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

PubWeight™: 1.85‹?› | Rank: Top 3%

🔗 View Article (PMID 9927043)

Published in Cancer Res on January 15, 1999

Authors

N Suh1, Y Wang, T Honda, G W Gribble, E Dmitrovsky, W F Hickey, R A Maue, A E Place, D M Porter, M J Spinella, C R Williams, G Wu, A J Dannenberg, K C Flanders, J J Letterio, D J Mangelsdorf, C F Nathan, L Nguyen, W W Porter, R F Ren, A B Roberts, N S Roche, K Subbaramaiah, M B Sporn

Author Affiliations

1: Norris Cotton Cancer Center and Department of Pharmacology Dartmouth Medical School, Hanover, New Hampshire 03755, USA.

Articles citing this

Transcriptional regulation of collagenase (MMP-1, MMP-13) genes in arthritis: integration of complex signaling pathways for the recruitment of gene-specific transcription factors. Arthritis Res (2001) 3.24

New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress. J Nat Prod (2011) 1.90

Synthetic oleanane triterpenoids: multifunctional drugs with a broad range of applications for prevention and treatment of chronic disease. Pharmacol Rev (2012) 1.71

Chemotherapeutic approaches for targeting cell death pathways. Oncologist (2006) 1.70

Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis. J Clin Invest (2014) 1.46

The triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic-acid methyl ester has potent anti-diabetic effects in diet-induced diabetic mice and Lepr(db/db) mice. J Biol Chem (2010) 1.44

Human neuroblastoma cells rapidly enter cell cycle arrest and apoptosis following exposure to C-28 derivatives of the synthetic triterpenoid CDDO. Cancer Biol Ther (2008) 1.44

Human immunodeficiency virus type 1-induced macrophage gene expression includes the p21 gene, a target for viral regulation. J Virol (2005) 1.37

Electrophilic peroxisome proliferator-activated receptor-gamma ligands have potent antifibrotic effects in human lung fibroblasts. Am J Respir Cell Mol Biol (2009) 1.30

Neuroprotective effects of the triterpenoid, CDDO methyl amide, a potent inducer of Nrf2-mediated transcription. PLoS One (2009) 1.29

Prevention and treatment of experimental estrogen receptor-negative mammary carcinogenesis by the synthetic triterpenoid CDDO-methyl Ester and the rexinoid LG100268. Clin Cancer Res (2008) 1.28

Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. Toxins (Basel) (2010) 1.19

Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer. Front Biosci (Landmark Ed) (2011) 1.19

Synthetic triterpenoids prolong survival in a transgenic mouse model of pancreatic cancer. Cancer Prev Res (Phila) (2010) 1.19

Proteomic analysis shows synthetic oleanane triterpenoid binds to mTOR. PLoS One (2011) 1.13

Potential of peroxisome proliferator-activated receptor gamma antagonist compounds as therapeutic agents for a wide range of cancer types. PPAR Res (2008) 1.01

Oleanolic acid and its synthetic derivatives for the prevention and therapy of cancer: preclinical and clinical evidence. Cancer Lett (2014) 1.01

Oleanane triterpenoid CDDO-Me induces apoptosis in multidrug resistant osteosarcoma cells through inhibition of Stat3 pathway. BMC Cancer (2010) 1.00

Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo. Blood (2008) 1.00

CDDO induces granulocytic differentiation of myeloid leukemic blasts through translational up-regulation of p42 CCAAT enhancer binding protein alpha. Blood (2007) 1.00

Role of peroxisome proliferator-activated receptor-gamma and its coactivator DRIP205 in cellular responses to CDDO (RTA-401) in acute myelogenous leukemia. Cancer Res (2010) 0.99

The Nrf2 triterpenoid activator, CDDO-imidazolide, protects kidneys from ischemia-reperfusion injury in mice. Kidney Int (2013) 0.98

Triterpenoids display single agent anti-tumor activity in a transgenic mouse model of chronic lymphocytic leukemia and small B cell lymphoma. PLoS One (2007) 0.98

Peroxisome proliferator-activated receptor-gamma ligands induce heme oxygenase-1 in lung fibroblasts by a PPARgamma-independent, glutathione-dependent mechanism. Am J Physiol Lung Cell Mol Physiol (2009) 0.96

The synthetic triterpenoid CDDO-Im inhibits fatty acid synthase expression and has antiproliferative and proapoptotic effects in human liposarcoma cells. Cancer Invest (2008) 0.96

The triterpenoid CDDO-Me inhibits bleomycin-induced lung inflammation and fibrosis. PLoS One (2013) 0.96

Preclinical evidences toward the use of triterpenoid CDDO-Me for solid cancer prevention and treatment. Mol Cancer (2014) 0.94

Fatty acid synthesis is a therapeutic target in human liposarcoma. Int J Oncol (2010) 0.91

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) 0.91

Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. J Med Chem (2011) 0.90

Synthetic triterpenoids target the Arp2/3 complex and inhibit branched actin polymerization. J Biol Chem (2010) 0.89

Bardoxolone methyl (CDDO-Me) as a therapeutic agent: an update on its pharmacokinetic and pharmacodynamic properties. Drug Des Devel Ther (2014) 0.89

RTA 408, A Novel Synthetic Triterpenoid with Broad Anticancer and Anti-Inflammatory Activity. PLoS One (2015) 0.86

The combination of the histone deacetylase inhibitor vorinostat and synthetic triterpenoids reduces tumorigenesis in mouse models of cancer. Carcinogenesis (2012) 0.85

Synthetic triterpenoid cyano enone of methyl boswellate activates intrinsic, extrinsic, and endoplasmic reticulum stress cell death pathways in tumor cell lines. Mol Cancer Ther (2011) 0.84

Effects of PPARγ Ligands on Leukemia. PPAR Res (2012) 0.84

Electrophilic PPARγ ligands inhibit corneal fibroblast to myofibroblast differentiation in vitro: a potentially novel therapy for corneal scarring. Exp Eye Res (2011) 0.84

The synthetic triterpenoid, CDDO-Me, modulates the proinflammatory response to in vivo lipopolysaccharide challenge. J Interferon Cytokine Res (2010) 0.84

Activation of peroxisome proliferator-activated receptor gamma contributes to the survival of T lymphoma cells by affecting cellular metabolism. Am J Pathol (2007) 0.84

The synthetic triterpenoid CDDO-Imidazolide suppresses experimental liver metastasis. Clin Exp Metastasis (2011) 0.84

CDDO-Imidazolide inhibits growth and survival of c-Myc-induced mouse B cell and plasma cell neoplasms. Mol Cancer (2006) 0.84

Peroxisome proliferator-activated receptor gamma (PPARgamma) and colorectal carcinogenesis. J Cancer Res Clin Oncol (2007) 0.84

Role of peroxisome proliferator-activated receptor gamma and its ligands in the treatment of hematological malignancies. PPAR Res (2008) 0.83

Bryonolic acid transcriptional control of anti-inflammatory and antioxidant genes in macrophages in vitro and in vivo. J Nat Prod (2012) 0.83

The triterpenoid CDDO-Me delays murine acute graft-versus-host disease with the preservation of graft-versus-tumor effects after allogeneic bone marrow transplantation. Biol Blood Marrow Transplant (2010) 0.83

Anticancer Role of PPARgamma Agonists in Hematological Malignancies Found in the Vasculature, Marrow, and Eyes. PPAR Res (2010) 0.83

The synthetic triterpenoid, CDDO, suppresses alloreactive T cell responses and reduces murine early acute graft-versus-host disease mortality. Biol Blood Marrow Transplant (2007) 0.83

Inhibition of NOS-2 expression in macrophages through the inactivation of NF-kappaB by andalusol. Br J Pharmacol (1999) 0.82

Electrophilic PPARγ Ligands Attenuate IL-1β and Silica-Induced Inflammatory Mediator Production in Human Lung Fibroblasts via a PPARγ-Independent Mechanism. PPAR Res (2011) 0.82

Inhibition of transglutaminase 2, a novel target for pulmonary fibrosis, by two small electrophilic molecules. Am J Respir Cell Mol Biol (2014) 0.82

Bryonolic acid: a large-scale isolation and evaluation of heme oxygenase 1 expression in activated macrophages. J Nat Prod (2010) 0.81

The triterpenoid CDDO inhibits expression of matrix metalloproteinase-1, matrix metalloproteinase-13 and Bcl-3 in primary human chondrocytes. Arthritis Res Ther (2003) 0.81

Oleanane triterpenoids in the prevention and therapy of breast cancer: current evidence and future perspectives. Phytochem Rev (2014) 0.81

Peroxisome proliferator-activated receptor gamma-dependent activity of indole ring-substituted 1,1-bis(3'-indolyl)-1-(p-biphenyl)methanes in cancer cells. Cancer Chemother Pharmacol (2009) 0.80

Prevention and Treatment of Colorectal Cancer by Natural Agents From Mother Nature. Curr Colorectal Cancer Rep (2013) 0.80

Dietary terpenoids and prostate cancer chemoprevention. Front Biosci (2008) 0.79

A synthetic triterpenoid CDDO-Im inhibits tumorsphere formation by regulating stem cell signaling pathways in triple-negative breast cancer. PLoS One (2014) 0.79

Bardoxolone methyl induces apoptosis and autophagy and inhibits epithelial-to-mesenchymal transition and stemness in esophageal squamous cancer cells. Drug Des Devel Ther (2015) 0.79

CDDO-imidazolide mediated inhibition of malignant cell growth in Waldenström macroglobulinemia. Leuk Res (2008) 0.78

Fatty Acids and Breast Cancer: Make Them on Site or Have Them Delivered. J Cell Physiol (2016) 0.77

Cancer Cell Growth Is Differentially Affected by Constitutive Activation of NRF2 by KEAP1 Deletion and Pharmacological Activation of NRF2 by the Synthetic Triterpenoid, RTA 405. PLoS One (2015) 0.77

Protection of HepG2 cells against acrolein toxicity by 2-cyano-3,12-dioxooleana-1,9-dien-28-imidazolide via glutathione-mediated mechanism. Exp Biol Med (Maywood) (2014) 0.75

Promoter methylation status and expression of PPAR-γ gene are associated with prognosis of acute-on-chronic hepatitis B liver failure. Clin Epigenetics (2015) 0.75

Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity. Tetrahedron (2008) 0.75

A novel synthetic oleanane triterpenoid suppresses adhesion, migration, and invasion of highly metastatic melanoma cells by modulating gelatinase signaling axis. Mol Carcinog (2014) 0.75

Time Course Expression Analysis of 1[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]imidazole Induction of Cytoprotection in Human Endothelial Cells. Gene Regul Syst Bio (2017) 0.75

Articles by these authors

Interpreting patterns of gene expression with self-organizing maps: methods and application to hematopoietic differentiation. Proc Natl Acad Sci U S A (1999) 39.79

Analysis of the mouse transcriptome based on functional annotation of 60,770 full-length cDNAs. Nature (2002) 28.79

Effects of radiotherapy and of differences in the extent of surgery for early breast cancer on local recurrence and 15-year survival: an overview of the randomised trials. Lancet (2005) 24.57

Gene transfer into mouse lyoma cells by electroporation in high electric fields. EMBO J (1982) 17.98

Complete genome sequence of enterohemorrhagic Escherichia coli O157:H7 and genomic comparison with a laboratory strain K-12. DNA Res (2001) 15.22

Release of reactive nitrogen intermediates and reactive oxygen intermediates from mouse peritoneal macrophages. Comparison of activating cytokines and evidence for independent production. J Immunol (1988) 14.21

Identification of interferon-gamma as the lymphokine that activates human macrophage oxidative metabolism and antimicrobial activity. J Exp Med (1983) 14.08

Transient left ventricular apical ballooning without coronary artery stenosis: a novel heart syndrome mimicking acute myocardial infarction. Angina Pectoris-Myocardial Infarction Investigations in Japan. J Am Coll Cardiol (2001) 12.56

Complete genome sequence of Methanobacterium thermoautotrophicum deltaH: functional analysis and comparative genomics. J Bacteriol (1997) 12.21

Transforming growth factor type beta: rapid induction of fibrosis and angiogenesis in vivo and stimulation of collagen formation in vitro. Proc Natl Acad Sci U S A (1986) 12.14

p63, a p53 homolog at 3q27-29, encodes multiple products with transactivating, death-inducing, and dominant-negative activities. Mol Cell (1998) 11.54

Transforming growth factor beta 1 null mutation in mice causes excessive inflammatory response and early death. Proc Natl Acad Sci U S A (1993) 10.82

Secretory products of macrophages. J Clin Invest (1987) 10.33

Human transforming growth factor-beta complementary DNA sequence and expression in normal and transformed cells. Nature (1985) 10.13

Production of transforming growth factor beta by human T lymphocytes and its potential role in the regulation of T cell growth. J Exp Med (1986) 9.86

Chromosomal translocation t(15;17) in human acute promyelocytic leukemia fuses RAR alpha with a novel putative transcription factor, PML. Cell (1991) 9.40

Transforming growth factor-beta in human platelets. Identification of a major storage site, purification, and characterization. J Biol Chem (1983) 9.32

Effect of radiotherapy after breast-conserving surgery on 10-year recurrence and 15-year breast cancer death: meta-analysis of individual patient data for 10,801 women in 17 randomised trials. Lancet (2011) 9.20

The relationship between glucose and incident cardiovascular events. A metaregression analysis of published data from 20 studies of 95,783 individuals followed for 12.4 years. Diabetes Care (1999) 9.16

Regulation of mouse sterol regulatory element-binding protein-1c gene (SREBP-1c) by oxysterol receptors, LXRalpha and LXRbeta. Genes Dev (2000) 9.09

WAF1/CIP1 is induced in p53-mediated G1 arrest and apoptosis. Cancer Res (1994) 9.00

Nuclear receptors and lipid physiology: opening the X-files. Science (2001) 8.76

Coronary-artery calcification in young adults with end-stage renal disease who are undergoing dialysis. N Engl J Med (2000) 8.47

Effect of radiotherapy after mastectomy and axillary surgery on 10-year recurrence and 20-year breast cancer mortality: meta-analysis of individual patient data for 8135 women in 22 randomised trials. Lancet (2014) 8.04

Regulation of immune responses by TGF-beta. Annu Rev Immunol (1998) 8.01

Positional cloning of the gene for multiple endocrine neoplasia-type 1. Science (1997) 7.95

Alterations of macrophage functions by mediators from lymphocytes. J Exp Med (1971) 7.95

Identification of nitric oxide synthase as a protective locus against tuberculosis. Proc Natl Acad Sci U S A (1997) 7.90

An oxysterol signalling pathway mediated by the nuclear receptor LXR alpha. Nature (1996) 7.86

Identification of a nuclear receptor for bile acids. Science (1999) 7.81

The frequency of chimeric molecules as a consequence of PCR co-amplification of 16S rRNA genes from different bacterial species. Microbiology (1996) 7.78

Nitric oxide. A macrophage product responsible for cytostasis and respiratory inhibition in tumor target cells. J Exp Med (1989) 7.72

Autocrine secretion and malignant transformation of cells. N Engl J Med (1980) 7.49

Isochorismate synthase is required to synthesize salicylic acid for plant defence. Nature (2001) 7.43

Knockout of glutamate transporters reveals a major role for astroglial transport in excitotoxicity and clearance of glutamate. Neuron (1996) 7.20

Frequency of formation of chimeric molecules as a consequence of PCR coamplification of 16S rRNA genes from mixed bacterial genomes. Appl Environ Microbiol (1997) 7.09

A new member of the frizzled family from Drosophila functions as a Wingless receptor. Nature (1996) 7.04

Production of large amounts of hydrogen peroxide by human tumor cells. Cancer Res (1991) 6.99

Role of LXRs in control of lipogenesis. Genes Dev (2000) 6.98

Requirement of ATM-dependent phosphorylation of brca1 in the DNA damage response to double-strand breaks. Science (1999) 6.93

Expression and secretion of type beta transforming growth factor by activated human macrophages. Proc Natl Acad Sci U S A (1987) 6.76

9-cis retinoic acid is a high affinity ligand for the retinoid X receptor. Cell (1992) 6.75

Cholesterol and bile acid metabolism are impaired in mice lacking the nuclear oxysterol receptor LXR alpha. Cell (1998) 6.70

PKD2, a gene for polycystic kidney disease that encodes an integral membrane protein. Science (1996) 6.56

Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers. Science (2000) 6.52

Molecular basis for feedback regulation of bile acid synthesis by nuclear receptors. Mol Cell (2000) 6.48

Differential expression and activation of a family of murine peroxisome proliferator-activated receptors. Proc Natl Acad Sci U S A (1994) 6.46

Transforming growth factor type beta induces monocyte chemotaxis and growth factor production. Proc Natl Acad Sci U S A (1987) 6.43

TFAR19, a novel apoptosis-related gene cloned from human leukemia cell line TF-1, could enhance apoptosis of some tumor cells induced by growth factor withdrawal. Biochem Biophys Res Commun (1999) 6.33

Effects of prenatal and postnatal methylmercury exposure from fish consumption on neurodevelopment: outcomes at 66 months of age in the Seychelles Child Development Study. JAMA (1998) 6.30

Mass screening for lung cancer with mobile spiral computed tomography scanner. Lancet (1998) 6.09

Autocrine growth factors and cancer. Nature (1985) 5.97

Type beta transforming growth factor: a bifunctional regulator of cellular growth. Proc Natl Acad Sci U S A (1985) 5.93

Readmission after hospitalization for congestive heart failure among Medicare beneficiaries. Arch Intern Med (1997) 5.93

New class of transforming growth factors potentiated by epidermal growth factor: isolation from non-neoplastic tissues. Proc Natl Acad Sci U S A (1981) 5.89

Retinoid X receptor interacts with nuclear receptors in retinoic acid, thyroid hormone and vitamin D3 signalling. Nature (1992) 5.76

A cluster of hydrophobic amino acid residues required for fast Na(+)-channel inactivation. Proc Natl Acad Sci U S A (1992) 5.60

Mice lacking Smad3 show accelerated wound healing and an impaired local inflammatory response. Nat Cell Biol (1999) 5.58

Leptomycin B is an inhibitor of nuclear export: inhibition of nucleo-cytoplasmic translocation of the human immunodeficiency virus type 1 (HIV-1) Rev protein and Rev-dependent mRNA. Chem Biol (1997) 5.49

Targeted disruption of SMAD3 results in impaired mucosal immunity and diminished T cell responsiveness to TGF-beta. EMBO J (1999) 5.49

Deficient hippocampal long-term potentiation in alpha-calcium-calmodulin kinase II mutant mice. Science (1992) 5.46

Hydrogen peroxide release from mouse peritoneal macrophages: dependence on sequential activation and triggering. J Exp Med (1977) 5.44

Blood transfusion in elderly patients with acute myocardial infarction. N Engl J Med (2001) 5.43

IAP-family protein survivin inhibits caspase activity and apoptosis induced by Fas (CD95), Bax, caspases, and anticancer drugs. Cancer Res (1998) 5.41

Human transforming growth factor-alpha: precursor structure and expression in E. coli. Cell (1984) 5.39

Extracellular cytolysis by activated macrophages and granulocytes. II. Hydrogen peroxide as a mediator of cytotoxicity. J Exp Med (1979) 5.38

Genetic diversity and disease control in rice. Nature (2000) 5.34

A role for the lissencephaly gene LIS1 in mitosis and cytoplasmic dynein function. Nat Cell Biol (2000) 5.29

Racial differences in the use of cardiac catheterization after acute myocardial infarction. N Engl J Med (2001) 5.29

Organizing principles for a diversity of GABAergic interneurons and synapses in the neocortex. Science (2000) 5.27

Some recent advances in the chemistry and biology of transforming growth factor-beta. J Cell Biol (1987) 5.25

Transforming growth factor beta is an important immunomodulatory protein for human B lymphocytes. J Immunol (1986) 5.19

Macrophages secrete a novel heparin-binding protein with inflammatory and neutrophil chemokinetic properties. J Exp Med (1988) 5.16

Transforming growth factor-beta: biological function and chemical structure. Science (1986) 5.08

Structural requirements of ligands for the oxysterol liver X receptors LXRalpha and LXRbeta. Proc Natl Acad Sci U S A (1999) 5.08

A genomic screen of autism: evidence for a multilocus etiology. Am J Hum Genet (1999) 4.96

Suppressor T cells generated by oral tolerization to myelin basic protein suppress both in vitro and in vivo immune responses by the release of transforming growth factor beta after antigen-specific triggering. Proc Natl Acad Sci U S A (1992) 4.94

LXR, a nuclear receptor that defines a distinct retinoid response pathway. Genes Dev (1995) 4.93

Suppression of experimental glomerulonephritis by antiserum against transforming growth factor beta 1. Nature (1990) 4.64

Differential signaling via the same axon of neocortical pyramidal neurons. Proc Natl Acad Sci U S A (1998) 4.59

POWER_SAGE: comparing statistical tests for SAGE experiments. Bioinformatics (2000) 4.56

BACE1 is the major beta-secretase for generation of Abeta peptides by neurons. Nat Neurosci (2001) 4.54

KILLER/DR5 is a DNA damage-inducible p53-regulated death receptor gene. Nat Genet (1997) 4.46

Hydrogen peroxide metabolism in human monocytes during differentiation in vitro. J Clin Invest (1981) 4.46

Vitamin C pharmacokinetics in healthy volunteers: evidence for a recommended dietary allowance. Proc Natl Acad Sci U S A (1996) 4.45