Caffeic acid phenethyl ester: Consequences of its hydrophobicity in the oxidative functions and cytokine release by leukocytes

Evidence-based Complementary and Alternative Medicine

Volumn 2014, Issue , 2014, Pages

  Paracatu, Luana Chiquetto ^a   Faria, Carolina Maria Quinello Gomes ^a   Quinello, Camila ^b   Rennó, Camila ^b   Palmeira, Patricia ^b   Zeraik, Maria Luiza ^a   Da Fonseca, Luiz Marcos ^a   Ximenes, Valdecir Farias ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

5 FLUOROTRYPTAMINE; APOCYNIN; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CAFFEIC ACID PHENETHYL ESTER; CHLOROGENIC ACID; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; INTERLEUKIN 10; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; SUPEROXIDE; TUMOR NECROSIS FACTOR ALPHA;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMOLUMINESCENCE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DEGRADATION; DPPH RADICAL SCAVENGING ASSAY; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROPHOBICITY; LEUKOCYTE ACTIVATION; NORMAL HUMAN; OXIDATION REDUCTION POTENTIAL; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; TRIENE DEGRADATION ASSAY;

EID: 84931023583     PISSN: 1741427X     EISSN: 17414288     Source Type: Journal    
DOI: 10.1155/2014/793629     Document Type: Article

References (52)

1. M. L. Khalil, "Biological activity of bee propolis in health and disease, " Asian Pacific Journal of Cancer Prevention, vol. 7, no. 1, pp. 22-31, 2006.
2. C. Gebhard, B. E. Stähli, S. Largiader et al., "Caffeic acid phenethyl ester inhibits endothelial tissue factor expression, " Biological and Pharmaceutical Bulletin, vol. 36, no. 6, pp. 1032- 1035, 2013.
3. K. C. Pramanik, S. K. Kudugunti, N. M. Fofaria, M. Y.Moridani, and S. K. Srivastava, "Caffeic acid phenethyl ester suppresses melanoma tumor growth by inhibiting PI3K/AKT/XIAP pathway, " Carcinogenesis, vol. 34, no. 9, pp. 2061-2070, 2013.
4. J. S. dos Santos and A. Monte-Alto-Costa, "Caffeic acid phenethyl ester improves burn healing in rats through anti inflammatory and antioxidant effects, " Journal of Burn Care and Research, vol. 34, no. 6, pp. 682-688, 2013.
5. K. Cui, W. Lu, L. Zhu, X. Shen, and J. Huang, "Caffeic acid phenethyl ester (CAPE), an active component of propolis, inhibits Helicobacter pylori peptide deformylase activity, " Biochemical and Biophysical Research Communications, vol. 435, no. 2, pp. 289-294, 2013.
6. P. Kleniewska, A. Piechota, B. Skibska, and A. Goraca, "The NADPH oxidase family and its inhibitors, " Archivum Immunologiae et Therapiae Experimentalis, vol. 60, no. 4, pp. 277-294, 2012.
7. D. C. Dale, L. Boxer, and W. Conrad Liles, "The phagocytes: neutrophils and monocytes, " Blood, vol. 112, no. 4, pp. 935-945, 2008.
8. A. Simonyi, Y. He, W. Sheng et al., "Targeting NADPHoxidase and phospholipases A2 in alzheimer's disease, " Molecular Neurobiology, vol. 41, no. 2-3, pp. 73-86, 2010.
9. H. Zhou, F. Zhang, S. Chen et al., "Rotenone activates phagocyte NADPH oxidase by binding to its membrane subunit gp91 phox, " Free Radical Biology and Medicine, vol. 52, no. 2, pp. 303- 313, 2012.
10. M. T. Fischer, R. Sharma, J. L. Lim et al., "NADPH oxidase expression in active multiple sclerosis lesions in relation to oxidative tissue damage and mitochondrial injury, " Brain, vol. 135, no. 3, pp. 886-899, 2012.
11. C. Lin and H. Wang, "NADPH oxidase is involved in H2O2- induced differentiation of human promyelocytic leukaemiaHL- 60 cells, " Cell Biology International, vol. 36, no. 4, pp. 391-395, 2012.
12. I. Takac, K. Schröder, and R. P. Brandes, "The nox family of NADPH Oxidases: friend or foe of the vascular system?" Current Hypertension Reports, vol. 14, no. 1, pp. 70-78, 2012.
13. G. R. Drummond, S. Selemidis, K. K. Griendling, and C. G. Sobey, "Combating oxidative stress in vascular disease: NADPH oxidases as therapeutic targets, " Nature Reviews Drug Discovery, vol. 10, no. 6, pp. 453-471, 2011.
14. J. Pečivová, T. Mačičková, K. Sviteková, and R. Nosál', "Quercetin inhibits degranulation and superoxide generation in PMA stimulated neutrophils, " Interdisciplinary Toxicology, vol. 5, no. 2, pp. 81-83, 2012.
15. F. Chen, L. Qian, B. Deng, Z. Liu, Y. Zhao, and Y. Le, "Resveratrol protects vascular endothelial cells from high glucose-induced apoptosis through inhibition of nadph oxidase activationdriven oxidative stress, "CNSNeuroscience and Therapeutics, vol. 19, no. 9, pp. 675-681, 2013.
16. M. Ciz, P. Denev, M. Kratchanova, O. Vasicek, G. Ambrozova, and A. Lojek, "Flavonoids inhibit the respiratory burst of neutrophils in mammals, " Oxidative Medicine and Cellular Longevity, vol. 2012, Article ID 181295, 6 pages, 2012.
17. I. H. Philippens, J. A. Wubben, B. Finsen, and B. A. T Hart, "Oral treatment with the NADPH oxidase antagonist apocynin mitigates clinical and pathological features of parkinsonism in the MPTP marmoset model, " Journal of Neuroimmune Pharmacology, vol. 8, no. 3, pp. 715-726, 2013.
18. C. M. Q. G. de Faria, A. C. Nazaré, M. S. Petronio et al., "Protocatechuic acid alkyl esters: hydrophobicity as a determinant factor for inhibition of NADPH oxidase, " Current Medicinal Chemistry, vol. 19, no. 28, pp. 4885-4893, 2012.
19. A. Lojek, L. Kubala, H. Čížová, and M. Číž, "A comparison of whole blood neutrophil chemiluminescence measured with cuvette and microtitre plate luminometers, " Luminescence, vol. 17, no. 1, pp. 1-4, 2002.
20. A. K. Ghose and G. M. Crippen, "Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2.Modeling dispersive and hydrophobic interactions, " Journal of Chemical Information and Computer Science, vol. 27, pp. 21-35, 1987.
21. M. L. Zeraik, V. F. Ximenes, L. O. Regasini et al., "4- Aminochalcones as novel inhibitors of the chlorinating activity of myeloperoxidase, " Current Medicinal Chemistry, vol. 19, no. 31, pp. 5405-5413, 2012.
22. W. Brand-Williams, M. E. Cuvelier, and C. Berset, "Use of a free radical method to evaluate antioxidant activity, " LWT-Food Science and Technology, vol. 28, no. 1, pp. 25-30, 1995.
23. M. Laguerre, L. J. López-Giraldo, J. Lecomte et al., "Conjugated autoxidizable triene (CAT) assay: A novel spectrophotometric method for determination of antioxidant capacity using triacylglycerol as ultraviolet probe, " Analytical Biochemistry, vol. 380, no. 2, pp. 282-290, 2008.
24. M. S. Petronio, M. L. Zeraik, L. M. da Fonseca, and V. F. Ximenes, "Apocynin: chemical and biophysical properties of a NADPH oxidase inhibitor, " Molecules, vol. 18, no. 3, pp. 2821- 2839, 2013.
25. D. English and B. R. Andersen, "Single step separation of red blood cells, granulocytes and mononuclear leukocytes on discontinuous density gradients of Ficoll Hypaque, " Journal of Immunological Methods, vol. 5, no. 3, pp. 249-252, 1974.
26. A. C. de Almeida, O. C. Marques, C. Arslanian, A. Condino- Neto, and V. F. Ximenes, "4-fluoro-2-methoxyphenol, an apocynin analog with enhanced inhibitory effect on leukocyte oxidant production and phagocytosis, " European Journal of Pharmacology, vol. 660, no. 2-3, pp. 445-453, 2011.
27. A. S. Tan and M.V. Berridge, "Superoxide produced by activated neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: A simple colorimetric assay for measuring respiratory burst activation and for screening antiinflammatory agents, " Journal of Immunological Methods, vol. 238, no. 1-2, pp. 59-68, 2000.
28. M. Zhou, Z. Diwu, N. Panchuk-Voloshina, and R. P. Haugland, "A stable nonfluorescent derivative of resorufin for the fluorometric determination of trace hydrogen peroxide: Applications in detecting the activity of phagocyte NADPH oxidase and other oxidases, " Analytical Biochemistry, vol. 253, no. 2, pp. 162- 168, 1997.
29. V. F. Ximenes, I. M. M. Paino, O. M. M. de Faria-Oliveira, L. M. da Fonseca, and I. L. Brunetti, "Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid, " Brazilian Journal of Medical and Biological Research, vol. 38, no. 11, pp. 1575-1583, 2005.
30. E. Rutkowska, K. PajIk, and K. Jóźwiak, "Lipophilicity- methods of determination and its role in medicinal chemistry, " Acta Poloniae Pharmaceutica, vol. 70, no. 1, pp. 3-18, 2013.
31. V. B. O'Donnell, D. G. Tew, O. T. G. Jones, and P. J. England, "Studies on the inhibitory mechanism of iodoniumcompounds with special reference to neutrophilNADPHoxidase, " Biochemical Journal, vol. 290, no. 1, pp. 41-49, 1993.
32. S. Gunckel, P. Santander, G. Cordano et al., "Antioxidant activity of gallates: An electrochemical study in aqueous media, " Chemico-Biological Interactions, vol. 114, no. 1-2, pp. 45-59, 1998.
33. C. C. Winterbourn, "The challenges of using fluorescent probes to detect and quantify specific reactive oxygen species in living cells, " Biochimica et Biophysica Acta, vol. 1840, no. 2, pp. 730- 738, 2014.
34. M. Barbacanne, J. Souchard, B. Darblade et al., "Detection of superoxide anion released extracellularly by endothelial cells using cytochrome c reduction, ESR, fluorescence and lucigeninenhanced chemiluminescence techniques, " Free Radical Biology and Medicine, vol. 29, no. 5, pp. 388-396, 2000.
35. J. Stefanska and R. Pawliczak, "Apocynin: molecular aptitudes, " Mediators of Inflammation, vol. 2008, Article ID 106507, 10 pages, 2008.
36. A. C. de Almeida, M. M. dos Santos Vilela, A. Condino-Neto, and V. F. Ximenes, "The importance of myeloperoxidase in apocynin-mediated NADPH oxidase inhibition, " ISRN Inflammation, vol. 2012, Article ID 260453, 7 pages, 2012.
37. A. J. Kettle, A. M. Albrett, A. L. Chapman et al., "Measuring chlorine bleach in biology and medicine, " Biochimica et Biophysica Acta, vol. 1840, no. 2, pp. 781-793, 2013.
38. A. C. de Almeida, O. C. Marques, C. Arslanian, A. Condino- Neto, and V. F. Ximenes, "4-Fluoro-2-methoxyphenol, an apocynin analog with enhanced inhibitory effect on leukocyte oxidant production and phagocytosis, " European Journal of Pharmacology, vol. 660, no. 2-3, pp. 445-453, 2011.
39. Y. Huang, L. Yan, S. Rong, H. Haller, and T. Kirch, "TNF-a induces endothelial dysfunction via PKC-dependentNADPH oxidase activation, " Journal of Huazhong University of Science and Technology. Medical Science, vol. 32, no. 5, pp. 642-647, 2012.
40. T. Long, G. Liu, Y. Wang, Y. Chen, Y. Zhang, and D. Qin, "TNF-a, erectile dysfunction, and NADPH oxidasemediated ROS generation in corpus cavernosum in high-fat diet/streptozotocin-induced diabetic rats, " Journal of Sexual Medicine, vol. 9, no. 7, pp. 1801-1814, 2012.
41. B. M. Barth, S. J. Gustafson, J. L. Hankins et al., "Ceramide kinase regulates TNF-stimulated NADPH oxidase activity and eicosanoid biosynthesis in neuroblastoma cells, " Cellular Signalling, vol. 24, no. 6, pp. 1126-1133, 2012.
42. C. Dewas, P. M. Dang, M. Gougerot-Pocidalo, and J. El-Benna, "TNF-a induces phosphorylation of p47phox in human neutrophils: Partial phosphorylation of p47phox is a common event of priming of human neutrophils by TNF-a and granulocytemacrophage colony-stimulating factor, " Journal of Immunology, vol. 171, no. 8, pp. 4392-4398, 2003.
43. A.Csiszar, M. Wang, E. G. Lakatta, and Z. Ungvari, "Inflammation and endothelial dysfunction during aging: role of NF-kB, " Journal of Applied Physiology, vol. 105, no.4, pp. 1333-1341, 2008.
44. A. Muñoz and M. Costa, "Nutritionally mediated oxidative stress and inflammation, " Oxidative Medicine and Cellular Longevity, vol. 2013, Article ID 610950, 11 pages, 2013.
45. M. S. Baliga, N. Joseph, M. V. Venkataranganna, A. Saxena, V. Ponemone, and R. Fayad, "Curcumin, an active component of turmeric in the prevention and treatment of ulcerative colitis: preclinical and clinical observations, " Food and Function, vol. 3, no. 11, pp. 1109-1117, 2012.
46. C. Lin and H. Wang, "NADPH oxidase is involved in H2O2- induced differentiation of human promyelocytic leukaemiaHL- 60 cells, " Cell Biology International, vol. 36, no. 4, pp. 391-395, 2012.
47. S. Juman, N. Yasui, K. Ikeda et al., "Caffeic acid phenethyl ester suppresses the production of pro-inflammatory cytokines in hypertrophic adipocytes through lipopolysaccharidestimulated macrophages, " Biological and Pharmaceutical Bulletin, vol. 35, no. 11, pp. 1941-1946, 2012.
48. T. Çakir, E. Özkan, E. Dulundu et al., "Caffeic acid phenethyl ester (CAPE) prevents methotrexate-induced hepatorenal oxidative injury in rats, " The Journal of Pharmacy and Pharmacology, vol. 63, no. 12, pp. 1566-1571, 2011.
49. K. Natarajan, S. Singh, T. R. Burke Jr., D. Grunberger, and B. B. Aggarwal, "Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kB, " Proceedings of the National Academy of Sciences of the United States of America, vol. 93, no. 17, pp. 9090-9095, 1996.
50. P. M. Dang, C. Elbim, J. Marie, M. Chiandotto, M. Gougerot-Pocidalo, and J. El-Benna, "Anti-inflammatory effect of interleukin-10 on human neutrophil respiratory burst involves inhibition of GM-CSF-induced p47PHOX phosphorylation through a decrease in ERK1/2 activity, " The FASEB Journal, vol. 20, no. 9, pp. 1504-1506, 2006.
51. M. Bergman, M. Djaldetti, H. Salman, and H. Bessler, "On the combined effect of statins and lycopene on cytokine production by human peripheral blood cells, " Heart and Vessels, vol. 25, no. 5, pp. 426-431, 2010.
52. N. Celli, B. Mariani, L. K. Dragani, S. Murzilli, C. Rossi, and D. Rotilio, "Development and validation of a liquid chromatographic-tandem mass spectrometric method for the determination of caffeic acid phenethyl ester in rat plasma and urine, " Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 810, no. 1, pp. 129-136, 2004.