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512-64-1,MFCD00156105
Catalog No.:AA00D7U8

512-64-1 | QUINOMYCIN A

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1mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00D7U8
Chemical Name:
QUINOMYCIN A
CAS Number:
512-64-1
Molecular Formula:
C51H64N12O12S2
Molecular Weight:
1101.2571
MDL Number:
MFCD00156105
SMILES:
CSC1SCC2N(C)C(=O)C(C)NC(=O)C(COC(=O)C(N(C(=O)C1N(C)C(=O)C(C)NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c1cnc2c(n1)cccc2)C)C(C)C)NC(=O)c1cnc2c(n1)cccc2
Properties
Computed Properties
 
Complexity:
2200  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
77  
Hydrogen Bond Acceptor Count:
18  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
7  
Undefined Atom Stereocenter Count:
9  
XLogP3:
2.7  

Literature

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Title: A novel role for the transcription factor HIF-1α in the formation of mast cell extracellular traps.

Journal: The Biochemical journal 20120815

Title: Iodine-deficiency-induced long lasting angiogenic reaction in thyroid cancers occurs via a vascular endothelial growth factor-hypoxia inducible factor-1-dependent, but not a reactive oxygen species-dependent, pathway.

Journal: Thyroid : official journal of the American Thyroid Association 20120701

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Title: Echinomycin decreases induction of vascular endothelial growth factor and hepatocyte regeneration in acetaminophen toxicity in mice.

Journal: Basic & clinical pharmacology & toxicology 20120401

Title: Hypoxic stress simultaneously stimulates vascular endothelial growth factor via hypoxia-inducible factor-1α and inhibits stromal cell-derived factor-1 in human endometrial stromal cells.

Journal: Human reproduction (Oxford, England) 20120201

Title: IGF-1 induces hypoxia-inducible factor 1α-mediated GLUT3 expression through PI3K/Akt/mTOR dependent pathways in PC12 cells.

Journal: Brain research 20120109

Title: Hypoxia regulates the expression of extracellular matrix associated proteins in equine dermal fibroblasts via HIF1.

Journal: Journal of dermatological science 20120101

Title: 3-Carbamoylquinoxalin-1-ium chloride.

Journal: Acta crystallographica. Section E, Structure reports online 20120101

Title: Targeting the lactate transporter MCT1 in endothelial cells inhibits lactate-induced HIF-1 activation and tumor angiogenesis.

Journal: PloS one 20120101

Title: An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using recyclable alumina-supported heteropolyoxometalates.

Journal: TheScientificWorldJournal 20120101

Title: Electrochemical behavior of quinoxalin-2-one derivatives at mercury electrodes and its analytical use.

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Journal: PloS one 20120101

Title: Physical and functional interactions between Runx2 and HIF-1α induce vascular endothelial growth factor gene expression.

Journal: Journal of cellular biochemistry 20111201

Title: Enhancement of differentiation efficiency of hESCs into vascular lineage cells in hypoxia via a paracrine mechanism.

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Journal: Endocrinology 20110701

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Journal: Journal of cellular and molecular medicine 20110301

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Journal: Bioorganic & medicinal chemistry 20110115

Title: Involvement of common intermediate 3-hydroxy-L-kynurenine in chromophore biosynthesis of quinomycin family antibiotics.

Journal: The Journal of antibiotics 20110101

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Title: 3-Methyl-1-(prop-2-en-1-yl)quinoxalin-2(1H)-one.

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Title: Pharmacological and genetic accumulation of hypoxia-inducible factor-1alpha enhances excitatory synaptic transmission in hippocampal neurons through the production of vascular endothelial growth factor.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100428

Title: Insulin induces REDD1 expression through hypoxia-inducible factor 1 activation in adipocytes.

Journal: The Journal of biological chemistry 20100219

Title: Identification of cyclooxygenase-2 as a major actor of the transcriptomic adaptation of endothelial and tumor cells to cyclic hypoxia: effect on angiogenesis and metastases.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100115

Title: Drug release from a chemically-anchored PEG/phospholipid monolayer onto polymer-coated metallic stents.

Journal: Journal of biomaterials science. Polymer edition 20100101

Title: Capture of a Transition State Using Molecular Dynamics: Creation of an Intercalation Site in dsDNA with Ethidium Cation.

Journal: Journal of nucleic acids 20100101

Title: A ferrocene-quinoxaline derivative as a highly selective probe for colorimetric and redox sensing of toxic mercury(II) cations.

Journal: Sensors (Basel, Switzerland) 20100101

Title: Rationally engineered total biosynthesis of a synthetic analogue of a natural quinomycin depsipeptide in Escherichia coli.

Journal: Chembiochem : a European journal of chemical biology 20090817

Title: Inhibition of hypoxia-inducible factor-1 function enhances the sensitivity of multiple myeloma cells to melphalan.

Journal: Molecular cancer therapeutics 20090801

Title: Gallium (III) triflate-catalyzed synthesis of heterocycles: quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives.

Journal: Future medicinal chemistry 20090801

Title: Escherichia coli allows efficient modular incorporation of newly isolated quinomycin biosynthetic enzyme into echinomycin biosynthetic pathway for rational design and synthesis of potent antibiotic unnatural natural product.

Journal: Journal of the American Chemical Society 20090708

Title: Signaling by hypoxia-inducible factors is critical for ovulation in mice.

Journal: Endocrinology 20090701

Title: Interaction of an echinomycin-DNA complex with manganese ions.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20090701

Title: Antitumor compounds from marine actinomycetes.

Journal: Marine drugs 20090601

Title: Recepteur d'origine nantais tyrosine kinase is a direct target of hypoxia-inducible factor-1alpha-mediated invasion of breast carcinoma cells.

Journal: The Journal of biological chemistry 20090522

Title: Indicator-based and indicator-free magnetic assays connected with disposable electrochemical nucleic acid sensor system.

Journal: Talanta 20090415

Title: Diversification of echinomycin molecular structure by way of chemoenzymatic synthesis and heterologous expression of the engineered echinomycin biosynthetic pathway.

Journal: Current opinion in chemical biology 20090401

Title: Manganese (II) induces chemical hypoxia by inhibiting HIF-prolyl hydroxylase: implication in manganese-induced pulmonary inflammation.

Journal: Toxicology and applied pharmacology 20090315

Title: Structure-activity studies of echinomycin antibiotics against drug-resistant and biofilm-forming Staphylococcus aureus and Enterococcus faecalis.

Journal: Bioorganic & medicinal chemistry letters 20090301

Title: TioS T-TE--a prototypical thioesterase responsible for cyclodimerization of the quinoline- and quinoxaline-type class of chromodepsipeptides.

Journal: The FEBS journal 20090301

Title: Hypoxia decreases insulin signaling pathways in adipocytes.

Journal: Diabetes 20090101

Title: Automated genome mining for natural products.

Journal: BMC bioinformatics 20090101

Title: Evaluation of molecular descriptors for antitumor drugs with respect to noncovalent binding to DNA and antiproliferative activity.

Journal: BMC pharmacology 20090101

Title: Control of oocyte release by progesterone receptor-regulated gene expression.

Journal: Nuclear receptor signaling 20090101

Title: Hypoxia-inducible factor-1alpha protects cultured cortical neurons from lipopolysaccharide-induced cell death via regulation of NR1 expression.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20081224

Title: A dialogue between the hypoxia-inducible factor and the tumor microenvironment.

Journal: Cancer microenvironment : official journal of the International Cancer Microenvironment Society 20081201

Title: NF-kappaB-dependency and consequent regulation of IL-8 in echinomycin-induced apoptosis of HT-29 colon cancer cells.

Journal: Cell biology international 20081001

Title: Exploring the biosynthesis of natural products and their inherent suitability for the rational design of desirable compounds through genetic engineering.

Journal: Bioscience, biotechnology, and biochemistry 20081001

Title: Enzymatic macrolactonization in the presence of DNA leading to triostin A analogs.

Journal: Chemistry & biology 20080825

Title: The effects of local DNA sequence on the interaction of ligands with their preferred binding sites.

Journal: Biochimie 20080701

Title: Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites.

Journal: The Journal of antibiotics 20080601

Title: [Recent progress in the study on antitumor drugs targeting hypoxia-inducible factor-1].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080601

Title: In vitro and in vivo activities of echinomycin against clinical isolates of Staphylococcus aureus.

Journal: The Journal of antimicrobial chemotherapy 20080101

Title: Improved production of triostin A in engineered Escherichia coli with furnished quinoxaline chromophore by design of experiments in small-scale culture.

Journal: Biotechnology progress 20080101

Title: Complete sequence of biosynthetic gene cluster responsible for producing triostin A and evaluation of quinomycin-type antibiotics from Streptomyces triostinicus.

Journal: Biotechnology progress 20080101

Title: Relative and absolute configuration of antitumor agent SW-163D.

Journal: Bioscience, biotechnology, and biochemistry 20071201

Title: Dual effect of echinomycin on hypoxia-inducible factor-1 activity under normoxic and hypoxic conditions.

Journal: The FEBS journal 20071101

Title: [Biosynthesis of natural products from microbes].

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

Title: Modulating hypoxia-inducible transcription by disrupting the HIF-1-DNA interface.

Journal: ACS chemical biology 20070817

Title: Probing ligand binding to duplex DNA using KMnO4 reactions and electrospray ionization tandem mass spectrometry.

Journal: Analytical chemistry 20070615

Title: The short-term effects on restenosis and thrombosis of echinomycin-eluting stents topcoated with a hydrophobic heparin-containing polymer.

Journal: Biomaterials 20070301

Title: Robust platform for de novo production of heterologous polyketides and nonribosomal peptides in Escherichia coli.

Journal: Organic & biomolecular chemistry 20070221

Title: Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies.

Journal: Natural product reports 20070201

Title: Biochemistry. Directing biosynthesis.

Journal: Science (New York, N.Y.) 20061027

Title: Identification and stereochemical assignment of the beta-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway.

Journal: Organic letters 20061012

Title: Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli.

Journal: Nature chemical biology 20060801

Title: Synergistic effects of CoCl(2) and ROCK inhibition on mesenchymal stem cell differentiation into neuron-like cells.

Journal: Journal of cell science 20060701

Title: Echinomycin and cobalt-phenanthroline as redox indicators of DNA hybridization at gold electrodes.

Journal: Frontiers in bioscience : a journal and virtual library 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Serendipitous SAD phasing of an echinomycin-(ACGTACGT)2 bisintercalation complex.

Journal: Acta crystallographica. Section D, Biological crystallography 20060401

Title: Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway.

Journal: The international journal of biochemistry & cell biology 20060201

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Title: Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity.

Journal: Cancer research 20051001

Title: Structures of complexes between echinomycin and duplex DNA.

Journal: Acta crystallographica. Section D, Biological crystallography 20050401

Title: Functional cross-talk between fatty acid synthesis and nonribosomal peptide synthesis in quinoxaline antibiotic-producing streptomycetes.

Journal: The Journal of biological chemistry 20050211

Title: Atomic force microscopy study of the structural effects induced by echinomycin binding to DNA.

Journal: Journal of molecular biology 20050128

Title: Identification of diverse microbial metabolites as potent inhibitors of HIV-1 Tat transactivation.

Journal: Chemistry & biodiversity 20050101

Title: In vitro antibacterial activity of echinomycin and a novel analogue, YK2000, against vancomycin-resistant enterococci.

Journal: International journal of antimicrobial agents 20041201

Title: Interaction of echinomycin with guanine: electrochemistry and spectroscopy studies.

Journal: Biophysical chemistry 20041101

Title: Echinomycin and a novel analogue induce apoptosis of HT-29 cells via the activation of MAP kinases pathway.

Journal: Pharmacological research 20040801

Title: Naturally occurring cyclohexane epoxides: sources, biological activities, and synthesis.

Journal: Chemical reviews 20040601

Title: Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues.

Journal: Bioorganic & medicinal chemistry letters 20040119

Title: Validation of a sensitive assay for thiocoraline in mouse plasma using liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030825

Title: Kakadumycins, novel antibiotics from Streptomyces sp NRRL 30566, an endophyte of Grevillea pteridifolia.

Journal: FEMS microbiology letters 20030729

Title: Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells.

Journal: Cancer cell 20030301

Title: Interaction of DNA with echinomycin at the mercury electrode surface as detected by impedance and chronopotentiometric measurements.

Journal: Talanta 20020401

Title: Interaction of Hoechst 33258 and echinomycin with nucleosomal DNA fragments containing isolated ligand binding sites.

Journal: Biochemistry 20020312

Title: Cyclic voltammetry of echinomycin and its interaction with double-stranded and single-stranded DNA adsorbed at the electrode.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20020101

Title: SW-163C and E, novel antitumor depsipeptides produced by Streptomyces sp. II. Structure elucidation.

Journal: The Journal of antibiotics 20010801

Title: Total syntheses of thiocoraline and BE-22179 and assessment of their DNA binding and biological properties.

Journal: Journal of the American Chemical Society 20010131

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