Lipophilic caffeic and ferulic acid derivatives presenting cytotoxicity against human breast cancer cells

Chemical Research in Toxicology

Volumn 24, Issue 5, 2011, Pages 763-774

  Serafim, Teresa L ^a   Carvalho, Filipa S ^a   Marques, Maria P M ^b,c   Calheiros, Rita ^b   Silva, Tiago ^e   Garrido, Jorge ^d,e   Milhazes, Nuno ^e,f   Borges, Fernanda ^e   Roleira, Fernanda ^g   Silva, Elisiário T ^g   Holy, Jon ^h   Oliveira, Paulo J ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c UNIVERSITY OF COIMBRA   (Portugal)

^d INSTITUTO SUPERIOR DE ENGENHARIA DO PORTO   (Portugal)

^e UNIVERSITY OF PORTO   (Portugal)

^f Health Sciences Superior Institute North   (Portugal)

^g UNIVERSITY OF COIMBRA   (Portugal)

^h UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CAFFEOYLHEXYLAMIDE; FERULIC ACID; FERULOYLHEXYLAMIDE; HEXYL CAFFEATE; HEXYL FERULATE; HYDROXYACID; MITOCHONDRIAL PERMEABILITY TRANSITION PORE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BIOENERGY; BREAST CANCER; CANCER CELL; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE PROGRESSION; CELL CYCLE S PHASE; CELL PROLIFERATION; CELL STRAIN MCF 7; CELL TYPE; COMPARATIVE STUDY; CONTROLLED STUDY; CYTOSTASIS; CYTOTOXICITY TEST; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; FEMALE; FIBROBLAST; HUMAN; HUMAN CELL; LIPOPHILICITY; LIVER MITOCHONDRION; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRIAL PERMEABILITY; NONHUMAN; OXYGEN CONSUMPTION; RAT; SIGNAL TRANSDUCTION;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; APOPTOSIS; BREAST NEOPLASMS; CAFFEIC ACIDS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; COUMARIC ACIDS; FEMALE; HUMANS; MITOCHONDRIA;

EID: 79956157475     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200126r     Document Type: Article

References (50)

1. Fresco, P., Borges, F., Diniz, C., and Marques, M. P. (2006) New insights on the anticancer properties of dietary polyphenols Med. Res. Rev. 26, 747-766 (Pubitemid 44735552)
2. Fresco, P., Borges, F., Marques, M. P., and Diniz, C. (2010) The anticancer properties of dietary polyphenols and its relation with apoptosis Curr. Pharm. Des. 16, 114-134
3. Huang, W. Y., Cai, Y. Z., and Zhang, Y. (2010) Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention Nutr. Cancer 62, 1-20
4. Lee, K. W. and Lee, H. J. (2006) The roles of polyphenols in cancer chemoprevention BioFactors 26, 105-121
5. Czuba, Z., Krol, W., Scheller, S., and Shani, J. (1992) Effect of cinnamic and acrylic acids' derivatives on luminol-enhanced chemiluminescence of neutrophils Z. Naturforsch., C: J. Biosci. 47, 753-756
6. Bravo, L. (1998) Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance Nutr. Rev. 56, 317-333 (Pubitemid 28532456)
7. Kelloff, G. J. (2000) Perspectives on cancer chemoprevention research and drug development Adv. Cancer Res. 78, 199-334
8. Serafim, T. L., Marques, M. P., Borges, F., and Oliveira, P. J. (2008) Mitochondria as a target for novel chemotherapeutic agents based on phenolic acids J. Theor. Exp. Pharm. 1, 3-13
9. Fiuza, S. M., Gomes, C., Teixeira, L. J., Girao da Cruz, M. T., Cordeiro, M. N., Milhazes, N., Borges, F., and Marques, M. P. (2004) Phenolic acid derivatives with potential anticancer properties: a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids Bioorg. Med. Chem. 12, 3581-3589 (Pubitemid 38746860)
10. Gomes, C. A., da Cruz, T. G., Andrade, J. L., Milhazes, N., Borges, F., and Marques, M. P. (2003) Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study J. Med. Chem. 46, 5395-5401 (Pubitemid 37490372)
11. Esteves, M., Siquet, C., Gaspar, A., Rio, V., Sousa, J. B., Reis, S., Marques, M. P., and Borges, F. (2008) Antioxidant versus cytotoxic properties of hydroxycinnamic acid derivatives: a new paradigm in phenolic research Arch. Pharm. (Weinheim) 341, 164-173
12. Marques, M. P. M., Borges, F., Sousa, J. B., Calheiros, R., Garrido, J., Gaspar, A., Antunes, F., Diniz, C., and Fresco, P. (2006) Cytotoxic and COX-2 inhibition properties of Hydroxycinnamic derivatives Lett. Drug Design Discovery 3, 316-320 (Pubitemid 43988113)
13. Gao, S. and Hu, M. (2010) Bioavailability challenges associated with development of anti-cancer phenolics Mini. Rev. Med. Chem. 10, 550-567
14. Crozier, A., Jaganath, I. B., and Clifford, M. N. (2009) Dietary phenolics: chemistry, bioavailability and effects on health Nat. Prod. Rep. 26, 1001-1043
15. Roleira, F. M., Siquet, C., Orru, E., Garrido, E. M., Garrido, J., Milhazes, N., Podda, G., Paiva-Martins, F., Reis, S., Carvalho, R. A., Silva, E. J., and Borges, F. (2010) Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties Bioorg. Med. Chem. 18, 5816-5825
16. Shaw, J. M. and Winge, D. R. (2009) Shaping the mitochondrion: mitochondrial biogenesis, dynamics and dysfunction. Conference on Mitochondrial Assembly and Dynamics in Health and Disease EMBO Rep. 10, 1301-1305
17. Weinberg, F. and Chandel, N. S. (2009) Mitochondrial metabolism and cancer Ann. N.Y. Acad. Sci. 1177, 66-73
18. Gogvadze, V., Orrenius, S., and Zhivotovsky, B. (2009) Mitochondria as targets for cancer chemotherapy Semin. Cancer Biol. 19, 57-66
19. Ralph, S. J. and Neuzil, J. (2009) Mitochondria as targets for cancer therapy Mol. Nutr. Food. Res. 53, 9-28
20. Pereira, C. V., Moreira, A. C., Pereira, S. P., Machado, N. G., Carvalho, F. S., Sardao, V. A., and Oliveira, P. J. (2009) Investigating drug-induced mitochondrial toxicity: a biosensor to increase drug safety? Curr. Drug Saf. 4, 34-54
21. Pereira, G. C., Branco, A. F., Matos, J. A., Pereira, S. L., Parke, D., Perkins, E. L., Serafim, T. L., Sardao, V. A., Santos, M. S., Moreno, A. J., Holy, J., and Oliveira, P. J. (2007) Mitochondrially targeted effects of berberine [Natural Yellow 18, 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3- benzodioxolo(5,6-a) quinolizinium] on K1735-M2 mouse melanoma cells: comparison with direct effects on isolated mitochondrial fractions J. Pharmacol. Exp. Ther. 323, 636-649 (Pubitemid 350005145)
22. Lin, Z. X., Hoult, J. R., and Raman, A. (1999) Sulphorhodamine B assay for measuring proliferation of a pigmented melanocyte cell line and its application to the evaluation of crude drugs used in the treatment of vitiligo J. Ethnopharmacol. 66, 141-150 (Pubitemid 29307912)
23. Serafim, T. L., Oliveira, P. J., Sardao, V. A., Perkins, E., Parke, D., and Holy, J. (2008) Different concentrations of berberine result in distinct cellular localization patterns and cell cycle effects in a melanoma cell line Cancer Chemother. Pharmacol. 61, 1007-1018 (Pubitemid 351423129)
24. Rolo, A. P., Oliveira, P. J., Moreno, A. J., and Palmeira, C. M. (2000) Bile acids affect liver mitochondrial bioenergetics: possible relevance for cholestasis therapy Toxicol. Sci. 57, 177-185
25. Gornall, A. G., Bardawill, C. J., and David, M. M. (1949) Determination of serum proteins by means of the biuret reaction J. Biol. Chem. 177, 751-766
26. Oliveira, P. J., Santos, D. J., and Moreno, A. J. (2000) Carvedilol inhibits the exogenous NADH dehydrogenase in rat heart mitochondria Arch. Biochem. Biophys. 374, 279-285 (Pubitemid 30120263)
27. Chance, B., Williams, G. R., and Hollunger, G. (1963) Inhibition of electron and energy transfer in mitochondria. III. Spectroscopic and respiratory effects of uncoupling agents J. Biol. Chem. 238, 439-444
28. Oliveira, P. J., Coxito, P. M., Rolo, A. P., Santos, D. L., Palmeira, C. M., and Moreno, A. J. (2001) Inhibitory effect of carvedilol in the high-conductance state of the mitochondrial permeability transition pore Eur. J. Pharmacol. 412, 231-237 (Pubitemid 32144938)
29. Kamo, N., Muratsugu, M., Hongoh, R., and Kobatake, Y. (1979) Membrane potential of mitochondria measured with an electrode sensitive to tetraphenyl phosphonium and relationship between proton electrochemical potential and phosphorylation potential in steady state J. Membr. Biol. 49, 105-121 (Pubitemid 10221193)
30. Oliveira, P. J., Esteves, T., Rolo, A. P., Palmeira, C. M., and Moreno, A. J. (2004) Carvedilol inhibits the mitochondrial permeability transition by an antioxidant mechanism Cardiovasc. Toxicol. 4, 11-20 (Pubitemid 38506960)
31. Broekemeier, K. M., Dempsey, M. E., and Pfeiffer, D. R. (1989) Cyclosporin A is a potent inhibitor of the inner membrane permeability transition in liver mitochondria J. Biol. Chem. 264, 7826-7830 (Pubitemid 19137258)
32. Halestrap, A. P. (2009) What is the mitochondrial permeability transition pore? J Mol. Cell. Cardiol. 46, 821-831
33. Fedotcheva, N. I., Kazakov, R. E., Kondrashova, M. N., and Beloborodova, N. V. (2008) Toxic effects of microbial phenolic acids on the functions of mitochondria Toxicol. Lett. 180, 182-188
34. Jung, B. I., Kim, M. S., Kim, H. A., Kim, D., Yang, J., Her, S., and Song, Y. S. (2010) Caffeic acid phenethyl ester, a component of beehive propolis, is a novel selective estrogen receptor modulator Phytother. Res. 24, 295-300
35. Rajan, P., Vedernikova, I., Cos, P., Berghe, D. V., Augustyns, K., and Haemers, A. (2001) Synthesis and evaluation of caffeic acid amides as antioxidants Bioorg. Med. Chem. Lett. 11, 215-217 (Pubitemid 32099643)
36. Son, S., Lobkowsky, E. B., and Lewis, B. A. (2001) Caffeic acid phenethyl ester (CAPE): synthesis and X-ray crystallographic analysis Chem. Pharm. Bull. (Tokyo) 49, 236-238 (Pubitemid 32174663)
37. Nomura, E., Hosoda, A., Morishita, H., Murakami, A., Koshimizu, K., Ohigashi, H., and Taniguchi, H. (2002) Synthesis of novel polyphenols consisted of ferulic and gallic acids, and their inhibitory effects on phorbol ester-induced Epstein-Barr virus activation and superoxide generation Bioorg. Med. Chem. 10, 1069-1075 (Pubitemid 34141304)
38. Alao, J. P., Lam, E. W., Ali, S., Buluwela, L., Bordogna, W., Lockey, P., Varshochi, R., Stavropoulou, A. V., Coombes, R. C., and Vigushin, D. M. (2004) Histone deacetylase inhibitor trichostatin A represses estrogen receptor alpha-dependent transcription and promotes proteasomal degradation of cyclin D1 in human breast carcinoma cell lines Clin. Cancer Res. 10, 8094-8104 (Pubitemid 39587551)
39. Peetla, C., Bhave, R., Vijayaraghavalu, S., Stine, A., Kooijman, E., and Labhasetwar, V. (2010) Drug resistance in breast cancer cells: biophysical characterization of and doxorubicin interactions with membrane lipids Mol. Pharm. 7, 2334-2348
40. Doyle, L. A. and Ross, D. D. (2003) Multidrug resistance mediated by the breast cancer resistance protein BCRP (ABCG2) Oncogene 22, 7340-7358 (Pubitemid 37487163)
41. Vaseva, A. V. and Moll, U. M. (2009) The mitochondrial p53 pathway Biochim. Biophys. Acta 1787, 414-420
42. Sardao, V. A., Oliveira, P. J., Holy, J., Oliveira, C. R., and Wallace, K. B. (2009) Doxorubicin-induced mitochondrial dysfunction is secondary to nuclear p53 activation in H9c2 cardiomyoblasts Cancer Chemother. Pharmacol. 64, 811-827
43. Szliszka, E., Czuba, Z. P., Domino, M., Mazur, B., Zydowicz, G., and Krol, W. (2009) Ethanolic extract of propolis (EEP) enhances the apoptosis-inducing potential of TRAIL in cancer cells Molecules 14, 738-754
44. Mayevsky, A. (2009) Mitochondrial function and energy metabolism in cancer cells: past overview and future perspectives Mitochondrion 9, 165-179
45. Gogvadze, V., Zhivotovsky, B., and Orrenius, S. (2010) The Warburg effect and mitochondrial stability in cancer cells Mol. Aspects Med. 31, 60-74
46. Sardao, V. A., Pereira, S. L., and Oliveira, P. J. (2008) Drug-induced mitochondrial dysfunction in cardiac and skeletal muscle injury Expert Opin. Drug Saf. 7, 129-146 (Pubitemid 351447696)
47. Huang, D. W., Shen, S. C., and Wu, J. S. (2009) Effects of caffeic acid and cinnamic acid on glucose uptake in insulin-resistant mouse hepatocytes J. Agric. Food Chem. 57, 7687-7692
48. Manach, C., Scalbert, A., Morand, C., Remesy, C., and Jimenez, L. (2004) Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 79, 727-747 (Pubitemid 41103873)
49. Wang, S. J., Zhang, Z. Q., Zhao, Y. H., Ruan, J. X., and Li, J. L. (2006) Simultaneous quantification of chlorogenic acid and caffeic acid in rat plasma after an intravenous administration of mailuoning injection using liquid chromatography/mass spectrometry Rapid Commun. Mass Spectrom. 20, 2303-2308 (Pubitemid 44199621)
50. Coimbra, M., Isacchi, B., van Bloois, L., Torano, J. S., Ket, A., Wu, X., Broere, F., Metselaar, J. M., Rijcken, C. J., Storm, G., Bilia, R., and Schiffelers, R. M. (2011) Improving solubility and chemical stability of natural compounds for medicinal use by incorporation into liposomes. Int. J. Pharm. [online early access], DOI: 10.1016/j.ijpharm.2011.01.056.