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1393-48-2,MFCD00135828
Catalog No.:AA006XK6

1393-48-2 | Thiostrepton

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500mg
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1g
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA006XK6
Chemical Name:
Thiostrepton
CAS Number:
1393-48-2
Molecular Formula:
C61H73N15O14S4
Molecular Weight:
1368.5844
MDL Number:
MFCD00135828
SMILES:
CCC([C@@H]1N[C@@H]2C=Cc3c([C@H]2O)nc(cc3[C@@H](O)C)C(=O)O[C@H](C)[C@@H]2NC(=O)c3csc(n3)[C@@H](NC(=O)[C@H]3CSC(=N3)/C(=C\C)/NC(=O)[CH]NC(=O)c3nc([C@@]4(NC(=O)[C@@H](NC(=O)C(=C)NC(=O)[C@@H](NC1=O)C)C)CCC(=N[C@H]4c1nc2sc1)[CH2])sc3)[C@]([C@H](O)C)(O)C)C
NSC Number:
759821
Properties
Computed Properties
 
Complexity:
3940  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
114  
Hydrogen Bond Acceptor Count:
31  
Hydrogen Bond Donor Count:
17  
Rotatable Bond Count:
12  
Undefined Atom Stereocenter Count:
17  
XLogP3:
0.6  

Literature

Title: FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.

Journal: Chemico-biological interactions 20130905

Title: Male and female Plasmodium falciparum mature gametocytes show different responses to antimalarial drugs.

Journal: Antimicrobial agents and chemotherapy 20130701

Title: Combination treatment with bortezomib and thiostrepton is effective against tumor formation in mouse models of DEN/PB-induced liver carcinogenesis.

Journal: Cell cycle (Georgetown, Tex.) 20120915

Title: Overexpression of FoxM1 offers a promising therapeutic target in diffuse large B-cell lymphoma.

Journal: Haematologica 20120701

Title: Thiostrepton is an inducer of oxidative and proteotoxic stress that impairs viability of human melanoma cells but not primary melanocytes.

Journal: Biochemical pharmacology 20120501

Title: Insights into quinaldic acid moiety formation in thiostrepton biosynthesis facilitating fluorinated thiopeptide generation.

Journal: Chemistry & biology 20120420

Title: Combination with bortezomib enhances the antitumor effects of nanoparticle-encapsulated thiostrepton.

Journal: Cancer biology & therapy 20120201

Title: Mutagenesis of the thiostrepton precursor peptide at Thr7 impacts both biosynthesis and function.

Journal: Chemical communications (Cambridge, England) 20120114

Title: ppGpp inhibits peptide elongation cycle of chloroplast translation system in vitro.

Journal: Plant molecular biology 20120101

Title: [Construction of a new bifunctional vector which contains EGFP-gene].

Journal: Mikrobiolohichnyi zhurnal (Kiev, Ukraine : 1993) 20120101

Title: Peroxiredoxin 3 is a redox-dependent target of thiostrepton in malignant mesothelioma cells.

Journal: PloS one 20120101

Title: In vivo production of thiopeptide variants.

Journal: Methods in enzymology 20120101

Title: [Bacteriocidal activity of Streptomyces cultures].

Journal: Mikrobiolohichnyi zhurnal (Kiev, Ukraine : 1993) 20120101

Title: Thiostrepton, proteasome inhibitors and FOXM1.

Journal: Cell cycle (Georgetown, Tex.) 20111215

Title: Micelle-encapsulated thiostrepton as an effective nanomedicine for inhibiting tumor growth and for suppressing FOXM1 in human xenografts.

Journal: Molecular cancer therapeutics 20111201

Title: Proteasome inhibitors suppress expression of NPM and ARF proteins.

Journal: Cell cycle (Georgetown, Tex.) 20111115

Title: FoxM1 knockdown sensitizes human cancer cells to proteasome inhibitor-induced apoptosis but not to autophagy.

Journal: Cell cycle (Georgetown, Tex.) 20111001

Title: Transcript-level responses of Plasmodium falciparum to thiostrepton.

Journal: Molecular and biochemical parasitology 20110901

Title: Development of a vector and host system and characterization of replication of plasmid pSQ10 in moderately halophilic Nocardiopsis.

Journal: Acta biochimica et biophysica Sinica 20110901

Title: The transcription factor FOXM1 is a cellular target of the natural product thiostrepton.

Journal: Nature chemistry 20110821

Title: Differential effects of thiopeptide and orthosomycin antibiotics on translational GTPases.

Journal: Chemistry & biology 20110527

Title: NMR structures of thiostrepton derivatives for characterization of the ribosomal binding site.

Journal: Angewandte Chemie (International ed. in English) 20110328

Title: Thiostrepton maturation involving a deesterification-amidation way to process the C-terminally methylated peptide backbone.

Journal: Journal of the American Chemical Society 20110309

Title: Genome-wide expression analysis of Middle Eastern colorectal cancer reveals FOXM1 as a novel target for cancer therapy.

Journal: The American journal of pathology 20110201

Title: Heterologous production of thiostrepton A and biosynthetic engineering of thiostrepton analogs.

Journal: Molecular bioSystems 20110101

Title: Proteasome inhibitors induce p53-independent apoptosis in human cancer cells.

Journal: The American journal of pathology 20110101

Title: Thiazole antibiotic thiostrepton synergize with bortezomib to induce apoptosis in cancer cells.

Journal: PloS one 20110101

Title: Aberrant activation of ERK/FOXM1 signaling cascade triggers the cell migration/invasion in ovarian cancer cells.

Journal: PloS one 20110101

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

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Semi-synthetic analogues of thiostrepton delimit the critical nature of tail region modifications in the control of protein biosynthesis and antibacterial activity.

Journal: Bioorganic & medicinal chemistry 20100615

Title: New potential anti-cancer agents synergize with bortezomib and ABT-737 against prostate cancer.

Journal: The Prostate 20100601

Title: Antiplasmodial thiostrepton derivatives: proteasome inhibitors with a dual mode of action.

Journal: Angewandte Chemie (International ed. in English) 20100426

Title: Thiazole antibiotics against breast cancer.

Journal: Cell cycle (Georgetown, Tex.) 20100315

Title: FOXM1 confers acquired cisplatin resistance in breast cancer cells.

Journal: Molecular cancer research : MCR 20100101

Title: Two heterologously expressed Planobispora rosea proteins cooperatively induce Streptomyces lividans thiostrepton uptake and storage from the extracellular medium.

Journal: Microbial cell factories 20100101

Title: D-cysteine occurrence in thiostrepton may not necessitate an epimerase.

Journal: Chemical communications (Cambridge, England) 20091214

Title: Chasing after antibiotic leads.

Journal: Chemistry & biology 20091030

Title: Identification of distinct thiopeptide-antibiotic precursor lead compounds using translation machinery assays.

Journal: Chemistry & biology 20091030

Title: Wild-type p53 protects normal cells against apoptosis induced by thiostrepton.

Journal: Cell cycle (Georgetown, Tex.) 20090901

Title: Structure of the thiostrepton resistance methyltransferase.S-adenosyl-L-methionine complex and its interaction with ribosomal RNA.

Journal: The Journal of biological chemistry 20090619

Title: A novel mode of FoxM1 regulation: positive auto-regulatory loop.

Journal: Cell cycle (Georgetown, Tex.) 20090615

Title: Thiostrepton biosynthesis: prototype for a new family of bacteriocins.

Journal: Journal of the American Chemical Society 20090401

Title: Thiopeptide biosynthesis featuring ribosomally synthesized precursor peptides and conserved posttranslational modifications.

Journal: Chemistry & biology 20090227

Title: A fluorescent probe for the 70 S-ribosomal GTPase-associated center.

Journal: Chembiochem : a European journal of chemical biology 20090126

Title: Thiazole antibiotics target FoxM1 and induce apoptosis in human cancer cells.

Journal: PloS one 20090101

Title: Thiopeptide antibiotic biosynthesis.

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: FoxM1 is a general target for proteasome inhibitors.

Journal: PloS one 20090101

Title: Inducible expression systems for mycobacteria.

Journal: Methods in molecular biology (Clifton, N.J.) 20090101

Title: Inhibition of mitochondrial protein translation sensitizes melanoma cells to arsenic trioxide cytotoxicity via a reactive oxygen species dependent mechanism.

Journal: Cancer chemotherapy and pharmacology 20081201

Title: Thiostrepton selectively targets breast cancer cells through inhibition of forkhead box M1 expression.

Journal: Molecular cancer therapeutics 20080701

Title: Novel anticancer compounds induce apoptosis in melanoma cells.

Journal: Cell cycle (Georgetown, Tex.) 20080615

Title: FoxM1 inhibitors as potential anticancer drugs.

Journal: Expert opinion on therapeutic targets 20080601

Title: Translational regulation via L11: molecular switches on the ribosome turned on and off by thiostrepton and micrococcin.

Journal: Molecular cell 20080411

Title: Thiostrepton inhibition of tRNA delivery to the ribosome.

Journal: RNA (New York, N.Y.) 20071201

Title: The structure of free L11 and functional dynamics of L11 in free, L11-rRNA(58 nt) binary and L11-rRNA(58 nt)-thiostrepton ternary complexes.

Journal: Journal of molecular biology 20070406

Title: The effects of anti-bacterials on the malaria parasite Plasmodium falciparum.

Journal: Molecular and biochemical parasitology 20070401

Title: An rplKDelta29-PALG-32 mutation leads to reduced expression of the regulatory genes ccaR and claR and very low transcription of the ceaS2 gene for clavulanic acid biosynthesis in Streptomyces clavuligerus.

Journal: Molecular microbiology 20060801

Title: EF-G-dependent GTPase on the ribosome. conformational change and fusidic acid inhibition.

Journal: Biochemistry 20060227

Title: Discovery of a biologically active thiostrepton fragment.

Journal: Journal of the American Chemical Society 20051102

Title: Interactions of the N-terminal domain of ribosomal protein L11 with thiostrepton and rRNA.

Journal: The Journal of biological chemistry 20050819

Title: Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks.

Journal: Journal of the American Chemical Society 20050810

Title: Total synthesis of thiostrepton. Assembly of key building blocks and completion of the synthesis.

Journal: Journal of the American Chemical Society 20050810

Title: Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics.

Journal: Bioorganic & medicinal chemistry letters 20050516

Title: The apicoplast of Plasmodium falciparum is translationally active.

Journal: Molecular microbiology 20050401

Title: Electronic structure calculations on the thiazole-containing antibiotic thiostrepton: molecular mechanics, semi-empirical and ab initio analyses.

Journal: Bioorganic & medicinal chemistry letters 20050301

Title: Interaction of thiostrepton and elongation factor-G with the ribosomal protein L11-binding domain.

Journal: The Journal of biological chemistry 20050128

Title: Natural merodiploidy involving duplicated rpoB alleles affects secondary metabolism in a producer actinomycete.

Journal: Molecular microbiology 20050101

Title: Kinetics and thermodynamics of RRF, EF-G, and thiostrepton interaction on the Escherichia coli ribosome.

Journal: Biochemistry 20041012

Title: Total synthesis of thiostrepton, part 2: construction of the quinaldic acid macrocycle and final stages of the synthesis.

Journal: Angewandte Chemie (International ed. in English) 20040927

Title: Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

Journal: Angewandte Chemie (International ed. in English) 20040927

Title: Suppressive effect of antibiotic siomycin on antibody production.

Journal: The Journal of antibiotics 20040901

Title: [Construction of efficient conjugal plasmids between Escherichia coli and Streptomycetes].

Journal: Sheng wu gong cheng xue bao = Chinese journal of biotechnology 20040901

Title: Isolation and characterization of the Rhodococcus opacus thiostrepton-inducible genes tipAL and tipAS: application for recombinant protein expression in Rhodococcus.

Journal: FEMS microbiology letters 20040801

Title: A novel system for expressing recombinant proteins over a wide temperature range from 4 to 35 degrees C.

Journal: Biotechnology and bioengineering 20040420

Title: The translation initiation functions of IF2: targets for thiostrepton inhibition.

Journal: Journal of molecular biology 20040123

Title: Release of ribosome-bound ribosome recycling factor by elongation factor G.

Journal: The Journal of biological chemistry 20031128

Title: Structure-based design of agents targeting the bacterial ribosome.

Journal: Bioorganic & medicinal chemistry letters 20030804

Title: Structural basis for contrasting activities of ribosome binding thiazole antibiotics.

Journal: Chemistry & biology 20030801

Title: Synthetic studies on thiostrepton: construction of thiostrepton analogues with the thiazoline-containing macrocycle.

Journal: Angewandte Chemie (International ed. in English) 20030728

Title: Specific binding of ribosome recycling factor (RRF) with the Escherichia coli ribosomes by BIACORE.

Journal: Molecular biology reports 20030601

Title: Dissociation of intact Escherichia coli ribosomes in a mass spectrometer. Evidence for conformational change in a ribosome elongation factor G complex.

Journal: The Journal of biological chemistry 20030110

Title: Biosynthesis inspired Diels-Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics.

Journal: Chemical communications (Cambridge, England) 20020821

Title: Stereocontrolled synthesis of the quinaldic acid macrocyclic system of thiostrepton.

Journal: Angewandte Chemie (International ed. in English) 20020603

Title: A biomimetically inspired synthesis of the dehydropiperidine domain of thiostrepton.

Journal: Angewandte Chemie (International ed. in English) 20020603

Title: Large-scale motions within ribosomal 50S subunits as demonstrated using photolabile oligonucleotides.

Journal: Bioorganic chemistry 20020601

Title: Initiation factor IF2, thiostrepton and micrococcin prevent the binding of elongation factor G to the Escherichia coli ribosome.

Journal: Journal of molecular biology 20020524

Title: Osmotic regulation of the Streptomyces lividans thiostrepton-inducible promoter, ptipA.

Journal: Microbiology (Reading, England) 20020201

Title: [Homologous recombination in Streptomyces lincolnensis B48].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20011001

Title: Structure of the macrocycle thiostrepton solved using the anomalous dispersion contribution of sulfur.

Journal: Acta crystallographica. Section D, Biological crystallography 20010501

Title: Anion recognition by thiostrepton.

Journal: Bioorganic & medicinal chemistry letters 20010312

Title: A Corynebacterium glutamicum mutant with a defined deletion within the rplK gene is impaired in (p)ppGpp accumulation upon amino acid starvation.

Journal: Microbiology (Reading, England) 20010301

Title: Induction of ppGpp synthesis in Streptomyces coelicolor A3(2) grown under conditions of nutritional sufficiency elicits actII-ORF4 transcription and actinorhodin biosynthesis.

Journal: Molecular microbiology 20010101

Title: [Cloning of the thiostrepton-resistance gene for replicating copies of Streptomycete plasmids].

Journal: Mikrobiolohichnyi zhurnal (Kiev, Ukraine : 1993) 20010101

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