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Volumn 5, Issue 7, 2012, Pages 973-981

Highly potent activation of Nrf2 by topical tricyclic bis(cyano enone): Implications for protection against UV radiation during thiopurine therapy

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENIC TRICYCLIC BIS(CYANO ENONE); ANTIINFLAMMATORY AGENT; AZATHIOPRINE; GENOMIC DNA; KELCH LIKE ECH ASSOCIATED PROTEIN 1; MERCAPTOPURINE; RADIOPROTECTIVE AGENT; TBE 31; TIOGUANINE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

EID: 84866445766     PISSN: 19406207     EISSN: 19406215     Source Type: Journal    
DOI: 10.1158/1940-6207.CAPR-12-0041     Document Type: Article
Times cited : (35)

References (48)
  • 1
    • 0034490852 scopus 로고    scopus 로고
    • Chemoprotection against cancer by induction of Phase 2 enzymes
    • Talalay P. Chemoprotection against cancer by induction of phase 2 enzymes. Biofactors 2000;12:5-11. (Pubitemid 32107378)
    • (2000) BioFactors , vol.12 , Issue.1-4 , pp. 5-11
    • Talalay, P.1
  • 2
    • 0344915418 scopus 로고
    • Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis
    • Talalay P, De Long MJ, Prochaska HJ. Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc Natl Acad Sci U S A 1988;85:8261-5.
    • (1988) Proc Natl Acad Sci U S A , vol.85 , pp. 8261-8265
    • Talalay, P.1    De Long, M.J.2    Prochaska, H.J.3
  • 3
    • 33847050801 scopus 로고    scopus 로고
    • Cell survival responses to environmental stresses via the Keap1-Nrf2-ARE pathway
    • Kensler TW, Wakabayashi N, Biswal S. Cell survival responses to environmental stresses via the Keap1-Nrf2-ARE pathway. Annu Rev Pharmacol Toxicol 2007;47:89-116.
    • (2007) Annu Rev Pharmacol Toxicol , vol.47 , pp. 89-116
    • Kensler, T.W.1    Wakabayashi, N.2    Biswal, S.3
  • 5
    • 78751703950 scopus 로고    scopus 로고
    • Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution
    • Taguchi K, Motohashi H, Yamamoto M. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 2011;16:123-40.
    • (2011) Genes Cells , vol.16 , pp. 123-140
    • Taguchi, K.1    Motohashi, H.2    Yamamoto, M.3
  • 6
    • 79954416526 scopus 로고    scopus 로고
    • The cytoprotective role of the Keap1-Nrf2 pathway
    • Baird L, Dinkova-Kostova AT. The cytoprotective role of the Keap1-Nrf2 pathway. Arch Toxicol 2011;85:241-72.
    • (2011) Arch Toxicol , vol.85 , pp. 241-272
    • Baird, L.1    Dinkova-Kostova, A.T.2
  • 8
    • 57349116768 scopus 로고    scopus 로고
    • Coordinate regulation of enzyme markers for infl ammation and for protection against oxidants and electrophiles
    • Liu H, Dinkova-Kostova AT, Talalay P. Coordinate regulation of enzyme markers for infl ammation and for protection against oxidants and electrophiles. Proc Natl Acad Sci U S A 2008;105:15926-31.
    • (2008) Proc Natl Acad Sci U S A , vol.105 , pp. 15926-15931
    • Liu, H.1    Dinkova-Kostova, A.T.2    Talalay, P.3
  • 9
    • 0032491276 scopus 로고    scopus 로고
    • Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages
    • DOI 10.1016/S0960-894X(98)00479-X, PII S0960894X9800479X
    • Honda T, Rounds BV, Gribble GW, Suh N, Wang Y, Sporn MB. Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages. Bioorg Med Chem Lett 1998;8:2711-4. (Pubitemid 28496657)
    • (1998) Bioorganic and Medicinal Chemistry Letters , vol.8 , Issue.19 , pp. 2711-2714
    • Honda, T.1    Rounds, B.V.2    Gribble, G.W.3    Suh, N.4    Wang, Y.5    Sporn, M.B.6
  • 10
    • 0033590265 scopus 로고    scopus 로고
    • Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages
    • Honda T, Rounds BV, Bore L, Favaloro FGJr, Gribble GW, Suh N, et al. Novel synthetic oleanane triterpenoids: a series of highly active inhibitors of nitric oxide production in mouse macrophages. Bioorg Med Chem Lett 1999;9:3429-34.
    • (1999) Bioorg Med Chem Lett , vol.9 , pp. 3429-3434
    • Honda, T.1    Rounds, B.V.2    Bore, L.3    Favaloro Jr., F.G.4    Gribble, G.W.5    Suh, N.6
  • 11
    • 0034597578 scopus 로고    scopus 로고
    • Synthetic oleanane and ursane triterpenoids with modified rings A and C: A series of highly active inhibitors of nitric oxide production in mouse macrophages
    • Honda T, Rounds BV, Bore L, Finlay HJ, Favaloro FG Jr, Suh N, et al. Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages. J Med Chem 2000;43:4233-46.
    • (2000) J Med Chem , vol.43 , pp. 4233-4246
    • Honda, T.1    Rounds, B.V.2    Bore, L.3    Finlay, H.J.4    Favaloro Jr., F.G.5    Suh, N.6
  • 12
    • 0037168032 scopus 로고    scopus 로고
    • Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: A novel class of highly active inhibitors of nitric oxide production in mouse macrophages
    • DOI 10.1021/jm025565f
    • Favaloro FG Jr, Honda T, Honda Y, Gribble GW, Suh N, Risingsong R, et al. Design and synthesis of tricyclic compounds with enone functionalities in rings A and C: a novel class of highly active inhibitors of nitric oxide production in mouse macrophages. J Med Chem 2002;45:4801-5. (Pubitemid 35192769)
    • (2002) Journal of Medicinal Chemistry , vol.45 , Issue.22 , pp. 4801-4805
    • Favaloro Jr., F.G.1    Honda, T.2    Honda, Y.3    Gribble, G.W.4    Suh, N.5    Risingsong, R.6    Sporn, M.B.7
  • 13
    • 0346907138 scopus 로고    scopus 로고
    • Efficient synthesis of (-)- And (+)-tricyclic compounds with enone functionalities in rings A and C. A novel class of orally active anti-inflammatory and cancer chemopreventive agents
    • Honda T, Favaloro FG Jr, Janosik T, Honda Y, Suh N, Sporn MB, et al. Efficient synthesis of (-)- and (+)-tricyclic compounds with enone functionalities in rings A and C. A novel class of orally active anti-inflammatory and cancer chemopreventive agents. Org Biomol Chem 2003;1:4384-91.
    • (2003) Org Biomol Chem , vol.1 , pp. 4384-4391
    • Honda, T.1    Favaloro Jr., F.G.2    Janosik, T.3    Honda, Y.4    Suh, N.5    Sporn, M.B.6
  • 14
    • 34247270839 scopus 로고    scopus 로고
    • Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: Highly potent anti-inflammatory and cytoprotective agents
    • DOI 10.1021/jm070141c
    • Honda T, Sundararajan C, Yoshizawa H, Su X, Honda Y, Liby KT, et al. Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents. J Med Chem 2007;50:1731-4. (Pubitemid 46626584)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.8 , pp. 1731-1734
    • Honda, T.1    Sundararajan, C.2    Yoshizawa, H.3    Su, X.4    Honda, Y.5    Liby, K.T.6    Sporn, M.B.7    Gribble, G.W.8
  • 15
    • 79952811165 scopus 로고    scopus 로고
    • Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents
    • Honda T, Yoshizawa H, Sundararajan C, David E, Lajoie MJ, Favaloro FG Jr, et al. Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. J Med Chem 2011;54:1762-78.
    • (2011) J Med Chem , vol.54 , pp. 1762-1778
    • Honda, T.1    Yoshizawa, H.2    Sundararajan, C.3    David, E.4    Lajoie, M.J.5    Favaloro Jr., F.G.6
  • 16
    • 53049090607 scopus 로고    scopus 로고
    • A novel acetylenic tricyclic bis-(cyano enone) potently induces phase 2 cytoprotective pathways and blocks liver carcinogenesis induced by aflatoxin
    • Liby K, Yore MM, Roebuck BD, Baumgartner KJ, Honda T, Sundararajan C, et al. A novel acetylenic tricyclic bis-(cyano enone) potently induces phase 2 cytoprotective pathways and blocks liver carcinogenesis induced by aflatoxin. Cancer Res 2008;68:6727-33.
    • (2008) Cancer Res , vol.68 , pp. 6727-6733
    • Liby, K.1    Yore, M.M.2    Roebuck, B.D.3    Baumgartner, K.J.4    Honda, T.5    Sundararajan, C.6
  • 17
    • 77958565864 scopus 로고    scopus 로고
    • An exceptionally potent inducer of cytoprotective enzymes: Elucidation of the structural features that determine inducer potency and reactivity with Keap1
    • Dinkova-Kostova AT, Talalay P, Sharkey J, Zhang Y, Holtzclaw WD, Wang XJ, et al. An exceptionally potent inducer of cytoprotective enzymes: elucidation of the structural features that determine inducer potency and reactivity with Keap1. J Biol Chem 2010;285:33747-55.
    • (2010) J Biol Chem , vol.285 , pp. 33747-33755
    • Dinkova-Kostova, A.T.1    Talalay, P.2    Sharkey, J.3    Zhang, Y.4    Holtzclaw, W.D.5    Wang, X.J.6
  • 18
    • 34247526984 scopus 로고    scopus 로고
    • Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer
    • DOI 10.1038/nrc2129, PII NRC2129
    • Liby KT, Yore MM, Sporn MB. Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer. Nat Rev Cancer 2007;7:357-69. (Pubitemid 46652485)
    • (2007) Nature Reviews Cancer , vol.7 , Issue.5 , pp. 357-369
    • Liby, K.T.1    Yore, M.M.2    Sporn, M.B.3
  • 19
    • 79953242026 scopus 로고    scopus 로고
    • New synthetic triterpenoids: Potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress
    • Sporn MB, Liby KT, Yore MM, Fu L, Lopchuk JM, Gribble GW. New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J Nat Prod 2011;74:537-45.
    • (2011) J Nat Prod , vol.74 , pp. 537-545
    • Sporn, M.B.1    Liby, K.T.2    Yore, M.M.3    Fu, L.4    Lopchuk, J.M.5    Gribble, G.W.6
  • 20
    • 37549024231 scopus 로고    scopus 로고
    • Thiopurines in current medical practice: Molecular mechanisms and contributions to therapy-related cancer
    • Karran P, Attard N. Thiopurines in current medical practice: molecular mechanisms and contributions to therapy-related cancer. Nat Rev Cancer 2008;8:24-36.
    • (2008) Nat Rev Cancer , vol.8 , pp. 24-36
    • Karran, P.1    Attard, N.2
  • 21
    • 55149118807 scopus 로고    scopus 로고
    • Risk of nonmelanoma skin cancer with azathioprine use
    • Maddox JS, Soltani K. Risk of nonmelanoma skin cancer with azathioprine use. Inflamm Bowel Dis 2008;14:1425-3.
    • (2008) Inflamm Bowel Dis , vol.14 , pp. 1425-1433
    • Maddox, J.S.1    Soltani, K.2
  • 22
    • 84856193112 scopus 로고    scopus 로고
    • Use of thiopurines in the treatment of inflammatory bowel disease is associated with an increased risk of non-melanoma skin cancer in an at-risk population: A cohort study
    • Setshedi M, Epstein D, Winter TA, Myer L, Watermeyer G, Hift R. Use of thiopurines in the treatment of inflammatory bowel disease is associated with an increased risk of non-melanoma skin cancer in an at-risk population: a cohort study. J Gastroenterol Hepatol 2012;27:385-9.
    • (2012) J Gastroenterol Hepatol , vol.27 , pp. 385-389
    • Setshedi, M.1    Epstein, D.2    Winter, T.A.3    Myer, L.4    Watermeyer, G.5    Hift, R.6
  • 24
    • 0036657493 scopus 로고    scopus 로고
    • Skin cancer in organ transplant recipients: Epidemiology, pathogenesis, and management
    • Berg D, Otley CC. Skin cancer in organ transplant recipients: Epidemiology, pathogenesis, and management. J Am Acad Dermatol 2002;47:1-17.
    • (2002) J Am Acad Dermatol , vol.47 , pp. 1-17
    • Berg, D.1    Otley, C.C.2
  • 25
  • 26
    • 77951210792 scopus 로고    scopus 로고
    • Guanine sulphinate is a major stable product of photochemical oxidation of DNA 6-thioguanine by UVA irradiation
    • Ren X, Li F, Jeffs G, Zhang X, Xu YZ, Karran P. Guanine sulphinate is a major stable product of photochemical oxidation of DNA 6-thioguanine by UVA irradiation. Nucleic Acids Res 2010;38:1832-40.
    • (2010) Nucleic Acids Res , vol.38 , pp. 1832-1840
    • Ren, X.1    Li, F.2    Jeffs, G.3    Zhang, X.4    Xu, Y.Z.5    Karran, P.6
  • 27
    • 77956489958 scopus 로고    scopus 로고
    • Photo-oxidation of 6-thioguanine by UVA: The formation of addition products with low molecular weight thiol compounds
    • Ren X, Xu YZ, Karran P. Photo-oxidation of 6-thioguanine by UVA: The formation of addition products with low molecular weight thiol compounds. Photochem Photobiol 2010;86:1038-45.
    • (2010) Photochem Photobiol , vol.86 , pp. 1038-1045
    • Ren, X.1    Xu, Y.Z.2    Karran, P.3
  • 30
    • 64549098978 scopus 로고    scopus 로고
    • Reactive oxygen species generated by thiopurine/UVA cause irreparable transcription-blocking DNA lesions
    • Brem R, Li F, Karran P. Reactive oxygen species generated by thiopurine/UVA cause irreparable transcription-blocking DNA lesions. Nucleic Acids Res 2009;37:1951-61.
    • (2009) Nucleic Acids Res , vol.37 , pp. 1951-1961
    • Brem, R.1    Li, F.2    Karran, P.3
  • 31
    • 79960270911 scopus 로고    scopus 로고
    • Crosslinking of DNA repair and replication proteins to DNA in cells treated with 6-thioguanine and UVA
    • Gueranger Q, Kia A, Frith D, Karran P. Crosslinking of DNA repair and replication proteins to DNA in cells treated with 6-thioguanine and UVA. Nucleic Acids Res 2011;39:5057-66.
    • (2011) Nucleic Acids Res , vol.39 , pp. 5057-5066
    • Gueranger, Q.1    Kia, A.2    Frith, D.3    Karran, P.4
  • 32
    • 0022354811 scopus 로고
    • Skin cancer in renal transplant recipients is associated with increased concentrations of 6-thioguanine nucleotide in red blood cells
    • DOI 10.1111/j.1365-2133.1985.tb02408.x
    • Lennard L, Thomas S, Harrington CI, Maddocks JL. Skin cancer in renal transplant recipients is associated with increased concentrations of 6-thioguanine nucleotide in red blood cells. Br J Dermatol 1985;113:723-9. (Pubitemid 16186885)
    • (1985) British Journal of Dermatology , vol.113 , Issue.6 , pp. 723-729
    • Lennard, L.1    Thomas, S.2    Harrington, C.I.3    Maddocks, J.L.4
  • 34
    • 0028963613 scopus 로고
    • Quantitation of 6-thioguanine residues in peripheral blood leukocyte DNA obtained from patients receiving 6-mercaptopurine-based maintenance therapy
    • Warren DJ, Andersen A, Slørdal L. Quantitation of 6-thioguanine residues in peripheral blood leukocyte DNA obtained from patients receiving 6-mercaptopurine-based maintenance therapy. Cancer Res 1995;55:1670-4.
    • (1995) Cancer Res , vol.55 , pp. 1670-1674
    • Warren, D.J.1    Andersen, A.2    Slørdal, L.3
  • 35
    • 0029842160 scopus 로고    scopus 로고
    • Quantitation of 6-thioguanine in peripheral blood leukocyte DNA in Crohn's disease patients on maintenance 6-mercaptopurine therapy
    • DOI 10.1139/cjpp-74-5-580
    • Cuffari C, Seidman EG, Latour S, Théorêt Y. Quantitation of 6-thioguanine in peripheral blood leukocyte DNA in Crohn's disease patients on maintenance 6-mercaptopurine therapy. Can J Physiol Pharmacol 1996;74:580-5. (Pubitemid 26341481)
    • (1996) Canadian Journal of Physiology and Pharmacology , vol.74 , Issue.5 , pp. 580-585
    • Cuffari, C.1    Seidman, E.G.2    Latour, S.3    Theoret, Y.4
  • 36
    • 80053909017 scopus 로고    scopus 로고
    • Oral azathioprine leads to higher incorporation of 6-thioguanine in DNA of skin than liver: The protective role of the Keap1/Nrf2/ARE pathway
    • Kalra S, Zhang Y, Knatko EV, Finlayson S, Yamamoto M, Dinkova-Kostova AT. Oral azathioprine leads to higher incorporation of 6-thioguanine in DNA of skin than liver: The protective role of the Keap1/Nrf2/ARE pathway. Cancer Prev Res 2011;4:1665-74.
    • (2011) Cancer Prev Res , vol.4 , pp. 1665-1674
    • Kalra, S.1    Zhang, Y.2    Knatko, E.V.3    Finlayson, S.4    Yamamoto, M.5    Dinkova-Kostova, A.T.6
  • 37
    • 0022186670 scopus 로고
    • Measurement of protein using bicinchoninic acid
    • DOI 10.1016/0003-2697(85)90442-7
    • Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, et al. Measurement of protein using bicinchoninic acid. Anal Biochem 1985;150:76-85. (Pubitemid 16258399)
    • (1985) Analytical Biochemistry , vol.150 , Issue.1 , pp. 76-85
    • Smith, P.K.1    Krohn, R.I.2    Hermanson, G.T.3
  • 38
    • 0023930873 scopus 로고
    • Direct measurement of NAD(P)H: Quinone reductase from cells cultured in microtiter wells: A screening assay for anticarcinogenic enzyme inducers
    • Prochaska HJ, Santamaria AB. Direct measurement of NAD(P)H:quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal Biochem 1988;169:328-36. (Pubitemid 18081406)
    • (1988) Analytical Biochemistry , vol.169 , Issue.2 , pp. 328-336
    • Prochaska, H.J.1    Santamaria, A.B.2
  • 39
    • 0019738962 scopus 로고
    • Glutathione S-transferases (rat and human)
    • Habig WH, Jakoby WB. Glutathione S-transferases (rat and human). Methods Enzymol 1981;77:218-31.
    • (1981) Methods Enzymol , vol.77 , pp. 218-231
    • Habig, W.H.1    Jakoby, W.B.2
  • 40
    • 57349108021 scopus 로고    scopus 로고
    • Ursodeoxycholic acid stimulates Nrf2-mediated hepatocellular transport, detoxifi cation, and antioxidative stress systems in mice
    • Okada K, Shoda J, Taguchi K, Maher JM, Ishizaki K, Inoue Y, et al. Ursodeoxycholic acid stimulates Nrf2-mediated hepatocellular transport, detoxifi cation, and antioxidative stress systems in mice. Am J Physiol Gastrointest Liver Physiol 2008;295:G735-47.
    • (2008) Am J Physiol Gastrointest Liver Physiol , vol.295
    • Okada, K.1    Shoda, J.2    Taguchi, K.3    Maher, J.M.4    Ishizaki, K.5    Inoue, Y.6
  • 41
    • 0035823559 scopus 로고    scopus 로고
    • Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine
    • Chen ZS, Lee K, Kruh GD. Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem 2001;276:33747-54.
    • (2001) J Biol Chem , vol.276 , pp. 33747-33754
    • Chen, Z.S.1    Lee, K.2    Kruh, G.D.3
  • 45
    • 66749112860 scopus 로고    scopus 로고
    • Genetic versus chemoprotective activation of Nrf2 signaling: Overlapping yet distinct gene expression profiles between Keap1 knockout and triterpenoid-treated mice
    • Yates MS, Tran QT, Dolan PM, Osburn WO, Shin S, McCulloch CC, et al. Genetic versus chemoprotective activation of Nrf2 signaling: Overlapping yet distinct gene expression profiles between Keap1 knockout and triterpenoid-treated mice. Carcinogenesis 2009;30:1024-31.
    • (2009) Carcinogenesis , vol.30 , pp. 1024-1031
    • Yates, M.S.1    Tran, Q.T.2    Dolan, P.M.3    Osburn, W.O.4    Shin, S.5    McCulloch, C.C.6
  • 46
    • 82255181180 scopus 로고    scopus 로고
    • HSF1-dependent upregulation of Hsp70 by sulfhydryl-reactive inducers of the KEAP1/NRF2/ARE pathway
    • Zhang Y, Ahn YH, Benjamin IJ, Honda T, Hicks RJ, Calabrese V, et al. HSF1-dependent upregulation of Hsp70 by sulfhydryl-reactive inducers of the KEAP1/NRF2/ARE pathway. Chem Biol 2011;18:1355-61.
    • (2011) Chem Biol , vol.18 , pp. 1355-1361
    • Zhang, Y.1    Ahn, Y.H.2    Benjamin, I.J.3    Honda, T.4    Hicks, R.J.5    Calabrese, V.6
  • 48
    • 1242308254 scopus 로고    scopus 로고
    • Current status and future potential of transdermal drug delivery
    • Prausnitz MR, Mitragotri S, Langer R. Current status and future potential of transdermal drug delivery. Nat Rev Drug Discov 2004;3:115-24. (Pubitemid 38239773)
    • (2004) Nature Reviews Drug Discovery , vol.3 , Issue.2 , pp. 115-124
    • Prausnitz, M.R.1    Mitragotri, S.2    Langer, R.3


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