Mechanism and stereoselectivity of HDAC i inhibition by (R)-9-hydroxystearic acid in colon cancer

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1821, Issue 10, 2012, Pages 1334-1340

  Parolin, Carola ^a   Calonghi, Natalia ^a   Presta, Enrica ^a   Boga, Carla ^a   Caruana, Paolo ^a   Naldi, Marina ^a   Andrisano, Vincenza ^a   Masotti, Lanfranco ^a   Sartor, Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

9 hydroxystearic acid; Colon cancer; Cyclin D1; Histone deacetylase; Protein interaction; Stereoselectivity

Indexed keywords

9 HYDROXYSTEARIC ACID; ANTINEOPLASTIC AGENT; CYCLIN D1; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE 2; HISTONE DEACETYLASE 3; HISTONE DEACETYLASE INHIBITOR; HISTONE H4; PROTEIN P21; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL DIVISION; CELL PROLIFERATION; COLON CANCER; CONFOCAL MICROSCOPY; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; HISTONE ACETYLATION; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; STEREOCHEMISTRY;

CELL PROLIFERATION; CYCLIN D1; CYCLIN-DEPENDENT KINASE INHIBITOR P21; HISTONE DEACETYLASE 1; HISTONE DEACETYLASE INHIBITORS; HT29 CELLS; HUMANS; PROTEIN CONFORMATION; STEARIC ACIDS; STEREOISOMERISM;

EID: 84865137587     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2012.07.007     Document Type: Article

References (36)

1. B.D. Strahl, and C.D. Allis The language of covalent histone modification Nature 403 2000 41 45
2. A.J. De Ruijter, A.H. van Gennip, H.N. Caron, S. Kemp, and A.B. Van Kuilenburg Histone deacetylases (HDACs): characterization of the classical HDAC family Biochem. J. 370 2003 737 749 (Pubitemid 36399066)
3. S. Thiagalingam, K.H. Cheng, H.J. Lee, N. Mineva, A. Thiagalingam, and J.F. Ponte Histone deacetylases: unique players in shaping the epigenetic histone code Ann. N. Y. Acad. Sci. 983 2003 84 100 (Pubitemid 36399322)
4. M.S. Longworth, and L.A. Laimins Histone deacetylase 3 localizes to the plasma membrane and is a substrate of Src Oncogene 25 2006 4495 4500 (Pubitemid 44141638)
5. O. Grubisha, B.C. Smith, and J.M. Denu Small molecule regulation of Sir2 protein deacetylases FEBS J. 272 2005 4607 4616 (Pubitemid 41366985)
6. J.M. Denu The Sir 2 family of protein deacetylases Curr. Opin. Chem. Biol. 9 2005 431 440
7. I.V. Gregoretti, Y.M. Lee, and H.V. Goodson Molecular evolution of the histone deacetylase family: functional implications of phylogenetic analysis J. Mol. Biol. 16 2004 17 31 (Pubitemid 38429783)
8. O. Witt, H.E. Deubzer, T. Milde, and I. Oehme HDAC family: what are the cancer relevant targets? Cancer Lett. 277 2009 8 21
9. C.B. Yoo, and P.A. Jones Epigenetic therapy of cancer: past, present and future Nat. Rev. Drug Discov. 5 2006 37 50
10. K. Kawamoto, S.T. Okino, R.F. Place, S. Urakami, H. Hirata, N. Kikuno, T. Kawakami, Y. Tanaka, D. Pookot, Z. Chen, S. Majid, H. Enokida, M. Nakagawa, and R. Dahiya Epigenetic modifications of RASSF1A gene through chromatin remodeling in prostate cancer Clin. Cancer Res. 13 2007 2541 2549
11. M.F. Fraga, and M. Esteller Towards the human cancer epigenome: a first draft of histone modifications Cell Cycle 4 2005 1377 1381 (Pubitemid 41437126)
12. K. Ishihama, M. Yamakawa, S. Semba, H. Takeda, S. Kawata, S. Kimura, and W. Kimura Expression of HDAC1 and CBP/p300 in human colorectal carcinomas J. Clin. Pathol. 60 2007 1205 1210 (Pubitemid 350084539)
13. Y.X. Chen, J.Y. Fang, H.Y. Zhu, R. Lu, Z.H. Cheng, and D.K. Qiu Histone acetylation regulates p21WAF1 expression in human colon cancer cell lines World J. Gastroenterol. 10 2004 2643 2646 (Pubitemid 39214494)
14. WAF1in HT29 cancer cells Biochem. Biophys. Res. Commun. 314 2004 138 142 (Pubitemid 38058380)
15. E. Pagnotta, N. Calonghi, C. Boga, and L. Masotti N-methylformamide and 9-hydroxystearic acid: two anti-proliferative and differentiating agents with different modes of action in colon cancer cells Anticancer Drugs 17 2006 521 526 (Pubitemid 44309968)
16. N. Calonghi, C. Cappadone, E. Pagnotta, C. Boga, C. Bertucci, J. Fiori, G. Tasco, R. Casadio, and L. Masotti Histone deacetylase 1: a target of 9-hydroxystearic acid in the inhibition of cell growth in human colon cancer J. Lipid Res. 46 2005 1596 1603 (Pubitemid 41099326)
17. B. Behrouzian, C.K. Savile, B. Dawson, P.H. Buist, and J. Shanklin Exploring the hydroxylation-dehydrogenation connection: novel catalytic activity of castor stearoyl-ACP Delta 9 desaturase J. Am. Chem. Soc. 124 2002 3277 3283 (Pubitemid 34270367)
18. M. Naldi, N. Calonghi, L. Masotti, C. Parolin, S. Valente, A. Mai, and V. Andrisano Histone post-translational modifications by HPLC-ESI-MS after HT29 cell treatment with histone deacetylase inhibitors Proteomics 9 2009 5437 5445
19. M. Naldi, V. Andrisano, J. Fiori, N. Calonghi, E. Pagnotta, C. Parolin, G. Pieraccini, and L. Masotti Histone proteins determined in a human colon cancer by high-performance liquid chromatography and mass spectrometry J. Chromatogr. A 1129 2006 73 81 (Pubitemid 44331864)
20. S. Olmo, R. Gotti, M. Naldi, V. Andrisano, N. Calonghi, C. Parolin, L. Masotti, and V. Cavrini Analysis of human histone H4 by capillary electrophoresis in a pullulan-coated capillary, LC-ESI-MS and MALDI-TOF-MS Anal. Bioanal. Chem. 390 2008 1881 1888
21. M.W. Pfaffl A new mathematical model for relative quantification in real-time RT-PCR Nucleic Acids Res. 29 2001 E45
22. M.W. Pfaffl, W. Graham, W. Horgan, and L. Dempfle Relative Expression Software Tool (REST©) for group wise comparison and statistical analysis of relative expression results in real-time PCR Nucleic Acids Res. 30 2002 E36
23. A.B. Gladden, and J.A. Diehl The cyclin D1-dependent kinase associates with the pre- replication complex and modulates RB-MCM7 binding J. Biol. Chem. 278 2003 9754 9760 (Pubitemid 36800474)
24. W. Yang, L. Dostal, and J.P.N. Rosazza Stereospecificity of microbial hydrations of oleic acid to 10-hydroxystearic acid Appl. Environ. Microbiol. 59 1993 281 284 (Pubitemid 23028404)
25. D. Gunstone, and L.J. Morris Vegetable oils. VII. Strophantus seed oils J. Sci. Food Agric. 10 1959 522 526
26. A.P. Tulloch Absolute configuration of 13-hydroxydocosanoic and 17-hydroxyoctadecanoic acids Can. J. Chem. 46 1968 3727 3730
27. T.H. Applewhite, R.G. Binder, and W. Gaffield Optical rotatory dispersion and absolute configuration of some long-chain hydroxy acids J. Org. Chem. 32 1967 1173 1178
28. L.C. Sambucetti, D.D. Fischer, S. Zabludoff, P.O. Kwon, H. Chamberlin, H. Trogani, H. Xu, and D. Cohen Histone deacetylase inhibition selectively alters the activity and expression of cell cycle proteins leading to specific chromatin acetylation and antiproliferative effects J. Biol. Chem. 274 1999 34940 34947 (Pubitemid 129509542)
29. V.M. Richon, T.W. Sandhoff, R.A. Rifkind, and P.A. Marks Histone deacetylase inhibitor selectively induces p21WAF1 expression and gene-associated histone acetylation Proc. Natl. Acad. Sci. U. S. A. 97 2000 10014 10019
30. G. Zupkovitz, R. Grausenburger, R. Brunmeir, S. Senese, J. Tischler, J. Jurkin, M. Rembold, D. Meunier, G. Egger, S. Lagger, S. Chiocca, F. Propst, G. Weitzer, and C. Seiser The cyclin-dependent kinase inhibitor p21 is a crucial target for histone deacetylase 1 as a regulator of cellular proliferation Mol. Cell. Biol. 30 2010 1171 1181
31. S. Senese, K. Zaragoza, S. Minardi, I. Muradore, S. Ronzoni, A. Passafaro, L. Bernard, G.F. Draetta, M. Alcalay, C. Seiser, and S. Chiocca Role for histone deacetylase 1 in human tumor cell proliferation Mol. Cell. Biol. 27 2007 4784 4795 (Pubitemid 47016131)
32. N. Calonghi, E. Pagnotta, C. Parolin, C. Tognoli, C. Boga, and L. Masotti 9-Hydroxystearic acid interferes with EGF signalling in a human colon adenocarcinoma Biochem. Biophys. Res. Commun. 342 2006 585 589
33. J.A. Diehl, F. Zindy, and C.J. Sherr Inhibition of cyclin D1 phosphorylation on threonine-286 prevents its rapid degradation via ubiquitin-proteasome pathway Genes Dev. 11 1997 957 972 (Pubitemid 27199876)
34. J.A. Diehl, M. Cheng, M.F. Roussel, and C.J. Sherr Glycogen synthase kinase-3beta regulates cyclin D1 proteolysis and subcellular localization Genes Dev. 12 1998 3499 3511 (Pubitemid 28553242)
35. J.P. Alao The regulation of cyclin D1 degradation: roles in cancer development and the potential for therapeutic invention Mol. Cancer 6 2007 24 40
36. F. Bienvenu, B. Barré, S. Giraud, S. Avril, and O. Coqueret Transcriptional regulation by a DNA-associated form of cyclin D1 Mol. Biol. Cell 16 2005 1850 1858 (Pubitemid 40471954)