Potent inhibitors of the human UDP-glucuronosyltransferase 2B7 derived from the sesquiterpenoid alcohol longifolol

ChemMedChem

Volumn 2, Issue 6, 2007, Pages 881-889

  Bichlmaier, Ingo ^a   Kurkela, Mika ^a   Joshi, Tanmaya ^b   Siiskonen, Antti ^a   Rüffer, Tobias ^c   Lang, Heinrich ^c   Finel, Moshe ^a   Yli Kauhaluoma, Jari ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^c CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Eudismic analysis; Inhibition; Metabolism; UGT

Indexed keywords

ALCOHOL DERIVATIVE; ENZYME INHIBITOR; GLUCURONOSYLTRANSFERASE; TERPENE; UDP GLUCURONOSYLTRANSFERASE, UGT2B7; UDP-GLUCURONOSYLTRANSFERASE, UGT2B7; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ALCOHOLS; DRUG DESIGN; ENZYME INHIBITORS; GLUCURONOSYLTRANSFERASE; HUMANS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 38849110269     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200600246     Document Type: Article

References (39)

1. For reviews, see: a) A. Radominska-Pandya, M. Ouzzine, S. Fournel-Gigleux, J. Magdalou, Methods Enzymol. 2005, 400, 116-147;
2. b) P. G. Wells, P. I. Mackenzie, J. R. Chowdhury, C. Guillemette, P. A. Gregory, Y. Ishii, A. J. Hansen, F. K. Kessler, P. M. Kim, N. R. Chowdhury, J. K. Ritter, Drug Metab. Dispos. 2004, 32, 281-290;
3. c) M. B. Fisher, M. F. Paine, T. J. Strelevitz, S. A. Wrighton, Drug Metab. Rev. 2001, 33, 273-297;
4. d) C. D. King, G. R. Rios, M. D. Green, T. R. Tephly, Curr. Drug Metab. 2000, 1, 143-161.
5. I. S. Owens, N. K. Basu, R. Banerjee, Methods Enzymol. 2005, 400, 1-22.
6. J. A. Williams, R. Hyland, B. C. Jones, D. A. Smith, S. Hurst, T. C. Goosen, V. Peterkin, J. Koup, S. E. Ball, Drug Metab. Dispos. 2004, 32, 1201-1208.
7. M. H. Court, Methods Enzymol. 2005, 400, 104-116.
8. S. D. Copley, Curr. Opin. Chem. Biol. 2003, 7, 265-272.
9. a) K. H. G. Verschueren, S. M. Franken, H. J. Rozeboom, K. H. Kalk, B. W. Dijkstra, J. Mol. Biol. 1993, 232, 856-872;
10. b) F. C. Lightstone, Z. Ya-Jun, A. H. Maulitz, T. C. Bruice, Proc. Natl. Acad. Sci. USA 1997, 94, 8417-8420;
11. c) G. D. Markham, D. W. Parkin, F. Mentch, V. L. Schramm, J. Biol. Chem. 1987, 262, 5609-5615.
12. J. R. Halpert, F. P. Guengerich, J. R. Bend, M. A. Correia, Toxicol. Appl. Pharmacol. 1994, 125, 163-175.
13. K. Grancharov, Z. Naydenova, S. Lozeva, E. Golovinsky, Pharmacol. Ther. 2001, 89, 171-186.
14. a) C. M. Timmers, M. Dekker, R. C. Buijsman, G. A. van der Marel, B. Ethell, G. Anderson, B. Burchell, G. J. Mulder, J. H. van Boom, Bioorg. Med. Chem. Lett. 1997, 7, 1501-1506;
15. b) D. Noort, E. A. Meijer, T. J. Visser, J. H. N. Meerman; G. A. van der Marel, J. H. van Boom, G. J. Mulder, Mol. Pharmacol. 1991, 40, 316-320.
16. a) V. L. Schramm, Curr. Opin. Struct. Biol. 2005, 15, 604-613;
17. b) V. L. Schramm, Annu. Rev. Biochem. 1998, 67, 693-720.
18. a) M. Said, D. Noort, J. Magdalou, J. C. Ziegler, G. A. van der Marel, J. H. van Boom, G. J. Mulder, G. Siest, Biochem. Biophys. Res. Commun. 1992, 187, 140-145;
19. b) D. Noort, M. W. Coughtrie, B. Burchell, G. A. van der Marel, J. H. van Boom, A. van der Gen, G. J. Mulder, Eur. J. Biochem. 1990, 188, 309-312;
20. c) D. K. Alargov, R. G. Gugova, P. S. Denkova, G. Müller, E. V. Golovinsky, Monatsh. Chem. 1999, 130, 937-943;
21. d) D. K. Alargov, Z. Naydenova, K. Grancharov, P. S. Denkova, E. V. Golovinsky, Monatsh. Chem. 1997, 128, 725-732;
22. e) D. K. Alargov, Z. Naydenova, K. Grancharov, P. Denkova, E. Golovinsky, Monatsh. Chem. 1998, 129, 755-760.
23. V. Uchaipichat, P. I. Mackenzie, D. J. Elliot, J. O. Miners, Drug Metab. Dispos. 2006, 34, 449-456.
24. I. Bichlmaier, M. Kurkela, A. Siiskonen, M. Finel, J. Yli-Kauhaluoma, Bioorg. Chem., submitted.
25. a) I. Bichlmaier, A. Siiskonen, M. Finel, J. Yli-Kauhaluoma, J. Med. Chem. 2006, 49, 1818-1827;
26. b) I. Bichlmaier, A. Siiskonen, M. Kurkela, M. Finel, J. Yli-Kauhaluoma, Biol. Chem. 2006, 387, 407-416.
27. C. S. Sell, A fragrant introduction to terpenoid chemistry, The Royal Society of Chemistry, Cambridge, 2003, pp. 203-214.
28. a) U. Ladziata, V. V. Zhdankin, ARKIVOC 2006, ix, 26-58;
29. b) M. Frigerio, M. Santagostino, S. A. Sputore, J. Org. Chem. 1999, 64, 4537-4538.
30. J. D. Parrish, D. R. Shelton, R. D. Little, Org. Lett. 2003, 5, 3615-3617.
31. T. Mizuta, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2005, 70, 2195-2199.
32. P. Samadder, R. Bittman, H. S. Byun, G. Arthur, J. Med. Chem. 2004, 47, 2710-2713.
33. H. Motulsky, A. Christopoulos, Fitting models to biological data using linear and nonlinear regression. A practical guide to curve fitting, Graph-Pad Software Inc., San Diego CA, 2003, pp. 143-146.
34. We propose the trivial names α-phenyllongifolol and β-phenyllongifolol for compound 16a andits epimer 16b, respectively. The Greek letters α and β denote the relative configuration at C1′. Consistently, compound 10a is α-methyllongifolol, its epimer 10b is β-methyllongifolol.
35. M. Kurkela, A. Garcia-Horsman, L. Luukkanen, S. Mörsky, J. Taskinen, M. Baumann, R. Kostiainen, J. Hirvonen and M. Finel, J. Biol. Chem. 2003, 278, 3536-3544.
36. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
37. G. M. Sheldrick, SHELXL-97, A program for crystal structure refinement, Göttingen, 1996.
38. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881.
39. R. A. Copeland, Evaluation of enzyme inhibitors in drug discovery; Wiley, Hoboken, 2005, p. 271.