Exploring the anticancer potential of pyrazolo[1,2-a]benzo[1,2,3,4] tetrazin-3-one derivatives: The effect on apoptosis induction, cell cycle and proliferation

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 345-356

  Mingoia, Francesco ^a   Di Sano, Caterina ^b   Di Blasi, Francesco ^b   Fazzari, Marco ^c,d   Martorana, Annamaria ^c   Almerico, Anna Maria ^c   Lauria, Antonino ^c  

^a CNR   (Italy)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c UNIVERSITY OF PALERMO   (Italy)

^d RiMED Foundation   (Italy)

Author keywords

Anticancer agents; Apoptosis inducers; Cell cycle; Pyrazolo 1,2 a benzo 1,2,3,4 tetrazinone; VLAK protocol

Indexed keywords

1 (2 AMINO 4 CYANOPHENYL) 5 METHYLPYRAZOL 3 ONE; 1 (2 AMINO 4 TRIFLUOROMETHYLPHENYL) 5 METHYLPYRAZOL 3 ONE; 1 (2 AMINO 4,5 DICHLOROPHENYL) 5 METHYLPYRAZOL 3 ONE; 1 (2 AMINOPHENYL) 4,5 DIMETHYLPYRAZOL 3 ONE; 1 (2 NITROPHENYL 4 TRIFLUOROMETHYL) 5 METHYLPYRAZOL 3 ONE; 1 (4 CYANO 2 NITROPHENYL) 5 METHYLPYRAZOL 3 ONE; 1 (4,5 DICHLORO 2 NITROPHENYL) 5 METHYLPYRAZOL 3 ONE; 1 (4,5 DIMETHYL 2 NITROPHENYL) 5 METHYL 1,2 DIHYDROPYRAZOL 3 ONE; 1,8,9 TRIMETHYL 3H PYRAZOLO[1,2 A]BENZOTETRAZIN 3 ONE; 8 CYANO 1 METHYL 3H PYRAZOLO[1,2 A]BENZOTETRAZIN 3 ONE; 8 TRIFLUOROMETHYL 1 METHYL 3H PYRAZOLO[1,2 A]BENZOTETRAZIN 3 ONE; 8,9 DICHLORO 1 METHYL 3H PYRAZOLO[1,2 A]BENZOTETRAZIN 3 ONE; ANTINEOPLASTIC AGENT; CHLORINE; PYRAZOLO[1,2 ALPHA]BENZO[1,2,3,4]TETRAZIN 3 ONE DERIVATIVE; STAUROSPORINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ATOM; CANCER CELL; CANCER INHIBITION; CELL CYCLE; CELL MEMBRANE DEPOLARIZATION; CELL PROLIFERATION; CELL VIABILITY; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; HUMAN; HUMAN CELL; IN VITRO STUDY; LUNG NON SMALL CELL CANCER; MITOCHONDRIAL MEMBRANE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HETEROCYCLIC COMPOUNDS, 3-RING; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877025575     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.046     Document Type: Article

References (40)

1. S. Fulda, L. Galluzzi, and G. Kroemer Targeting mitochondria for cancer therapy Nat. Rev. Drug Discovery 9 2010 447 464
2. S. Fulda Evasion of apoptosis as a cellular stress response in cancer Int. J. Cell. Biol. 2010 370835
3. S. Fulda, and K.-M. Debatin Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy Oncogene 25 2006 4798 4811 (Pubitemid 44187627)
4. D.T. Hung, T.F. Jamison, and S.L. Shreiber Understanding and controlling the cell cycle with natural products Chem. Biol. 3 1996 623 639 (Pubitemid 26351772)
5. L.H. Hartwell, and M.B. Kastan Cell cycle control and cancer Science 266 1994 1821 1828
6. M. Seguado, and J.A. Tercero The S-phase checkpoint: targeting the replication fork Biol. Cell. 101 2009 617 627
7. K. Vermeulen, Zwi N. Berneman, and Dirk R. Van Bockstaele Cell cycle and apoptosis Cell. Proliferation 36 2003 165 175 (Pubitemid 36808272)
8. S. Maddica, S. Rao Ande, S. Panigrahi, T. Paranjothy, K. Weglarczyc, A. Zuse, M. Esraghi, K.D. Manda, E. Wiechec, and M. Los Cell survival, cell death and cell cycle pathways are interconnected: implications for cancer therapy Drug Resist. Updates 10 2007 13 29 (Pubitemid 46636381)
9. A.M. Almerico, and A.J. Boulton An unusual substitution reaction in a benzotetrazine derivative J. Chem. Soc. Chem. Commun. 1985 204 205
10. E.S. Newlands, M.F.G. Stevens, S.R. Wedge, R.T. Wheelhouse, and C. Brock Temozolomide a review of its discovery, chemical properties pre-clinical development and clinical trials Cancer Treat. Rep. 23 1997 35 61 (Pubitemid 27273454)
11. N.M. Bleehen, E.S. Newlands, S.M. Lee, N. Thatcher, P. Selby, A.H. Calvert, G.J.S. Rustin, M. Brampton, and M.F. G Stevens Cancer research campaign phase II trial of temozolomide in metastatic melanoma J. Clin. Oncol. 13 1995 910 913
12. P. Diana, P. Barraja, A. Lauria, A. Montalbano, A.M. Almerico, G. Dattolo, and G. Cirrincione New class of azolo-tetrazinones with potent antitumor activity Bioorg. Med. Chem. 11 2003 2371 2380
13. K. Engin, D.B. Leeper, J.R. Cater, A.J. Thistlethwaite, Tupchong, and J.D. McFarlane Extracellular pH distribution in human tumours Int. J. Hyperthermia 11 1995 211 216
14. D. Neri, and C. Supuran Interfering with pH regulation in tumours as a therapeutic strategy Nat. Drug Discovery 10 2011 767 777
15. A.M. Almerico, F. Mingoia, P. Diana, P. Barraja, A. Lauria, A. Montalbano, G. Cirrincione, and G. Dattolo 1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2, 3,4] tetrazin-3-ones. Design, synthesis, and biological activity of new antitumor agents J. Med. Chem. 48 2005 2859 2866 (Pubitemid 40548100)
16. A. Lauria, M. Tutone, and A.M. Almerico Virtual lock-and-key approach: the in silico revival of Fischer model by means of molecular descriptors Eur. J. Med. Chem. 46 2011 4274 4280
17. A. Lauria, C. Patella, G. Dattolo, and A.M. Almerico Design and synthesis of 4-substituted indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine derivatives with antitumor activity J. Med. Chem. 51 2008 2037 2046 (Pubitemid 351503259)
18. A. Lauria, M. Ippolito, and A.M. Almerico Inside the Hsp90 inhibitors binding mode through induced fit docking J. Mol. Graphics Modell. 27 2009 712 722
19. A. Lauria, M. Ippolito, M. Fazzari, M. Tutone, F. Di Blasi, F. Mingoia, and A.M. Almerico IKK-β inhibitors: an analysis of drug receptor interaction by using molecular docking and pharmacophore 3D QSAR approaches J. Mol. Graphics Modell. 29 2010 72 81
20. A. Lauria, M. Ippolito, and A.M. Almerico Combined use of PCA and QSAR/QSPR to predict the drugs mechanism of action. An application to the NCI ACAM Database QSAR Comb. Sci. 28 2009 387 395
21. A. Lauria, M. Ippolito, and A.M. Almerico Principal component analysis on molecular descriptors as an alternative point of view in the search of new Hsp90 inhibitors J. Comp. Biol. Chem. 33 2009 386 390
22. A. Lauria, C. Patella, I. Abbate, A. Martorana, and A.M. Almerico Lead optimization through VLAK protocol: new annelated pyrrolo-pyrimidine derivatives as antitumor agents Eur. J. Med. Chem. 55 2012 375 383
23. A. Lauria, M. Bruno, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico Annelated pyrrolo-pyrimidines from amino-cyano-pyrroles and BMMAs as leads for new DNA-interactive ring systems Bioorg. Med. Chem. 13 2005 1545 1553 (Pubitemid 40215241)
24. A. Lauria, I. Abbate, C. Patella, A. Martorana, G. Dattolo, and A.M. Almerico New Annelated Thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines, with potent anticancer activity, designed through VLAK protocol Eur. J. Med. Chem. 62 2013 416 424
25. J.N. Weinstein, K.W. Kohn, M.R. Grever, V.N. Viswanadhan, L.V. Rubinstein, A.P. Monks, D.A. Scudiero, L. Welch, A.D. Koutsoukos, A.J. Chiausa, and K.D. Paull Neural computing in cancer drug development: predicting mechanism of action Science 258 1992 447 451
26. W.W. Osdol, T.G. Myers, K.D. Paull, K.W. Kohn, and J.N. Weinstein Use of the Kohonen self-organizing map to study the mechanisms of action of chemotherapeutic agents J. Natl. Cancer Inst. 86 1994 1853 1859
27. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 82 1990 1107 1112 (Pubitemid 20213250)
28. M.D. Fyaz Ismail Important fluorinated drugs in experimental and clinical use J. Fluorine Chem. 118 2002 27 33
29. M.R. Grever, S.A. Schepartz, and B.A. Chabner The National Cancer Institute: cancer drug discovery and development program Semin. Oncol. 19 1992 622 638 (Pubitemid 23004840)
30. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, and M. Boyd Feasibility of a high-flux anticancer drug screen utilizing a diverse panel of human tumor cell lines in culture J. Natl. Cancer Inst. 83 1991 757 766
31. http://dtp.nci.nih.gov/branches/btb/ivclsp.html.
32. D. Floryk, and J. Houstek Tetramethyl rhodamine methyl ester (TMRM) is suitable for cytofluorometric measurements of mitochondrial membrane potential in cells treated with digitonin J. Biosci. Rep. 19 1999 27 34 (Pubitemid 29248702)
33. R.J. Youle, and A. Strasser The BCL-2 protein family: opposing activities that mediate cell death Nat. Rev. Mol. Cell Biol. 9 1 2008 47 59
34. G. Palou, R. Palou, A. Guerra-Moreno, A. Duch, A. Travesa, and D.G. Quintana Cyclin regulation by the S phase checkpoint J. Biol. Chem. 285 2010 26431 26440
35. LigPrep, Version 2.4 2010 Schrödinger LLC New York, NY
36. A.R. Katrinsky, V.S. Lobanov, and M. Karelson Quantum-chemical descriptors in QSAR/QSPR studies Chem. Rev. 96 1996 1027 1043 (Pubitemid 126641476)
37. C. Venturello, and R. D'Alosio A new synthesis of 2,5-dimethyl-3(2H) furanone Synthesis 1977 754 755
38. C. Venturello, and R. D'Alosio 2-Arylazo-2-5-dimethyl-3-oxo-2,3- dihydrofurans. Useful intermediates in the synthesis of 1-aryl-5-methyl-3- pyrazolones Synthesis 1979 283 287
39. Z. Darzynkiewicz, G. Juan, and E. Bedner Determining cell cycle stages by flow cytometry J.S. Bonifacino, M. Dasso, J.B. Harford, J. Lippincott-Schwartz, K.M. Yamada, Current Protocols in Cell Biology 2001 John Wiley & Sons New York pp. 8.4.1-8.4.18
40. R. Romagnoli, P.G. Baraldi, C. Lopez Cara, M. Kimatrai Salvador, R. Bortolozzi, G. Basso, G. Viola, J. Balzarini, A. Brancale, Xian-Hua Fu, Jun Li, Su-Zhan Zhang, and E. Hamel One-pot synthesis and biological evaluation of 2-pyrrolidinyl-4-amino-5-(3',4',5'-trimethoxybenzoyl)thiazole: a unique, highly active antimicrotubule agent J. Eur. Med. Chem. 46 2011 6015 6024