Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species

European Journal of Medicinal Chemistry

Volumn 57, Issue , 2012, Pages 268-274

  Vianna, D R ^a   Hamerski, L ^b   Figueiro F ^a   Bernardi, A ^a   Visentin, L C ^b   Pires, E N S ^a   Teixeira, H F ^a   Salbego, C G ^a   Eifler Lima, V L ^a   Battastini, A M O ^a   Von Poser, G L ^a   Pinto, A C ^b  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

5 Oxygenated 6,7 methylenedioxycoumarin; Apoptosis; Crystal structure; Cytotoxic activity; Glioma; Hippocampal organotypic culture; Pterocaulon

Indexed keywords

5 (2,3 DIHYDROXY 3 METHYLBUTYLOXY) 6,7 METHYLENEDIOXYCOUMARIN; 5 (3 METHYL 2 BUTENYLOXY) 6,7 METHYLENEDIOXYCOUMARIN; 5 METHOXY 6,7 METHYLENEDIOXYCOUMARIN; CARBENE; COUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG ISOLATION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; GLIOMA CELL; HIPPOCAMPUS; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; MEDICINAL PLANT; NONHUMAN; PTEROCAULON BALANSAE; PTEROCAULON LORENTZII; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; ASTERACEAE; BENZODIOXOLES; CELL LINE, TUMOR; CELL SURVIVAL; CENTRAL NERVOUS SYSTEM NEOPLASMS; COUMARINS; CYTOTOXINS; GLIOMA; HIPPOCAMPUS; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; MALE; ORGAN SPECIFICITY; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE CULTURE TECHNIQUES;

EID: 84867292705     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.007     Document Type: Article

References (39)

1. A.C. Stein, M. Sortino, C. Avancini, S. Zacchino, and G. von Poser Ethnoveterinary medicine in the search for antimicrobial agents: antifungal activity of some species of Pterocaulon (Asteraceae) J. Ethnopharmacol. 99 2005 211 214
2. E. Mongelli, S. Pampuro, J. Coussio, H. Salomon, and G. Ciccia Cytotoxic and DNA interaction activities of extracts from medicinal plants used in Argentina J. Ethnopharmacol. 71 2000 145 151
3. C. Ródio, D.D.R. Vianna, K.P. Kowalski, L.F. Panatieri, G. von Poser, and M.B. Rott In vitro evaluation of the amebicidal activity of Pterocaulon polystachyum (Asteraceae) against trophozoites of Acanthamoeba castellanii Parasitol. Res. 104 2008 191 194
4. C.S. Silveira, F.O. Martins, C.A. Costa, M.T.V. Romanos, M.A.C. Kaplan, and F.S. Menezes In vitro cytotoxic, antioxidant and antiviral effects of Pterocaulon alopecuroides and Bidens segetum extracts Rev. Bras Farmacogn. 19 2009 343 348
5. S.L. Debenedetti, P.S. Palacios, E.L. Nadinic, J.D. Coussio, N. De Kimpe, and M. Boeykens 5-(3-Methyl-2-butenyloxy)-6,7-methylenedioxycoumarin, a 5,6,7-trioxygenated coumarin from Pterocaulon virgatum J. Nat. Prod. 57 1994 1539 1542
6. D. Maes, S. Debenedetti, and N. De Kimpe New coumarins from Pterocaulon virgatum (L.) DC Biochem. Syst. Ecol. 34 2006 165 169
7. S. Chimichi, M. Boccalini, B. Cosimelli, G. Viola, D. Vedaldi, and F. Dall'Acqua New geiparvarin analogues from 7-(2-oxoethoxy) coumarins as efficient in vitro antitumoral agents Tetrahedron Lett. 43 2002 7473 7476
8. S. Rosselli, A.M. Maggio, N. Faraone, V. Spadaro, S.L. Morris-Natschke, and K.F. Bastow The cytotoxic properties of natural coumarins isolated from roots of Ferulago campestris (Apiaceae) and of synthetic ester derivatives of aegelinol Nat. Prod. Commun. 4 2009 1701 1706
9. H. Zhang, T.Z. Yu, Y.L. Zhao, D.W. Fan, L. Ding, and S.D. Zhang Cytotoxic activity of some novel dicoumarin derivatives in vitro Chem. Res. Chin. Univ. 25 2009 644 647
10. T.J. Kang, S.Y. Lee, R.P. Singh, R. Agarwal, and D.S. Yim Anti-tumor activity of oxypeucedanin from Ostericum koreanum against human prostate carcinoma DU145 cells Acta Oncol. 48 2009 895 900
11. G.J. Zlabinger Coumarin as an immunomodulator R. O'Kennedy, R.D. Thornes, Coumarins Biology, Applications and Mode of Action 1997 John Wiley & Sons Ltd Chichester 103 124
12. E.B. Yang, Y.N. Zhao, K. Zhang, and P. Mack Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor Biochem. Biophys. Res. Commun. 260 1999 682 685
13. C.Y. Chu, Y.Y. Tsai, C.J. Wang, W.L. Lin, and T.H. Tseng Induction of apoptosis by esculetin in human leukemia cells Eur. J. Pharmacol. 416 2001 25 32
14. E.C. Holland Gliomagenesis: genetic alterations and mouse models Nat. Rev. Genet. 2 2001 120 129
15. S. Sathornsumetee, D.A. Reardon, A. Desjardins, J.A. Quinn, J.J. Vredenburgh, and J.N. Rich Molecularly targeted therapy for malignant glioma Cancer 110 2007 13 24
16. P.Y. Wen, and S. Kesari Malignant gliomas in adults N. Engl. J. Med. 359 2008 492 507
17. M.E. Riveiro, C. Shayo, F. Monczor, N. Fernández, A. Baldi, and N. De Kimpe Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon Polystachyum. Cancer Lett. 210 2004 179 188
18. L.J. Farrugia WinGX suite for small-molecule single-crystal crystallography J. Appl. Crystallogr. 32 1999 837 838
19. B.V. Nonius "Collect" Data Collection Software 1998 Delft The Netherlands
20. A.J.M. Duisenberg, R.W.W. Hooft, A.M.M. Schreurs, and J. Kroon Accurate cells from area-detector images J. Appl. Crystallogr. 33 2000 893 898
21. A.J.M. Duisenberg Indexing in single-crystal diffractometry with an obstinate list of reflections J. Appl. Crystallogr. 25 1992 92 96
22. A.J.M. Duisenberg, L.M.J. Kroon-Batenburg, and A.M.M. Schreurs An intensity evaluation method: EVAL-14 J. Appl. Crystallogr. 36 2003 220 229
23. G.M. Sheldrick SADABS; Program for Empirical Absorption Correction of Area Detector Data 1996 University of Göttingen Germany
24. G.M. Sheldrick SHELXS97; Program for Crystal Structure Solution 1997 University of Göttingen Germany
25. G.M. Sheldrick SHELXL97; Program for Crystal Structure Refinement 1997 University of Göttingen Germany
26. L. Stoppini, P.A. Buchs, and D. Muller A simple method for organotypic cultures of nervous tissue J. Neurosci. Methods 37 1991 173 182
27. L.M. Valentin, R. Rodnight, A.B. Geyer, A.P. Horn, A. Tavares, H. Cimarosti, C.A. Netto, and C.G. Salbego Changes in heat shock protein 27 phosphorylation and immunocontent in response to preconditioning to oxygen and glucose deprivation in organotypic hippocampal cultures Neuroscience 118 2003 379 386
28. J. Noraberg, B.W. Kristensen, and J. Zimmer Markers for neuronal degeneration in organotypic slice cultures Brain Res. Protoc. 3 1999 278 290
29. R.D.H. Murray, J. Mendez, and S.A. Brown Natural Coumarins: Ocurrence, Chemistry and Biochemistry 1982 John Wiley & Sons Ltd New York
30. C.L. Barnes ORTEP-3 for windows - a version of ORTEP-III with a Graphical User Interface (GUI) J. Appl. Crystallogr. 30 1997 565 566
31. H.K. Fun, S.R. Jebas, M. Parveen, Z. Khanam, and R.M. Ghalib 7,7′,8,8′-Tetra-meth-oxy-4,4′-dimethyl-3,5′-bichromene- 2,2′-dione Acta Crystallogr. Sect. E: Struct. Rep. Online 65 2009 o1322 o1323
32. A.L. Spek Single-crystal structure validation with the program PLATON J. Appl. Crystallogr. 36 2003 7 13
33. K.A. Nolan, H. Zhao, P.F. Faulder, A.D. Frenkel, D.J. Timson, D. Siegel, D. Ross, T.R. Burke Jr., I.J. Stratford, and R.A. Bryce Coumarin-based inhibitors of human NAD(P)H: quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity J. Med. Chem. 50 2007 6316 6325 http://apps.webofknowledge.com/ OneClickSearch.do?product=WOS&search-mode=OneClickSearch&colName= WOS&SID=4CfEe6hKoPGp2GPJ4C4&field=AU&value=Lessa,%20JA
34. A. Maresca, C. Temperini, L. Pochet, B. Masereel, A. Scozzafava, and C.T. Supuran Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins J. Med. Chem. 53 2010 335 344
35. I.E. Holopainen Organotypic hippocampal slice cultures: a model system to study basic cellular and molecular mechanisms of neuronal cell death, neuroprotection, and synaptic plasticity Neurochem. Res. 30 2005 1521 1528
36. A. Bernardi, R.L. Frozza, E. Jäger, F. Figueiró, L. Bavaresco, C. Salbego, A.R. Pohlmann, S.S. Guterres, and A.M.O. Battastini Selective cytotoxicity of indomethacin and indomethacin ethyl ester-loaded nanocapsules against glioma cell lines: an in vitro study Eur. J. Pharmacol. 586 2008 24 34
37. J.S. Lopez-Gonzalez, H. Prado-Garcia, D. Aguilar-Cazares, J.Á. Molina-Guarneros, J. Morales-Fuentes, and J.J. Mandoki Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines Lung Cancer 43 2004 275 283
38. H.Y. Zhanga Wang LF theoretical elucidation of structure-activity relationship for coumarins to scavenge peroxyl radical J. Mol. Struct. (Theochem) 673 2004 199 202
39. A. Maresca, C. Temperini, H. Vu, N.B. Pham, S.A. Poulsen, A. Scozzafava, R.J. Quinn, and C.T. Supuran Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors J. Am. Chem. Soc 131 2009 3057 3062