Enhanced bioactivity of silybin B methylation products

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 3, 2013, Pages 742-747

  Sy Cordero, Arlene A ^a   Graf, Tyler N ^a   Runyon, Scott P ^b   Wani, Mansukh C ^b   Kroll, David J ^c   Agarwal, Rajesh ^d   Brantley, Scott J ^e   Paine, Mary F ^e   Polyak, Stephen J ^f   Oberlies, Nicholas H ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

^b RTI INTERNATIONAL   (United States)

^c NORTH CAROLINA CENTRAL UNIVERSITY   (United States)

^d UNIVERSITY OF COLORADO   (United States)

^e UNC Hamner Institute for Drug Safety Sciences   (United States)

^f UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Flavonolignans; Methylation; Milk thistle; Silybin B; Silybum marianum

Indexed keywords

5,7,4'' GAMMA TETRA O METHYLSILYBIN B; 5,7,4'' GAMMA TRI O METHYLSILYBIN B; 5,7,4'' TRI O METHYLSILYBIN B; 7 O METHYLSILYBIN B; 7,4'' DI O METHYLSILYBIN B; ACETONE; CYTOCHROME P450 2C9; DIMETHYL SULFATE; FLAVONOLIGNAN; POTASSIUM CARBONATE; SILIBININ; SILYBIN B; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; DEMETHYLATION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HEPATITIS C; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIVER MICROSOME; PROSTATE CANCER; SPECTROMETRY; SPECTROSCOPY; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTIVIRAL AGENTS; ARYL HYDROCARBON HYDROXYLASES; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HEPACIVIRUS; HUMANS; METHYLATION; MICROBIAL SENSITIVITY TESTS; MICROSOMES, LIVER; MOLECULAR STRUCTURE; SILYMARIN; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS C VIRUS; SILYBUM MARIANUM;

EID: 84872289493     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.035     Document Type: Article

References (25)

1. D.J. Kroll, H.S. Shaw, and N.H. Oberlies Integr. Cancer Ther. 6 2007 110
2. P.R. Davis-Searles, Y. Nakanishi, N.C. Kim, T.N. Graf, N.H. Oberlies, M.C. Wani, M.E. Wall, R. Agarwal, and D.J. Kroll Cancer Res. 65 2005 4448
3. G. Deep, N.H. Oberlies, D.J. Kroll, and R. Agarwal Carcinogenesis 28 2007 1533
4. G. Deep, N.H. Oberlies, D.J. Kroll, and R. Agarwal Oncogene 27 2008 3986
5. G. Deep, N.H. Oberlies, D.J. Kroll, and R. Agarwal Int. J. Cancer 123 2008 41
6. G. Deep, K. Raina, R.P. Singh, N.H. Oberlies, D.J. Kroll, and R. Agarwal Int. J. Cancer 123 2008 2750
7. G. Deep, S.C. Gangar, N.H. Oberlies, D.J. Kroll, and R. Agarwal Mol. Carcinog. 49 2010 902
8. G. Deep, S.C. Gangar, S. Rajamanickam, K. Raina, M. Gu, C. Agarwal, N.H. Oberlies, and R. Agarwal PLoS ONE 7 2012 e34630
9. T.N. Graf, M.C. Wani, R. Agarwal, D.J. Kroll, and N.H. Oberlies Planta Med. 73 2007 1495
10. A. Sy-Cordero, T.N. Graf, Y. Nakanishi, M.C. Wani, R. Agarwal, D.J. Kroll, and N.H. Oberlies Planta Med. 76 2010 644
11. S.J. Brantley, N.H. Oberlies, D.J. Kroll, and M.F. Paine J. Pharmacol. Exp. Ther. 1081 2010 332
12. C. Morishima, M.C. Shuhart, C.C. Wang, D.M. Paschal, M.C. Apodaca, Y. Liu, D.D. Sloan, T.N. Graf, N.H. Oberlies, D.Y. Lee, K.R. Jerome, and S.J. Polyak Gastroenterology 138 2010 671
13. S.J. Polyak, C. Morishima, V. Lohmann, S. Pal, D.Y. Lee, Y. Liu, T.N. Graf, and N.H. Oberlies Proc. Natl. Acad. Sci. U.S.A. 107 2010 5995
14. J. Wagoner, A. Negash, O.J. Kane, L.E. Martinez, Y. Nahmias, N. Bourne, D.M. Owen, J. Grove, C. Brimacombe, J.A. McKeating, E.I. Pecheur, T.N. Graf, N.H. Oberlies, V. Lohmann, F. Cao, J.E. Tavis, and S.J. Polyak Hepatology 2010 1912 51
15. J. Wagoner, C. Morishima, T.N. Graf, N.H. Oberlies, E. Teissier, E.I. Pecheur, J.E. Tavis, and S.J. Polyak PLoS ONE 6 2011 e16464
16. Polyak, S. J.; Oberlies, N. H.; Pecheur, E. I.; Ferenci, P.; Pawlotsky, J. M. Antivir. Ther. 2012, accepted for publication 07/11/2012.
17. Z. Wen, T.E. Dumas, S.J. Schrieber, R.L. Hawke, M.W. Fried, and P.C. Smith Drug Metab. Dispos. 36 2008 65
18. T.W. Flaig, M. Glode, D. Gustafson, A. van Bokhoven, Y. Tao, S. Wilson, L.J. Su, Y. Li, G. Harrison, R. Agarwal, E.D. Crawford, M.S. Lucia, and M. Pollak Prostate 70 2010 848
19. E. Theodosiou, M.H. Katsoura, H. Loutrari, K. Purchartova, V. Kren, F.N. Kolisis, and H. Stamatis Biocatal. Biotransformation 27 2009 161
20. R. Gazak, P. Sedmera, M. Marzorati, S. Riva, and V. Kren J. Mol. Catal. B Enzym. 50 2008 87
21. L.X. Yang, K.X. Huang, H.B. Li, J.X. Gong, F. Wang, Y.B. Feng, Q.F. Tao, Y.H. Wu, X.K. Li, X.M. Wu, S. Zeng, S. Spencer, Y. Zhao, and J. Qu J. Med. Chem. 52 2009 7732
22. P. Dzubak, M. Hajduch, R. Gazak, A. Svobodova, J. Psotova, D. Walterova, P. Sedmera, and V. Kren Bioorg. Med. Chem. 14 2006 3793
23. N.C. Kim, T.N. Graf, C.M. Sparacino, M.C. Wani, and M.E. Wall Org. Biomol. Chem. 1 2003 1684
24. N.C. Kim, T.N. Graf, C.M. Sparacino, M.C. Wani, and M.E. Wall Org. Biomol. Chem. 1 2003 3470
25. J. Zhong, P. Gastaminza, G. Cheng, S. Kapadia, T. Kato, D.R. Burton, S.F. Wieland, S.L. Uprichard, T. Wakita, and F.V. Chisari Proc. Natl. Acad. Sci. U.S.A. 102 2005 9294