Chalcone-coumarin derivatives as potential anti-cancer drugs: An in vitro and in vivo investigation

Anti-Cancer Agents in Medicinal Chemistry

Volumn 14, Issue 7, 2014, Pages 963-974

  Jamier, Vincent ^a,b   Marut, Wioleta ^a   Valente, Sergio ^c   Chéreau, Christiane ^c   Chouzenoux, Sandrine ^a   Nicco, Carole ^a   Lemaréchal, Hervé ^a   Weill, Bernard ^a   Kirsch, Gilbert ^c   Jacob, Claus ^b   Batteux, Frederic ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b SAARLAND UNIVERSITY   (Germany)

^c UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Cancer; Coumarin; Cytotoxicity; Oxidative stress; Structure activity relationship

Indexed keywords

7-HYDROXY-4-(3-(4-HYDROXYPHENYL)-3-OXOPROP-1-ENYL)-2H-CHROMEN-2-ONE; 7-METHOXY-4-(3-OXO-3-PHENYLPROP-1-ENYL)-2H-CHROMEN-2-ONE; ANTINEOPLASTIC AGENT; CHALCONE DERIVATIVE; COUMARIN DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ANIMAL; BAGG ALBINO MOUSE; CANCER TRANSPLANTATION; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; FEMALE; HUMAN; IC50; KIDNEY; LIVER; METABOLISM; NECROSIS; PATHOLOGY; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHALCONES; COUMARINS; FEMALE; HETEROGRAFTS; HUMANS; INHIBITORY CONCENTRATION 50; KIDNEY; LIVER; MICE, INBRED BALB C; NECROSIS; NEOPLASM TRANSPLANTATION; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84905639421     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/1871520613666131224124445     Document Type: Article

References (38)

1. Crozier, A.; Jaganath, I.B.; Clifford M.N. Dietary phenolics: Chemistry, bioavailability and effects on health. Nat. Prod. Rep., 2009, 26, 1001-1043.
2. Jacob, C.; Jamier, V.; Ba, L.A. Redox active secondary metabolites. Curr. Opin. Chem. Biol., 2011, 15, 149-155.
3. Thornes, R.D.; Edlow, D.W.; Wood, S. Jr. Inhibition of locomotion of cancer cells in vivo by anticoagulant therapy. I. Effects of sodium warfarin on V2 cancer cells, granulocytes, lymphocytes and macrophages in rabbits. Johns Hopkins Med. J., 1968, 123, 305-316.
4. Pelkonen, O.; Rautio, A.; Raunio, H.; Pasanen, M. CYP2A6: A human coumarin 7-hydroxylase. Toxicology, 2000, 144, 139-147.
5. Bruyere, C.; Genovese, S.; Lallemand, B.; Ionescu-Motatu, A.; Curini, M.; Kiss, R.; Epifano, F. Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines. Bioorg. Med. Chem. Lett., 2011, 21, 4174-4179.
6. Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr. Med. Chem., 2006, 13, 199-222.
7. Wu, L.; Wang, X.; Xu, W.; Farzaneh, F.; Xu, R. The structure and pharmacological functions of coumarins and their derivatives. Curr. Med. Chem., 2009, 16, 4236-4260.
8. Jimenez-Orozco, F.A.; Lopez-Gonzalez, J.S.; Nieto-Rodriguez, A.; Velasco-Velazquez, M.A.; Molina-Guarneros, J.A.; Mendoza-Patino, N.; García-Mondragón, M.J.; Elizalde-Galvan, P.; León-Cedeño, F.; Mandoki, J.J. Decrease of cyclin D1 in the human lung adenocarcinoma cell line A-427 by 7-hydroxycoumarin. Lung Cancer, 2001, 34, 185-194.
9. Valente, S.; Bana, E.; Viry, E.; Bagrel, D.; Kirsch, G. Synthesis and biological evaluation of novel coumarin-based inhibitors of Cdc25 phosphatases. Bioorg. Med. Chem. Lett., 2010, 20, 5827-5830.
10. Valente, S.; Kirsch, G. Facile synthesis of 4-acetyl-coumarins, thiocoumarin and quinolin-2(1H)-one via very high alpha-regioselective heck coupling on tosylates. Tetrahedron Lett., 2011, 52, 3429-3432.
11. Laurila, P.; Virtanen, I.; Wartiovaara, J.; Stenman, S. Fluorescent Antibodies and lectins stain intracellular structures in fixed cells treated with non-ionic detergent. J. Histochem. Cytochem., 1978, 26, 251-257.
12. Alexandre, J.; Nicco, C.; Chereau, C.; Laurent, A.; Weill, B.; Goldwasser, F.; Batteux, F. Improvement of the therapeutic index of anticancer drugs by the superoxide dismutase mimic mangafodipir. J. Natl. Cancer Inst., 2006, 98, 236-244.
13. Rice, G.C.; Bump, E.A.; Shrieve, D.C.; Lee, W.; Kovacs, M. Quantitative analysis of cellular glutathione by flow cytometry utilizing monochlorobimane: Some applications to radiation and drug resistance in vitro and in vivo. Cancer Res., 1986, 46, 6105-6110.
14. Ito, K.; Sawanobori, J. 4-diazomethyl-7-methoxycoumarin as a new type of stable aryldiazomethane reagent. Synth. Commun., 1982, 12, 665-671.
15. Binda, C.; Wang, J.; Pisani, L.; Caccia, C.; Carotti, A.; Salvati, P.; Edmondson, D.E.; Mattevi, A. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: Safinamide and coumarin analogs. J. Med. Chem., 2007, 50, 5848-5852.
16. Marques-Lopez, E.; Herrera, R.P.; Marks, T.; Jacobs, W.C.; Konning, D.; De Figueiredo, R.M.; Christmann, M. Crossed intramolecular rauhut-currier-type reactions via dienamine activation. Org. Lett., 2009, 11, 4116-4119.
17. Kuroda, J.I.; Inamoto, K.; Hiroya, K.; Doi, T. N-heterocyclic carbene derived nickel-pincer complexes: Efficient and applicable catalysts for suzuki-miyaura coupling reactions of aryl/alkenyl tosylates and mesylates. Eur. J. Org. Chem., 2009, 2251-2261.
18. Idziorek, T.; Estaquier, J.; Debels, F.; Ameisen, J.C. Yopro-1 permits cytofluorometric analysis of programmed cell-death (apoptosis) without interfering with cell viability. J. Immunol. Methods, 1995, 185, 249-258.
19. Madari, H.; Panda, D.; Wilson, L.; Jacobs, R.S. Dicoumarol: A unique microtubule stabilizing natural product that is synergistic with Taxol. Cancer Res., 2003, 63, 1214-1220.
20. Shahverdi, A.R.; Saadat, F.; Khorramizadeh, M.R.; Iranshahi, M.; Khoshayand, M.R. Two matrix metalloproteinases inhibitors from Ferula persica var. persica. Phytomedicine, 2006, 13, 712-717.
21. Lee, S.H.; Park, C.; Jin, C.Y.; Kim, G.Y.; Moon SK.; Hyun, J.W.; Lee, W.H.; Choi, B.T.; Kwon, T.K.; Yoo, Y.H.; Choi, YH. Involvement of extracellular signal-related kinase signaling in esculetin induced G1 arrest of human leukemia U937 cells. Biomed. Pharmacother., 2008, 62, 723-729.
22. Lopez-Gonzalez, J.S.; Prado-Garcia, H.; Aguilar-Cazares, D.; Molina-Guarneros, J.A.; Morales-Fuentes, J.; Mandoki, J.J. Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines. Lung Cancer, 2004, 43, 275-283.
23. Starcevic, S.; Brozic, P.; Turk, S.; Cesar, J.; Rizner, T.L.; Gobec, S. Synthesis and biological evaluation of (6-and 7-phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17 beta-hydroxysteroid dehydrogenase type 1. J. Med. Chem., 2011, 54, 248-261.
24. Jiao, J.; Xiang, H.; Liao, Q. Recent advancement in nonsteroidal aromatase inhibitors for treatment of estrogen-dependent breast cancer. Curr. Med. Chem., 2010, 17, 3476-3487.
25. Stefanachi, A.; Favia, A.D.; Nicolotti, O.; Leonetti, F.; Pisani, L.; Catto, M.; Zimmer, C.; Hartmann, R.W.; Carotti, A. Design, synthesis, and biological evaluation of imidazolyl derivatives of 4,7-disubstituted coumarins as aromatase inhibitors selective over 17-alpha-hydroxylase/c17-20 lyase. J. Med. Chem., 2011, 54, 1613-1625.
26. Su, D.; Cheng, Y.; Liu, M.; Liu, D.Z.; Cui, H.; Zhang, B.; Zhou, S.; Yang, T.; Mei, Q. Comparision of piceid and resveratrol in antioxidation and antiproliferation activities in vitro. PloS one, 2013, 8(1), e54505.
27. Laurent, A.; Nicco, C.; Chereau, C.; Goulvestre, C.; Alexandre, J.; Alves, A.; Lévy, E.; Goldwasser, F.; Panis, Y.; Soubrane, O.; Weill, B.; Batteux, F. Controlling tumor growth by modulating endogenous production of reactive oxygen species. Cancer Res., 2005, 65, 948-956.
28. Trachootham, D.; Alexandre, J.; Huang, P. Targeting cancer cells by ROS-mediated mechanisms: A radical therapeutic approach? Nat. Rev. Drug Discov., 2009, 8, 579-591.
29. Jacob, C.; Winyard, P.G. Redox signaling and regulation in biology and medicine. Weinheim. Wiley-VCH, 2009.
30. Schafer, F.Q.; Buettner, G.R. Redox environment of the cell as viewed through the redox state of the glutathione disulfide/ glutathione couple. Free Radical Bio. Med., 2001, 30, 1191-1212.
31. Born, S.L.; Rodriguez, P.A.; Eddy, C.L.; LehmanMcKeeman, L.D. Synthesis and reactivity of coumarin 3,4-epoxide. Drug Metab. Dispos., 1997, 25, 1318-1323.
32. Lake, B.G. Coumarin metabolism, toxicity and carcinogenicity: Relevance for human risk assessment. Food Chem. Toxicol., 1999, 37, 423-453.
33. Vassallo, J.D.; Hicks, S.M.; Born, S.L.; Daston, G.P. Roles for epoxidation and detoxification of coumarin in determining species differences in Clara cell toxicity. Toxicol. Sci., 2004, 82, 26-33.
34. Kostova, I.P.; Manolov, I.I.; Nicolova, I.N.; Danchev, N.D. New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity. Farmaco., 2001, 56, 707-713.
35. Tagalakis, V.; Blostein, M.; Robinson-Cohen, C.; Kahn, S.R. The effect of anticoagulants on cancer risk and survival: Systematic review. Cancer Treat. Rev., 2007, 33, 358-368.
36. Bhattacharyya, S.S.; Paul, S.; Mandal, S.K.; Banerjee, A.; Boujedaini, N.; Khuda-Bukhsh, A.R. A synthetic coumarin (4-Methyl-7 hydroxy coumarin) has anti-cancer potentials against DMBA-induced skin cancer in mice. Eur. J. Pharmacol., 2009, 614, 128-136.
37. Lacy, A.; O'Kennedy, R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr. Pharm. Design, 2004, 10, 3797-3811.
38. Kostova, I. Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem. Anti-Cancer Agents, 2005, 5, 29-46.