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52665-74-4,MFCD18432704
Catalog No.:AA00DDRR

52665-74-4 | MANUMYCIN A

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1mg
≥98%
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$159.00   $111.00
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5mg
≥98%
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$589.00   $412.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DDRR
Chemical Name:
MANUMYCIN A
CAS Number:
52665-74-4
Molecular Formula:
C31H38N2O7
Molecular Weight:
550.6426
MDL Number:
MFCD18432704
SMILES:
CCCC[C@H](/C=C(/C=C(/C(=O)NC1=C[C@@](O)(/C=C/C=C/C=C/C(=O)NC2=C(O)CCC2=O)[C@H]2[C@@H](C1=O)O2)\C)\C)C
Properties
Properties
 
Storage:
Light sensitive;-20 ℃;Inert atmosphere;  

Computed Properties
 
Complexity:
1260  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
5  
Heavy Atom Count:
40  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
12  
XLogP3:
4.1  

Literature

Title: Areca nut components affect COX-2, cyclin B1/cdc25C and keratin expression, PGE2 production in keratinocyte is related to reactive oxygen species, CYP1A1, Src, EGFR and Ras signaling.

Journal: PloS one 20140101

Title: Tandem enzymatic oxygenations in biosynthesis of epoxyquinone pharmacophore of manumycin-type metabolites.

Journal: Chemistry & biology 20130725

Title: In vitro antifungal activity of farnesyltransferase inhibitors against clinical isolates of Aspergillus and Candida.

Journal: Annals of clinical microbiology and antimicrobials 20130101

Title: Role of RhoB in the regulation of pulmonary endothelial and smooth muscle cell responses to hypoxia.

Journal: Circulation research 20120525

Title: Effect of starter unit availability on the spectrum of manumycin-type metabolites produced by Streptomyces nodosus ssp. asukaensis.

Journal: Journal of applied microbiology 20111101

Title: Signaling cascades mediate astrocyte death induced by zinc.

Journal: Toxicology letters 20110728

Title: The farnesyltransferase inhibitors tipifarnib and lonafarnib inhibit cytokines secretion in a cellular model of mevalonate kinase deficiency.

Journal: Pediatric research 20110701

Title: Prevention of transplant coronary artery disease by prenylation inhibitors.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20110701

Title: Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes.

Journal: Archives of biochemistry and biophysics 20110315

Title: Enhanced antiproliferative and apoptotic response of HT-29 adenocarcinoma cells to combination of photoactivated hypericin and farnesyltransferase inhibitor manumycin A.

Journal: International journal of molecular sciences 20110101

Title: Polygonatum cyrtonema lectin induces murine fibrosarcoma L929 cell apoptosis and autophagy via blocking Ras-Raf and PI3K-Akt signaling pathways.

Journal: Biochimie 20101201

Title: BCR-ABL but not JAK2 V617F inhibits erythropoiesis through the Ras signal by inducing p21CIP1/WAF1.

Journal: The Journal of biological chemistry 20101008

Title: Plumbagin activates ERK1/2 and Akt via superoxide, Src and PI3-kinase in 3T3-L1 cells.

Journal: European journal of pharmacology 20100725

Title: Targeting farnesyl-transferase as a novel therapeutic strategy for mevalonate kinase deficiency: in vitro and in vivo approaches.

Journal: Pharmacological research 20100601

Title: Selective cytotoxicity of glycyrrhetinic acid against tumorigenic r/m HM-SFME-1 cells: potential involvement of H-Ras downregulation.

Journal: Toxicology letters 20100215

Title: Reversal of age-dependent nuclear morphology by inhibition of prenylation does not affect lifespan in Caenorhabditis elegans.

Journal: Nucleus (Austin, Tex.) 20100101

Title: Farnesyltransferase inhibitors reduce Ras activation and ameliorate acetaminophen-induced liver injury in mice.

Journal: Hepatology (Baltimore, Md.) 20091101

Title: Phosphorylation of histone H3 at Ser10: its role in cell transformation by v-Src.

Journal: Biochemical and biophysical research communications 20090904

Title: Manumycin inhibits STAT3, telomerase activity, and growth of glioma cells by elevating intracellular reactive oxygen species generation.

Journal: Free radical biology & medicine 20090815

Title: Hypoinsulinemia alleviates the GRF1/Ras/Akt anti-apoptotic pathway and induces alterations of mitochondrial ras trafficking in neuronal cells.

Journal: Neurochemical research 20090601

Title: Autophagy induced by farnesyltransferase inhibitors in cancer cells.

Journal: Cancer biology & therapy 20081001

Title: [Effects of manumycin combined with methoxyamine on apoptosis in myeloid leukemia U937 cells].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20080801

Title: Receptor-mediated tobacco toxicity: acceleration of sequential expression of alpha5 and alpha7 nicotinic receptor subunits in oral keratinocytes exposed to cigarette smoke.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080501

Title: Expression of rTSbeta as a 5-fluorouracil resistance marker in patients with primary breast cancer.

Journal: Oncology reports 20080401

Title: Endothelin-1 induction of Glut1 transcription in 3T3-L1 adipocytes involves distinct PKCepsilon- and p42/p44 MAPK-dependent pathways.

Journal: Biochimica et biophysica acta 20080201

Title: Simvastatin alleviates diabetes-induced VEGF-mediated nephropathy via the modulation of Ras signaling pathway.

Journal: Renal failure 20080101

Title: Oridonin induced autophagy in human cervical carcinoma HeLa cells through Ras, JNK, and P38 regulation.

Journal: Journal of pharmacological sciences 20071201

Title: Diastereoselective spiroannulation of phenolic substrates: advances towards the asymmetric formation of the manumycin m-C7N core skeleton.

Journal: Molecules (Basel, Switzerland) 20070925

Title: Inactivation of ras and changes of mitochondrial membrane potential contribute to oridonin-induced autophagy in a431 cells.

Journal: Journal of pharmacological sciences 20070901

Title: Combination chemotherapy including combretastatin A4 phosphate and paclitaxel is effective against anaplastic thyroid cancer in a nude mouse xenograft model.

Journal: The Journal of clinical endocrinology and metabolism 20070801

Title: Methylglyoxal-induced fibronectin gene expression through Ras-mediated NADPH oxidase activation in renal mesangial cells.

Journal: Nephrology (Carlton, Vic.) 20070801

Title: Requirement of reactive oxygen species generation in apoptosis of leukemia cells induced by 2-methoxyestradiol.

Journal: Acta pharmacologica Sinica 20070701

Title: Farnesyltransferase inhibitor, manumycin a, prevents atherosclerosis development and reduces oxidative stress in apolipoprotein E-deficient mice.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20070601

Title: Ras activation modulates methylglyoxal-induced mesangial cell apoptosis through superoxide production.

Journal: Renal failure 20070101

Title: Fibroblast growth factor-2 suppresses oridonin-induced L929 apoptosis through extracellular signal-regulated kinase-dependent and phosphatidylinositol 3-kinase-independent pathway.

Journal: Journal of pharmacological sciences 20061101

Title: Equilibrium in lung schistosomula sphingomyelin breakdown and biosynthesis allows very small molecules, but not antibody, to access proteins at the host-parasite interface.

Journal: The Journal of parasitology 20060801

Title: Combining a matrix metalloproteinase inhibitor, a farnesyltransferase inhibitor, and a taxane improves survival in an anaplastic thyroid cancer model.

Journal: Cancer letters 20060718

Title: Ras modulation of superoxide activates ERK-dependent fibronectin expression in diabetes-induced renal injuries.

Journal: Kidney international 20060501

Title: Redox control of manumycin A-induced apoptosis in anaplastic thyroid cancer cells: involvement of the xenobiotic apoptotic pathway.

Journal: Cancer biology & therapy 20060301

Title: Binding of manumycin A inhibits IkappaB kinase beta activity.

Journal: The Journal of biological chemistry 20060203

Title: Roles of Ras and extracellular signal-regulated kinase-dependent IkappaBalpha degradation in oridonin-enhanced phagocytosis of apoptotic cells by human macrophage-like U937 cells.

Journal: International immunopharmacology 20060201

Title: HMG-CoA reductase inhibitors upregulate heme oxygenase-1 expression in murine RAW264.7 macrophages via ERK, p38 MAPK and protein kinase G pathways.

Journal: Cellular signalling 20060101

Title: Modulation of parathyroid hormone-related protein levels (PTHrP) in anaplastic thyroid cancer.

Journal: Surgery 20050901

Title: Bcl-2-associated X protein is the main mediator of manumycin a-induced apoptosis in anaplastic thyroid cancer cells.

Journal: The Journal of clinical endocrinology and metabolism 20050601

Title: Requirement of multiple signaling pathways for the augmented production of hyaluronan by v-Src.

Journal: Nagoya journal of medical science 20050601

Title: Farnesyltransferase inhibitors induce DNA damage via reactive oxygen species in human cancer cells.

Journal: Cancer research 20050501

Title: Enhancement of manumycin A-induced apoptosis by methoxyamine in myeloid leukemia cells.

Journal: Leukemia 20050401

Title: Toll-like receptor 2 and mitogen- and stress-activated kinase 1 are effectors of Mycobacterium avium-induced cyclooxygenase-2 expression in macrophages.

Journal: The Journal of biological chemistry 20041231

Title: YC-1-induced cyclooxygenase-2 expression is mediated by cGMP-dependent activations of Ras, phosphoinositide-3-OH-kinase, Akt, and nuclear factor-kappaB in human pulmonary epithelial cells.

Journal: Molecular pharmacology 20040901

Title: Peptidoglycan induces nuclear factor-kappaB activation and cyclooxygenase-2 expression via Ras, Raf-1, and ERK in RAW 264.7 macrophages.

Journal: The Journal of biological chemistry 20040514

Title: Further studies on the biosynthesis of the manumycin-type antibiotic, asukamycin, and the chemical synthesis of protoasukamycin.

Journal: Journal of the American Chemical Society 20040331

Title: Circadian regulation of cGMP-gated channels of vertebrate cone photoreceptors: role of cAMP and Ras.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040211

Title: p21ras activation following hypoxia-ischemia in the newborn rat brain is dependent on nitric oxide synthase activity but p21ras does not contribute to neurologic injury.

Journal: Brain research. Developmental brain research 20031219

Title: Proteomic identification of heat shock protein 70 as a candidate target for enhancing apoptosis induced by farnesyl transferase inhibitor.

Journal: Proteomics 20031001

Title: Ras is a mediator of TGFbeta1 signaling in developing chick ciliary ganglion neurons.

Journal: Brain research 20030822

Title: Manumycin inhibits cell proliferation and the Ras signal transduction pathway in human hepatocellular carcinoma cells.

Journal: International journal of molecular medicine 20030601

Title: A novel metal-chelating inhibitor of protein farnesyltransferase.

Journal: Bioorganic & medicinal chemistry letters 20030505

Title: Modified radiosensitivity of pancreatic cancer xenografts by farnesyl protein transferase inhibitor and MEK inhibitor.

Journal: Oncology reports 20030101

Title: Involvement of NMDA receptors and a p21Ras-like guanosine triphosphatase in the constitutive activation of nuclear factor-kappa-B in cortical neurons.

Journal: Experimental brain research 20021201

Title: Inhibition of glucose- and calcium-induced insulin secretion from betaTC3 cells by novel inhibitors of protein isoprenylation.

Journal: The Journal of pharmacology and experimental therapeutics 20021001

Title: High-performance liquid chromatographic assay validation of Manumycin A in mouse plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020905

Title: Manumycin inhibits farnesyltransferase and induces apoptosis of drug-resistant interleukin 6-producing myeloma cells.

Journal: British journal of haematology 20020701

Title: [Correlation between inhibitory effect of Manumycin on human hepatoma cancer cell HepG2 and Ras signal transduction pathway].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20020401

Title: Biosynthesis and attachment of novel bacterial polyketide synthase starter units.

Journal: Natural product reports 20020201

Title: Increased expression of heat shock protein 70 in adherent ovarian cancer and mesothelioma following treatment with manumycin, a farnesyl transferase inhibitor.

Journal: Anticancer research 20020101

Title: Suppression of cell spreading by v-Crk requires Ras-MEK-MAP kinase signaling.

Journal: Oncogene 20010913

Title: Role of inhibitors of isoprenylation in proliferation, phenotype and apoptosis of human retinal pigment epithelium.

Journal: Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20010301

Title: Hara M, et al. Identification of Ras farnesyltransferase inhibitors by microbial screening. Proc Natl Acad Sci U S A. 1993 Mar 15;90(6):2281-5.

Title: Bernier M, et al. Binding of manumycin A inhibits IkappaB kinase beta activity. J Biol Chem. 2006 Feb 3;281(5):2551-61.

Title: Kim KH, et al. Manumycin A induces apoptosis in malignant pleural mesothelioma through regulation of Sp1 and activation of the mitochondria-related apoptotic pathway. Oncol Rep. 2016 Jul;36(1):117-24.

Title: Datta, A. et al. Manumycin A suppresses exosome biogenesis and secretion via targeted inhibition of Ras/Raf/ERK1/2 signaling and hnRNP H1 in Castration resistant prostate cancer cells. Cancer Let. 408, 73–81 (2017).

Title: Zhang H, et al. Advances in the discovery of exosome inhibitors in cancer. J Enzyme Inhib Med Chem. 2020;35(1):1322-1330.

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