Protective effects of 6-hydroxy-1-methylindole-3-acetonitrile on cisplatin-induced oxidative nephrotoxicity via Nrf2 inactivation

Food and Chemical Toxicology

Volumn 62, Issue , 2013, Pages 159-166

  Moon, Ji Hee ^a   Shin, Ji Sun ^a,b   Kim, Jong Bin ^a   Baek, Nam In ^a   Cho, Young Wuk ^b   Lee, Yong Sup ^a   Kay, Hee Yeon ^c   Kim, Soo dong ^d   Lee, Kyung Tae ^a  

^a Kyung Hee University   (South Korea)

^b Kyung Hee University Hospital   (South Korea)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Dong A University   (South Korea)

Author keywords

6 Hydroxy 1 methylindole 3 acetonitrile; Nephrotoxicity; Nrf2; ROS

Indexed keywords

6 HYDROXY 1 METHYLINDOLE 3 ACETONITRILE; CATALASE; CISPLATIN; CREATININE; GLUTATHIONE; GLUTATHIONE REDUCTASE; HEME OXYGENASE 1; INDOLE DERIVATIVE; LACTATE DEHYDROGENASE; MALONALDEHYDE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; 6-HYDROXY-1-METHYLINDOLE-3-ACETONITRILE; NFE2L2 PROTEIN, RAT; PROTECTIVE AGENT;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRASSICA RAPA; CONTROLLED STUDY; CYTOTOXICITY; DRUG DETERMINATION; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME REPRESSION; GENE TRANSLOCATION; KIDNEY CELL; KIDNEY INJURY; LLC PK1 CELL; MALE; NEPHROTOXICITY; NONHUMAN; OXIDATIVE STRESS; PROTEIN BINDING; PROTEIN EXPRESSION; RAT; RENAL PROTECTION; TREATMENT RESPONSE; UREA NITROGEN BLOOD LEVEL; ACUTE KIDNEY INJURY; ANIMAL; CELL LINE; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; EPITHELIUM CELL; KIDNEY DISEASES; METABOLISM; SPRAGUE DAWLEY RAT;

ACUTE KIDNEY INJURY; ANIMALS; BLOOD UREA NITROGEN; BRASSICA RAPA; CELL LINE; CISPLATIN; CREATININE; EPITHELIAL CELLS; GLUTATHIONE; HEME OXYGENASE-1; INDOLES; KIDNEY DISEASES; L-LACTATE DEHYDROGENASE; MALE; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; PROTECTIVE AGENTS; RATS, SPRAGUE-DAWLEY; REACTIVE OXYGEN SPECIES;

EID: 84884126004     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2013.08.039     Document Type: Article

References (51)

1. Ahn H., Lee E., Kim K., Lee C. Effect of glutathione and its related enzymes on chemosensitivity of renal cell carcinoma and bladder carcinoma cell lines. J. Urol. 1994, 151:263-267.
2. Aleksunes L.M., Goedken M.J., Rockwell C.E., Thomale J., Manautou J.E., Klaassen C.D. Transcriptional regulation of renal cytoprotective genes by Nrf2 and its potential use as a therapeutic target to mitigate cisplatin-induced nephrotoxicity. J. Pharmacol. Exp. Ther. 2010, 335:2-12.
3. An S., Han J.I., Kim M.J., Park J.S., Han J.M., Baek N.I., Chung H.G., Choi M.S., Lee K.T., Jeong T.S. Ethanolic extracts of Brassica campestris spp. rapa roots prevent high-fat diet-induced obesity via beta(3)-adrenergic regulation of white adipocyte lipolytic activity. J. Med. Food. 2010, 13:406-414.
4. Baldew G.S., McVie J.G., van der Valk M.A., Los G., de Goeij J.J., Vermeulen N.P. Selective reduction of cis-diamminedichloroplatinum(II) nephrotoxicity by ebselen. Cancer Res. 1990, 50:7031-7036.
5. Baldew G.S., Boymans A.P., Mol J.G., Vermeulen N.P. The influence of ebselen on the toxicity of cisplatin in LLC-PK1 cells. Biochem. Pharmacol. 1992, 22:382-387.
6. Blachley J.D., Hill J.B. Renal and electrolyte disturbances associated with cisplatin. Ann. Intern. Med. 1981, 95:628-632.
7. Carlberg I., Mannervik B. Glutathione reductase. Methods Enzymol. 1985, 113:484-490.
8. Cetin R., Devrim E., Kiliçoǧlu B., Avci A., Candir O., Durak I. Cisplatin impairs antioxidant system and causes oxidation in rat kidney tissues: possible protective roles of natural antioxidant foods. J. Appl. Toxicol. 2006, 26:42-46.
9. Cho J.M., Manandhar S., Lee H.R., Park H.M., Kwak M.K. Role of the Nrf2-antioxidant system in cytotoxicity mediated by anticancer cisplatin: implication to cancer cell resistance. Cancer Lett. 2008, 260:96-108.
10. Costa D., Gomes A., Reis S., Lima J.L., Fernandes E. Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. Life Sci. 2005, 76:2841-2848.
11. Costantino L., Barlocco D. Privileged structures as leads in medicinal chemistry. Curr. Med. Chem. 2006, 13:65-85.
12. Davis C.A., Nick H.S., Agarwal A. Manganese superoxide dismutase attenuates Cisplatin-induced renal injury: importance of superoxide. J. Am. Soc. Nephrol. 2001, 12:2683-2690.
13. Eyer P., Podhradský D. Evaluation of the micromethod for determination of glutathione using enzymatic cycling and Ellman's reagent. Anal. Biochem. 1986, 153:57-66.
14. Fonseca T., Gigante B., Marques M.M., Gilchrist T.L., De Clercq E. Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid. Bioorg. Med. Chem. 2004, 12:103-112.
15. Howell S.B., Taetle R. Effect of sodium thiosulfate on cis-dichlorodiammineplatinum(II) toxicity and antitumor activity in L1210 leukemia. Cancer Treat Rep. 1980, 64:611-616.
16. Itoh K., Tong K.I., Yamamoto M. Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free Radic. Biol. Med. 2004, 36:1208-1213.
17. Jiang T., Chen N., Zhao F., Wang X.J., Kong B., Zheng W., Zhang D.D. High levels of Nrf2 determine chemoresistance in type II endometrial cancer. Cancer Res. 2010, 70:5486-5496.
18. Jung U.J., Baek N.I., Chung H.G., Bang M.H., Jeong T.S., Lee K.T., Kang Y.J., Lee M.K., Kim H.J., Yeo J., Choi M.S. Effects of the ethanol extract of the roots of Brassica rapa on glucose and lipid metabolism in C57BL/KsJ-db/db mice. Clin. Nutr. 2007, 27:158-167.
19. Kim Y.H., Kim Y.W., Oh Y.J., Back N.I., Chung S.A., Chung H.G., Jeong T.S., Choi M.S., Lee K.T. Protective effect of the ethanol extract of the roots of Brassica rapa on cisplatin-induced nephrotoxicity in LLC-PK1 cells and rats. Biol. Pharm. Bull. 2006, 29:2436-2441.
20. Kuhlmann M.K., Burkhardt G., Köhler H. Insights into potential cellular mechanisms of cisplatin nephrotoxicity and their clinical application. Nephrol. Dial. Transpl. 1997, 12:2478-2480.
21. Kuo C.C., Hsieh H.P., Pan W.Y., Chen C.P., Liou J.P., Lee S.J., Chang Y.L., Chen L.T., Chen C.T., Chang J.Y. BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004, 64:4621-4628.
22. 2 productions in LPS-induced RAW 264.7 cells. Bioorg. Med. Chem. Lett. 2013, 23:2571-2574.
23. Lieberthal W., Triaca V., Levine J. Mechanisms of death induced by cisplatin in proximal tubular epithelial cells: apoptosis vs. necrosis. Am. J. Physiol. 1996, 270:700-708.
24. Maines M.D. Heme oxygenase: function, multiplicity, regulatory mechanisms, and clinical applications. FASEB J. 1988, 2:2557-2568.
25. Masuda H., Tanaka T., Takahama U. Cisplatin generates superoxide anion by interaction with DNA in a cell-free system. Biochem. Biophys. Res. Commun. 1994, 203:1175-1180.
26. Misra H.P., Fridovich I. Superoxide dismutase and peroxidase: a positive activity stain applicable to polyacrylamide gel electropherograms. Arch. Biochem. Biophys. 1977, 183:511-515.
27. Mistry P., Merazga Y., Spargo D.J., Riley P.A., McBrien D.C. The effects of cisplatin on the concentration of protein thiols and glutathione in the rat kidney. Cancer Chemother. Pharmacol. 1991, 28:277-282.
28. Nguyen T., Sherratt P.J., Pickett C.B. Regulatory mechanisms controlling gene expression mediated by the antioxidant response element. Annu. Rev. Pharmacol. Toxicol. 2003, 43:233-260.
29. Niture S.K., Jain A.K., Jaiswal A.K. Antioxidant-induced modification of INrf2 cysteine 151 and PKC-delta-mediated phosphorylation of Nrf2 serine 40 are both required for stabilization and nuclear translocation of Nrf2 and increased drug resistance. J. Cell Sci. 2009, 122:4452-4464.
30. Pabla N., Dong G., Jiang M., Huang S., Kumar M.V., Messing R.O., Dong Z. Inhibition of PKCδ reduces cisplatin-induced nephrotoxicity without blocking chemotherapeutic efficacy in mouse models of cancer. J. Clin. Invest. 2011, 121:2709-2722.
31. Pedras M.S. The chemical ecology of crucifers and their fungal pathogens: boosting plant defenses and inhibiting pathogen invasion. Chem. Rec. 2008, 8:109-115.
32. Radwan M.A., Ragab E.A., Sabry N.M., El-Shenawy S.M. Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents. Bioorg. Med. Chem. 2007, 15:3832-3841.
33. Ries F., Klastersky J. Nephrotoxicity induced by cancer chemotherapy with special emphasis on cisplatin toxicity. Am. J. Kidney Dis. 1986, 8:368-379.
34. Romani A., Vignolini P., Isolani L., Ieri F., Heimler D. HPLC-DAD/MS characterization of flavonoids and hydroxycinnamic derivatives in turnip tops (Brassica rapa L. Subsp. sylvestris L.). J. Agric. Food Chem. 2006, 54:1342-1346.
35. Rosenberg B. Fundamental studies with cisplatin. Cancer 1985, 55:2303-2316.
36. Salahudeen A., Badr K., Morrow J., Roberts J. Hydrogen peroxide induces 21-aminosteroid-inhibitable F2-isoprostane production and cytolysis in renal tubular epithelial cells. J. Am. Soc. Nephrol. 1995, 6:1300-1303.
37. Satoh M., Kashihara N., Fujimoto S., Horike H., Tokura T., Namikoshi T., Sasaki T., Makino H. A novel free radical scavenger, edarabone, protects against cisplatin-induced acute renal damage in vitro and in vivo. J. Pharmacol. Exp. Ther. 2003, 305:1183-1190.
38. Schonhof I., Krumbein A., Brückner B. Genotypic effects on glucosinolates and sensory properties of broccoli and cauliflower. Nahrung 2004, 48:25-33.
39. Shibahara S. Regulation of heme oxygenase gene expression. Semin. Hematol. 1988, 25:370-376.
40. Shin J.S., Noh Y.S., Lee Y.S., Cho Y.W., Baek N.I., Choi M.S., Jeong T.S., Kang E., Chung H.G., Lee K.T. Arvelexin from Brassica rapa suppresses NF-κB-regulated pro-inflammatory gene expression by inhibiting activation of IκB kinase. Br. J. Pharmacol. 2011, 164:145-158.
41. Shin J.S., Yun C.H., Cho Y.W., Baek N.I., Choi M.S., Jeong T.S., Chung H.G., Lee K.T. Indole-containing fractions of Brassica rapa inhibit inducible nitric oxide synthase and pro-inflammatory cytokine expression by inactivating nuclear factor-κB. J. Med. Food 2011, 14:1527-1537.
42. Shin J.S., Yun K.J., Chung K.S., Seo K.H., Park H.J., Cho Y.W., Baek N.I., Jang D., Lee K.T. Monotropein isolated from the roots of Morinda officinalis ameliorates proinflammatory mediators in RAW 264.7 macrophages and dextran sulfate sodium (DSS)-induced colitis via NF-κB inactivation. Food Chem. Toxicol. 2013, 53:263-271.
43. Sohn S.I., Rim H.K., Kim Y.H., Choi J.H., Park J.H., Park H.J., Choi J.W., Kim S.D., Jeong S.Y., Lee K.T. The ameliorative effect of 23-hydroxytormentic acid isolated from Rubus coreanus on cisplatin-induced nephrotoxicity in rats. Biol. Pharm. Bull. 2011, 34:1508-1513.
44. Speir E., Yu Z.X., Ferrans V.J., Huang E.S., Epstein S.E. Aspirin attenuates cytomegalovirus infectivity and gene expression mediated by cyclooxygenase-2 in coronary artery smooth muscle cells. Circ. Res. 1998, 83:210-216.
45. Sundar L., Chang F.N. Antimicrobial activity and biosynthesis of indole antibiotics produced by Xenorhabdus nematophilus. J. Gen. Microbiol. 1993, 139:3139-3148.
46. Suzuki C.A., Cherian M.G. The interactions of cis-diamminedichloroplatinum with metallothionein and glutathione in rat liver and kidney. Toxicology 1990, 64:113-127.
47. Weijl N.I., Cleton F.J., Osanto S. Free radicals and antioxidants in chemotherapy-induced toxicity. Cancer Treat Rev. 1997, 23:209-240.
48. Wheeler C.R., Salzman J.A., Elsayed N.M., Omaye S.T., Korte D.W. Automated assays for superoxide dismutase, catalase, glutathione peroxidase, and glutathione reductase activity. Anal. Biochem. 1990, 184:193-199.
49. Wu Q., Bang M.H., Lee D.Y., Cho J.G., Jeong R.H., Shrestha S., Lee K.T., Chung H.G., Ahn E.M., Baek N.I. New indoles from the roots of Brassica rapa ssp. campestris. Chem. Nat. Comp. 2012, 48:281-284.
50. Zhang J.G., Lindup W.E. Role of mitochondria in cisplatin-induced oxidative damage exhibited by rat renal cortical slices. Biochem. Pharmacol. 1993, 45:2215-2222.
51. Zhang J., Piantadosi C.A. Mitochondrial oxidative stress after carbon monoxide hypoxia in the rat brain. J. Clin. Invest. 1992, 90:119-1199.