Trimethylaurintricarboxylic acid inhibits human DNA methyltransferase 1: Insights from enzymatic and molecular modeling studies

Journal of Molecular Modeling

Volumn 18, Issue 4, 2012, Pages 1583-1589

  Yoo, Jakyung ^a   Medina Franco, José L ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

Cancer; DNMT; Docking; Enzyme inhibition; Epigenetics; Methyltransferase

Indexed keywords

5,5 METHYLENEDISALICYLIC ACID; AMINO ACID; AURINTRICARBOXYLIC ACID; DNA METHYLTRANSFERASE 1; METHYLTRANSFERASE INHIBITOR; NSC 14778; NSC 97317; SALSALATE; TRIMETHYLAURINTRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DNA METHYLATION; DRUG BINDING; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME BINDING; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; MOLECULAR MODEL; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN PROTEIN INTERACTION;

AURINTRICARBOXYLIC ACID; CATALYTIC DOMAIN; DNA (CYTOSINE-5-)-METHYLTRANSFERASE; DNA METHYLATION; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; PROTEIN STRUCTURE, TERTIARY;

EID: 84861231717     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1191-4     Document Type: Article

References (36)

1. Robertson KD (2001) DNA methylation, methyltransferases, and cancer. Oncogene 20:3139-3155 (Pubitemid 32553570)
2. Yokochi T, Robertson KD (2002) Preferential methylation of unmethylated DNA by mammalian de novo DNA methyltransferase Dnmt3a. J Biol Chem 277:11735-11745 (Pubitemid 34952728)
3. Goll MG, Bestor TH (2005) Eukaryotic cytosine methyltransferases. Annu Rev Biochem 74:481-514 (Pubitemid 40995515)
4. Sippl W, Jung M (2009) DNA Methyltransferase inhibitors, vol. 42 Epigenetic Targets in Drug Discovery. Wiley-VCH, Weinheim
5. Stresemann C, Lyko F (2008) Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer 123:8-13 (Pubitemid 351705186)
6. Kelly TK, De Carvalho DD, Jones PA (2010) Epigenetic modifications as therapeutic targets. Nat Biotechnol 28:1069-1078
7. Portela A, Esteller M (2010) Epigenetic modifications and human disease. Nat Biotechnol 28:1057-1068
8. Zawia NH, Lahiri DK, Cardozo-Pelaez F (2009) Epigenetics, oxidative stress, and Alzheimer disease. Free Radical Biol Med 46:1241-1249
9. Miller CA, Gavin CF, White JA, Parrish RR, Honasoge A, Yancey CR, Rivera IM, Rubio MD, Rumbaugh G, Sweatt JD (2010) Cortical DNA methylation maintains remote memory. Nat Neurosci 13:664-666
10. Narayan P, Dragunow M (2010) Pharmacology of epigenetics in brain disorders. Br J Pharmacol 159:285-303
11. Cheng XD, Blumenthal RM (2008) Mammalian DNA methyltransferases: A structural perspective. Structure 16:341-350 (Pubitemid 351324115)
12. Lan J, Hua S, He XN, Zhang Y (2010) DNA methyltransferases and methyl-binding proteins of mammals. Acta Biochim Biophys Sin 42:243-252
13. Jurkowska RZ, Jurkowski TP, Jeltsch A (2011) Structure and function of mammalian DNA methyltransferases. ChemBioChem 12:206-222
14. Vilkaitis G, Merkiene E, Serva S, Weinhold E, Klimasauskas S (2001) The mechanism of DNA cytosine-5 methylation - Kinetic and mutational dissection of HhaI methyltransferase. J Biol Chem 276:20924-20934
15. Schermelleh L, Spada F, Easwaran HP, Zolghadr K, Margot JB, Cardoso MC, Leonhardt H (2005) Trapped in action: direct visualization of DNA methyltransferase activity in living cells. Nat Methods 2:751-756 (Pubitemid 41486206)
16. Issa JPJ, Kantarjian HM, Kirkpatrick P (2005) Azacitidine. Nat Rev Drug Discovery 4:275-276 (Pubitemid 41130933)
17. Schrump DS, Fischette MR, Nguyen DM, Zhao M, Li XM, Kunst TF, Hancox A, Hong JA, Chen GA, Pishchik V, Figg WD, Murgo AJ, Steinberg SM (2006) Phase I study of decitabine-mediated gene expression in patients with cancers involving the lungs, esophagus, or pleura. Clin Cancer Res 12:5777-5785 (Pubitemid 44629609)
18. Issa J-PJ, Kantarjian HM (2009) Targeting DNA methylation. Clinical Cancer Res 15:3938-3946
19. Lyko F, Brown R (2005) DNA methyltransferase inhibitors and the development of epigenetic cancer therapies. J Natl Cancer Inst 97:1498-1506 (Pubitemid 41631949)
20. Yu N, Wang M (2008) Anticancer drug discovery targeting DNA hypermethylation. Curr Med Chem 15:1350-1375 (Pubitemid 351997787)
21. Hauser AT, Jung M (2008) Targeting epigenetic mechanisms: Potential of natural products in cancer chemoprevention. Planta Med 74:1593-1601
22. Siedlecki P, Boy RG, Musch T, Brueckner B, Suhai S, Lyko F, Zielenkiewicz P (2006) Discovery of two novel, small-molecule inhibitors of DNA methylation. J Med Chem 49:678-683 (Pubitemid 43157497)
23. Kuck D, Caulfield T, Lyko F, Medina-Franco JL (2010) Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells. Mol Cancer Ther 9:3015-3023
24. Medina-Franco JL, Caulfield T (2011) Advances in the computational development of DNA methyltransferase inhibitors. Drug Discovery Today 16:418-425
25. Kuck D, Singh N, Lyko F, Medina-Franco JL (2010) Novel and selective DNA methyltransferase inhibitors: Docking-based virtual screening and experimental evaluation. Bioorg Med Chem 18:822-829
26. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag L-S, Sanschagrin P, Shenkin PS, Schwede T (2010) Novel inhibitors of dengue virus methyltransferase: Discovery by in vitro-driven virtual screening on a desktop computer grid. J Med Chem 53:1483-1495
27. Milani M, Mastrangelo E, Bollati M, Selisko B, Decroly E, Bouvet M, Canard B, Bolognesi M (2009) Flaviviral methyltransferase/ RNA interaction: Structural basis for enzyme inhibition. Antiviral Res 83:28-34
28. Bouvet M, Debarnot C, Imbert I, Selisko B, Snijder EJ, Canard B, Decroly E (2010) In vitro reconstitution of SARS-coronavirus mRNA cap methylation. Plos Pathogens 6:13
29. Developmental Therapeutics Program. National Cancer Institute (NCI) http://dtp.cancer.gov
30. Reaction Biology Corporation. http://www.reactionbiology.com
31. Yoo J, Medina-Franco JL (2011) Homology modeling, docking and structure-based pharmacophore of inhibitors of DNA methyltransferase. J Comput Aided Mol Des 25:555-567
32. Yoo J, Medina-Franco JL (2011) Rundfeldt C (ed) Discovery and optimization of inhibitors of DNA methyltransferase as novel drugs for cancer therapy. Drug Development. InTech (in press)
33. The UniProt C The Universal Protein Resource (UniProt) (2010) Nucleic Acids Res 38(suppl 1):D142-D148
34. Song J, Rechkoblit O, Bestor TH, Patel DJ (2011) Structure of DNMT1-DNA complex reveals a role for autoinhibition in maintenance DNA methylation. Science 331:1036-1040
35. Loving K, Salam NK, Sherman W (2009) Energetic analysis of fragment docking and application to structure-based pharmacophore hypothesis generation. J Comput Aided Mol Des 23:541-554
36. Salam NK, Nuti R, Sherman W (2009) Novel method for generating structure-based pharmacophores using energetic analysis. J Chem Inf Model 49:2356-2368