Arginine-Based Molecular Transporters: The Synthesis and Chemical Evaluation of Releasable Taxol-Transporter Conjugates

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3459-3462

  Kirschberg, Thorsten A ^a   VanDeusen, Chris L ^b   Rothbard, Jonathan B ^a   Yang, Michael ^a   Wender, Paul A ^b  

^a Cellgate Incorporated   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ARGININE; PACLITAXEL; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONJUGATE; EVALUATION; PH; SOLUBILITY; SYNTHESIS;

ACETYLATION; ANTINEOPLASTIC AGENTS; ARGININE; HALF-LIFE; HYDROGEN-ION CONCENTRATION; MEMBRANE TRANSPORT PROTEINS; MOLECULAR STRUCTURE; PACLITAXEL; SOLUBILITY; STEREOISOMERISM;

EID: 0344824453     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035234c     Document Type: Article

References (50)

1. Taxol is the registered trademark for the molecule with the generic name paclitaxel.
2. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
3. (a) Diaz, J. F.; Andreu, J. M. Biochem. 1993, 32, 2747-2755.
4. (b) Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667.
5. For the most recent total synthesis, see: Kusama, H.; Hara, R.; Kawahara, S.; Nishimori, T.; Kashima, H.; Nakamura, N.; Morihira, K.; Kuwajima, I. J. Am. Chem. Soc. 2000, 122, 3811-3820. For earlier syntheses from the groups of Holton, Nicolaou, Danishefsky, Wender, and Mukaiyama, see ref 7 in the above-cited paper.
6. Rodi, D. J.; Janes, R. W.; Sanganee, H. J.; Holton, R. A.; Wallace, B. A.; Makowski, L. J. Mol. Biol. 1999, 285, 197-203.
7. (a) Paclitaxel (Taxol): Current Practices and Future Directions in Breast Cancer Management; Seminars in Oncology; Yarboro, J. W., Bornstein, R. S., Mastrangelo, M. J., Eds.; W. B. Saunders: Philadelphia, PA, 1996; Vol. 23 (1-Suppl. 14), pp 23-31.
8. (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995.
9. Taxol Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995.
10. Terwogt, J. M. M.; Nuijen, B.; Ten Bokkel Huinink, W. W.; Beijnen, J. H. Cancer Treatment Rev. 1997, 23, 87-95.
11. (a) Takahashi, T.; Tsukamoto, H.; Yamada, H. Bioorg. Med. Chem. Lett. 1998, 8, 113-116.
12. (b) Li, C.; Yu, D.-F.; Newman, R. A.; Cabral, F.; Stephens, L. C.; Hunter, N.; Milas, L.; Wallace, S. Cancer Res. 1998, 58, 2404-2409.
13. Greenwald, R. B.; Pendri, A.; Bolikal, D. J. Org. Chem. 1995, 60, 331-336.
14. Mathew, A. E.; Mejillano, M. R.; Nath, J. P.; Himes, R. H.; Stella, V. J. J. Med. Chem. 1992, 35, 145-151.
15. (a) Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179-181.
16. (b) Golik, J.; Wong, H. S. L.; Chen, S. H.; Doyle, T. W.; Wright, J. J. K.; Knipe, J.; Rose, W. C.; Casazza, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1996, 6, 1837-1842.
17. Vyas, D. M.; Wong, H.; Crosswell, A. R.; Casazza, A. M.; Knipe, J. O.; Mamber, S. W.; Doyle, T. W. Bioorg. Med. Chem. Lett. 1993, 3, 1357-1360.
18. Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
19. (a) De Bont, D. B. A.; Leenders, R. G. G.; Haisma, H. J.; van der Meulen-Muileman, I.; Scheeren, H. W.; Bioorg. Med. Chem. Lett. 1997, 5, 4405-414.
20. (b) Rodrigues, M. L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B. K. Chem. Biol. 1995, 2, 223-227.
21. Ueda, Y.; Wong, H.; Matiskella, J. D.; Mikkikineni, A. B.; Farina, V.; Fairchild, C.; Rose, W. C.; Mamber, S. W.; Long, B. H.; Kerns, E. H.; Casazza, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1994, 4, 1861-1864.
22. Nicolaou, K. C.; Guy, R. K.; Pitsinos, E. N.; Wrasidlo, W. Angew. Chem., Int. Ed. Engl. 1994, 33, 3, 1583-1587.
23. (e) Nicolaou, K. C.; Riemer, C.; Kerr, M. A.; Rideout, D.; Wrasidlo, W. Nature 1993, 364, 464-466.
24. (f) Ueda, Y.; Mikkilineni, A. B.; Knipe, J. O.; Rose, W. C.: Casazza, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1993, 3, 1761-1766.
25. (g) Zhao, Z.; Kingston, D. G. I. J. Nat. Prod. 1991, 54, 1607-1611.
26. Langel, U., Ed. Cell Penetrating Peptides; CRC Press: Boca Raton, FL, 2002.
27. (a) Lindgren, M.; Haellbrink, M.; Prochiantz, A.; Langel, Ue. Trends Pharm. Sci. 2000, 21, 99-103.
28. (b) Frankel, A. D.; Pabo, C. O. Cell 1988, 55, 1189-1193.
29. Bhorade, R.; Weissleder, R.; Nakakoshi, T.; Moore, A.; Tung, C.-H. Bioconjugate Chem. 2000, 11, 301-305.
30. Josephson, L.; Tung, C-H.; Moore, A.; Weissleder, R. Bioconjugate Chem. 1999, 10, 186-191.
31. (e) Fawell, S.; Seery, J.; Daikh, Y.; Moore, C.; Chen, L. L.; Pepinsky, B.; Barsoum, J. Proc. Natl. Aca. Sci. U.S.A. 1994, 91, 664-668.
32. (a) Mitchell, D. J.; Kim, D. T.; Steinman, L.; Fathman, C. G.; Rothbard, J. B. J. Peptide Res. 2000, 56, 318-325.
33. (b) Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Science U.S.A. 2000, 97, 13003-13008.
34. Rothbard, J. B.; Kreider, E.; VanDeusen, C. L.; Wright, L. R.; Wylie, B. L.; Wender, P. A. J. Med. Chem. 2002, 45, 3612-3618.
35. Umezawa, N.; Gelman, M. A.; Haigis, M. C.; Raines, R. T.; Gellmann, S. H. J. Am. Chem. Soc. 2002, 124, 368-369.
36. (e) Wender, P. A.; Rothbard, J. B.; Jessop, T. C.; Kreider, E. L.; Wylie, B. L. J. Am. Chem. Soc. 2002, 124, 13382-13383.
37. (f) Rueping, M.; Mahajan, Y.; Sauer, M.; Seebach, D. ChemBioChem 2002, 3, 257-259.
38. (g) Futaki, S.; Ohashi, W.; Suzuki, T.; Niwa, M.; Tanaka, S.; Ueda, K.; Harashima, H.; Sugiura, Y. Bioconjugate Chem. 2001, 12, 1005-1011.
39. Wender, P. A.; Jessop, T. C.; Pattabiraman, K.; Pelkey, E. T.; VanDeusen, C. L. Org Lett. 2001, 3, 3229-3232.
40. Rothbard, J. B.; Garlington, S.; Lin. Q.; Kirschberg, T.; Kreider, E.; McGrane, P. L.; Wender, P. A.; Khavari, P. A. Nature Med. 2000, 6, 1253-1257.
41. Testa, B.; Mayer, J. M. Drug Metab. Rev. 1998, 30, 787-807.
42. Recently, a similar approach was used as a solid-phase linker strategy: Ando, H.; Manabe, S.; Nakahara, Y.; Ito, Y. Angew. Chem., Int. Ed. 2001, 40, 4725-4728.
43. This compound was mentioned in ref 8c but was described to be too unstable for synthetic application in an aqueous environment.
44. Free primary and secondary amines are excluded.
45. a of cysteine thiols, see: Lutlof, M. P.; Tirelli, N.; Cerritelli, S.; Cavalli, L.; Hubbell, J. A. Bioconjugate Chem. 2001, 72, 1051-1056.
46. In general, the use of DCC gave reduced yields in these coupling reactions.
47. Plapinger, R. E.; Nachlas, M. M.; Seligman, M. L.; Seligman, A. M. J. Org. Chem. 1965, 30, 1781-1785.
48. For most biological applications TFA counterions are undesirable.
49. Magri, N. F.; Kingston, D. G. I. J. Nat. Prod. 1988, 51, 298-306.
50. Aqueous solubility: Taxol < 4 μg/mL; conjugate 6 > 100 mg/mL. For the taxol value, see ref 10e.