A boronated benzamide as melanoma-seeking agent

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 3, 1997, Pages 361-364

  Parry, Daniel ^a   Papon, Janine ^a   Moins, Nicole ^a   Moreau, Marie France ^a   Morin, Christophe ^b  

^a INSERM   (France)

^b UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; BORON 10; CARBON 14; N (2 DIETHYLAMINOETHYL) 4 (2 BORONO 1,3 DIOXAN 2 YL)BENZAMIDE; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLOOD BRAIN BARRIER; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG TUMOR LEVEL; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; ISOTOPE LABELING; MELANOMA; MOUSE; NEUTRON CAPTURE THERAPY; NONHUMAN; XENOGRAFT;

ANIMALIA;

EID: 0031552102     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00013-9     Document Type: Article

References (30)

1. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
2. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
3. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
4. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
5. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
6. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
7. 1. For reviews on BNCT see inter alia : Barth, R.F.; Soloway, R.G. Sci. Am. 1990, 263, 68-73. Morris, J.H. Chem. Brit. 1991, 331-334. Carlsson, J.; Sjöberg, S.; Larsson, B.S, Acta Oncol. 1992, 31, 803-813. Hawthorne, F. Ang. Chem. 1993, 105, 997-1003 (Int. Ed. Engl. 1993, 32, 950-984). Lesnikowski, Z.J.; Schinazi, R. Polish J. Chem. 1995, 269, 827-840. Mehta, S.C.; Lu, D.R. Pharm. Res.1996, 13, 344-351.
8. 2. For a review about boron analogues of biomolecules see: Morin, C. Tetrahedron 1994, 50, 12521-12569.
9. 3. Mishima, Y.; Honda, C.; Ichihashi, M.; Obara, H.; Hiratsuka, J.; Fukuda, H.. Karashima, H.; Kobayashi, T.; Kanda, K.; Yoshino, K. Lancet 1989 (August 12), 388-389. Mishima, Y.; Ichihashi, M.; Hatta, S.;Honda, C; Yamamura, K.; Nakagawa, T. Honda, Pigment Cell Res. 1989, 2, 226-234.
10. 3. Mishima, Y.; Honda, C.; Ichihashi, M.; Obara, H.; Hiratsuka, J.; Fukuda, H.. Karashima, H.; Kobayashi, T.; Kanda, K.; Yoshino, K. Lancet 1989 (August 12), 388-389. Mishima, Y.; Ichihashi, M.; Hatta, S.;Honda, C; Yamamura, K.; Nakagawa, T. Honda, Pigment Cell Res. 1989, 2, 226-234.
11. 4. Michelot, J.M.; Moreau, M.-F.; Labarre, P.G.; Madelmont, J.-C.; Veyre, A.J.; Papon, J.M.; Parry, D.F.; Bonafous, J.F.; Boire, J.P.; Desplanches G.G.; Bertrand, S.Z.; Meyniel, G. J. Nucl. Med; 1991, 32, 1573-1577. Michelot, J.M.; Moreau, M.-F.; Veyre, A.J.; Bonafous, J.F.; Bacin, F.J.; Madelmont, J.-C.; Bussiere,F.; Souteyrand, P.A.; Mauclaire, L.P.; Chossat, F.M.; Papon, J.M.; Labarre, P.G.; Kaufmann, P.; Plagne,R.J. J. Nucl. Med. 1993, 34, 1260-1266. Moreau, M.-F.; Michelot, J.; Papon, J.; Bayle, M.; Labarre, P.;Madelmont, J.-C.; Parry, D.; Boire, J.Y.; Moins, N.; Seguin, H.; Veyre, A.; Mauclaire, L. Nucl. Med. Biol.1995, 22, 737-747. Moreau, M.F.; Parry, D.: Bayle, M.; Papon, J.; Labarre, P.; Veyre, A.J. J. LabelledCompd. Radiopharm. 1995, 36, 805-813.
12. 4. Michelot, J.M.; Moreau, M.-F.; Labarre, P.G.; Madelmont, J.-C.; Veyre, A.J.; Papon, J.M.; Parry, D.F.; Bonafous, J.F.; Boire, J.P.; Desplanches G.G.; Bertrand, S.Z.; Meyniel, G. J. Nucl. Med; 1991, 32, 1573-1577. Michelot, J.M.; Moreau, M.-F.; Veyre, A.J.; Bonafous, J.F.; Bacin, F.J.; Madelmont, J.-C.; Bussiere,F.; Souteyrand, P.A.; Mauclaire, L.P.; Chossat, F.M.; Papon, J.M.; Labarre, P.G.; Kaufmann, P.; Plagne,R.J. J. Nucl. Med. 1993, 34, 1260-1266. Moreau, M.-F.; Michelot, J.; Papon, J.; Bayle, M.; Labarre, P.;Madelmont, J.-C.; Parry, D.; Boire, J.Y.; Moins, N.; Seguin, H.; Veyre, A.; Mauclaire, L. Nucl. Med. Biol.1995, 22, 737-747. Moreau, M.F.; Parry, D.: Bayle, M.; Papon, J.; Labarre, P.; Veyre, A.J. J. LabelledCompd. Radiopharm. 1995, 36, 805-813.
13. 4. Michelot, J.M.; Moreau, M.-F.; Labarre, P.G.; Madelmont, J.-C.; Veyre, A.J.; Papon, J.M.; Parry, D.F.; Bonafous, J.F.; Boire, J.P.; Desplanches G.G.; Bertrand, S.Z.; Meyniel, G. J. Nucl. Med; 1991, 32, 1573-1577. Michelot, J.M.; Moreau, M.-F.; Veyre, A.J.; Bonafous, J.F.; Bacin, F.J.; Madelmont, J.-C.; Bussiere,F.; Souteyrand, P.A.; Mauclaire, L.P.; Chossat, F.M.; Papon, J.M.; Labarre, P.G.; Kaufmann, P.; Plagne,R.J. J. Nucl. Med. 1993, 34, 1260-1266. Moreau, M.-F.; Michelot, J.; Papon, J.; Bayle, M.; Labarre, P.;Madelmont, J.-C.; Parry, D.; Boire, J.Y.; Moins, N.; Seguin, H.; Veyre, A.; Mauclaire, L. Nucl. Med. Biol.1995, 22, 737-747. Moreau, M.F.; Parry, D.: Bayle, M.; Papon, J.; Labarre, P.; Veyre, A.J. J. LabelledCompd. Radiopharm. 1995, 36, 805-813.
14. 4. Michelot, J.M.; Moreau, M.-F.; Labarre, P.G.; Madelmont, J.-C.; Veyre, A.J.; Papon, J.M.; Parry, D.F.; Bonafous, J.F.; Boire, J.P.; Desplanches G.G.; Bertrand, S.Z.; Meyniel, G. J. Nucl. Med; 1991, 32, 1573-1577. Michelot, J.M.; Moreau, M.-F.; Veyre, A.J.; Bonafous, J.F.; Bacin, F.J.; Madelmont, J.-C.; Bussiere,F.; Souteyrand, P.A.; Mauclaire, L.P.; Chossat, F.M.; Papon, J.M.; Labarre, P.G.; Kaufmann, P.; Plagne,R.J. J. Nucl. Med. 1993, 34, 1260-1266. Moreau, M.-F.; Michelot, J.; Papon, J.; Bayle, M.; Labarre, P.;Madelmont, J.-C.; Parry, D.; Boire, J.Y.; Moins, N.; Seguin, H.; Veyre, A.; Mauclaire, L. Nucl. Med. Biol.1995, 22, 737-747. Moreau, M.F.; Parry, D.: Bayle, M.; Papon, J.; Labarre, P.; Veyre, A.J. J. LabelledCompd. Radiopharm. 1995, 36, 805-813.
15. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
16. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
17. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
18. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
19. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
20. 5. John, C.S.; Saga, T.; Kinuya, S.; Le, N.; Jeong, J.M.; Paik, C.H.; Reba, R.C.; Varma, V.M.; McAfee,J.G. Nucl. Med. Biol. 1993, 20, 75-79. John, C.S.; Bowen, W.D.; Saga, T.; Kinuya, S.; Viner, B.J.;Baumgold, J.; Paik, C.H.; Reba, R.C.; Neumann, R.D.; Varma, V.M.; McAfee, J.G. J. Nucl. Med. 1993,34, 2169-2175. John, C.S.; Vilner, B.J.; Bowen, W.D. J. Med. Chem. 1994, 37,1737-1739. John, C.S.; Vilner, B.J.; Gulden, M.E.; Efange, S.M.N.; Langason, R.; Moody, T.W.; Bowen, W.D. Cancer Res.1995, 55, 3022-3027. Dence, C.S.; John, C.S.; Goree, R.E.; Bowen, W.D.; Welch, M.J. J. LabelledCompd. Radiopharm. 1995, 37, 263-265. John, C.S.; Gulden, M.E.; Vilner, B.J.; Venugopal, R.; Bowen,W.D. J. Labelled Compd. Radiopharm. 1995, 37, 269-271.
21. 6. Coenen, H.H.; Brandau, W.; Dittmann, H.; Dutschka, K.; Niehoff, T.; Pulawski, T.; Zôlzer, P.; Sciuk, F.; Streffer, C. J. Labelled Compd. Radiopharm. 1995, 37, 260-262.
22. 7. Hanson R.N.; Elmaleh, D.R. J. Labelled Compd. Radiopharm. 1995, 37, 275-276.
23. 8. Nicholl, C.; Mohammed, A.; Eisenhut, M. J. Labelled Compd. Radiopharm. 1995, 37, 277-279.
24. 3); due to quadrupolar relaxation, the carbon attached to boron is not detected.
25. 10. Matsubara, H.; Seto, K.; Tahara, T.; Takahashi, S. Bull. Chem. Soc. Jpn. 1989,62, 3896-3901.
26. 11. Törsell, K. Acta Chem. Scand. 1954, 8, 1779-1786. Helms, A.; Heiler, D.; McLendon, G. J. Am.Chem. Soc. 1992,114, 6227-6238.
27. 11. Törsell, K. Acta Chem. Scand. 1954, 8, 1779-1786. Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992,114, 6227-6238.
28. 12. Allen, C.F.H.; VanAllan, J.A. Org. Synth. . 1947,27, 20-21 (Coll. Vol. III, 1955, 20).
29. - radioactivity was counted (proportional counter : Ambis 4000) on animal slices (40 μm). The values shown are the means of two experiments.
30. 14. Moreau, M.-F.; Michelot, J.; Veyre, A.; Madelmont, J.-C.; Godenèche, D.; Labarra, P.; Parry, D.; Meyniel, G. US Patent 5, 190, 741.