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287194-40-5,MFCD11100254
Catalog No.:AA002W6D

287194-40-5 | (-)-DHMEQ

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2mg
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1 week  
$241.00   $169.00
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5mg
98%
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$368.00   $258.00
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10mg
98%
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$527.00   $369.00
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25mg
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$924.00   $647.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002W6D
Chemical Name:
(-)-DHMEQ
CAS Number:
287194-40-5
Molecular Formula:
C13H11NO5
Molecular Weight:
261.2301
MDL Number:
MFCD11100254
SMILES:
O=C1C=C(NC(=O)c2ccccc2O)[C@@H]([C@H]2[C@@H]1O2)O
Properties
Properties
 
Form:
Solid  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
446  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  

Downstream Synthesis Route
2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-<i>N</i>-(2-hydroxy-5-oxo-7-oxa-bicyclo4.1.0hept-3-en-3-yl)-benzamide 
  287194-40-5 

[1]Matsumoto,Naoki;Ariga,Akiko;To-E,Sakino;Nakamura,Hikaru;Agata,Naoki;Hirano,Shin-Ichi;Inoue,Jun-Ichiro;Umezawa,Kazuo[BioorganicandMedicinalChemistryLetters,2000,vol.10,#9,p.865-869]

2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo4.1.0hept-3-en-3-yl)benzamide 
 
(2R,3R,4R)-2,3-epoxy-4-hydroxy-5-N-(2-hydroxybenzyl)aminocyclohex-5-en-1-one 
  287194-40-5 

[1]Suzuki,Yoshikazu;Sugiyama,Chie;Ohno,Osamu;Umezawa,Kazuo[Tetrahedron,2004,vol.60,#33,p.7061-7066]

[1]Suzuki,Yoshikazu;Sugiyama,Chie;Ohno,Osamu;Umezawa,Kazuo[Tetrahedron,2004,vol.60,#33,p.7061-7066]

[2]Matsumoto,Naoki;Ariga,Akiko;To-E,Sakino;Nakamura,Hikaru;Agata,Naoki;Hirano,Shin-Ichi;Inoue,Jun-Ichiro;Umezawa,Kazuo[BioorganicandMedicinalChemistryLetters,2000,vol.10,#9,p.865-869]

[1]Suzuki,Yoshikazu;Sugiyama,Chie;Ohno,Osamu;Umezawa,Kazuo[Tetrahedron,2004,vol.60,#33,p.7061-7066]

2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo4.1.0hept-3-en-3-yl)benzamide 
  287194-40-5 

[1]Matsumoto,Naoki;Ariga,Akiko;To-E,Sakino;Nakamura,Hikaru;Agata,Naoki;Hirano,Shin-Ichi;Inoue,Jun-Ichiro;Umezawa,Kazuo[BioorganicandMedicinalChemistryLetters,2000,vol.10,#9,p.865-869]

Literature

Title: Exposure to a combination of formaldehyde and DINP aggravated asthma-like pathology through oxidative stress and NF-κB activation.

Journal: Toxicology 20180701

Title: Ligand-dependent EGFR activation induces the co-expression of IL-6 and PAI-1 via the NFkB pathway in advanced-stage epithelial ovarian cancer.

Journal: Oncogene 20120913

Title: The novel NF-κB inhibitor DHMEQ synergizes with celecoxib to exert antitumor effects on human liver cancer cells by a ROS-dependent mechanism.

Journal: Cancer letters 20120901

Title: Enhancement of radiosensitivity by a unique novel NF-κB inhibitor, DHMEQ, in prostate cancer.

Journal: British journal of cancer 20120807

Title: Dehydroxymethylepoxyquinomicin (DHMEQ), a novel NF-kappaB inhibitor, inhibits allergic inflammation and airway remodelling in murine models of asthma.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20120801

Title: Inhibition of nuclear factor-κB by dehydroxymethylepoxyquinomicin induces schedule-dependent chemosensitivity to anticancer drugs and enhances chemoinduced apoptosis in osteosarcoma cells.

Journal: Anti-cancer drugs 20120701

Title: Involvement of NF-κB-mediated expression of galectin-3-binding protein in TNF-α-induced breast cancer cell adhesion.

Journal: Oncology reports 20120601

Title: Immunomodulatory effect of nuclear factor-κB inhibition by dehydroxymethylepoxyquinomicin in combination with donor-specific blood transfusion.

Journal: Transplantation 20120427

Title: Involvement of DNA binding domain in the cellular stability and importin affinity of NF-κB component RelB.

Journal: Organic & biomolecular chemistry 20120421

Title: A novel NF-κB inhibitor, dehydroxymethylepoxyquinomicin, ameliorates inflammatory colonic injury in mice.

Journal: Journal of Crohn's & colitis 20120301

Title: Antitumor effect of dehydroxymethylepoxyquinomicin, a small molecule inhibitor of nuclear factor-κB, on glioblastoma.

Journal: Neuro-oncology 20120101

Title: Suppression of inflammatory cytokine secretion by an NF-ĸB inhibitor DHMEQ in nasal polyps fibroblasts.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20120101

Title: 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.

Journal: Chemical & pharmaceutical bulletin 20120101

Title: 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.

Journal: Cancer science 20111101

Title: Design and synthesis of biotinylated DHMEQ for direct identification of its target NF-κB components.

Journal: Bioorganic & medicinal chemistry letters 20111101

Title: Dehydroxymethylepoxyquinomicin (DHMEQ) can suppress tumour necrosis factor-α production in lipopolysaccharide-injected mice, resulting in rescuing mice from death in vivo.

Journal: Clinical and experimental immunology 20111101

Title: Possible role of peritoneal NF-κB in peripheral inflammation and cancer: lessons from the inhibitor DHMEQ.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20110701

Title: Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a new activator of antioxidant transcription factor Nrf2.

Journal: Organic & biomolecular chemistry 20110621

Title: [NF-kappaB inhibitor].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20110601

Title: Inhibition of nuclear factor-kappaB suppresses peritoneal dissemination of gastric cancer by blocking cancer cell adhesion.

Journal: Cancer science 20110501

Title: Anti-tumor activity of dehydroxymethylepoxyquinomicin against human oral squamous cell carcinoma cell lines in vitro and in vivo.

Journal: Oral oncology 20110501

Title: Inhibition of immune activation by a novel nuclear factor-kappa B inhibitor in HTLV-I-associated neurologic disease.

Journal: Blood 20110324

Title: Apoptosis in mouse amniotic epithelium is induced by activated macrophages through the TNF receptor type 1/TNF pathway.

Journal: Biology of reproduction 20110201

Title: Hydrogen and N-acetyl-L-cysteine rescue oxidative stress-induced angiogenesis in a mouse corneal alkali-burn model.

Journal: Investigative ophthalmology & visual science 20110121

Title: Coffee induces breast cancer resistance protein expression in Caco-2 cells.

Journal: Biological & pharmaceutical bulletin 20110101

Title: The side population, as a precursor of Hodgkin and Reed-Sternberg cells and a target for nuclear factor-κB inhibitors in Hodgkin's lymphoma.

Journal: Cancer science 20101101

Title: A new NF-κB inhibitor based on the amino-epoxyquinol core of DHMEQ.

Journal: Bioorganic & medicinal chemistry letters 20101001

Title: Donor pretreatment with DHMEQ improves islet transplantation.

Journal: The Journal of surgical research 20100901

Title: Topical application of dehydroxymethylepoxyquinomicin improves allergic inflammation via NF-kappaB inhibition.

Journal: The Journal of allergy and clinical immunology 20100801

Title: Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, prevents inflammatory injury induced by interferon-gamma and histamine in NCTC 2544 keratinocytes.

Journal: Clinical and experimental pharmacology & physiology 20100701

Title: Inhibition of active HIV-1 replication by NF-kappaB inhibitor DHMEQ.

Journal: Microbes and infection 20100501

Title: Characterizing the involvement of the nuclear factor-kappa B (NF kappa B) transcription factor in uveal melanoma.

Journal: Investigative ophthalmology & visual science 20100401

Title: Amelioration of experimental autoimmune uveoretinitis with nuclear factor-{kappa}B Inhibitor dehydroxy methyl epoxyquinomicin in mice.

Journal: Investigative ophthalmology & visual science 20100401

Title: Potent cytotoxic effect of a novel nuclear factor-kappaB inhibitor dehydroxymethylepoxyquinomicin on human bladder cancer cells producing various cytokines.

Journal: Urology 20100401

Title: Gene set enrichment analysis provides insight into novel signalling pathways in breast cancer stem cells.

Journal: British journal of cancer 20100105

Title: A small molecule inhibitor of NF-kappaB, dehydroxymethylepoxyquinomicin (DHMEQ), suppresses growth and invasion of nasopharyngeal carcinoma (NPC) cells.

Journal: Cancer letters 20100101

Title: Dehydroxymethylepoxyquinomicin inhibits expression and production of inflammatory mediators in interleukin-1beta-induced human chondrocytes.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101

Title: Efficient cellular uptake of the novel NF-kappaB inhibitor (-)-DHMEQ and irreversible inhibition of NF-kappaB in neoplastic cells.

Journal: Oncology research 20100101

Title: Induction of oncogene addiction shift to NF-kappaB by camptothecin in solid tumor cells.

Journal: Biochemical and biophysical research communications 20091204

Title: Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.

Journal: Bioorganic & medicinal chemistry letters 20090915

Title: Unusual intramolecular N-->O acyl group migration occurring during conjugation of (-)-DHMEQ with cysteine.

Journal: Bioorganic & medicinal chemistry letters 20090915

Title: Impairment of plasmacytoid dendritic cells for IFN production by the ligand for immunoglobulin-like transcript 7 expressed on human cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090915

Title: Possible involvement of chemokine-induced platelet activation in thrombophilic diathesis of antiphospholipid syndrome.

Journal: Annals of the New York Academy of Sciences 20090901

Title: Antitumor effects of dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, in human liver cancer cells are mediated through a reactive oxygen species-dependent mechanism.

Journal: Molecular pharmacology 20090801

Title: Inhibition of inflammatory mediator secretion by (-)-DHMEQ in mouse bone marrow-derived macrophages.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20090601

Title: Transient inhibition of NF-kappaB by DHMEQ induces cell death of primary effusion lymphoma without HHV-8 reactivation.

Journal: Cancer science 20090401

Title: Induction of histidine decarboxylase in macrophages inhibited by the novel NF-kappaB inhibitor (-)-DHMEQ.

Journal: Biochemical and biophysical research communications 20090206

Title: Chemosensitization and immunosensitization of resistant cancer cells to apoptosis and inhibition of metastasis by the specific NF-kappaB inhibitor DHMEQ.

Journal: Current pharmaceutical design 20090101

Title: Growth suppression and apoptosis induction in synovial sarcoma cell lines by a novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin (DHMEQ).

Journal: Cancer letters 20081218

Title: Identification of the RelA domain responsible for action of a new NF-kappaB inhibitor DHMEQ.

Journal: Biochemical and biophysical research communications 20081114

Title: Dehydroxymethylepoxyquinomicin, a novel nuclear Factor-kappaB inhibitor, enhances antitumor activity of taxanes in anaplastic thyroid cancer cells.

Journal: Endocrinology 20081101

Title: The NF-kappaB inhibitors (bortezomib and DHMEQ) sensitise rituximab-resistant AIDS-B-non-Hodgkin lymphoma to apoptosis by various chemotherapeutic drugs.

Journal: Leukemia & lymphoma 20081001

Title: Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.

Journal: Journal of medicinal chemistry 20080925

Title: DHMEQ, a novel NF-kappaB inhibitor, suppresses growth and type I collagen accumulation in keloid fibroblasts.

Journal: Journal of dermatological science 20080901

Title: The novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin, prevents local and remote organ injury following intestinal ischemia/reperfusion in rats.

Journal: The Journal of surgical research 20080901

Title: A simple and reliable method for determining plasma concentration of dehydroxymethylepoxyquinomicin by high performance liquid chromatography with mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080801

Title: 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.

Journal: Immunology 20080601

Title: Induction of apoptosis in Epstein-Barr virus-infected B-lymphocytes by the NF-kappaB inhibitor DHMEQ.

Journal: Microbes and infection 20080601

Title: Effects of DHMEQ, a novel nuclear factor-kappab inhibitor, on beta cell dysfunction in INS-1 cells.

Journal: Endocrine journal 20080501

Title: The novel NF-kappaB activation inhibitor dehydroxymethyl-epoxyquinomicin suppresses anti-Thy1.1-induced glomerulonephritis in rats.

Journal: Nephron. Experimental nephrology 20080101

Title: Dehydroxymethylepoxyquinomicin (DHMEQ) therapy reduces tumor formation in mice inoculated with tax-deficient adult T-cell leukemia-derived cell lines.

Journal: Cancer letters 20071118

Title: Targeting NF-kappaB and induction of apoptosis by novel NF-kappaB inhibitor dehydroxymethylepoxyquinomicin (DHMEQ) in Burkitt lymphoma cells.

Journal: Leukemia research 20071101

Title: [Screening of bioactive metabolites that suppress inflammation].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20071001

Title: Suppression of diabetes-induced retinal inflammation by blocking the angiotensin II type 1 receptor or its downstream nuclear factor-kappaB pathway.

Journal: Investigative ophthalmology & visual science 20070901

Title: Nuclear factor-kB in thyroid carcinogenesis and progression: a novel therapeutic target for advanced thyroid cancer.

Journal: Arquivos brasileiros de endocrinologia e metabologia 20070701

Title: IkappaBalpha independent induction of NF-kappaB and its inhibition by DHMEQ in Hodgkin/Reed-Sternberg cells.

Journal: Laboratory investigation; a journal of technical methods and pathology 20070401

Title: Reversal of resistance to cytotoxic cancer therapies: DHMEQ as a chemo-sensitizing and immuno-sensitizing agent.

Journal: Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20070101

Title: NF-kappaB inhibitor dehydroxymethylepoxyquinomicin suppresses osteoclastogenesis and expression of NFATc1 in mouse arthritis without affecting expression of RANKL, osteoprotegerin or macrophage colony-stimulating factor.

Journal: Arthritis research & therapy 20070101

Title: Control of allograft rejection by applying a novel nuclear factor-kappaB inhibitor, dehydroxymethylepoxyquinomicin.

Journal: Transplantation 20061227

Title: A selective NFkappaB inhibitor, DHMEQ, reduced atherosclerosis in ApoE-deficient mice.

Journal: Journal of atherosclerosis and thrombosis 20061201

Title: [Clinical and hematological characteristics of adult T-cell leukemia/lymphoma].

Journal: [Rinsho ketsueki] The Japanese journal of clinical hematology 20061201

Title: Inhibition of macrophage activation and phagocytosis by a novel NF-kappaB inhibitor, dehydroxymethylepoxyquinomicin.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20061101

Title: Significance of autologous interleukin-6 production in the HA22T/VGH cell model of hepatocellular carcinoma.

Journal: Annals of the New York Academy of Sciences 20061101

Title: Inhibition of tumor growth by NF-kappaB inhibitors.

Journal: Cancer science 20061001

Title: DHMEQ, a novel NF-kappaB inhibitor, induces apoptosis and cell-cycle arrest in human hepatoma cells.

Journal: International journal of oncology 20060901

Title: DHMEQ, a new NF-kappaB inhibitor, induces apoptosis and enhances fludarabine effects on chronic lymphocytic leukemia cells.

Journal: Leukemia 20060501

Title: Blocking NF-kappaB as a potential strategy to treat adult T-cell leukemia/lymphoma.

Journal: Drug news & perspectives 20060501

Title: 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.

Journal: International journal of oncology 20060401

Title: 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.

Journal: International journal of oncology 20060401

Title: 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.

Journal: Head & neck 20060201

Title: 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.

Journal: Leukemia research 20060101

Title: Enhancement of the caspase-independent apoptotic sensitivity of pancreatic cancer cells by DHMEQ, an NF-kappaB inhibitor.

Journal: International journal of oncology 20051101

Title: 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.

Journal: Blood 20051001

Title: In vivo antitumor activity of the NF-kappaB inhibitor dehydroxymethylepoxyquinomicin in a mouse model of adult T-cell leukemia.

Journal: Carcinogenesis 20050801

Title: Prevention of cancer cachexia by a novel nuclear factor {kappa}B inhibitor in prostate cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050801

Title: Inhibition of inflammatory cytokine secretion from mouse microglia cells by DHMEQ, an NF-kappaB inhibitor.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20050701

Title: Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, induces apoptosis in multiple myeloma cells in an IkappaBalpha-independent manner.

Journal: Molecular cancer therapeutics 20050701

Title: Inhibition of RANKL-induced osteoclastogenesis by (-)-DHMEQ, a novel NF-kappaB inhibitor, through downregulation of NFATc1.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050401

Title: A novel NF-kappaB inhibitor DHMEQ selectively targets constitutive NF-kappaB activity and induces apoptosis of multiple myeloma cells in vitro and in vivo.

Journal: International journal of cancer 20050310

Title: Targeting of nuclear factor kappaB Pathways by dehydroxymethylepoxyquinomicin, a novel inhibitor of breast carcinomas: antitumor and antiangiogenic potential in vivo.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050201

Title: Effect of a small molecule inhibitor of nuclear factor-kappaB nuclear translocation in a murine model of arthritis and cultured human synovial cells.

Journal: Arthritis research & therapy 20050101

Title: Inhibition of cellular adhesion in human umbilical vein endothelial cells by NF-kappaB inhibitor DHMEQ under flow.

Journal: Oncology research 20050101

Title: Induction of thyroid cancer cell apoptosis by a novel nuclear factor kappaB inhibitor, dehydroxymethylepoxyquinomicin.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041015

Title: Antitumor effect of a novel nuclear factor-kappa B activation inhibitor in bladder cancer cells.

Journal: Expert review of anticancer therapy 20031201

Title: Novel nuclear factor kappa B activation inhibitor prevents inflammatory injury in unilateral ureteral obstruction.

Journal: The Journal of urology 20030401

Title: Suppression of hormone-refractory prostate cancer by a novel nuclear factor kappaB inhibitor in nude mice.

Journal: Cancer research 20030101

Title: Preparation of radioactively labeled dehydroxymethyl-epoxyquinomicin, an NF-kappa B function inhibitor.

Journal: Drugs under experimental and clinical research 20030101

Title: Synthesis and structure-activity relationship of dehydroxymethylepoxyquinomicin analogues as inhibitors of NF-kappaB functions.

Journal: Bioorganic & medicinal chemistry 20021201

Title: Molecular design and biological activities of NF-kappaB inhibitors.

Journal: Molecules and cells 20021031

Title: Inhibition of tumor necrosis factor-alpha -induced nuclear translocation and activation of NF-kappa B by dehydroxymethylepoxyquinomicin.

Journal: The Journal of biological chemistry 20020705

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