Protection or cytotoxicity mediated by a novel quinonoid-polyphenol compound?

General Physiology and Biophysics

Volumn 34, Issue 1, 2015, Pages 51-64

  Milackova, Ivana ^a   Rackova, Lucia ^a   Majekova, Magdalena ^a   Mrvova, Natasa ^a   Stefek, Milan ^a  

^a INSTITUTE OF EXPERIMENTAL PHARMACOLOGY AND TOXICOLOGY   (Slovakia)

Author keywords

CHNQ; Hormesis; Oxidative stress; Quinones

Indexed keywords

CHLORONAPHTHOQUINONE; POLYPHENOL DERIVATIVE; QUERCETIN DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; ANTIOXIDANT; FLAVONOID; HYDROGEN PEROXIDE; NAPHTHOQUINONE; NEUTRAL RED; OXIDIZING AGENT; POLYPHENOL; TETRAZOLIUM; THIAZOLE DERIVATIVE; THIAZOLYL BLUE;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL PROTECTION; CONTROLLED STUDY; DRUG CYTOTOXICITY; FIBROBLAST; HUMAN; HUMAN CELL; LOW DRUG DOSE; MOLECULAR MODEL; NEWBORN; OXIDATIVE STRESS; AGING; APOPTOSIS; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; HORMESIS; IMMUNOHISTOCHEMISTRY; NECROSIS;

AGING; ANTIOXIDANTS; APOPTOSIS; CELLS, CULTURED; FLAVONOIDS; HORMESIS; HUMANS; HYDROGEN PEROXIDE; IMMUNOHISTOCHEMISTRY; MODELS, MOLECULAR; NAPHTHOQUINONES; NECROSIS; NEUTRAL RED; OXIDANTS; OXIDATIVE STRESS; POLYPHENOLS; QUINONES; TETRAZOLIUM SALTS; THIAZOLES;

EID: 84925297636     PISSN: 02315882     EISSN: 13384325     Source Type: Journal    
DOI: 10.4149/gpb_2014028     Document Type: Article

References (61)

1. Adams S., Green P., Claxton R., Simcox S., Williams M. V., Walsh K., Leeuwenburgh C. (2001): Reactive carbonyl formation by oxidative and non-oxidative pathways. Front. Biosci. 6, 17-24 http://dx.doi.org/10.2741/Adams
2. Akhtar M. W., Sunico C. R., Nakamura T., Lipton S. A. (2012): Redox regulation of protein function via cysteine S-nitrosylation and its relevance to neurodegenerative diseases. Int. J. Cell Biol. 2012, 463756 http://dx.doi.org/10.1155/2012/463756
3. Awad H. M., Boersma M. G., Vervoort J., Rietjens I. M. (2000): Peroxidase-catalyzed formation of quercetin quinone methideglutathione adducts. Arch. Biochem. Biophys. 378, 224-233 http://dx.doi.org/10.1006/abbi.2000.1832
4. Bast A., Haenen G. R. (2002): The toxicity of antioxidants and their metabolites. Environ. Toxicol. Pharmacol. 11, 251-258 http://dx.doi.org/10.1016/S1382-6689(01)00118-1
5. Bergman E. D., Ginsberg D., Rappo R. (1959): The Michael Reaction in Organic Reactions. (Ed. Blatt A. H.), John Wiley and Sons Inc, New York
6. Birringer M. (2011): Hormetics: dietary triggers of an adaptive stress response. Pharm Res. 28, 2680-2694 http://dx.doi.org/10.1007/s11095-011-0551-1
7. Bolton J. L., Turnipseed S. B., Thompson J. A. (1997): Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models. Chem. Biol. Interact. 107, 185-200 http://dx.doi.org/10.1016/S0009-2797(97)00079-3
8. Calabrese E. J., Baldwin L. (1997): The dose determines the stimulation (and poison): development of a chemical hormesis database. Int. J. Toxicol. 16, 545-559 http://dx.doi.org/10.1080/109158197226874
9. Calingasan N. Y., Uchida K., Gibson G. E. (1999): Protein-bound acrolein: A novel marker of oxidative stress in Alzheimer's disease. J. Neurochem. 72, 751-756 http://dx.doi.org/10.1046/j.1471-4159.1999.0720751.x
10. Chevion M., Berenshtein E., Stadtman E. R. (2000): Human studies related to protein oxidation: protein carbonyl content as a marker of damage. Free Radic. Res. 33, 99-108
11. Chondrogianni N., Kapeta S., Chinou I., Vassilatou K., Papassideri I., Gonos E. S. (2010): Anti-ageing and rejuvenating effects of quercetin. Exp. Gerontol. 45, 763-771 http://dx.doi.org/10.1016/j.exger.2010.07.001
12. Dalle-Donne I., Rossi R., Giustarini D., Milzani A., Colombo R. (2003): Protein carbonyl groups as biomarkers of oxidative stress. Clin. Chim. Acta 329, 23-38 http://dx.doi.org/10.1016/S0009-8981(03)00003-2
13. Dinkova-Kostova A. T., Massiah M. A., Bozak R. E., Hicks R. J., Talalay P. (2001): Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc. Natl. Acad. Sci. 98, 3404-3409 http://dx.doi.org/10.1073/pnas.051632198
14. El-Mahdy M.A., Zhu Q., Wang Q.-E., Wani G., Wani A. A. (2005): Thymoquinone induces apoptosis through activation of caspase-8 and mitochondrial events in p53-null myeloblastic leukemia HL-60 cells. Int. J. Cancer 117, 409-417 http://dx.doi.org/10.1002/ijc.21205
15. Gasch A., Werner-Washburne M. (2002): The genomics of yeast responses to environmental stress and starvation. Func. Int. Gen. 2, 181-192 http://dx.doi.org/10.1007/s10142-002-0058-2
16. Gomez-Monterrey I., Campiglia P., Bertamino A., Aquino C., Sala M., Grieco P., Dicitore A., Porta A. et al. (2010): A novel quinone-based derivative (DTNQ-Pro) induces apoptotic death via modulation of heat shock protein expression in Caco-2 cells. Br. J. Pharmacol. 160, 931-940 http://dx.doi.org/10.1111/j.1476-5381.2010.00718.x
17. Harman D. (1972): A biologic clock: the mitochondria? J. Am. Geriatr. Soc. 20, 145-147
18. Itoh K., Chiba T., Takahashi S., Ishii T., Igarashi K., Katoh Y., Oyake T., Hayashi N., Satoh K., Hatayama I., Yamamoto M., Nabeshima Y. (1997): An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem. Biophys. Res. Commun. 236, 313-322 http://dx.doi.org/10.1006/bbrc.1997.6943
19. Itoh K., Wakabayashi N., Katoh Y., Ishii T., Igarashi K., Engel J. D., Yamamoto M. (1999): Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amoni-terminal Neh2 domain. Genes Dev. 13, 76-86 http://dx.doi.org/10.1101/gad.13.1.76
20. Kayembe J. S., Taba, K. M., Ntumba, K., Tshiongo, M. T. C., Kazadi, T. K. (2010): In vitro anti-malarial activity of 20 quinones isolated from four plants used by traditional healers in the Democratic Republic of Congo. J. Med. Plants Res. 4, 991-994
21. Kobayashi A., Kang M. I., Watai Y., Tong K. I., Shibata T., Uchida K., Yamamoto M. (2006): Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1. Mol. Cell Biol. 26, 221-229 http://dx.doi.org/10.1128/MCB.26.1.221-229.2006
22. Kultz D. (2005): Molecular and evolutionary basis of the cellular stress response. Annu. Rev. Physiol. 67, 225-257 http://dx.doi.org/10.1146/annurev.physiol.67.040403.103635
23. Kuwana T., Bouchier-Hayes L., Chipuk J. E., Bonzon C., Sullivan B. A., Green D. R., Newmeyer D. D. (2005): BH3 domains of BH3-only proteins differentially regulate Bax-mediated mitochondrial membrane permeabilization both directly and indirectly. Mol. Cell 17, 525-535 http://dx.doi.org/10.1016/j.molcel.2005.02.003
24. Lapidot T., Walker M. D., Kanner J. (2002): Antioxidant and prooxidant effects of phenolics on pancreatic beta-cells in vitro. J. Agric. Food Chem. 50, 7220-7225 http://dx.doi.org/10.1021/jf020615a
25. Le Bras M., Clément M. V., Pervaiz S., Brenner C. (2005) Reactive oxygen species and the mitochondrial signaling pathway of cell death. Histol. Histopathol. 20, 205-219
26. Lee J. M., Johnson J. A. (2004): An important role of Nrf2-ARE pathway in the cellular defense mechanism. J. Biochem. Mol. Biol. 37, 139-143 http://dx.doi.org/10.5483/BMBRep.2004.37.2.139
27. Levine R. L. (2002): Carbonyl modified proteins in cellular regulation, aging, and disease. Free Radic. Biol. Med. 32, 790-796 http://dx.doi.org/10.1016/S0891-5849(02)00765-7
28. Li W.W., Heinze J., Haehnel W. (2005): Site-specific binding of quinones to proteins through thiol addition and addition-elimination reactions. J. Am. Chem. Soc. 127, 6140-6141 http://dx.doi.org/10.1021/ja050974x
29. Lin C. F., Chen C. L., Chang W. T., Jan M. S., Hsu L. J., Wu R. H., Tang M. J., Chang W. C., Lin Y. S. (2004): Sequential caspase-2 and caspase-8 activation upstream of mitochondria during ceramideand etoposide-induced apoptosis. J. Biol. Chem. 279, 40755-40761 http://dx.doi.org/10.1074/jbc.M404726200
30. Massaoka M. H., Matsuo A. L., Fiqueiredo C. R., Farias C. F., Girola N., Arruda D. C., Scutti J. A., et al. (2012): Jacaranone induces apoptosis in melanoma cells via ROS-mediated downregulation of Akt and p38 MAPK activation and displays antitumor activity in vivo. PLoS One 7, e38698 http://dx.doi.org/10.1371/journal.pone.0038698
31. Mathers J., Fraser J. A., McMahon M., Saunders R. D., Hayes J. D., McLellan L. I. (2004): Antioxidant and cytoprotective responses to redox stress. Biochem. Soc. Symp. 71, 157-176
32. Metodiewa D., Jaiswal A. K., Cenas N., Dickancaite E., Segura Aguilar J. (1999): Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product. Free Radic. Biol. Med. 26, 107-116 http://dx.doi.org/10.1016/S0891-5849(98)00167-1
33. Milackova I., Kovacikova L., Veverka M., Gallovic J., Stefek M. (2013): Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay. Interdiscipl. Toxicol. 6, 13-17 http://dx.doi.org/10.2478/intox-2013-0003
34. Murota K., Terao J. (2003): Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism. Arch. Biochem. Biophys. 417, 12-17 http://dx.doi.org/10.1016/S0003-9861(03)00284-4
35. O'Brien P. J. (1991): Molecular mechanisns of quinone cytotoxicity. Chem.-Biol. Interactions. 80, 1-41 http://dx.doi.org/10.1016/0009-2797(91)90029-7
36. Pietsch K., Saul N., Chakrabarti S., Sturzenbaum S. R., Menzel R., Steinberg C. E. (2011): Hormetins, antioxidants and prooxidants: defining quercetin-, caffeic acid-and rosmarinic acid-mediated life extension in C. elegans. Biogerontology 12, 329-347 http://dx.doi.org/10.1007/s10522-011-9334-7
37. Prasad V., Chandele A., Jagtap J. C., Kumar S., Shastry P. (2006): ROS-triggered caspase 2 activation and feedback amplification loop in β-carotene-induced apoptosis. Free Radic. Biol. Med. 41, 431-442 http://dx.doi.org/10.1016/j.freeradbiomed.2006.03.009
38. Przybysz A. J., Chloe K. P., Roberts L. J., Strange K. (2009): Increased age reduces DAF-16 and SKN-1 signaling and the hormetic response of Caenorhabditis elegans to the xenobiotic juglone. Mech. Ageing Dev. 130, 357-369 http://dx.doi.org/10.1016/j.mad.2009.02.004
39. Qiu X., Schonthal A., Cadenas E. (1998): Anticancer quinones induce pRb-preventable G2/M cell cycle arrest and apoptosis. Free Radic. Biol. Med. 24, 848-854 http://dx.doi.org/10.1016/S0891-5849(97)00368-7
40. Rackova L., Snirc V., Jung T., Stefek M., Karasu C., Grune T. (2009): Metabolism induced oxidative stress is a mediator of glucose toxicity in HT22 neuronal cells. Free Radic. Res. 24, 1-11
41. Renvoize C., Biola A., Pallardy M., Breard J. (1998): Apoptosis: identification of dying cells. Cell. Biol. Toxicol. 14, 111-120 http://dx.doi.org/10.1023/A:1007429904664
42. Repiská V., Varga I., Lehocký I., Bo″hmer D., Blaško M., Polák Š., Adamkov M., Danišovič L. (2010): Biological and morphological characterization of human neonatal fibroblast cell culture B-HNF-1. Biologia 65, 919-924 http://dx.doi.org/10.2478/s11756-010-0095-6
43. Requena J. R., Chao C. C., Levine R. L., Stadtman E. R. (2001): Glutamic and aminoadipic semialdehydes are the main carbonyl products of metal-catalyzed oxidation of proteins. Proc. Natl. Acad. Sci. U.S.A. 98, 69-74 http://dx.doi.org/10.1073/pnas.98.1.69
44. Reznick A. Z., Cross C. E., Hu M. L., Suzuki Y. J., Khwaja S., Safadi A., Motchnik P. A., Packer L., Halliwell B. (1992): Modification of plasma proteins by cigarette smoke as measured by protein carbonyl formation. Biochem. J. 286, 607-611
45. Prasad V., Chandele A., Jagtap J. C., Sudheer K. P., Shastry P. (2006): ROS-triggered caspase 2 activation and feedback amplification loop in beta-carotene-induced apoptosis. Free Radic. Biol. Med. 41, 431-442 http://dx.doi.org/10.1016/j.freeradbiomed.2006.03.009
46. Ribble D., Goldstein N. B., Norris D. A., Shellman Y. G. (2005): A simple technique for quantifying apoptosis in 96-well plates. BMC Biotechnol. 5, 12-19 http://dx.doi.org/10.1186/1472-6750-5-12
47. Ristow M., Schmeisser S. (2011): Extending life span by increasing oxidative stress. Free Radic. Biol. Med. 51, 327-336 http://dx.doi.org/10.1016/j.freeradbiomed.2011.05.010
48. Satoh T., McKercher S. R., Lipton S. A. (2013): Nrf2/ARE-mediated antioxidant actions of pro-electrophilic drugs. Free Radic. Biol. Med. 65, 645-657 http://dx.doi.org/10.1016/j.freeradbiomed.2013.07.022
49. Sedding D. G. (2008): FoxO transcription factors in oxidative stress response and ageing-a new fork on the way to longevity? Biol. Chem. 389, 279-283 http://dx.doi.org/10.1515/BC.2008.033
50. Shao Y., Molnar L. F., Jung Y., Kussmann J., Ochsenfeld C., Brown S. T., Gilbert A. T. B., Slipchenko L. V., Levchenko S. V., O'Neill D. P., et al. (2006): Advances in methods and algorithms in a modern quantum chemistry program package. Phys. Chem. Chem. Phys. 8, 3172-3191 http://dx.doi.org/10.1039/b517914a
51. Shibayama-Imazu T., Sonoda I., Sakairi S., Aiuchi T., Ann W., Nakajo S., Itabe H., Nakaya K. (2006): Production of superoxide and dissipation of mitochondrial transmembrane potential by vitamin K2 trigger apoptosis in human ovarian cancer TYK-nu cells. Apoptosis 11, 1535-1543 http://dx.doi.org/10.1007/s10495-006-7979-5
52. Si H., Liu D. (2014): Dietary anti-aging phytochemicals and mechanisms associated with prolonged survival. J. Nut. Biochem. 25, 581-591 http://dx.doi.org/10.1016/j.jnutbio.2014.02.001
53. Son T. G., Camandola S., Arumugam T. V., Cutler R. G., Telljohann R. S., Mughal M. R., Moore T. A, Luo W., Yu Q. S., Johnson D. A., Johnson J. A., Greig N. H., Mattson M. P. (2010): Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia. J. Neurochem. 112, 1316-1326 http://dx.doi.org/10.1111/j.1471-4159.2009.06552.x
54. Son T. G., Camandola S., Mattson M. P. (2008): Hormetic Dietary Phytochemicals. Neuromolecular Med. 10, 236-246 http://dx.doi.org/10.1007/s12017-008-8037-y
55. Stefek M., Kovacikova L., Milackova I., Veverka M., Svajdlenka E., Veverkova E. (2012): Quercetin derivatives, their pharmaceutical composition and use. Industrial Property Office of the Slovak Republic, Patent Application, PP 5006-2012
56. Tandon V. K., Kumar S. (2013): Recent development on naphthoquinone derivatives and their therapeutic applications as anticancer agents. Expert. Opin. Ther. Pat. 23, 1087-1108 http://dx.doi.org/10.1517/13543776.2013.798303
57. Thomson R. H. (1971): Naturally Occuring Quinones. Academic Press, New York
58. Vargas A. J., Burd R. (2010): Hormesis and synergy: pathways and mechanisms of quercetin in cancer prevention and management. Nutr. Rev. 68, 418-428 http://dx.doi.org/10.1111/j.1753-4887.2010.00301.x
59. Veverka M., Gallovic J., Svajdlenka E., Veverkova E., Pronayova N., Milackova I., Stefek M. (2013): Novel quercetin derivatives: synthesis and screening for antioxidant activity and aldose reductase inhibition. Chem. Papers 67, 76-83 http://dx.doi.org/10.2478/s11696-012-0240-5
60. Xu K., Wang P., Wang L., Liu C., Xu S., Cheng Y., Wang Y., Li Q., Lei H. (2014): Quinone derivatives from the genus Rubia and their bioactivities. Chem. Biodivers. 11, 341-363 http://dx.doi.org/10.1002/cbdv.201200173
61. Yin X. M. (2000): Signal transduction mediated by Bid, a pro-death Bcl-2 family proteins, connects the death receptor and mitochondria apoptosis pathways. Cell Res. 10, 161-167 http://dx.doi.org/10.1038/sj.cr.7290045