente M.G.H., Wickramasinghe A., Nurco D.J., Wang H.J.H., Nawrocky M.M., Makar M.S., and Miura M. Bioorg. Med. Chem. 11 (2003) 1
35. Bobadova-Parvanova P., Oku Y., Wickramasinghe A., Hall R.W., and Vicente M.G.H. J. Porphyrins Phthalocyanines 8 (2004) 996
36. Rockwell S.C., Kallman R.F., and Fajardo L.F. J. Natl. Cancer Inst. 49 (1972) 735
37. Fairchild R.G., Gabel D., Laster B.H., Greenberg D., Kiszenick W., and Micca P.L. Med. Phys. 13 (1986) 50
38. Traynham J.G., and Pascual O.S. J. Org. Chem. 21 (1956) 1362