Skip to main content
SpringerLink
Log in

Preparation and Biological Evaluation of Synthetic and Polymer-Encapsulated Congeners of the Antitumor Agent Pactamycin: Insight into Functional Group Effects and Biological Activity

  • Chapter
  • First Online:
Stereoselective Desymmetrization Methods in the Assembly of Complex Natural Molecules

Part of the book series: Springer Theses ((Springer Theses))

  • 396 Accesses

Abstract

An expeditious total synthesis of the aminocyclitol antibiotic pactamycin was described in Chap. 1, enabling fifteen-step preparation of the natural product from commercially available materials. Pactamycin, while bearing a remarkable array of valuable biological traits, is hindered in medicinal development by its high cytotoxicity.

Reprinted in part with permission from Sharpe, R. J.; Malinowski, J. T.; Sorana, F.; Luft, J. C.; Bowerman, C. J.; DeSimone, J. M.; Johnson, J. S. Bioorg. Med. Chem. 2015, 23, 1849.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Notes

  1. 1.

    Summary methods for synthesis of unsymmetrical dialkylureas: [22–29].

References

  1. M. MacCoss, T.A. Baillie, Science 2004, 303 (1810)

    Google Scholar 

  2. E. Patridge, P. Gareiss, M.S. Kinch, D. Hoyer, Drug Discov. Today, In Press (2015)

    Google Scholar 

  3. R. Bade, H.-F. Chan, J. Reynisson, Eur. J. Med. Chem. 45, 5646 (2010)

    Article  CAS  Google Scholar 

  4. M.S. Butler, A.A.B. Robertson, M.A. Cooper, Nat. Prod. Rep. 31, 1612 (2014)

    Article  CAS  Google Scholar 

  5. S. Schreiber, Science 2000, 287 (1964)

    Google Scholar 

  6. T.R. Hurley, T.A. Smitka, J.H. Wilton, R.H. Bunge, G.C. Hokanson, J.C. French, J. Antibiot. 1986, 39 (1086)

    Google Scholar 

  7. T. Ito, N. Roongsawang, N. Shirasaka, W. Lu, P.M. Flatt, N. Kasanah, C. Miranda, T. Mahmud, ChemBioChem 10, 2253 (2009)

    Article  CAS  Google Scholar 

  8. W. Lu, N. Roongsawang, T. Mahmud, Chem. Biol. 18, 425 (2011)

    Article  CAS  Google Scholar 

  9. K.H. Almabruk, W. Lu, Y. Li, M. Abugreen, J.X. Kelly, T. Mahmud, Org. Lett. 15, 1678 (2013)

    Article  CAS  Google Scholar 

  10. M.E.R. O’Brien, Ann. Oncol. 15, 440 (2004)

    Article  Google Scholar 

  11. W.J. Gradishar, S. Tjulandin, N. Davidson, H. Shaw, N. Desai, P. Bhar, M. Hawkins, J. O’Shaughnessy, J. Clin. Oncol. 23, 7794 (2005)

    Article  CAS  Google Scholar 

  12. A.Z. Wang, R. Langer, O.C. Farokhzad, Annu. Rev. Med. 63, 185 (2012)

    Article  CAS  Google Scholar 

  13. R.A. Petros, J.M. DeSimone, Nat. Rev. Drug Discov. 9, 615 (2010)

    Article  CAS  Google Scholar 

  14. W.P. Caron, K.P. Morgan, B.A. Zamboni, W.C. Zamboni, Clin. Cancer Res. 19, 3309 (2013)

    Article  CAS  Google Scholar 

  15. J. Hrkach, D. Von Hoff, M. Mukkaram Ali, E. Andrianova, J. Auer, T. Campbell, D. De Witt, M. Figa, M. Figueiredo, A. Horhota, S. Low, K. McDonnell, E. Peeke, B. Retnarajan, A. Sabnis, E. Schnipper, J.J. Song, Y.H. Song, J. Summa, D. Tompsett, G. Troiano, T. Van Geen Hoven, J. Wright, P. LoRusso, P.W. Kantoff, N.H. Bander, C. Sweeney, O.C. Farokhzad, R. Langer, S. Zale, Sci. Transl. Med. 4, 12839 (2012)

    Article  Google Scholar 

  16. G. Batist, K.A. Gelmon, K.N. Chi, W.H. Miller, S.K.L. Chia, L.D. Mayer, C.E. Swenson, A.S. Janoff, A.C. Louie, Clin. Cancer Res. 15, 692 (2009)

    Article  CAS  Google Scholar 

  17. S. Svenson, M. Wolfgang, J. Hwang, J. Ryan, S. Eliasof, J. Control. Release 153, 49 (2011)

    Article  CAS  Google Scholar 

  18. J.P. Rolland, B.W. Maynor, L.E. Euliss, A.E. Exner, G.M. Denison, J.M. DeSimone, J. Am. Chem. Soc. 127, 10096 (2005)

    Article  CAS  Google Scholar 

  19. K.S. Chu, A.N. Schorzman, M.C. Finniss, C.J. Bowerman, L. Peng, J.C. Luft, A.J. Madden, A.Z. Wang, W.C. Zamboni, J.M. DeSimone, Biomaterials 34, 8424 (2013)

    Article  CAS  Google Scholar 

  20. K.S. Chu, M.C. Finniss, A.N. Schorzman, J.L. Kuijer, J.C. Luft, C.J. Bowerman, M.E. Napier, Z.A. Haroon, W.C. Zamboni, J.M. Desimone, Nano Lett. 14, 1472 (2014)

    Article  CAS  Google Scholar 

  21. K.M. Gharpure, K.S. Chu, C. Bowerman,T. Miyake, S. Pradeep, L.S. Mangala, H.-D. Han, R. Rupaimoole, G.N. Armaiz-Pena, T.B. Rahhal, S.Y. Wu, C. Luft, M.E. Napier, G. Lopez-Berestein, J.M. Desimone, A.K. Sood, Mol. Cancer Ther. (2014)

    Google Scholar 

  22. S. Ozaki, Chem. Rev. 72, 457 (1972)

    Article  Google Scholar 

  23. I. Gallou, M. Eriksson, X. Zeng, C. Senanayake, V. Farina, J. Org. Chem. 70, 6960 (2005)

    Article  CAS  Google Scholar 

  24. Y. Matsumura, Y. Satoh, O. Onomura, T. Maki, J. Org. Chem. 65, 1549 (2000)

    Article  CAS  Google Scholar 

  25. S. Gastaldi, S.M. Weinreb, D. Stien, J. Org. Chem. 65, 3239 (2000)

    Article  CAS  Google Scholar 

  26. C. Han, J.A. Porco, Org. Lett. 9, 1517 (2007)

    Article  CAS  Google Scholar 

  27. Q. Liu, N.W. Luedtke, Y. Tor, Tetrahedron Lett. 42, 1445 (2001)

    Article  CAS  Google Scholar 

  28. S.L. Peterson, S.M. Stucka, C.J. Dinsmore, Org. Lett. 12, 1340 (2010)

    Article  CAS  Google Scholar 

  29. P. Dubé, N.F.F. Nathel, M. Vetelino, M. Couturier, C.L. Aboussafy, S. Pichette, M.L. Jorgensen, M. Hardink, Org. Lett. 11, 5622 (2009)

    Article  Google Scholar 

  30. T. Tsujimoto, T. Nishikawa, D. Urabe, M. Isobe, Synlett 433 (2005)

    Google Scholar 

  31. S. Knapp, Y. Yu, Org. Lett. 9, 1359 (2007)

    Article  CAS  Google Scholar 

  32. T.J. Haussener, R.E. Looper, Org. Lett. 14, 3632 (2012)

    Article  CAS  Google Scholar 

  33. N. Matsumoto, T. Tsujimoto, A. Nakazaki, M. Isobe, T. Nishikawa, RSC Adv. 2, 9448 (2012)

    Article  CAS  Google Scholar 

  34. J.T. Malinowski, S.J. McCarver, J.S. Johnson, Org. Lett. 14, 2878 (2012)

    Article  CAS  Google Scholar 

  35. S. Hanessian, R.R. Vakiti, S. Dorich, S. Banerjee, F. Lecomte, J.R. Del Valle, J. Zhang, B. Deschênes-Simard, Angew. Chem. Int. Ed. 50, 3497 (2011)

    Article  CAS  Google Scholar 

  36. S. Hanessian, R. Vakiti, S. Dorich, S. Banerjee, B. Deschênes-Simard, J. Org. Chem. 77, 9458 (2012)

    Article  CAS  Google Scholar 

  37. S. Hanessian, R.R. Vatiki, A.K. Chattopadhyay, S. Dorich, C. Lavallée, Bioorg. Med. Chem. 21, 1775 (2013)

    Article  CAS  Google Scholar 

  38. D.S. Tourigny, I.S. Fernández, A.C. Kelley, R.R. Vakiti, A.K. Chattopadhyay, S. Dorich, S. Hanessian, V. Ramakrishnan, J. Mol. Biol. 425, 3907 (2013)

    Article  CAS  Google Scholar 

  39. J.T. Malinowski, R.J. Sharpe, J.S. Johnson, Science 340, 180 (2013)

    Article  CAS  Google Scholar 

  40. R.J. Sharpe, J.T. Malinowski, J.S. Johnson, J. Am. Chem. Soc. 135, 17990 (2013)

    Article  CAS  Google Scholar 

  41. S. Salvestrini, P. Di Cerbo, S. Capasso, J. Chem. Soc. Perkin Trans. 2(11), 1889 (2002)

    Google Scholar 

  42. G.B. Payne, J. Org. Chem. 27, 3819 (1962)

    Article  CAS  Google Scholar 

  43. R. Shen, C.T. Lin, J.A. Porco, J. Am. Chem. Soc. 124, 5650 (2002)

    Article  CAS  Google Scholar 

  44. G. Dinos, D.N. Wilson, Y. Teraoka, W. Szaflarski, P. Fucini, D. Kalpaxis, K.H. Nierhaus, Mol. Cell 13, 113 (2004)

    Article  CAS  Google Scholar 

  45. A.P. Carter, W.M. Clemons Jr., D.E. Brodersen, R.J. Morgan-Warren, B.T. Wimberly, V. Ramakrishnan, Nature 407, 340 (2000)

    Article  CAS  Google Scholar 

  46. M. Iwatsuki, A. Nishihara-Tsukashima, A. Ishiyama, M. Namatame, Y. Watanabe, S. Handasah, H. Pranamuda, B. Marwoto, A. Matsumoto, Y. Takahashi, K. Otoguro, S. Ōmura, J. Antibiot. 65, 169 (2012)

    Article  CAS  Google Scholar 

  47. D.D. Weller, K.L. Rinehart Jr., J. Am. Chem. Soc. 100, 6757 (1978)

    Article  CAS  Google Scholar 

  48. K.L. Rinehart Jr., M. Potgieter, J. Am. Chem. Soc. 103, 2099 (1981)

    Article  CAS  Google Scholar 

  49. M.J. Waring, Expert Opin. Drug Discov. 5, 235 (2010)

    Article  CAS  Google Scholar 

  50. K.S. Chu, W. Hasan, S. Rawal, M.D. Walsh, E.M. Enlow, J.C. Luft, A.S. Bridges, J.L. Kuijer, M.E. Napier, W.C. Zamboni, J.M. DeSimone, Nanomedicine 9, 686 (2013)

    CAS  Google Scholar 

  51. See Table 2.8 in Section 2.5 of this Chapter

    Google Scholar 

  52. See Figure 2.8 in Section 2.5 of this Chapter

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Advanced Research Chemist, Eastman Chemical Company, Johnson City, TN, USA

    Robert J. Sharpe

Authors
  1. Robert J. Sharpe
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Robert J. Sharpe .

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Sharpe, R.J. (2016). Preparation and Biological Evaluation of Synthetic and Polymer-Encapsulated Congeners of the Antitumor Agent Pactamycin: Insight into Functional Group Effects and Biological Activity. In: Stereoselective Desymmetrization Methods in the Assembly of Complex Natural Molecules. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-39025-3_2

Download citation

Publish with us

Policies and ethics

Search

Navigation