Novel folate-hydroxamate based antimetabolites: Synthesis and biological evaluation

Medicinal Chemistry

Volumn 7, Issue 4, 2011, Pages 265-274

  Carrasco, Marta P ^a   Enyedy, Eva A ^a   Krupenko, Natalia I ^b   Krupenko, Sergey A ^b   Nuti, Elisa ^c   Tuccinardi, Tiziano ^c   Santamaria, Salvatore ^c   Rossello, Armando ^c   Martinelli, Adriano ^c   Santos, M Amélia ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

Antiproliferative; Cancer therapy; Dihydrofolate reductase inhibitors; Dual enzyme inhibitors; Folates and antifolates; Histone deacetylase inhibitors; Methotrexate

Indexed keywords

4 AMINOBENZOIC ACID CAPROIC HYDROXAMIC ACID; ANTIMETABOLITE; DIHYDROFOLATE REDUCTASE INHIBITOR; FOLATE 4 AMINOBENZOIC ACID CAPROIC HYDROXAMIC ACID; FOLATE 4 AMINOBENZOIC ACID HYDROXAMIC ACID; FOLATE CAPROIC HYDROXAMIC ACID; FOLIC ACID DERIVATIVE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; METHOTREXATE CAPROIC HYDROXAMIC ACID; METHOTREXATE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; METASTASIS; MITOSIS INHIBITION; MOLECULAR DOCKING; PRIORITY JOURNAL;

ANTIMETABOLITES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; FOLIC ACID; FOLIC ACID ANTAGONISTS; HELA CELLS; HISTONE DEACETYLASES; HUMANS; HYDROXAMIC ACIDS; MALE; METHOTREXATE; MOLECULAR TARGETED THERAPY; NEOPLASMS; REPRESSOR PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 79959348452     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340611796150923     Document Type: Article

References (32)

1. Yoshida, M.; Kijima, M.; Akita, M.; Beppu, T. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. J. Biol. Chem., 1990, 265, 17174-17179.
2. Korcsmáros, T.; Szalay, M.S.; Böde, C.; Kovács, I.A.; Csermely, P. How to design multi-target drugs. Expert Opin. Drug Discov., 2007, 2, 799-808.
3. Brown, D.; Superti-Furga, G. Rediscovering the sweet spot in drug discovery, Drug Discov. Today., 2003, 8, 1067-1077. (Pubitemid 38124472)
4. Bertino, J.R. Karnofsky memorial lecture. Ode to methotrexate. J. Clin. Oncol., 1993, 11, 5-14.
5. Smorenburg, C.H.; Sparreboom, A.; Bontenjal, M.; Verweij, J. Combination chemotherapy of the taxanes and antimetabolites: its use and limitations. Eur. J. Cancer, 2001, 37, 2310-2323. (Pubitemid 33097466)
6. Schnell, J.R.; Dyson, H.J.; Wright, P.E. Structure, dynamics, and catalytic function of Dihydrofolate Reductase. Annu. Rev. Biophys. Biomol. Struct., 2004, 33, 119-140. (Pubitemid 38829954)
7. Hildmann, C.; Riester, D.; Schwienhorst, A. Histone deacetylases: an important class of cellular regulators with a variety of functions. Appl. Microbiol. Biotechnol., 2007, 75, 487-497. (Pubitemid 46776553)
8. Takimoto, C.H. New Antifolates: Pharmacology and Clinical Applications. The Oncologist, 1996, 1, 68-81. (Pubitemid 126669374)
9. Finn, P.W. Histone Deacetylase Inhibitors, in Drug Design of Zinc- Enzyme Inhibitors; Supuran, C.T.; Winum, J.-Y. Ed.; John Wiley & Sons Inc, 2009, pp. 859-879.
10. Marks, P.A.; Xu, W.-S. Histone deacetylase inhibitors: Potential in cancer therapy. J. Cell. Biochem., 2009, 107, 600-608.
11. Buchwald, M.; Krämer, O.H.; Heinzel, T. HDACi - Targets beyond chromatin. Cancer Lett., 2009, 280, 160-167.
12. Bora-Tatar, G.; Dayangaç-Erden, D.; Demir, A.S.; Dalkara, S.; Yelekçi, K.; Erdem-Yurter, H. Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies. Bioorg. Med. Chem., 2009, 17, 5219-5228.
13. Grolla, A.A.; Podestà, V.; Chini, M.G.; Di Micco, S.; Vallario, A.; Genezzani, A.A.; Canonico, P.L.; Bifulco, G.; Tron, G.C.; Sorba, G.; Pirali, T. Synthesis, Biological Evaluation, and Molecular Docking of Ugi Products Containing a Zinc-Chelating Moiety as Novel Inhibitors of Histone Deacetylases. J. Med. Chem., 2009, 52, 2776-2785.
14. Marks, P.A. Discovery and development of SAHA as an anticancer agent. Oncogene., 2007, 26, 1351-1356. (Pubitemid 46328465)
15. Zimmermann, G.R.; Lehár, J.; Keith, C.T. Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov. Today, 2007, 12, 34-42. (Pubitemid 46014485)
16. Tumber, A.; Collins, L.S.; Petersen, K.D.; Thougaard, A.; Christiansen, S.J.; Dejligbjerg, M.; Jensen, P.B.; Sehested, M.; Ritchie, J.W.A. The histone deacetylase inhibitor PXD101 synergises with 5-fluorouracil to inhibit colon cancer cell growth in vitro and in vivo. Cancer Chemother. Pharmacol., 2007, 60, 275-283. (Pubitemid 46742543)
17. Bots, M.; Johnstone, R.W. Rational Combinations Using HDAC Inhibitors. Clin. Cancer Res., 2009, 15, 3970-3977.
18. Mukherjee, P.; Pradhan, A.; Shah, F., Tekwani, B.L.; Avery, M.A. Structural insights into the Plasmodium falciparum histone deacetylase 1 (PfHDAC-1): A novel target for the development of antimalarial therapy. Biorg. Med. Chem., 2008, 16, 5254-5365.
19. Richon, V.M.; Garcia-Vargas, J.; Hardwick, J. S. Development of vorinostat: Current applications and future perspectives for cancer therapy. Cancer Lett., 2009, 280, 201-210.
20. Marques, S.M.; Nuti, E.; Rossello, A.; Supuran, C.T.; Tuccinardi, T.; Martinelli, A.; Santos, M.A. Dual inhibitors of matrix metalloproteinases and carbonic anhydrases: iminodiacetyl-based hydroxamate-benzenesulfonamide conjugates. J. Med. Chem., 2008, 51, 7968-7979.
21. Santos, M.A.; Enyedy, E.A.; Rossello, A.; Carelli, P.; Krupenko, N.I.; Krupenko, S.A. Methotrexate γ-hydroxamate derivatives as potential dual target antitumor drugs. Bioorg. Med. Chem., 2007, 15, 1266-1274. (Pubitemid 46038141)
22. Marques, S.M.; Enyedy, E.A.; Supuran, C.T.; Krupenko, N.I.; Krupenko, S.A.; Santos, M.A. Pteridine-sulfonamide conjugates as dual inhibitors of carbonic anhydrases and dihydrofolate reductase with potential antitumor activity. Bioorg. Med. Chem., 2010, 18, 5081-5089.
23. Low, P.S.; Kularatne, S.A. Folate-targeted therapeutic and imaging agents for cancer. Curr. Opin. Chem. Biol., 2009, 13, 256-262.
24. Reynolds, R.C.; Campbell, S.R.; Fairchild, R.G.; Kisliuk, R.L.; Micca, P.L.; Queener, S.F.; Riordan, J.M.; Sedwick, W.D.; Waud, W.R.; Leung, A.K.; Dixon, R.W.; Suling, W.J.; Borhani, D.W. Novel boron-containing, non-classical antifolates: synthesis and preliminary biological and structural evaluation. J. Med. Chem., 2007, 50, 3283-3289. (Pubitemid 47065977)
25. Finnin, M.S.; Donigian, J.R.; Cohen, A.; Richon, V.M.; Rifkind, R.A.; Marks, P.A.; Breslow, R.; Pavletich, N.P. Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature, 1999, 401, 188-193. (Pubitemid 29436325)
26. Vannini, A.; Volpari, C.; Gallinari, P.; Jones, P.; Mattu, M.; Carfí, A.; De Francesco, R.; Steinkühler, C.; Di Marco, S. Substrate binding to histone deacetylases as shown by the crystal structure of the HDAC8-substrate complex. EMBO Reports, 2007, 8, 879-884. (Pubitemid 350001433)
27. Armarego, W.; Perring, D. Purification of Laboratory Chemicals. Butterworth-Heinemann Press, 1999.
28. SoftMax Pro 4.7.1 by Molecular Device.
29. GraFit version 4 by Erithecus Software.
30. Maestro, version 7.5; Schrödinger Inc.: Portland, OR, 2005.
31. Macromodel, version 8.5; Schrödinger Inc.: Portland, OR, 1999.
32. Jones, G.; Willett, P.; Glen, R.C.; Leach, A.R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol., 1997, 267, 727-748. (Pubitemid 27170693)