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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, Yoshizawa H, Gribble GW, Williams CR, Risingsong R, Royce DB, Dinkova-Kostova AT, Stephenson KK, Egner PA, Yates MS, Groopman JD, Kensler TW, Sporn MB.

Cancer Res. 2008 Aug 15;68(16):6727-33. doi: 10.1158/0008-5472.CAN-08-1123.


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, Janosik T, Su X, Honda Y, Roebuck BD, Gribble GW.

J Med Chem. 2011 Mar 24;54(6):1762-78. doi: 10.1021/jm101445p. Epub 2011 Mar 1.


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, Gribble GW.

Org Biomol Chem. 2003 Dec 21;1(24):4384-91. Epub 2003 Oct 31.


Potent protection against aflatoxin-induced tumorigenesis through induction of Nrf2-regulated pathways by the triterpenoid 1-[2-cyano-3-,12-dioxooleana-1,9(11)-dien-28-oyl]imidazole.

Yates MS, Kwak MK, Egner PA, Groopman JD, Bodreddigari S, Sutter TR, Baumgartner KJ, Roebuck BD, Liby KT, Yore MM, Honda T, Gribble GW, Sporn MB, Kensler TW.

Cancer Res. 2006 Feb 15;66(4):2488-94.


Novel synthetic pyridyl analogues of CDDO-Imidazolide are useful new tools in cancer prevention.

Cao M, Onyango EO, Williams CR, Royce DB, Gribble GW, Sporn MB, Liby KT.

Pharmacol Res. 2015 Oct;100:135-47. doi: 10.1016/j.phrs.2015.07.024. Epub 2015 Jul 31.


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

Kalra S, Knatko EV, Zhang Y, Honda T, Yamamoto M, Dinkova-Kostova AT.

Cancer Prev Res (Phila). 2012 Jul;5(7):973-81. doi: 10.1158/1940-6207.CAPR-12-0041. Epub 2012 Jun 1.


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, David E, Schiavoni KH, Finlayson S, Mierke DF, Honda T.

J Biol Chem. 2010 Oct 29;285(44):33747-55. doi: 10.1074/jbc.M110.163485. Epub 2010 Aug 26.


Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent.

Honda T, Dinkova-Kostova AT, David E, Padegimas EM, Sundararajan C, Visnick M, Bumeister R, Christian Wigley W.

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2188-91. doi: 10.1016/j.bmcl.2011.03.018.


Chemoprevention of colon carcinogenesis by oleanolic acid and its analog in male F344 rats and modulation of COX-2 and apoptosis in human colon HT-29 cancer cells.

Janakiram NB, Indranie C, Malisetty SV, Jagan P, Steele VE, Rao CV.

Pharm Res. 2008 Sep;25(9):2151-7. doi: 10.1007/s11095-008-9582-7. Epub 2008 Apr 12.


Complete protection against aflatoxin B(1)-induced liver cancer with a triterpenoid: DNA adduct dosimetry, molecular signature, and genotoxicity threshold.

Johnson NM, Egner PA, Baxter VK, Sporn MB, Wible RS, Sutter TR, Groopman JD, Kensler TW, Roebuck BD.

Cancer Prev Res (Phila). 2014 Jul;7(7):658-65. doi: 10.1158/1940-6207.CAPR-13-0430. Epub 2014 Mar 24.


The acetylenic tricyclic bis(cyano enone), TBE-31 inhibits non-small cell lung cancer cell migration through direct binding with actin.

Chan E, Saito A, Honda T, Di Guglielmo GM.

Cancer Prev Res (Phila). 2014 Jul;7(7):727-37. doi: 10.1158/1940-6207.CAPR-13-0403. Epub 2014 May 7.


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.

Favaloro FG Jr, Honda T, Honda Y, Gribble GW, Suh N, Risingsong R, Sporn MB.

J Med Chem. 2002 Oct 24;45(22):4801-5.


Of mice, rats, and men: could Nrf2 activation protect against aflatoxin heptocarcinogenesis in humans?

Eaton DL, Schaupp CM.

Cancer Prev Res (Phila). 2014 Jul;7(7):653-7. doi: 10.1158/1940-6207.CAPR-14-0119. Epub 2014 Jun 16.


Transgenic expression of aflatoxin aldehyde reductase (AKR7A1) modulates aflatoxin B1 metabolism but not hepatic carcinogenesis in the rat.

Roebuck BD, Johnson DN, Sutter CH, Egner PA, Scholl PF, Friesen MD, Baumgartner KJ, Ware NM, Bodreddigari S, Groopman JD, Kensler TW, Sutter TR.

Toxicol Sci. 2009 May;109(1):41-9. doi: 10.1093/toxsci/kfp003. Epub 2009 Jan 23.


New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase.

Li W, Zheng S, Higgins M, Morra RP Jr, Mendis AT, Chien CW, Ojima I, Mierke DF, Dinkova-Kostova AT, Honda T.

J Med Chem. 2015 Jun 11;58(11):4738-48. doi: 10.1021/acs.jmedchem.5b00393. Epub 2015 May 20.


Novel tricyclic compounds having acetylene groups at C-8a and cyano enones in rings A and C: highly potent anti-inflammatory and cytoprotective agents.

Honda T, Sundararajan C, Yoshizawa H, Su X, Honda Y, Liby KT, Sporn MB, Gribble GW.

J Med Chem. 2007 Apr 19;50(8):1731-4. Epub 2007 Mar 17.


Synthesis, chemical reactivity as Michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents.

Zheng S, Santosh Laxmi YR, David E, Dinkova-Kostova AT, Shiavoni KH, Ren Y, Zheng Y, Trevino I, Bumeister R, Ojima I, Wigley WC, Bliska JB, Mierke DF, Honda T.

J Med Chem. 2012 May 24;55(10):4837-46. doi: 10.1021/jm3003922. Epub 2012 May 7.


Novel semisynthetic analogues of betulinic acid with diverse cytoprotective, antiproliferative, and proapoptotic activities.

Liby K, Honda T, Williams CR, Risingsong R, Royce DB, Suh N, Dinkova-Kostova AT, Stephenson KK, Talalay P, Sundararajan C, Gribble GW, Sporn MB.

Mol Cancer Ther. 2007 Jul;6(7):2113-9.


A novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity.

Suh N, Wang Y, Honda T, Gribble GW, Dmitrovsky E, Hickey WF, Maue RA, Place AE, Porter DM, Spinella MJ, Williams CR, Wu G, Dannenberg AJ, Flanders KC, Letterio JJ, Mangelsdorf DJ, Nathan CF, Nguyen L, Porter WW, Ren RF, Roberts AB, Roche NS, Subbaramaiah K, Sporn MB.

Cancer Res. 1999 Jan 15;59(2):336-41.


The novel synthetic triterpenoid, CDDO-imidazolide, inhibits inflammatory response and tumor growth in vivo.

Place AE, Suh N, Williams CR, Risingsong R, Honda T, Honda Y, Gribble GW, Leesnitzer LM, Stimmel JB, Willson TM, Rosen E, Sporn MB.

Clin Cancer Res. 2003 Jul;9(7):2798-806.

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