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Advances in Hematology
Volume 2009 (2009), Article ID 704928, 5 pages
http://dx.doi.org/10.1155/2009/704928
Research Article

An NMR Study of the Bortezomib Degradation under Clinical Use Conditions

1Dipartimento di Chimica Organica e Biochimica, Università Degli Studi di Napoli Federico II, Via Cynthia 6, Monte Sant'Angelo, 80126 Napoli, Italy
2Dipartimento di Biochimica e Biotecnologie Mediche, Divisione di Ematologia, Università Degli Studi di Napoli Federico II, 80131 Napoli, Italy
3Farmacia Centralizzata, Azienda Ospedaliera, Universitaria “Federico II”, 80131 Napoli, Italy

Received 14 November 2008; Accepted 9 February 2009

Academic Editor: David H. Vesole

Copyright © 2009 Adele Bolognese et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. M. P. Groziak, “Boron therapeutics on the horizon,” American Journal of Therapeutics, vol. 8, no. 5, pp. 321–328, 2001. View at Google Scholar
  2. P. G. Richardson, C. Mitsiades, R. Schlossman et al., “Bortezomib in the front-line treatment of multiple myeloma,” Expert Review of Anticancer Therapy, vol. 8, no. 7, pp. 1053–1072, 2008. View at Publisher · View at Google Scholar · View at PubMed
  3. P. G. Richardson, T. Hideshima, C. Mitsiades, and K. Anderson, “Proteasome inhibition in hematologic malignancies,” Annals of Medicine, vol. 36, no. 4, pp. 304–314, 2004. View at Publisher · View at Google Scholar
  4. J. Mikhael and H. Chang, “Bortezomib: proteasome inhibition as a novel mechanism of cancer therapy-implications for hematological malignancies,” Letters in Drug Design & Discovery, vol. 4, no. 2, pp. 82–86, 2007. View at Publisher · View at Google Scholar
  5. H. C. Brown, in Boranes in Organic Chemistry, pp. 320–326, Cornell University Press, Ithaca, NY, USA, 1972.
  6. M. B. Smith and J. March, March's Advanced Organic Chemistry, John Wiley & Sons, Hoboken, NJ, USA, 6th edition, 2007.
  7. M. Yamashita, Y. Yamamoto, K.-Y. Akiba et al., “Syntheses and structures of hypervalent pentacoordinate carbon and boron compounds bearing an anthracene skeleton—elucidation of hypervalent interaction based on X-ray analysis and DFT calculation,” Journal of the American Chemical Society, vol. 127, no. 12, pp. 4354–4371, 2005. View at Publisher · View at Google Scholar · View at PubMed
  8. M. Groll, C. R. Berkers, H. L. Ploegh, and H. Ovaa, “Crystal structure of the boronic acid-based proteasome inhibitor bortezomib in complex with the yeast 20S proteasome,” Structure, vol. 14, no. 3, pp. 451–456, 2006. View at Publisher · View at Google Scholar · View at PubMed
  9. S. B. Mirvis, “Air oxidation of triakylboranes,” Journal of the American Chemical Society, vol. 83, pp. 3051–3056, 1961. View at Google Scholar
  10. H. C. Brown, M. M. Midland, and G. W. Kabalka, “The stoichiometrically controlled reaction of organoboranes with oxygen under very mild conditions to achieve essentially quantitative conversion into alcohols,” Journal of the American Chemical Society, vol. 93, no. 4, pp. 1024–1025, 1971. View at Publisher · View at Google Scholar
  11. D. G. Hall, in Boronic Acids, pp. 482–495, Wiley-VCH, Chichester, UK, 2006.
  12. S. Wu, W. Waugh, and V. J. Stella, “Degradation pathways of a peptide boronic acid derivative, 2-Pyz-(CO)-Phe-Leu-B(OH)2,” Journal of Pharmaceutical Sciences, vol. 89, no. 6, pp. 758–765, 2000. View at Publisher · View at Google Scholar
  13. P. André, S. Cisternino, F. Chiadmi et al., “Stability of bortezomib 1-mg/mL solution in plastic syringe and glass vial,” The Annals of Pharmacotherapy, vol. 39, no. 9, pp. 1462–1466, 2005. View at Publisher · View at Google Scholar · View at PubMed
  14. P. Cmoch, “Identification of 2-chloropyrazine oxidation products and several derivatives by multinuclear magnetic resonance,” Magnetic Resonance in Chemistry, vol. 41, no. 9, pp. 693–698, 2003. View at Publisher · View at Google Scholar
  15. T. Pekol, J. S. Daniels, J. Labutti et al., “Human metabolism of the proteasome inhibitor bortezomib: identification of circulating metabolites,” Drug Metabolism and Disposition, vol. 33, no. 6, pp. 771–777, 2005. View at Publisher · View at Google Scholar · View at PubMed
  16. M. Verdoes, B. I. Florea, W. A. van der Linden et al., “Mixing of peptides and electrophilic traps gives rise to potent, broad-spectrum proteasome inhibitors,” Organic & Biomolecular Chemistry, vol. 5, no. 9, pp. 1416–1426, 2007. View at Publisher · View at Google Scholar · View at PubMed