Natural sesquiterpene lactones as inhibitors of Myb-dependent gene expression: Structure-activity relationships

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 313-320

  Schomburg, Caroline ^a   Schuehly, Wolfgang ^b   Da Costa, Fernando B ^c   Klempnauer, Karl Heinz ^a   Schmidt, Thomas J ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF GRAZ   (Austria)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Anticancer; c Myb; Pharmacophore; QSAR; Sesquiterpene lactone; Structure activity relationship

Indexed keywords

11ALPHA,13 DIHYDROHELENALIN ACETATE; 11ALPHA,13 DIHYDROHELENALIN ISOVALERATE; 15 ACETOXY 6 DEOXYCHAMISSONOLIDE; 4 O ACETYL 6 DEOXYCHAMISSONOLIDE; 4,6 DI O ACETYLCHAMISSONOLIDE; 6 DEOXYCHAMISSONOLIDE; 8 EPIXANTHATIN; 8 EPIXANTHATIN 1BETA,5BETA EPOXIDE; ALANTOLACTONE; ANTINEOPLASTIC AGENT; ARGLABIN; ARNIFOLIN; CARABRONE; CHAMISSONOLIDE; DEACETYL 4 O TIGLOYLCHAMISSONOLIDE; DEACETYL 6 DEOXYCHAMISSONOLIDE; DEHYDROCOSTUSLACTONE; FURANOHELIANGOLIDE GOYAZENSOLIDE; HELENALIN; HELENALIN ACETATE; HELENALIN ISOBUTYRATE; MEXICANIN 1; PERUVIN; PROTEIN C MYB; PSEUDOGUAIANOLIDE HELENALIN ACETATE; PSILOSTACHYIN A; PUNGIOLIDE A; PUNGIOLIDE B; SESQUITERPENE LACTONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; GENE ACTIVATION; GENE EXPRESSION; NONHUMAN; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TRANSCRIPTION INITIATION;

ACETYLTRANSFERASES; ANIMALS; CELL LINE; CELL SURVIVAL; CHICKENS; COMPUTER SIMULATION; DOSE-RESPONSE RELATIONSHIP, DRUG; GENE EXPRESSION; GREEN FLUORESCENT PROTEINS; INHIBITORY CONCENTRATION 50; LACTONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PROMOTER REGIONS, GENETIC; PROTO-ONCOGENE PROTEINS C-MYB; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874934270     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.018     Document Type: Article

References (27)

1. K. Weston Myb proteins in life, death and differentiation Curr. Opin. Genet. Dev. 8 1998 76 81
2. J.S. Lipsick, and D.M. Wang Transformation by v-Myb Oncogene 18 1999 3047 3055
3. I.-H. Oh, and E.P. Reddy The myb gene family in cell growth, differentiation and apoptosis Oncogene 18 1999 3017 3033
4. R.J. Ramsay, and T.J. Gonda Myb function in normal and cancer cells Nat. Rev. Cancer 8 2008 523 534
5. M.L. Mucenski, K. McLain, A.B. Kier, S.H. Swerdlow, C.M. Schreiner, T.A. Miller, D.W. Pietryga, W.J. Scott Jr., and S.S. Potter A functional c-myb gene is required for normal murine fetal hepatic hematopoiesis Cell 65 1991 677 689
6. N. Emambokus, A. Vegiopoulos, B. Harman, E. Jenkinson, G. Anderson, and J. Frampton Progression through key stages of haemopoiesis is dependent on distinct threshold levels of c-Myb EMBO J. 22 2003 4478 4488
7. T.P. Bender, C.S. Kremer, M. Kraus, T. Buch, and K. Rajewsky Critical functions for c-Myb at three checkpoints during thymocyte development Nat. Immunol. 5 2004 721 729
8. M.R. Carpinelli, D.J. Hilton, D. Metcalf, J.L. Antonchuk, C.D. Hyland, S.L. Mifsud, L. Di Rago, A.A. Hilton, T.A. Willson, A.W. Roberts, R.G. Ramsay, N.A. Nicola, and W.S. Alexander Suppressor screen in Mpl-/- mice: c-Myb mutation causes supraphysiological production of platelets in the absence of thrombopoietin signaling Proc. Natl. Acad. Sci. USA 101 2004 6553 6558
9. M.L. Sandberg, S.E. Sutton, M.T. Pletcher, T. Wiltshire, L.M. Tarantino, J.B. Hogenesch, and M.P. Cooke c-Myb and p300 regulate hematopoietic stem cell proliferation and differentiation Dev. Cell 8 2005 153 166
10. M.D. Thomas, C.S. Kremer, K.S. Ravichandran, K. Rajewsky, and T.P. Bender c-Myb is critical for B cell development and maintenance of follicular B cells Immunity 23 2005 275 286
11. J. Sitzmann, K. Noben-Trauth, and K.-H. Klempnauer Expression of mouse c-myb during embryonic development Oncogene 11 1995 2273 2279
12. J. Malaterre, M. Carpinelli, M. Ernst, W. Alexander, M. Cooke, S. Sutton, S. Dworkin, J.K. Heath, J. Frampton, G. McArthur, H. Clevers, D. Hilton, T. Mantamadiotis, and R.G. Ramsay c-Myb is required for progenitor cell homeostasis in colonic crypts Proc. Natl. Acad. Sci. USA 104 2007 3829 3834
13. J.J. Rushton, L.M. Davis, W. Lei, X. Mo, A. Leutz, and S.A. Ness Distinct changes in gene expression induced by A-Myb, B-Myb and c-Myb proteins Oncogene 22 2003 308 313
14. G. Lang, J.R. White, M.J. Argent-Katwala, C.G. Allinson, and K. Weston Myb proteins regulate the expression of diverse target genes Oncogene 24 2005 1375 1384
15. F. Liu, W. Lei, J.P. O'Rourke, and S.A. Ness Oncogenic mutations cause dramatic, qualitative changes in the transcriptional activity of c-Myb Oncogene 2 2006 5795 5805
16. T. Berge, V. Matre, E.M. Brendeford, T. Saether, B. Lüscher, and O.S. Gabrielsen Revisiting a selection of target genes for the hematopoietic transcription factor c-Myb using chromatin immunoprecipitation and c-Myb knockdown Blood Cells Mol. Dis. 39 2007 278 286
17. T. Bujnicki, C. Wilczek, C. Schomburg, F. Feldmann, P. Schlenke, C. Müller-Tidow, T.J. Schmidt, and K.-H. Klempnauer Inhibition of Myb-dependent gene expression by the sesquiterpene lactone mexicanin-I Leukemia 26 2012 615 622
18. T.J. Schmidt Toxic activities of sesquiterpene lactones-structural and biochemical aspects Curr. Org. Chem. 3 1999 577 605
19. T.J. Schmidt Quantitative structure-cytotoxicity relationships within a series of helenanolide type sesquiterpene lactones. (Helenanolide type sesquiterpene lactones, IV Pharm. Pharmacol. Lett. 9 1999 9 13
20. T.J. Schmidt, and J. Heilmann Quantitative structure-cytotoxicity relationships of sesquiterpene lactones derived from partial charge (Q)-based fractional accessible surface area descriptors (Q-frASAs) Quant. Struct.-Act. Relat. (QSAR) 21 2002 276 287
21. T.J. Schmidt Structure-activity relationships of sesquiterpene lactones Atta-ur-Rahman Studies in Natural Products Chemistry vol. 33 2006 Elsevier Amsterdam 309 392
22. T.J. Schmidt, A.M.M. Nour, S.A. Khalid, M. Kaiser, and R. Brun Quantitative structure-antiprotozoal activity relationships of sesquiterpene lactones Molecules 14 2009 2062 2076
23. Chemical Computing Group Molecular Operating Environment (MOE) rel. 2011.10 2011 Chemical Computing Group Inc 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7
24. I. Merfort Perspectives on sesquiterpene lactones in inflammation and cancer Curr. Drug Targets 12 2011 1560 1573
25. M.R.O. Kreuger, S. Grootjans, M.W. Biavatti, P. Vandenabeele, and K. D'Herde Sesquiterpene lactones as drugs with multiple targets in cancer treatment: focus on parthenolide Anti-cancer Drugs 23 2012 883 896
26. O. Chayka, J. Kintscher, D. Braas, and K.-H. Klempnauer v-Myb mediates cooperation of a cell-specific enhancer with the mim-1 promoter Mol. Cell. Biol. 25 2005 499 511
27. C. Wilczek, O. Chayka, A. Plachetka, and K.-H. Klempnauer Myb-induced chromatin remodeling at a dual enhancer/promoter element involves non-coding RNA transcription and is disrupted by oncogenic mutations of v-myb J. Biol. Chem. 284 2009 35314 35324