Identification of Degradation Product of Deguelin and Its Stability Using Liquid Chromatography and Electrospray/Mass Spectrometry

Journal of Liquid Chromatography and Related Technologies

Volumn 27, Issue 6, 2004, Pages 1057-1069

  Shin, Young Geun ^a,c   Udeani, George O ^a   Kosmeder II, Jerome W ^a   Zhao, Guo Min ^a   Dagar, Sumeet ^a   Onyuksel, Hayat ^a   Moriarty, Robert M ^b   Cordell, Geoffrey A ^a,b   Moon, Richard C ^a   Kinghorn, A Douglas ^a,b   Pezzuto, John M ^a,b,d  

^a UNIVERSITY OF ILLINOIS   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c GLAXOSMITHKLINE   (United States)

^d PURDUE UNIVERSITY   (United States)

Author keywords

Degradation; Deguelin; LC MS; Stability; Tephrosin

Indexed keywords

DEGRADATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; TUMORS;

AUTO-OXIDATION; DEGRADATION PRODUCTS;

ORGANIC COMPOUNDS;

CORN OIL; CREMOPHOR; DEGUELIN; LIPOSOME; POLYSORBATE 80; TAMOXIFEN CITRATE; YOHIMBINE;

ANALYTIC METHOD; ARTICLE; AUTOOXIDATION; CATALYSIS; DECOMPOSITION; ELECTROSPRAY MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; NONHUMAN; PHOSPHOLIPID VESICLE; PROTEIN ANALYSIS; PROTEIN DEGRADATION; PROTEIN STABILITY; SAMPLING; TRANSCRIPTION REGULATION;

ZEA MAYS;

EID: 12144288146     PISSN: 10826076     EISSN: None     Source Type: Journal    
DOI: 10.1081/JLC-120030178     Document Type: Article

References (28)

1. Anonymous. Cancer Facts and Figures; American Cancer Society: Atlanta, 1999.
2. Hong, W.K.; Sporn, M.B. Recent advances in chemoprevention of cancer. Science 1997, 278, 1073-1077.
3. Greenwald, P.; Kelloff, G.; Burch-Whirman, C.; Kramer, B.S. Chemoprevention. Cancer J. Clin. 1995, 45, 31-49.
4. Dunn, B.K.; Kramer, B.S.; Ford, L.G. Phase III, large-scale chemoprevention trials. Approach to chemoprevention clinical trials and phase III clinical trials of tamoxifen as a chemopreventive for breast cancer. The U.S. National Cancer Institute experience. Hematol. Oncol. Clin. North Am. 1998, 12, 1019-1036.
5. Thompson, J.M.; Coltman, C.A., Jr.; Crowley, J. Chemoprevention of prostate cancer: the prostate cancer trials. Prostate 1997, 33, 217-221.
6. Kelloff, G.J.; Boone, C.W.; Steele, V.E.; Fay, J.R.; Lubet, R.A.; Crowell, J.W.; Sigman, C.C. Mechanistic considerations in chemopreventive drug development. J. Cell. Biochem. Suppl. 1994, 20, 1-24.
7. Jang, M.S.; Cai, E.N.; Udeani, G.O.; Slowing, K.V.; Thomas, C.F.; Beecher, C.W.W.; Fong, H.H.S.; Famsworth, N.R.; Kinghorn, A.D.; Mehta, R.G.; Moon, R.C.; Pezzuto, J.M. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
8. Pezzuto, J.M. Cancer chemopreventive agents: from plant materials to clinical trials. In Human Medicinal Agents from Plants; Kinghorn, A.D., Baladrin, M.F., Eds.; American Chemical Society: Washington DC, 1993; 205-217.
9. Pezzuto, J.M. Natural product cancer chemopreventive agents. In Phytochemistry: Phytochemistry of Medicinal Plants; Arnason, J.T., Mata, R., Romeo, J.T., Eds.; Plenum Press: New York, 1995;19-45.
10. Kinghorn, A.D.; Fong, H.H.S.; Farnsworth, N.R.; Mehta, R.G.; Moon, R.C.; Moriarty, R.M.; Pezzuto, J.M. Cancer chemopreventive agents discovered by activity-guided fractionation: a review. Curr. Org. Chem. 1998, 2, 597-612
11. Udeani, G.O.; Gerhäuser, C.; Thomas, C.F.; Moon, R.C.; Kosmeder, J.W.; Kinghorn, A.D.; Moriarty, R.M.; Pezzuto, J.M. Cancer chemopreventive activity mediated by deguelin, a naturally occurring rotenoid. Cancer Res. 1997, 57, 3424-3428.
12. Gerhäuser, C.; Mar, W.; Lee, S.K.; Suh, N.; Luo, Y.D.; Kosmeder, J.W.; Luyengi, L.; Fong, H.H.S.; Kinghorn, A.D.; Moriarty, R.M.; Mehta, R.G.; Constantinou, A.; Moon, R.C.; Pezzuto, J.M. Rotenoids mediate potent cancer chemopreventive activity through transcriptional regulation of ornithine decarboxylase. Nature Med. 1995, 1, 260-266.
13. Gerhäuser, C.; Lee, S.K.; Kosmeder, J.W.; Moriarty, R.M.; Hamel, E. ; Mehta, R.G.; Moon, R.C.; Pezzuto, J.M. Regulation of ornithine decarboxylase induction by deguelin, a, natural product cancer chemopreventive agent. Cancer Res. 1997, 57, 3429-3435.
14. Udeani, G.O.; Zhao, G.M.; Kosmeder, J.W.; Beecher, C.W.W.; Kinghorn, A.D.; Moriarty, R.M.; Moon, R.C.; Pezzuto, J.M. Preclinical pharmacokinetics of deguelin, a naturally occurring chemopreventive agent. Proc. Am. Assoc. Cancer Res. 1998, 39, 290.
15. Udeani, G.O.; Zhao, G.M.; Kastrissios, H.; Kinghorn, A.D.; Beecher, C.W.W.; Moon, R.C.; Pezzuto, J.M. Ornithine decarboxylase: a potential biomarker in dosage modulation of the chemopreventive agent deguelin. J. Clin. Pharmacol. 1998, 38, 862.
16. Adams, J.D.; Flora, K.P.; Goldspiel, B.R.; Wilson, J.W.; Arbuck, S.G.; Finley, R. Taxol: a history of pharmaceutical development and current pharmaceutical concerns. J. Natl. Cancer Inst. Monogr. 1993, 15, 141-147.
17. Kohler, D.R.; Goldspiel, B.R. Paclitaxel (taxol). Pharmacotherapy 1994, 14, 3-34.
18. Goldspiel, B.R. Pharmaceutical issues: preparation, administration, stability, and compatibility with other medications. Ann. Pharmacother. 1994, 28, S23-S26.
19. Udeani, G.O.; Zhao, G.M.; Shin, Y.G.; Kosmeder, J.W.; Beecher, C.W.W.; Kinghorn, A.D.; Moriarty, R.M.; Moon, R.C.; Pezzuto, J.M. Pharmacokinetics of deguelin, a cancer chemopreventive agent in rats. Cancer Chemother. Pharmacol. 2001, 47, 263-268.
20. Anzeveno, P.B. Retenoid interconversion: synthesis of deguelin from rotenone. J. Org. Chem. 1979, 44, 2578-2580.
21. Sejourne, F.; Rubinstein, I.; Suzuki, H.; Onyuksel, H. Development of a novel bioactive formulation of vasoactive intestinal peptide in sterically stabilized liposomes. Pharm. Res. 1997, 14, 362-365.
22. Patel, M.; Rubinstein, I.; Ikezaki, H.; Onyuksel, H. Simplified preparation of vasoactive intestinal peptide in sterically stabilized liposomes. Proc. Int. Symp. Control Rel. Bioact. Mat. 1997, 24, 913-914.
23. Onyuksel, H.; Ikezaki, H.; Patel, M.; Rubinstein, I. A novel bioactive formulation of vasoactive intestinal peptide in micelles. Pharm. Res. 1999, 16, 155-160.
24. Luyengi, L.; Lee, I.-S.; Mar, W.; Fong, H.H.S.; Pezzuto, J.M.; Kinghorn, A.D. Rotenoids and chalcones from Mundulea sericea that inhibit phobol ester-induced ornithine decarboxylase activity. Phytochemistry 1994, 36, 1523-1526.
25. Terada, H.; Kokumai, M.; Konoshima, T.; Kozuka, M.; Haruna, M. Structural elucidation and-chemical conversion of amorphispironone, a novel spironone from Amorpha fruticosa, to rotenoids. Chem. Pharm. Bull. 1993, 41, 187-190.
26. Carlson, D.G.; Weisleder, D.; Tallent, W.H. NMR investigations of rotenoids. Tetrahedron 1973, 29; 2731-2741.
27. Cheng, H.-M.; Yamamoto, I.; Casida, J.E. Rotenone photodecomposition. J. Agric. Food Chem. 1972, 20, 850-856.
28. Fuster, M.D.; Lampi, A.M.; Hopia, A.; Kamal-Eldin, A. Effects of α- and γ-tocopherols on the autoxidation of purified sunflower triacylglycerols. Lipids 1998, 33, 715-722.