Phenylbenzopyrones structure-activity studies identify betuletol derivatives as potential antitumoral agents

European Journal of Pharmacology

Volumn 548, Issue 1-3, 2006, Pages 9-20

  Rubio, Sara ^a   Quintana, José ^a   López, Mariana ^a   Eiroa, José Luis ^a   Triana, Jorge ^a   Estévez, Francisco ^a  

^a UNIVERSITY OF LAS PALMAS DE GRAN CANARIA   (Spain)

Author keywords

Apoptosis; Caspases; Cytotoxic activity; DNA fragmentation; Flavonoids; poly(ADP ribose) polymerase

Indexed keywords

3,3' DIMETHYLQUERCETIN; 4',5,7 TRIACETOXY 3,6 DIMETHOXYFLAVONE; 4',5,7 TRIHYDROXY 3,6 DIMETHOXYFLAVONE; 5,7 DIACETOXY 4' HYDROXY 3,6 DIMETHOXYFLAVONE; 5,7 DIHYDROXY 3,3',4' TRIMETHOXYFLAVONE; 7 ACETOXY 4',5 DIHYDROXY 3,6 DIMETHOXYFLAVONE; ANTINEOPLASTIC AGENT; APIGENIN; AXILLARIN; BENZYLOXYCARBONYLISOLEUCYLGLUTAMYLTHREONYLASPARTYL FLUOROMETHYL KETONE; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; BETULETOL 3 METHYL ETHER; BETULETOL 3 METHYL ETHER DIACETATE; BUTELOL 3,5,7 TRIMETHYL ETHER; CASPASE 8 INHIBITOR; CRYPTOSTROBIN; DIHYDROKAEMPFEROL 7,4' DIMETHYL ETHER; DIHYDROQUERCETIN 7,3' DIMETHYL ETHER; ERIODICTYOL; ERIODICTYOL TETRACETATE; FLAVANOID; ISOKAEMPFERIDE; NARINGENIN; QUERCETIN; QUERCETIN 3 METHYL ETHER; QUERCETIN 3 METHYL ETHER TETRACETATE; QUERCETIN 3,3' DIMETHYL ETHER TRIACETATE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL LINE; CELL STRAIN HL 60; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG SCREENING; HELA CELL; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASES; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CYTOCHROMES C; DNA FRAGMENTATION; ETHERS; FLAVONOIDS; HUMANS; MITOCHONDRIA; POLY(ADP-RIBOSE) POLYMERASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33748704067     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2006.07.020     Document Type: Article

References (37)

1. Block G., Patterson B., and Subar A. Fruit, vegetables and cancer prevention: a review of the epidemiological evidence. Nutr. Cancer 18 (1992) 1-29
2. Boldin M., Goncharov T., Goltsev Y., and Wallach D. Involvement of MACH, a novel MORT1/FADD-interacting protease, in Fas/APO-1- and TNF receptor-induced cell death. Cell 85 (1996) 803-815
3. Borner C. The Bcl-2 protein family: sensors and checkpoints for life-or-death decisions. Mol. Immunol. 39 (2003) 615-647
4. Budihardjo I., Oliver H., Lutter M., Luo X., and Wang X. Biochemical pathways of caspase activation during apoptosis. Annu. Rev. Cell Dev. Biol. 15 (1999) 269-290
5. 13C N.M.R. Study of (±)-cryptostrobin and related substances. Revision of the structures of the natural products (±)-lawinal, unonal, 7-O-methylunonal and isounonal. Aust. J. Chem. 35 (1982) 1851-1858
6. Chipuk J.E., and Green D.R. Do inducers of apoptosis trigger caspase-independent cell death?. Nat. Rev., Mol. Cell Biol. 6 (2005) 268-275
7. Cohen G.M. Caspases: the executioners of apoptosis. Biochem. J. 326 (1997) 1-16
8. Friesen C., Herr I., Krammer P.H., and Debatin K.M. Involvement of the CD95 (APO-1/FAS) receptor/ligand system in drug-induced apoptosis in leukemia cells. Nat. Med. 2 (1996) 574-577
9. González A.G., Bermejo J., Triana J., López M., and Eiroa J.L. Sesquiterpene lactones from Tanacetum ferulaceum. Phytochemistry 29 (1990) 2339-2341
10. González A.G., Bermejo J., Triana J., Eiroa J.L., and López M. Germacranolides from Allagopappus viscosissimus. Phytochemistry 31 (1992) 330-331
11. González A.G., Bermejo J., Triana J., López M., and Eiroa J.L. Sesquiterpene lactones and other constituents of Tanacetum species. Phytochemistry 31 (1992) 1821-1822
12. González A.G., Bermejo J., Triana J., Eiroa J.L., and López M. Sesquiterpene lactones and other constituents of Allagopappus species. J. Nat. Prod. 58 (1995) 432-437
13. Haldar S., Jena N., and Croce C.M. Inactivation of Bcl-2 by phosphorylation. Proc. Natl. Acad. Sci. U. S. A. 92 (1995) 4507-4511
14. Igney F.H., and Krammer P.H. Death and anti-death: tumour resistance to apoptosis. Nat. Rev., Cancer 2 (2002) 277-288
15. Kandaswami C., Perkins E., Soloniuk D.S., Drzewiecki G., and Middleton E. Ascorbic acid-enhanced antiproliferative effect of flavonoids on squamous cell carcinoma in vitro. Anticancer Drugs 4 (1993) 91-96
16. Kawaii S., Tomono Y., Katase E., Ogawa K., and Yano M. Antiproliferative activity of flavonoids on several cancer cell lines. Biosci. Biotechnol. Biochem. 63 (1999) 896-899
17. Kim K.M., and Lee Y.J. Role of HER-2/neu signaling in sensitivity to tumor necrosis factor-related apoptosis-inducing ligand: enhancement of TRAIL-mediated apoptosis by amiloride. J. Cell. Biochem. 96 (2005) 376-389
18. Kluck R.M., Bozy-Wetzel E., Green D.R., and Newmeyer D.D. The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis. Science 275 (1997) 1132-1136
19. Ko C.H., Shen S.C., Lin H.Y., Hou W.C., Lee W.R., Yang L.L., and Chen Y.C. Flavanones structure related inhibition on TPA-induced tumor promotion through suppression of extracellular signal-regulated protein kinases: involvement of prostaglandin E2 in anti-promotive process. J. Cell. Physiol. 193 (2002) 93-102
20. Krammer P.H. CD95's deadly mission in the immune system. Nature 407 (2000) 789-795
21. Kuntz S., Wenzel U., and Daniel H. Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines. Eur. J. Nutr. 38 (1999) 133-142
22. 2+-dependent endonuclease. Biochem. Pharmacol. 63 (2002) 225-236
23. Li P., Nijhawan D., Budihardjo I., Srinivasula S.M., Ahmad M., Alnemri E.S., and Wang X. Cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell 91 (1997) 479-489
24. Liu X., Kim C., Yang J., Jemmerson R., and Wang X. Induction of apoptotic program in cell-free extracts: requirement for dATP and cytochrome c. Cell 86 (1996) 147-157
25. Marsden V.S., and Strasser A. Control of apoptosis in the immune system: Bcl-2, BH3-only proteins and more. Annu. Rev. Immunol. 21 (2003) 71-105
26. Middleton E., Kandaswami C., and Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52 (2000) 673-751
27. Motwani M., Delohery T.M., and Schwartz G.K. Sequential dependent enhancement of caspase activation and apoptosis by flavopiridol on paclitaxel-treated human gastric and breast cancer cells. Clin. Cancer Res. 5 (1999) 1876-1883
28. Muzio M., Chinnaiyan A.M., Kischkel F.C., O'Rourke K., Schevchenko A., Ni J., Scaffidi C., Bretz J.D., Zhang M., Gentz R., Mann M., Krammer P.H., Peter M.E., and Dixit V.M. FLICE, a novel FADD-homologous ICE/CED-3-like protease, is recruited to the CD95 (Fas/APO-1) death-inducing signalling complex. Cell 85 (1996) 817-827
29. Nicholson D.W., and Thornberry N.A. Caspases: killer proteases. Trends Biochem. Sci. 22 (1997) 299-306
30. Rivero A., Quintana J., Eiroa J.L., López M., Triana J., Bermejo J., and Estévez F. Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. Eur. J. Pharmacol. 482 (2003) 77-84
31. Srinivasula S., Ahmad M., Alnemri T., and Alnemri E. Autoactivation of procaspase-9 by Apaf-1 mediated oligomerization. Mol. Cell 1 (1998) 949-957
32. Stennicke H.R., Jurgensmeier J.M., Shin H., Deveraux Q., Wolf B.B., Yang X., Zhou Q., Ellerby H.M., Ellerby L.M., Bredesen D., Green D.R., Reed J.C., Froelich C.J., and Salvesen G.S. Procaspase-3 is a major physiologic target of caspase-8. J. Biol. Chem. 273 (1998) 27084-27090
33. Szewczyk A., and Wojtczak L. Mitochondria as a pharmacological target. Pharmacol. Rev. 54 (2002) 101-127
34. Thornberry N.A., and Lazebnik Y. Caspases: enemies within. Science 281 (1998) 1312-1316
35. Triana J., López M., Pérez F.J., González-Platas J., Quintana J., Estévez F., León F., and Bermejo J. Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities. J. Nat. Prod. 68 (2005) 523-531
36. Van Gurp M., Festjens N., van Loo G., Saelens X., and Vandenabeele P. Mitochondrial intermembrane proteins in cell death. Biochem. Biophys. Res. Commun. 304 (2003) 487-497
37. Yang J., Liu X., Bhalla K., Kim C.N., Ibrado A.M., Cai J., Peng T.I., Jones D.P., and Wang X. Prevention of apoptosis by Bcl-2: release of cytochrome c from mitochondria blocked. Science 275 (1997) 1129-1132