NMR and mass spectrometric characterization of vinblastine, vincristine and some new related impurities - part I

Journal of Pharmaceutical and Biomedical Analysis

Volumn 84, Issue , 2013, Pages 293-308

  Dubrovay, Zsófia ^a   Háda, Viktor ^a   Béni, Zoltán ^a   Szántay, Csaba ^a  

^a GEDEON RICHTER LTD   (Hungary)

Author keywords

High resolution MS; Structure elucidation; Ultra high field NMR; Vinblastine; Vincristine

Indexed keywords

VINBLASTINE; VINCRISTINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NITROGEN NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

EID: 84880809557     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.08.019     Document Type: Article

References (38)

1. The Alkaloids, Antitumor Bisindole Alkaloids from Catharanthus roseus (L.) 1990, vol. 37. Academic Press, San Diego.
2. Béni Z., Háda V., Dubrovay Zs., Szántay Cs. Structure elucidation of indole-indoline type alkaloids: a retrospective account from the point of view of current NMR and MS technology. J. Pharm. Biomed. Anal. 2012, 69:106-124.
3. Görög S., Szántay Cs. Spectroscopic methods in drug quality control and development. Encyclopedia of Spectroscopy and Spectrometry, vol. 3 2010, 2640-2650. Elsevier, Oxford. 2nd ed.
4. Szántay Cs., Béni Z., Balogh G., Gáti T. The changing role of NMR spectroscopy in off-line impurity identification: a conceptual view. Trends Anal. Chem. 2006, 25:806-820.
5. Szántay Cs., Balázs M., Bölcskei H., Szántay Cs. Synthesis of vinca alkaloids and related compounds, part LVI. 15',20'-Anhydrovinblastine borane complex, structural investigations using NMR methods. Tetrahedron 1991, 47:1265-1274.
6. Hunter B.K., Hall L.D., Sanders J.K.M. The conformation of vinblastine in solution as determined by NOE difference spectroscopy. J. Chem. Soc., Perkin Trans. I 1983, 657-665.
7. Kuehne M.E., Matson P.A., Bornmann W.G. Enantioselective syntheses of vinblastine, leurosidine, vincovaline, and 20'-epi-vincovaline. J. Org. Chem. 1991, 56:513-528.
8. Blaskó G., Cordell G.A. Isolation, structure elucidation, and biosynthesis of the bisindole alkaloids of Catharanthus. The Alkaloids, Antitumor Bisindole alkaloids from Catharanthus roseus (L.) 1990, vol. 37:1-69. Academic Press, San Diego, (Chapter 1).
9. 1H NMR study and conformational aspects of 20'-deoxy-20'-epivindesine. Magn. Reson. Chem. 1986, 24:35-40.
10. 1H NMR study of vinblastine. Bull. Soc. Chim. Belg. 1980, 89:629-636.
11. Ribet J.-P., Zalavari P., Commenges G., Fahy J., Duflos A., Schambe P. Analyse structurale de la vinorelbine en solution déterminée par spectrométrie de résonance magnétique nucléaire. Ann. Pharm. Fr. 1997, 55:20-34.
12. 13C NMR spectra of vinflunine. Magn. Reson. Chem. 2001, 39:43-48.
13. (8'-noranhydrovinblastine). J. Heterocycl. Chem. 1995, 32:1255-1259.
14. Andrews C.W., Wisowaty J., Davis A.O., Crouch R.C., Martin G.E. Molecular modeling, NMR spectroscopy, and conformational analysis of 3',4'-anhydrovinblastine. J. Heterocycl. Chem. 1995, 32:1011-1017.
15. 13C NMR spectroscopy. J. Nat. Prod. 1992, 55:285-293.
16. 15N correlation via unsymmetrical indirect covariance NMR: application to vinblastine. J. Nat. Prod. 2007, 70:1966-1970.
17. 13C NMR study of two vincristine derivatives at 300MHz. Bull. Soc. Chim. Belg. 1989, 92:125-132.
18. Ishikawa H., Colby D.A., Seto S., Va P., Tam A., Kakei H., Rayl T.J., Hwang I., Boger D.L. J. Am. Chem. Soc. 2009, 13:4904-4916.
19. Ahn S.H., Duffel M.W., Rosazza J.P.N. Oxidations of vincristine catalyzed by peroxidase and ceruloplasmin. J. Nat. Prod. 1997, 60:1125-1129.
20. Mák M., Tamás J., Honty K., Szabó L., Szántay Cs. Mass spectral behaviour of some semisynthetic derivatives of vinblastine-type alkaloids. Biomed. Environ. Mass Spectrom. 1989, 18:576-580.
21. Favretto D., Piovan A., Cappelletti E.M. Electrospray ionization mass spectra and collision induced mass spectra of antitumour Catharanthus alkaloids. Rapid Commun. Mass Spectrom. 1998, 12:982-984.
22. Xing J., Xie C., Lou H. Recent applications of liquid chromatography-mass spectrometry in natural products bioanalysis. J. Pharmaceut. Biomed. Anal. 2007, 44:368-378.
23. Feng X., Siegel M.M. FTICR-MS applications for the structure determination of natural products. Anal. Bioanal. Chem. 2007, 389:1341-1363.
24. Nussbaumer S., Geiser L., Sadeghipour F., Hochstrasser D., Bonnabry P., Veuthey J.-L., Fleury-Souverain S. Wipe sampling procedure coupled to LC-MS/MS analysis for the simultaneous determination of 10 cytotoxic drugs on different surfaces. Anal. Bioanal. Chem. 2012, 402:2499-2509.
25. Ling G., Zhang P., Sun J., Zhang W., Fu Q., Zhang T., Deng Y., He Z. An LC-MS/MS method for simultaneous determination of vincristine and verapamil in rat plasma after oral administration of a dual agent formulation. Biomed. Chromatogr. 2011, 25:963-969.
26. Hamscher G., Mohring S.A.I., Knobloch A., Eberle N., Nau H., Nolte I., Simon D. Determination of drug residues in urine of dogs receiving anti-cancer chemotherapy by liquid chromatography-electrospray ionization-tandem mass spectrometry: is there an environmental or occupational risk?. J. Anal. Toxicol. 2010, 34:142-148.
27. Guilhaumou R., Solas C., Rome A., Giocanti M., Andre N., Lacarelle B. Validation of an electrospray ionization LC/MS/MS method for quantitative analysis of vincristine in human plasma samples. J. Chromatogr. B 2010, 878:423-427.
28. Damen C.W.N., Rosing H., Schellens J.H.M., Beijnen J.H. High-performance liquid chromatography coupled with mass spectrometry for the quantitative analysis of vinca-alkaloids in biological matrices: a concise survey from the literature. Biomed. Chromatogr. 2010, 24:83-90.
29. Ferreres F., Pereira D.M., Valentão P., Oliveira J.M.A., Faria J., Gaspar L., Sottomayor M., Andrade P.B. Simple and reproducible HPLC-DAD-ESI-MS/MS analysis of alkaloids in Catharanthus roseus roots. J. Pharmaceut. Biomed. Anal. 2010, 51:65-69.
30. Yin J., Yang Y., Li K., Zhang J., Shao B. Analysis of anticancer drugs in sewage water by selective SPE and UPLC-ESI-MS-MS. J. Chromatogr. Sci. 2010, 48:781-789.
31. Nussbaumer S., Fleury-Souverain S., Antinori P., Sadeghipour F., Hochstrasser D.F., Bonnabry P., Veuthey J.-L., Geiser L. Simultaneous quantification of ten cytotoxic drugs by a validated LC-ESI-MS/MS method. Anal. Bioanal. Chem. 2010, 398:3033-3042.
32. Damen C.W.N., Israëls T., Caron H.N., Schellens J.H.M., Rosing H., Beijnen J.H. Validated assay for the simultaneous quantification of total vincristine and actinomycin-D concentrations in human EDTA plasma and of vincristine concentrations in human plasma ultrafiltrate by high-performance liquid chromatography coupled with tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23:763-774.
33. Damen C.W.N., Rosing H., Schellens J.H.M., Beijnen J.H. Application of dried blood spots combined with high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry for simultaneous quantification of vincristine and actinomycin-D. Anal. Bional. Chem. 2009, 394:1171-1182.
34. Dennison J.B., Kulanthaivel P., Barbuch R.J., Renbarger J.L., Ehlhardt W.J., Hall S.D. Selective metabolism of vincristine in vitro by CYP3A5. Drug Metab. Dispos. 2006, 34:1317-1327.
35. Neuss N., Gorman M., Svoboda G.H., Maciak G., Beer C.T. Vinca alkaloids. III. Characterization of leurosine and vincaleukoblastine, new alkaloids from Vinca Rosea Linn. J. Am. Chem. Soc. 1959, 81:4754-4755.
36. Vinblastine Sulphate and Vincristine Sulphate 2011, European Pharmacopoeia, Strasbourg, pp. 3200-3202. 7th ed.
37. Moncrief J.W., Lipscomb W.N. Structures of leurocristine (vincristine) and vincaleukoblastine. X-ray analysis of leurocristine methiodide. J. Am. Chem. Soc. 1965, 87:4963-4964.
38. Bau R., Jin K.K. Crystal structure of vinblastine. J. Chem. Soc., Perkin Trans. 2000, 1:2079-2082.