Home Other Building Blocks (-)-DHMEQ

(-)-DHMEQ

CAS No.:
287194-40-5
Catalog Number:
AG002W95
Molecular Formula:
C13H11NO5
Molecular Weight:
261.2301
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
2mg
98%
1 week
United States
$290
- +
5mg
98%
1 week
United States
$423
- +
10mg
98%
1 week
United States
$557
- +
25mg
98%
1 week
United States
$1057
- +
Product Description
Catalog Number:
AG002W95
Chemical Name:
(-)-DHMEQ
CAS Number:
287194-40-5
Molecular Formula:
C13H11NO5
Molecular Weight:
261.2301
MDL Number:
MFCD11100254
IUPAC Name:
2-hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
InChI:
InChI=1S/C13H11NO5/c15-8-4-2-1-3-6(8)13(18)14-7-5-9(16)11-12(19-11)10(7)17/h1-5,10-12,15,17H,(H,14,18)/t10-,11+,12-/m0/s1
InChI Key:
IUOMATKBBPCLFR-TUAOUCFPSA-N
SMILES:
O=C1C=C(NC(=O)c2ccccc2O)[C@@H]([C@H]2[C@@H]1O2)O
Properties
Complexity:
446  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
261.064g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
261.233g/mol
Monoisotopic Mass:
261.064g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
99.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0
Literature
Title Journal
Exposure to a combination of formaldehyde and DINP aggravated asthma-like pathology through oxidative stress and NF-κB activation. Toxicology 20180701
Ligand-dependent EGFR activation induces the co-expression of IL-6 and PAI-1 via the NFkB pathway in advanced-stage epithelial ovarian cancer. Oncogene 20120913
The novel NF-κB inhibitor DHMEQ synergizes with celecoxib to exert antitumor effects on human liver cancer cells by a ROS-dependent mechanism. Cancer letters 20120901
Enhancement of radiosensitivity by a unique novel NF-κB inhibitor, DHMEQ, in prostate cancer. British journal of cancer 20120807
Dehydroxymethylepoxyquinomicin (DHMEQ), a novel NF-kappaB inhibitor, inhibits allergic inflammation and airway remodelling in murine models of asthma. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20120801
Inhibition of nuclear factor-κB by dehydroxymethylepoxyquinomicin induces schedule-dependent chemosensitivity to anticancer drugs and enhances chemoinduced apoptosis in osteosarcoma cells. Anti-cancer drugs 20120701
Involvement of NF-κB-mediated expression of galectin-3-binding protein in TNF-α-induced breast cancer cell adhesion. Oncology reports 20120601
Immunomodulatory effect of nuclear factor-κB inhibition by dehydroxymethylepoxyquinomicin in combination with donor-specific blood transfusion. Transplantation 20120427
Involvement of DNA binding domain in the cellular stability and importin affinity of NF-κB component RelB. Organic & biomolecular chemistry 20120421
A novel NF-κB inhibitor, dehydroxymethylepoxyquinomicin, ameliorates inflammatory colonic injury in mice. Journal of Crohn's & colitis 20120301
Antitumor effect of dehydroxymethylepoxyquinomicin, a small molecule inhibitor of nuclear factor-κB, on glioblastoma. Neuro-oncology 20120101
Suppression of inflammatory cytokine secretion by an NF-ĸB inhibitor DHMEQ in nasal polyps fibroblasts. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20120101
A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2S,3S,4S)-DHMEQ. Chemical & pharmaceutical bulletin 20120101
Bioimaging analysis of nuclear factor-κB activity in Philadelphia chromosome-positive acute lymphoblastic leukemia cells reveals its synergistic upregulation by tumor necrosis factor-α-stimulated changes to the microenvironment. Cancer science 20111101
Design and synthesis of biotinylated DHMEQ for direct identification of its target NF-κB components. Bioorganic & medicinal chemistry letters 20111101
Dehydroxymethylepoxyquinomicin (DHMEQ) can suppress tumour necrosis factor-α production in lipopolysaccharide-injected mice, resulting in rescuing mice from death in vivo. Clinical and experimental immunology 20111101
Possible role of peritoneal NF-κB in peripheral inflammation and cancer: lessons from the inhibitor DHMEQ. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20110701
Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a new activator of antioxidant transcription factor Nrf2. Organic & biomolecular chemistry 20110621
[NF-kappaB inhibitor]. Nihon rinsho. Japanese journal of clinical medicine 20110601
Inhibition of nuclear factor-kappaB suppresses peritoneal dissemination of gastric cancer by blocking cancer cell adhesion. Cancer science 20110501
Anti-tumor activity of dehydroxymethylepoxyquinomicin against human oral squamous cell carcinoma cell lines in vitro and in vivo. Oral oncology 20110501
Inhibition of immune activation by a novel nuclear factor-kappa B inhibitor in HTLV-I-associated neurologic disease. Blood 20110324
Apoptosis in mouse amniotic epithelium is induced by activated macrophages through the TNF receptor type 1/TNF pathway. Biology of reproduction 20110201
Hydrogen and N-acetyl-L-cysteine rescue oxidative stress-induced angiogenesis in a mouse corneal alkali-burn model. Investigative ophthalmology & visual science 20110121
Coffee induces breast cancer resistance protein expression in Caco-2 cells. Biological & pharmaceutical bulletin 20110101
The side population, as a precursor of Hodgkin and Reed-Sternberg cells and a target for nuclear factor-κB inhibitors in Hodgkin's lymphoma. Cancer science 20101101
A new NF-κB inhibitor based on the amino-epoxyquinol core of DHMEQ. Bioorganic & medicinal chemistry letters 20101001
Donor pretreatment with DHMEQ improves islet transplantation. The Journal of surgical research 20100901
Topical application of dehydroxymethylepoxyquinomicin improves allergic inflammation via NF-kappaB inhibition. The Journal of allergy and clinical immunology 20100801
Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, prevents inflammatory injury induced by interferon-gamma and histamine in NCTC 2544 keratinocytes. Clinical and experimental pharmacology & physiology 20100701
Inhibition of active HIV-1 replication by NF-kappaB inhibitor DHMEQ. Microbes and infection 20100501
Characterizing the involvement of the nuclear factor-kappa B (NF kappa B) transcription factor in uveal melanoma. Investigative ophthalmology & visual science 20100401
Amelioration of experimental autoimmune uveoretinitis with nuclear factor-{kappa}B Inhibitor dehydroxy methyl epoxyquinomicin in mice. Investigative ophthalmology & visual science 20100401
Potent cytotoxic effect of a novel nuclear factor-kappaB inhibitor dehydroxymethylepoxyquinomicin on human bladder cancer cells producing various cytokines. Urology 20100401
Gene set enrichment analysis provides insight into novel signalling pathways in breast cancer stem cells. British journal of cancer 20100105
A small molecule inhibitor of NF-kappaB, dehydroxymethylepoxyquinomicin (DHMEQ), suppresses growth and invasion of nasopharyngeal carcinoma (NPC) cells. Cancer letters 20100101
Dehydroxymethylepoxyquinomicin inhibits expression and production of inflammatory mediators in interleukin-1beta-induced human chondrocytes. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101
Efficient cellular uptake of the novel NF-kappaB inhibitor (-)-DHMEQ and irreversible inhibition of NF-kappaB in neoplastic cells. Oncology research 20100101
Induction of oncogene addiction shift to NF-kappaB by camptothecin in solid tumor cells. Biochemical and biophysical research communications 20091204
Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB. Bioorganic & medicinal chemistry letters 20090915
Unusual intramolecular N-->O acyl group migration occurring during conjugation of (-)-DHMEQ with cysteine. Bioorganic & medicinal chemistry letters 20090915
Impairment of plasmacytoid dendritic cells for IFN production by the ligand for immunoglobulin-like transcript 7 expressed on human cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20090915
Possible involvement of chemokine-induced platelet activation in thrombophilic diathesis of antiphospholipid syndrome. Annals of the New York Academy of Sciences 20090901
Antitumor effects of dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, in human liver cancer cells are mediated through a reactive oxygen species-dependent mechanism. Molecular pharmacology 20090801
Inhibition of inflammatory mediator secretion by (-)-DHMEQ in mouse bone marrow-derived macrophages. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20090601
Transient inhibition of NF-kappaB by DHMEQ induces cell death of primary effusion lymphoma without HHV-8 reactivation. Cancer science 20090401
Induction of histidine decarboxylase in macrophages inhibited by the novel NF-kappaB inhibitor (-)-DHMEQ. Biochemical and biophysical research communications 20090206
Chemosensitization and immunosensitization of resistant cancer cells to apoptosis and inhibition of metastasis by the specific NF-kappaB inhibitor DHMEQ. Current pharmaceutical design 20090101
Growth suppression and apoptosis induction in synovial sarcoma cell lines by a novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin (DHMEQ). Cancer letters 20081218
Identification of the RelA domain responsible for action of a new NF-kappaB inhibitor DHMEQ. Biochemical and biophysical research communications 20081114
Dehydroxymethylepoxyquinomicin, a novel nuclear Factor-kappaB inhibitor, enhances antitumor activity of taxanes in anaplastic thyroid cancer cells. Endocrinology 20081101
The NF-kappaB inhibitors (bortezomib and DHMEQ) sensitise rituximab-resistant AIDS-B-non-Hodgkin lymphoma to apoptosis by various chemotherapeutic drugs. Leukemia & lymphoma 20081001
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues. Journal of medicinal chemistry 20080925
DHMEQ, a novel NF-kappaB inhibitor, suppresses growth and type I collagen accumulation in keloid fibroblasts. Journal of dermatological science 20080901
The novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin, prevents local and remote organ injury following intestinal ischemia/reperfusion in rats. The Journal of surgical research 20080901
A simple and reliable method for determining plasma concentration of dehydroxymethylepoxyquinomicin by high performance liquid chromatography with mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080801
DHMEQ, a novel nuclear factor-kappaB inhibitor, induces selective depletion of alloreactive or phytohaemagglutinin-stimulated peripheral blood mononuclear cells, decreases production of T helper type 1 cytokines, and blocks maturation of dendritic cells. Immunology 20080601
Induction of apoptosis in Epstein-Barr virus-infected B-lymphocytes by the NF-kappaB inhibitor DHMEQ. Microbes and infection 20080601
Effects of DHMEQ, a novel nuclear factor-kappab inhibitor, on beta cell dysfunction in INS-1 cells. Endocrine journal 20080501
The novel NF-kappaB activation inhibitor dehydroxymethyl-epoxyquinomicin suppresses anti-Thy1.1-induced glomerulonephritis in rats. Nephron. Experimental nephrology 20080101
Dehydroxymethylepoxyquinomicin (DHMEQ) therapy reduces tumor formation in mice inoculated with tax-deficient adult T-cell leukemia-derived cell lines. Cancer letters 20071118
Targeting NF-kappaB and induction of apoptosis by novel NF-kappaB inhibitor dehydroxymethylepoxyquinomicin (DHMEQ) in Burkitt lymphoma cells. Leukemia research 20071101
[Screening of bioactive metabolites that suppress inflammation]. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20071001
Suppression of diabetes-induced retinal inflammation by blocking the angiotensin II type 1 receptor or its downstream nuclear factor-kappaB pathway. Investigative ophthalmology & visual science 20070901
Nuclear factor-kB in thyroid carcinogenesis and progression: a novel therapeutic target for advanced thyroid cancer. Arquivos brasileiros de endocrinologia e metabologia 20070701
IkappaBalpha independent induction of NF-kappaB and its inhibition by DHMEQ in Hodgkin/Reed-Sternberg cells. Laboratory investigation; a journal of technical methods and pathology 20070401
Reversal of resistance to cytotoxic cancer therapies: DHMEQ as a chemo-sensitizing and immuno-sensitizing agent. Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20070101
NF-kappaB inhibitor dehydroxymethylepoxyquinomicin suppresses osteoclastogenesis and expression of NFATc1 in mouse arthritis without affecting expression of RANKL, osteoprotegerin or macrophage colony-stimulating factor. Arthritis research & therapy 20070101
Control of allograft rejection by applying a novel nuclear factor-kappaB inhibitor, dehydroxymethylepoxyquinomicin. Transplantation 20061227
A selective NFkappaB inhibitor, DHMEQ, reduced atherosclerosis in ApoE-deficient mice. Journal of atherosclerosis and thrombosis 20061201
[Clinical and hematological characteristics of adult T-cell leukemia/lymphoma]. [Rinsho ketsueki] The Japanese journal of clinical hematology 20061201
Inhibition of macrophage activation and phagocytosis by a novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20061101
Significance of autologous interleukin-6 production in the HA22T/VGH cell model of hepatocellular carcinoma. Annals of the New York Academy of Sciences 20061101
Inhibition of tumor growth by NF-kappaB inhibitors. Cancer science 20061001
DHMEQ, a novel NF-kappaB inhibitor, induces apoptosis and cell-cycle arrest in human hepatoma cells. International journal of oncology 20060901
DHMEQ, a new NF-kappaB inhibitor, induces apoptosis and enhances fludarabine effects on chronic lymphocytic leukemia cells. Leukemia 20060501
Blocking NF-kappaB as a potential strategy to treat adult T-cell leukemia/lymphoma. Drug news & perspectives 20060501
Survivin associates with cell proliferation in renal cancer cells: regulation of survivin expression by insulin-like growth factor-1, interferon-gamma and a novel NF-kappaB inhibitor. International journal of oncology 20060401
Antitumor effects of the novel NF-kappaB inhibitor dehydroxymethyl-epoxyquinomicin on human hepatic cancer cells: analysis of synergy with cisplatin and of possible correlation with inhibition of pro-survival genes and IL-6 production. International journal of oncology 20060401
Effects of a novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin (DHMEQ), on growth, apoptosis, gene expression, and chemosensitivity in head and neck squamous cell carcinoma cell lines. Head & neck 20060201
In vitro and in vivo antitumor activity of the NF-kappaB inhibitor DHMEQ in the human T-cell leukemia virus type I-infected cell line, HUT-102. Leukemia research 20060101
Enhancement of the caspase-independent apoptotic sensitivity of pancreatic cancer cells by DHMEQ, an NF-kappaB inhibitor. International journal of oncology 20051101
Dual targeting of transformed and untransformed HTLV-1-infected T cells by DHMEQ, a potent and selective inhibitor of NF-kappaB, as a strategy for chemoprevention and therapy of adult T-cell leukemia. Blood 20051001
In vivo antitumor activity of the NF-kappaB inhibitor dehydroxymethylepoxyquinomicin in a mouse model of adult T-cell leukemia. Carcinogenesis 20050801
Prevention of cancer cachexia by a novel nuclear factor {kappa}B inhibitor in prostate cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 20050801
Inhibition of inflammatory cytokine secretion from mouse microglia cells by DHMEQ, an NF-kappaB inhibitor. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20050701
Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, induces apoptosis in multiple myeloma cells in an IkappaBalpha-independent manner. Molecular cancer therapeutics 20050701
Inhibition of RANKL-induced osteoclastogenesis by (-)-DHMEQ, a novel NF-kappaB inhibitor, through downregulation of NFATc1. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050401
A novel NF-kappaB inhibitor DHMEQ selectively targets constitutive NF-kappaB activity and induces apoptosis of multiple myeloma cells in vitro and in vivo. International journal of cancer 20050310
Targeting of nuclear factor kappaB Pathways by dehydroxymethylepoxyquinomicin, a novel inhibitor of breast carcinomas: antitumor and antiangiogenic potential in vivo. Clinical cancer research : an official journal of the American Association for Cancer Research 20050201
Effect of a small molecule inhibitor of nuclear factor-kappaB nuclear translocation in a murine model of arthritis and cultured human synovial cells. Arthritis research & therapy 20050101
Inhibition of cellular adhesion in human umbilical vein endothelial cells by NF-kappaB inhibitor DHMEQ under flow. Oncology research 20050101
Induction of thyroid cancer cell apoptosis by a novel nuclear factor kappaB inhibitor, dehydroxymethylepoxyquinomicin. Clinical cancer research : an official journal of the American Association for Cancer Research 20041015
Antitumor effect of a novel nuclear factor-kappa B activation inhibitor in bladder cancer cells. Expert review of anticancer therapy 20031201
Novel nuclear factor kappa B activation inhibitor prevents inflammatory injury in unilateral ureteral obstruction. The Journal of urology 20030401
Suppression of hormone-refractory prostate cancer by a novel nuclear factor kappaB inhibitor in nude mice. Cancer research 20030101
Preparation of radioactively labeled dehydroxymethyl-epoxyquinomicin, an NF-kappa B function inhibitor. Drugs under experimental and clinical research 20030101
Synthesis and structure-activity relationship of dehydroxymethylepoxyquinomicin analogues as inhibitors of NF-kappaB functions. Bioorganic & medicinal chemistry 20021201
Molecular design and biological activities of NF-kappaB inhibitors. Molecules and cells 20021031
Inhibition of tumor necrosis factor-alpha -induced nuclear translocation and activation of NF-kappa B by dehydroxymethylepoxyquinomicin. The Journal of biological chemistry 20020705
Properties