Degradation of rapamycin and its ring-opened isomer: Role of base catalysis

Arkivoc

Volumn 2007, Issue 12, 2007, Pages 110-131

  Il'ichev, Yuri V ^a   Alquier, Lori ^a   Maryanoff, Cynthia A ^a  

^a JOHNSON AND JOHNSON   (United States)

Author keywords

Base catalysis; Degradation; Kinetics; Rapamycin; Secorapamycin

Indexed keywords

EID: 34248154791     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.c09     Document Type: Article

References (48)

1. Vezina, C.; Kudelski, A.; Sehgal, S. N. J. Antibiot. (Tokyo) 1975, 28, 721.
2. (b) Sehgal, S. N.; Baker, H.; Vezina, C. J. Antibiot. (Tokyo) 1975, 28, 727.
3. Martel, R. R.; Klicius, J.; Galet, S. Can. J. Physiol. Pharmacol. 1977, 55, 48.
4. Caufield, C. E. Curr. Pharmaceut. Design 1995, 1, 145.
5. Napoli, K. L.; Taylor, P. J. Therap. Drug Monitor. 2001, 23, 559.
6. Swindells, D. C. N.; White, P. S.; Findlay, J. A. Can. J. Chem. 1978, 56, 2491.
7. Van Duyne, G. D.; Standaert, R. F.; Schreiber, S. L.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 7433.
8. Deivanayagam, C. C.; Carson, M.; Thotakura, A.; Narayana, S. V.; Chodavarapu, R. S. Acta Crystallogr., Sect. D 2000, 56, 266.
9. Fulton, K. F.; Jackson, S. E.; Buckle, A. M. Biochemistry 2003, 42, 2364.
10. Holt, D. A.; Konialian, A. L.; Brandt, M.; Levy, M. A.; Bossard, M. J.; Luengo, J. I.; Newman-Tarr, T.; Badger, A. Bioorg. Med. Chem. Lett. 1993, 3, 1977.
11. Wang, C. P.; Chan, K. W.; Schiksnis, R. A.; Scatina, J.; Sisenwine, S. F. J. Liq. Chromat. 1994, 17, 3383.
12. (a) Wang, C. P.; Lim, H.-K.; Chan, K. W.; Scatina, J.; Sisewine, S. F. J. Liq. Chromat. 1995, 18, 2559.
13. (b) Wang, C. P.; Lim, H.-K.; Chan, K. W.; Scatina, J.; Sisenwine, S. F. J. Liq. Chromat. Rel. Technol. 1997, 20, 1689.
14. (a) Paine, M. F.; Leung, L. Y.; Lim, H. K.; Liao, K.; Oganesian, A.; Zhang, M.-Y.; Thummel, K. E.; Watkins, P. B. J. Pharmacol. Exper. Therapeutics 2002, 301, 174.
15. (b) Paine, M. F.; Leung, L. Y.; Watkins, P. B. Ther. Drug Monit. 2004, 26, 463.
16. Luengo, J. I.; Konialian, A. L.; Holt, D. A. Tetrahedron Lett. 1993, 34, 991.
17. Yohannes, D.; Myers, C. D.; Danishefsky, S. J. Tetrahedron Lett. 1993, 34, 2075.
18. Steffan, R. J.; Kearney, R. M.; Hu, D. C.; Failli, A. A.; Skotnicki, J. S.; Schiksnis, R. A.; Mattes, J. F.; Chan, K. W.; Caufield, C. E. Tetrahedron Lett. 1993, 34, 3699.
19. Skotnicki, J. S.; Failli, A. A.; Steffan, R. J.; Kearney, R. M. U.S. Patent, 9 pp US 5252579A, 19931012.
20. Hallensleben, K.; Raida, M.; Habermehl, G. J. Am. Soc. Mass Spectr. 2000, 11, 516.
21. Buchberger, W.; Ferdig, M.; Sommer, R.; Vo, T. D. T. Electrophoresis 2005, 26, 161.
22. Zhou, C. C.; Stewart, K. D.; Dhaon, M. K. Magn. Res. Chem. 2005, 43, 41.
23. (a) Noda, I. Appl. Spectrosc. 1993, 47, 1329.
24. (b) Noda, I., Appl. Spectrosc. 2000, 54, 994.
25. (c) Noda, I. Vibr. Spectrosc. 2004, 36, 143.
26. Ozaki, Y.; Liu, Y.; Noda, I. Appl. Spectrosc. 1997, 51, 526 and references therein.
27. (a) Nabet, A.; Pézolet, I. Appl. Spectrosc. 1997, 51, 466.
28. (b) Meskers, S.; Ruysschaert, J.-M.; Goormaghtigh, E. J Am. Chem. Soc. 1999, 121, 5115.
29. (c) Fabian, H.; Mantsch, H. H.; Schultz, C. P. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 13153.
30. (a) Elmore, D. L.; Dluhy, R. A. Coll. Surf. A 2000, 171, 225.
31. (b) Elmore, D. L.; Shanmukh, S.; Dluhy, R. A. J. Phys. Chem. A 2002, 106, 3420.
32. (a) Ren, Y.; Shimoyama, M.; Ninomiya, T; Matsukawa, K.; Inoue, H.; Noda, I.; Ozaki, Y. J. Phys. Chem. B. 1999, 103, 6475.
33. (b) Noda, I.; Marcott, C. J. Phys. Chem. A 2002, 106, 3371.
34. Izawa, K.; Ogasawara, T.; Masuda, H.; Okabayashi, H.; Noda, I. Macromolecules 2002, 35, 92.
35. Izawa, K.; Ogasawara, T.; Masuda, H.; Okabayashi, H.; O'Connor, C. J.; Noda, I. Phys. Chem. Chem. Phys 2002, 4, 1053.
36. Izawa, K.; Ogasawara, T.; Masuda, H.; Okabayashi, H.; O'Connor, C. J.; Noda, I. J. Phys. Chem. B 2002, 106, 2867.
37. Although a weak signal with RT around 15.3 min and m/z values corresponding to rapamycin can be detected, it is likely to be a different isomeric compound because a similar signal was observed for secorapamycin solutions.
38. Kruppa, G.; Schnier, P. D.; Tabei, K.; Van Orden, S.; Siegel, M. M. Anal. Chem. 2002, 74, 3877.
39. No time-dependent change in the isomer ratio (∼9.5) could be detected in the rapamycin solutions with different concentrations of ammonium acetate. However, it takes ca 5 days to reach approximately the same ratio in 30/70 v/v MeCN solution containing 7 mM acetate buffer with apparent pH of 4.95.
40. The trans/cis ratio was estimated from the integrals for the H2 signals assigned to trans- and cis-rotamers. The estimation procedure is associated with significant uncertainty because of the signal overlap.
41. Wu, W.-J.; Raleigh, D. P. J. Org. Chem. 1998, 63, 6689.
42. Swarbrick, M. E.; Gosselin, F.; Lubell, W. D. J. Org. Chem. 1999, 64, 1993.
43. Kessler, H.; Haessner, R.; Schueler, W. Helv. Chim. Acta 1993, 76, 117.
44. Concellón, J. M.; Rodríguez-Solla, H.; Concellón, C.; Díaz, P. Synlett 2006, (6), 837.
45. Askin, D.; Reamer, R. A.; Jones, T. K.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1989, 30, 671.
46. Baumann, K.; Bacher, M.; Steck, A.; Wagner, T. Tetrahedron 2004, 60, 5965.
47. Rubin, M. B.; Gleiter, R. Chem. Rev. 2000, 100, 1121.
48. Noda, I. Appl. Spectrosc. 2003, 57, 1049.