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522-17-8,MFCD01740600
Catalog No.:AA00D7WK

522-17-8 | Deguelin

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5mg
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10mg
≥98%
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$150.00   $105.00
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25mg
≥98%
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$355.00   $248.00
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50mg
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100mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00D7WK
Chemical Name:
Deguelin
CAS Number:
522-17-8
Molecular Formula:
C23H22O6
Molecular Weight:
394.4172
MDL Number:
MFCD01740600
SMILES:
COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C=CC(Oc1cc2)(C)C
Properties
Properties
 
BP:
560.1°C at 760 mmHg  
Form:
Solid  
MP:
>90°C (dec.)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
674  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
6  
Rotatable Bond Count:
2  
XLogP3:
3.7  

Literature

Title: Antitumor effects of deguelin on H460 human lung cancer cells in vitro and in vivo: Roles of apoptotic cell death and H460 tumor xenografts model.

Journal: Environmental toxicology 20170101

Title: Protective role of hypoxia-inducible factor-1α-dependent CD39 and CD73 in fulminant acute liver failure.

Journal: Toxicology and applied pharmacology 20170101

Title: Synthesis and Evaluation of a Novel Deguelin Derivative, L80, which Disrupts ATP Binding to the C-terminal Domain of Heat Shock Protein 90.

Journal: Molecular pharmacology 20150801

Title: Deguelin, a selective silencer of the NPM1 mutant, potentiates apoptosis and induces differentiation in AML cells carrying the NPM1 mutation.

Journal: Annals of hematology 20150201

Title: Deguelin inhibits the migration and invasion of lung cancer A549 and H460 cells via regulating actin cytoskeleton rearrangement.

Journal: International journal of clinical and experimental pathology 20150101

Title: Deguelin inhibits the migration and invasion of U-2 OS human osteosarcoma cells via the inhibition of matrix metalloproteinase-2/-9 in vitro.

Journal: Molecules (Basel, Switzerland) 20141015

Title: Deguelin suppresses pancreatic tumor growth and metastasis by inhibiting epithelial-to-mesenchymal transition in an orthotopic model.

Journal: Oncogene 20130822

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Deguelin, an Akt inhibitor, down-regulates NF-κB signaling and induces apoptosis in colon cancer cells and inhibits tumor growth in mice.

Journal: Digestive diseases and sciences 20121101

Title: Delivering instilled hydrophobic drug to the bladder by a cationic nanoparticle and thermo-sensitive hydrogel composite system.

Journal: Nanoscale 20121021

Title: Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.

Journal: Phytochemistry 20120601

Title: Induction of DNA damage by deguelin is mediated through reducing DNA repair genes in human non-small cell lung cancer NCI-H460 cells.

Journal: Oncology reports 20120401

Title: The greening of pesticide-environment interactions: some personal observations.

Journal: Environmental health perspectives 20120401

Title: Comparison of several extraction procedures for the determination of biopesticides in soil samples by ultrahigh pressure LC-MS/MS.

Journal: Journal of separation science 20120401

Title: Synthesis of deguelin-biotin conjugates and investigation into deguelin's interactions.

Journal: Bioorganic & medicinal chemistry 20120115

Title: A new prenylated flavanone from Derris trifoliata Lour.

Journal: Molecules (Basel, Switzerland) 20120111

Title: Chronic Akt blockade aggravates pathological hypertrophy and inhibits physiological hypertrophy.

Journal: American journal of physiology. Heart and circulatory physiology 20120101

Title: Wnt signaling pathways in urological cancers: past decades and still growing.

Journal: Molecular cancer 20120101

Title: Multi-level targeting of the phosphatidylinositol-3-kinase pathway in non-small cell lung cancer cells.

Journal: PloS one 20120101

Title: Mitochondrial electron transport chain in heavy metal-induced neurotoxicity: effects of cadmium, mercury, and copper.

Journal: TheScientificWorldJournal 20120101

Title: Role of phosphatidylinositol-3-kinase pathway in head and neck squamous cell carcinoma.

Journal: Journal of oncology 20120101

Title: Radiation, inflammation, and immune responses in cancer.

Journal: Frontiers in oncology 20120101

Title: Deguelin attenuates reperfusion injury and improves outcome after orthotopic lung transplantation in the rat.

Journal: PloS one 20120101

Title: Anticancer efficacy of deguelin in human prostate cancer cells targeting glycogen synthase kinase-3 β/β-catenin pathway.

Journal: International journal of cancer 20111215

Title: Exploring the boundaries of additivity: mixtures of NADH: quinone oxidoreductase inhibitors.

Journal: Chemical research in toxicology 20110815

Title: Role for pAKT in rat urinary bladder with cyclophosphamide (CYP)-induced cystitis.

Journal: American journal of physiology. Renal physiology 20110801

Title: Radish (Raphanus sativus L. leaf) ethanol extract inhibits protein and mRNA expression of ErbB(2) and ErbB(3) in MDA-MB-231 human breast cancer cells.

Journal: Nutrition research and practice 20110801

Title: [Effects of deguelin on proliferation and apoptosis of MCF-7 breast cancer cells by phosphatidylinositol 3-kinase/Akt signaling pathway].

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20110501

Title: Activation of STAT1 is required for interferon-alpha-mediated cell death.

Journal: Experimental cell research 20110101

Title: NNK-Induced Lung Tumors: A Review of Animal Model.

Journal: Journal of oncology 20110101

Title: X-linked inhibitor of apoptosis positive nuclear labeling: a new independent prognostic biomarker of breast invasive ductal carcinoma.

Journal: Diagnostic pathology 20110101

Title: SRC-3 has a role in cancer other than as a nuclear receptor coactivator.

Journal: International journal of biological sciences 20110101

Title: Deguelin--an inhibitor to tumor lymphangiogenesis and lymphatic metastasis by downregulation of vascular endothelial cell growth factor-D in lung tumor model.

Journal: International journal of cancer 20101115

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Deguelin promotes apoptosis and inhibits angiogenesis of gastric cancer.

Journal: Oncology reports 20101001

Title: Inhibition of Cell Proliferation and MAP Kinase and Akt Pathways in Oral Squamous cell Carcinoma by Genistein and Biochanin A.

Journal: Evidence-based complementary and alternative medicine : eCAM 20100901

Title: Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20100823

Title: [Separation and preparation of two rotenoids from the roots of Derris by high-speed counter-current chromatography].

Journal: Se pu = Chinese journal of chromatography 20100801

Title: Natural toxins for use in pest management.

Journal: Toxins 20100801

Title: IGF1 activates cell cycle arrest following irradiation by reducing binding of ΔNp63 to the p21 promoter.

Journal: Cell death & disease 20100601

Title: Deguelin suppresses cell proliferation via the inhibition of survivin expression and STAT3 phosphorylation in HTLV-1-transformed T cells.

Journal: Leukemia research 20100301

Title: Cardiotoxicity of anticancer drugs: the need for cardio-oncology and cardio-oncological prevention.

Journal: Journal of the National Cancer Institute 20100106

Title: A novel inhibitor of the PI3K/Akt pathway based on the structure of inositol 1,3,4,5,6-pentakisphosphate.

Journal: British journal of cancer 20100105

Title: The role of the Akt/mTOR pathway in tobacco carcinogen-induced lung tumorigenesis.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100101

Title: Differential chemosensitization of P-glycoprotein overexpressing K562/Adr cells by withaferin A and Siamois polyphenols.

Journal: Molecular cancer 20100101

Title: A comprehensive panel of three-dimensional models for studies of prostate cancer growth, invasion and drug responses.

Journal: PloS one 20100101

Title: Suppression of lung tumorigenesis by leucine zipper/EF hand-containing transmembrane-1.

Journal: PloS one 20100101

Title: Parkinson's disease: is it a toxic syndrome?

Journal: Neurology research international 20100101

Title: 1-Nitropyrene stabilizes the mRNA of cytochrome P450 1a1, a carcinogen-metabolizing enzyme, via the Akt pathway.

Journal: Chemical research in toxicology 20091201

Title: Deguelin inhibits growth of breast cancer cells by modulating the expression of key members of the Wnt signaling pathway.

Journal: Cancer prevention research (Philadelphia, Pa.) 20091101

Title: A novel look into estrogen receptor-negative breast cancer prevention with the natural, multifunctional signal transduction inhibitor deguelin.

Journal: Cancer prevention research (Philadelphia, Pa.) 20091101

Title: Optimising resolution for a preparative separation of Chinese herbal medicine using a surrogate model sample system.

Journal: Journal of chromatography. A 20090626

Title: Nitric oxide inhibitory principles from Derris trifoliata stems.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20090601

Title: Involvement of SRC-3 in deguelin-induced apoptosis in Jurkat cells.

Journal: International journal of hematology 20090601

Title: Deguelin blocks cells survival signal pathways and induces apoptosis of HL-60 cells in vitro.

Journal: International journal of hematology 20090601

Title: Discovering chemical modifiers of oncogene-regulated hematopoietic differentiation.

Journal: Nature chemical biology 20090401

Title: Liposomal encapsulation of deguelin: evidence for enhanced antitumor activity in tobacco carcinogen-induced and oncogenic K-ras-induced lung tumorigenesis.

Journal: Cancer prevention research (Philadelphia, Pa.) 20090401

Title: Synergistic effect of ERK inhibition on tetrandrine-induced apoptosis in A549 human lung carcinoma cells.

Journal: Journal of veterinary science 20090301

Title: Targeting heat shock protein 90 overrides the resistance of lung cancer cells by blocking radiation-induced stabilization of hypoxia-inducible factor-1alpha.

Journal: Cancer research 20090215

Title: A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.

Journal: PloS one 20090101

Title: Acute inhibition of selected membrane-proximal mouse T cell receptor signaling by mitochondrial antagonists.

Journal: PloS one 20090101

Title: Angiogenesis in pre-malignant conditions.

Journal: British journal of cancer 20081209

Title: Simultaneous blockade of AP-1 and phosphatidylinositol 3-kinase pathway in non-small cell lung cancer cells.

Journal: British journal of cancer 20081209

Title: Deguelin inhibits retinal neovascularization by down-regulation of HIF-1alpha in oxygen-induced retinopathy.

Journal: Journal of cellular and molecular medicine 20081201

Title: A novel derivative of the natural agent deguelin for cancer chemoprevention and therapy.

Journal: Cancer prevention research (Philadelphia, Pa.) 20081201

Title: Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.

Journal: Journal of natural products 20081001

Title: Phenolic constituents of Amorpha fruticosa that inhibit NF-kappaB activation and related gene expression.

Journal: Journal of natural products 20081001

Title: Deguelin inhibits human hepatocellular carcinoma by antiangiogenesis and apoptosis.

Journal: Oncology reports 20080701

Title: Enhancement radiosensitization of breast cancer cells by deguelin.

Journal: Cancer biotherapy & radiopharmaceuticals 20080601

Title: Antiangiogenic effect of deguelin on choroidal neovascularization.

Journal: The Journal of pharmacology and experimental therapeutics 20080201

Title: Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20080118

Title: Identification of novel antiangiogenic anticancer activities of deguelin targeting hypoxia-inducible factor-1 alpha.

Journal: International journal of cancer 20080101

Title: Deguelin represses both the expression of nucleophosmin and some nucleoporins: Nup88 and Nup214 in Jurkat cells.

Journal: Biological & pharmaceutical bulletin 20080101

Title: Studies on cellular resilience and adaptation following acute and repetitive exposure to ozone in cultured human epithelial (HeLa) cells.

Journal: Redox report : communications in free radical research 20080101

Title: Implication of AMP-activated protein kinase and Akt-regulated survivin in lung cancer chemopreventive activities of deguelin.

Journal: Cancer research 20071215

Title: Direct evidence for the action of phosphatidylinositol (3,4,5)-trisphosphate-mediated signal transduction in the 2-cell mouse embryo.

Journal: Biology of reproduction 20071101

Title: Deguelin inhibits expression of IkappaBalpha protein and induces apoptosis of B-CLL cells in vitro.

Journal: Leukemia 20070801

Title: The phosphoinositide 3-kinase pathway in human cancer: genetic alterations and therapeutic implications.

Journal: Current genomics 20070801

Title: Structural basis for depletion of heat shock protein 90 client proteins by deguelin.

Journal: Journal of the National Cancer Institute 20070620

Title: Anti-cancer effects of deguelin on human leukemia K562 and K562/ADM cells In Vitro.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20070401

Title: AKT and CDK5/p35 mediate brain-derived neurotrophic factor induction of DARPP-32 in medium size spiny neurons in vitro.

Journal: The Journal of biological chemistry 20070309

Title: [Effect of deguelin on proliferation and apoptosis of lymphoma Daudi cells and its mechanism].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20070301

Title: The Akt inhibitor deguelin, is an angiopreventive agent also acting on the NF-kappaB pathway.

Journal: Carcinogenesis 20070201

Title: Rotenoids and flavonoids with anti-invasion of HT1080, anti-proliferation of U937, and differentiation-inducing activity in HL-60 from Erycibe expansa.

Journal: Bioorganic & medicinal chemistry 20070201

Title: [Effect of deguelin on expression of nup98 in K562 cells].

Journal: Zhongguo shi yan xue ye xue za zhi 20070201

Title: [Deguelin regulates cell cycle and nuclear pore complex protein Nup98 and Nup88 in U937 cells in vitro].

Journal: Zhonghua xue ye xue za zhi = Zhonghua xueyexue zazhi 20070201

Title: Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells.

Journal: Molecular pharmacology 20070101

Title: Soluble Fas ligand inhibits angiogenesis in rheumatoid arthritis.

Journal: Arthritis research & therapy 20070101

Title: Mechanism of uptake and retention of F-18 BMS-747158-02 in cardiomyocytes: a novel PET myocardial imaging agent.

Journal: Journal of nuclear cardiology : official publication of the American Society of Nuclear Cardiology 20070101

Title: Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand.

Journal: Chemical & pharmaceutical bulletin 20061101

Title: Deguelin, an Akt inhibitor, suppresses IkappaBalpha kinase activation leading to suppression of NF-kappaB-regulated gene expression, potentiation of apoptosis, and inhibition of cellular invasion.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20061015

Title: Deguelin inhibits expression of IkappaBalpha protein in Raji and U937 cells.

Journal: Acta pharmacologica Sinica 20060401

Title: Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.

Journal: Journal of cellular biochemistry 20060201

Title: Efficacy of deguelin and silibinin on benzo(a)pyrene-induced lung tumorigenesis in A/J mice.

Journal: Neoplasia (New York, N.Y.) 20051201

Title: Deguelin as a chemopreventive agent in mouse lung tumorigenesis induced by tobacco smoke carcinogens.

Journal: Journal of the National Cancer Institute 20051116

Title: Chemopreventive effects of deguelin, a novel Akt inhibitor, on tobacco-induced lung tumorigenesis.

Journal: Journal of the National Cancer Institute 20051116

Title: Cross-talk between the two divergent insulin signaling pathways is revealed by the protein kinase B (Akt)-mediated phosphorylation of adapter protein APS on serine 588.

Journal: The Journal of biological chemistry 20051111

Title: Fast and versatile multiresidue method for the analysis of botanical insecticides on fruits and vegetables by HPLC/DAD/MS.

Journal: Journal of agricultural and food chemistry 20051102

Title: Deguelin regulates nuclear pore complex proteins Nup98 and Nup88 in U937 cells in vitro.

Journal: Acta pharmacologica Sinica 20051001

Title: Regulating expressions of cyclin D1, pRb, and anti-cancer effects of deguelin on human Burkitt's lymphoma Daudi cells in vitro.

Journal: Acta pharmacologica Sinica 20050701

Title: Deguelin, A PI3K/AKT inhibitor, enhances chemosensitivity of leukaemia cells with an active PI3K/AKT pathway.

Journal: British journal of haematology 20050601

Title: Effect of deguelin on UVB-induced skin carcinogenesis.

Journal: Journal of chemotherapy (Florence, Italy) 20050601

Title: Mechanisms of interleukin-4 effects on calcium signaling in airway smooth muscle cells.

Journal: The Journal of pharmacology and experimental therapeutics 20050401

Title: Resistance to endotoxic shock in endothelial nitric-oxide synthase (eNOS) knock-out mice: a pro-inflammatory role for eNOS-derived no in vivo.

Journal: The Journal of biological chemistry 20050318

Title: 7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata.

Journal: Phytochemistry 20050301

Title: Rotenone, deguelin, their metabolites, and the rat model of Parkinson's disease.

Journal: Chemical research in toxicology 20041101

Title: Molecular mechanisms of deguelin-induced apoptosis in transformed human bronchial epithelial cells.

Journal: Biochemical pharmacology 20040915

Title: Natural inhibitors of carcinogenesis.

Journal: Planta medica 20040801

Title: Apoptosis induction by the natural product cancer chemopreventive agent deguelin is mediated through the inhibition of mitochondrial bioenergetics.

Journal: Apoptosis : an international journal on programmed cell death 20040701

Title: Cancer chemopreventive activity of rotenoids from Derris trifoliata.

Journal: Planta medica 20040601

Title: Co-targeting IGF-1R and c-kit: synergistic inhibition of proliferation and induction of apoptosis in H 209 small cell lung cancer cells.

Journal: British journal of cancer 20040504

Title: Deguelin-induced inhibition of cyclooxygenase-2 expression in human bronchial epithelial cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040201

Title: Rotenone and rotenoids in cubè resins, formulations, and residues on olives.

Journal: Journal of agricultural and food chemistry 20040128

Title: Cancer chemopreventive activity of rotenoids from Derris trifoliata.

Journal: Planta medica 20040101

Title: Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation.

Journal: Organic letters 20031030

Title: Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.

Journal: Pest management science 20031001

Title: Deguelin suppresses the formation of carcinogen-induced aberrant crypt foci in the colon of CF-1 mice.

Journal: International journal of cancer 20030310

Title: AKT and the phosphatidylinositol 3-kinase/AKT pathway: important molecular targets for lung cancer prevention and treatment.

Journal: Journal of the National Cancer Institute 20030219

Title: Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells.

Journal: Journal of the National Cancer Institute 20030219

Title: Deguelin inhibits the growth of colon cancer cells through the induction of apoptosis and cell cycle arrest.

Journal: European journal of cancer (Oxford, England : 1990) 20021201

Title: Discovery of cancer preventive agents from natural products: from plants to prevention.

Journal: Current oncology reports 20021101

Title: [Modification of the analytical method for rotenoids in plants].

Journal: Se pu = Chinese journal of chromatography 20020301

Title: Pharmacokinetics of deguelin, a cancer chemopreventive agent in rats.

Journal: Cancer chemotherapy and pharmacology 20010301

Title: Review article number 135 biosynthesis in the rotenoid group of natural products: applications of isotope methodology.

Journal: Phytochemistry 19981120

Title: NADH: ubiquinone oxidoreductase inhibitors block induction of ornithine decarboxylase activity in MCF-7 human breast cancer cells.

Journal: Pharmacology & toxicology 19981101

Title: Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent.

Journal: Cancer research 19970815

Title: Anomalous structure-activity relationships of 13-homo-13-oxarotenoids and 13-homo-13-oxadehyrorotenoids.

Journal: Chemical research in toxicology 19970801

Title: Mehta R, et al. Deguelin action involves c-Met and EGFR signaling pathways in triple negative breast cancer cells. PLoS One. 2013 Jun 10;8(6):e65113.

Title: Yang YL, et al. Deguelin induces both apoptosis and autophagy in cultured head and neck squamous cell carcinoma cells. PLoS One. 2013;8(1):e54736.

Title: Li Z, et al. Deguelin, a natural rotenoid, inhibits mouse myeloma cell growth in vitro via induction of apoptosis. Oncol Lett. 2012 Oct;4(4):677-681.

Title: Kang HW, et al. Deguelin, an Akt inhibitor, down-regulates NF-κB signaling and induces apoptosis in colon cancer cells and inhibits tumor growth in mice. Dig Dis Sci. 2012 Nov;57(11):2873-82.

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