Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Design and Synthesis of Resin-Conjugated Tamiflu Analogs for Affinity Chromatography

  • Kimura, Yasuaki (Graduate School of Pharmaceutical Sciences, The University of Tokyo) ;
  • Yamatsugu, Kenzo (Graduate School of Pharmaceutical Sciences, The University of Tokyo) ;
  • Kanai, Motomu (Graduate School of Pharmaceutical Sciences, The University of Tokyo) ;
  • Echigo, Noriko (Faculty of Pharmaceutical Sciences, Tokushima Bunri University) ;
  • Kuzuhara, Takashi (Faculty of Pharmaceutical Sciences, Tokushima Bunri University) ;
  • Shibasaki, Masakatsu (Graduate School of Pharmaceutical Sciences, The University of Tokyo)
  • Published : 2010.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Two types of resin-conjugated Tamiflu analogs were synthesized by modifying our original synthetic route of oseltamivir phosphate (Tamiflu). The prepared resins bound to influenza virus neuraminidase, the main target of Tamiflu. The resins will be useful for isolating and identifying presumed endogenous vertebrate proteins that interact with Tamiflu, which might relate to the rarely observed abnormal behavior exhibited by some influenza patients treated with Tamiflu.

Keywords

References

  1. Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681. https://doi.org/10.1021/ja963036t
  2. Yueng, Y.-Y.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310. https://doi.org/10.1021/ja0616433
  3. Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312. https://doi.org/10.1021/ja061696k
  4. Cong, X.; Yao, Z.-J. J. Org. Chem. 2006, 71, 5365. https://doi.org/10.1021/jo060633h
  5. Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 259. https://doi.org/10.1021/ol062663c
  6. Yamatsugu, K.; Kamijo, S.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2007, 48, 1403. https://doi.org/10.1016/j.tetlet.2006.12.093
  7. Bromfield, K. M.; Graden, H.; Hagberg, D. P.; Olsson, T.; Kann, N. Chem. Commun. 2007, 3183.
  8. Satoh, N.; Akiba, T.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2007, 46, 5734. https://doi.org/10.1002/anie.200701754
  9. Shie, J.-J.; Fang, J.-M.; Wang, S.-Y.; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Su, C.-Y.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11892. https://doi.org/10.1021/ja073992i
  10. Kipassa, N. T.; Okamura, H.; Kina, K.; Hamasa, T.; Iwagawa, T. Org. Lett. 2008, 10, 815. https://doi.org/10.1021/ol7029646
  11. Trost, B. M.; Zhang, T. Angew. Chem., Int. Ed. 2008, 47, 3759. https://doi.org/10.1002/anie.200800282
  12. Zutter, U.; Iding, H.; Spurr, P.; Wirz, B. J. Org. Chem. 2008, 73, 4895. https://doi.org/10.1021/jo800264d
  13. Shie, J.-J.; Fang, J.-M.; Wong, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5788. https://doi.org/10.1002/anie.200801959
  14. Yamatsugu, K.; Yin, L.; Kamijo, S.; Kimura, Y.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2009, 48, 1070. https://doi.org/10.1002/anie.200804777
  15. Matveenko, M.; Willis, A. C.; Banwell, M. G. Tetrahedron Lett. 2008, 49, 7018. https://doi.org/10.1016/j.tetlet.2008.09.130
  16. Ishikawa, H.; Suzuki, T.; Hayashi, Y. Angew. Chem., Int. Ed. 2009, 48, 1304. https://doi.org/10.1002/anie.200804883
  17. Mandai, T.; Oshitari, T. Synlett 2009, 783.
  18. Oshitari, T.; Mandai, T. Synlett 2009, 787.
  19. Satoh, N.; Akiba, T.; Yokoshima, S.; Fukuyama, T. Tetrahedron 2009, 65, 3239. https://doi.org/10.1016/j.tet.2008.09.103
  20. Nie, L.-D.; Ko, X.-X.; Ko, K. H.; Lu,W.-D. J. Org. Chem. 2009, 74, 3970. https://doi.org/10.1021/jo900218k
  21. Sullivan, B.; Carrera, I.; Drouin, M.; Hudlicky, T. Angew. Chem., Int. Ed. 2009, 48, 4229. https://doi.org/10.1002/anie.200901345
  22. Hai, S.; Ying-Jie, L.; Yu-Lin, W.; Yikang, W. Synlett 2009, 2473.
  23. Yamatsugu, K.; Kanai, M.; Shibasaki, M. Tetrahedron 2009, 65, 6017
  24. Farina, N.; Brown, J. D. Angew. Chem., Int. Ed. 2006, 45, 7300.
  25. Shibasaki, M.; Kanai, M. Eur. J. Org. Chem. 2008, 1839.
  26. Magano, J. Chem. Rev. 2009, 109, 4398 https://doi.org/10.1021/cr800449m
  27. Izumi, Y.; Tokuda, K.; O’Dell, K. A.; Zorumski, C. F.; Narahashi, T. Neurosci. Lett. 2007, 426, 54. https://doi.org/10.1016/j.neulet.2007.08.054
  28. Ishii, K.; Hamamoto, H.; Sasaki, T.; Ikegaya, Y.; Yamatsugu, K.; Kanai, M.; Shibasaki, M.; Sekimizu, K. Drug Discov. Ther. 2008, 2, 24.
  29. Ose, A.; Kusuhara, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M.; Takuya, F.; Yamamoto, A.; Sugiyama, Y. Drug Metab. Dispos. 2008, 36, 427. https://doi.org/10.1124/dmd.107.018556
  30. Morita, M.; Sone, T.; Yamatsugu, K.; Sohotome, Y.; Matsunaga, S.; Kanai, M.; Watanabe, Y.; Shibasaki, M. Bioorg. Med. Chem. Lett. 2008, 18, 600. https://doi.org/10.1016/j.bmcl.2007.11.079
  31. Konno, F.; Arai, T.; Zhang, M.-R.; Hatori, A.; Yamamoto, K.; Ogawa, M.; Ito, G.; Odawara, C.; Yamasaki, T.; Kato, K.; Suzuki, K. Bioorg. Med. Chem. Lett. 2008, 18, 1260. https://doi.org/10.1016/j.bmcl.2008.01.037
  32. Usami, A.; Sasaki, T.; Satoh, N.; Akiba, S.; Yokoshima, S.; Fukuyama, T.; Yamatsugu, K.; Kanai, M.; Shibasaki, M.; Matsuki, N.; Ikegaya, Y. J. Pharamacol. Sci. 2008, 106, 659. https://doi.org/10.1254/jphs.SC0070467
  33. Ono, H.; Nagano, Y.; Matsunami, N.; Sugiyama, S.; Yamamoto, S.; Tanabe, M. Biol. Pharm. Bull. 2008, 31, 638. https://doi.org/10.1248/bpb.31.638
  34. Yoshino, T.; Nishijima, K.; Shioda, K.; Yui, K.; Kato, S. Neurosci. Lett. 2008, 438, 67. https://doi.org/10.1016/j.neulet.2008.04.011
  35. Hata, K.; Koseki, K.; Yamaguchi, K.; Moriya, S.; Suzuki, Y.; Yingsakmongkon, S.; Hirai, G.; Sodeoka, M.; von Itzstein, M.; Miyagi, T. Antimicrob. Agents Chemother. 2008, 52, 3484. https://doi.org/10.1128/AAC.00344-08
  36. Jhee, S. S.; Yen, M.; Ershefsky, L.; Leibowitz, M.; Schulte, M.; Kaeser, B.; Boak, L.; Patel, A.; Hoffmann, G.; Prinssen, E. P.; Rayner, C. R. Antimicrob. Agents Chemother. 2008, 52, 3678.
  37. Toovy, S.; Rayner, C.; Prinssen, E.; Chu, T.; Donner, B.; Thakrar, B.; Dutkowski, R.; Hoffmann, G.; Breidenbach, A.; Lindemann, L.; Carey, E.; Boak, L; Gieschke, R.; Sachs, S.; Solsky, J.; Small, I.; Reddy, D. Drug Safety 2008, 31, 1097. https://doi.org/10.2165/0002018-200831120-00006
  38. Ose, A.; Ito, M.; Kusuhara, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M.; Hosokawa, M.; Schuetz, J. D.; Sugiyama, Y. Drug Metab. Dispos. 2009, 37, 315. https://doi.org/10.1124/dmd.108.024018
  39. Hatori A.; Arai, T.; Yamamoto, K.; Yamasaki, T.; Kawamura, K.; Yul. J.; Konno, F.; Nakao, R.; Suzuki, K.; Zhang, M. -R. Nucl. Med. Biol. 2009, 36, 47. https://doi.org/10.1016/j.nucmedbio.2008.10.008
  40. Izumi, Y.; Tokuda, K.; O’Dell, K. A.; Zorumski, C. F.; Narahashi, T. Hum. Exp. Toxicol. 2009, 27, 911. https://doi.org/10.1177/0960327109102367
  41. Arai, T.; Konno, F.; Ogawa, M.; Zhang, M. R.; Suzuki, K. J. Labelled Compd. Radiopharm. 2009, 52, 350. https://doi.org/10.1002/jlcr.1604
  42. Hoffmann, G.; Funk, C.; Fowler, S.; Otteneder, M. B.; Breidenbach, A.; Rayner, C. R.; Chu, T.; Prinssen, E. P. Antimicrob. Agents Chemother. 2009, 53, 4753. https://doi.org/10.1128/AAC.01541-08
  43. Oshima, S.; Nemoto, E.; Kuramochi, M.; Saitoh, Y.; Kobayshi, D. J. Pharm. Pharmacol. 2009, 61, 1397. https://doi.org/10.1211/jpp/61.10.0018
  44. Kimura, Y.; Yamatsugu, K.; Kanai, M.; Echigo, N.; Kuzuhara, T.; Shibasaki, M. Tetrahedron Lett. 2009, 50, 3205. https://doi.org/10.1016/j.tetlet.2009.01.142
  45. Rusell, R. J.; Haire, L. F.; Stevens, D. J.; Collins, P. J.; Lin, Y. P.; Blackburn, G. M.; Hay, A. J.; Gamblin, S. J.; Skehel, J. J. Nature 2006, 443, 45. https://doi.org/10.1038/nature05114
  46. Collins, P. J.; Haire, L. F.; Lin, Y. P.; Liu, J.; Rusell, R. J.; Walker, P. A.; Skehel, J. J.; Martin, S. R.; Hay, A. J.; Gamblin, S. J. Nature 2008, 453, 1258. https://doi.org/10.1038/nature06956
  47. Gracias, V.; Frank, K. E.; Milligan, G. L.; Aube, J. Tetrahedron 1997, 53, 16241. https://doi.org/10.1016/S0040-4020(97)01012-0
  48. Ullrich, T.; Ghobrial, M.; Peters, C.; Billich, A.; Guerini, D.; Nussbaumer, P. Chem. Med. Chem. 2007, 3, 356.

Cited by

  1. Recent Development in Synthetic Strategies for Oseltamivir Phosphate vol.51, pp.3-4, 2011, https://doi.org/10.1002/ijch.201100001
  2. Rapid and simple detection of Tamiflu-resistant influenza virus: Development of oseltamivir derivative-based lateral flow biosensor for point-of-care (POC) diagnostics vol.8, pp.1, 2018, https://doi.org/10.1038/s41598-018-31311-x