23110-15-8,MFCD00864660
Catalog No.:AA006YF7

23110-15-8 | Fumagillin

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥95%
in stock  
$138.00   $96.00
- +
10mg
in stock  
$170.00   $119.00
- +
25mg
in stock  
$294.00   $206.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA006YF7
Chemical Name:
Fumagillin
CAS Number:
23110-15-8
Molecular Formula:
C26H34O7
Molecular Weight:
458.5440
MDL Number:
MFCD00864660
SMILES:
COC1C(CCC2(C1C1(C)OC1CC=C(C)C)CO2)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
Properties
Computed Properties
 
Complexity:
879  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
4  
Formal Charge:
0  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
11  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
4  

Downstream Synthesis Route
fumagillol 
 
(2E,4E,6E,8E)-Deca-2,4,6,8-tetraenedioyldichloride 
  23110-15-8 

[1]Taber,DouglassF.;Christos,ThomasE.;Rheingold,ArnoldL.;Guzei,IliaA.[JournaloftheAmericanChemicalSociety,1999,vol.121,#23,p.5589-5590]

23110-15-8   
(2E,4E,6E,8E)-Deca-2,4,6,8-tetraenedioicacidmono-{(3R,4S,5S,6R)-4-(2R,3R)-3-(3,3-dimethyl-oxiranylmethyl)-2-methyl-oxiranyl-5-methoxy-1-oxa-spiro2.5oct-6-yl}ester 

[1]Halász,Judit;Podányi,Benjamin;Vasvári-Debreczy,Lelle;Szabó,Anna;Hajdú,Félix;Böcskei,Zsolt;Hegedus-Vajda,Judit;Gyorbíró,Andrea;Hermecz,István[Tetrahedron,2000,vol.56,#51,p.10081-10085]

23110-15-8   
fumagillol 

[1]Grenning,AlexanderJ.;Snyder,JohnK.;Porco,JohnA.[OrganicLetters,2014,vol.16,#3,p.792-795]

[2]Locationinpatent:experimentalpartLee,HongWoo;Kang,SungKwon;Yoo,ChoongLeol;Lee,SeungUk[Heterocycles,2009,vol.78,#7,p.1837-1846]

[3]Asami,Yukihiro;Kakeya,Hideaki;Onose,Rie;Chang,Yie-Hwa;Toi,Masakazu;Osada,Hiroyuki[Tetrahedron,2004,vol.60,#33,p.7085-7091]

[4]Vansteelandt,Marieke;Blanchet,Elodie;Egorov,Maxim;Petit,Fabien;Toupet,Loic;Bondon,Arnaud;Monteau,Fabrice;Bizec,Bruno;Thomas,OlivierP.;Pouchus,YvesFrancois;Bot,RonanLe;Grovel,Olivier[JournalofNaturalProducts,2013,vol.76,#2,p.297-301]

[5]Blanchet,Elodie;Vansteelandt,Marieke;LeBot,Ronan;Egorov,Maxim;Guitton,Yann;Pouchus,YvesFrançois;Grovel,Olivier[EuropeanJournalofMedicinalChemistry,2014,vol.79,p.244-250]

[1]Asami,Yukihiro;Kakeya,Hideaki;Onose,Rie;Chang,Yie-Hwa;Toi,Masakazu;Osada,Hiroyuki[Tetrahedron,2004,vol.60,#33,p.7085-7091]

23110-15-8   
N-methyl-N'-nitrosoguanidine 
  1399360-30-5 

[1]CurrentPatentAssignee:LARIMARTHERAPEUTICSINC-WO2012/122264,2012,A1Locationinpatent:Page/Pagecolumn54

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Title: Magnetic circular dichroism study of a dicobalt(II) methionine aminopeptidase/fumagillin complex and dicobalt II-II and II-III model complexes.

Journal: Inorganic chemistry 20081117

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Title: Microsporidial keratoconjunctivitis in a healthy patient with a history of LASIK surgery.

Journal: Cornea 20030401

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Journal: Ophthalmology 20010501

Title: General aspects of anti-angiogenesis and cancer therapy.

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Journal: Contraception 20010201

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Journal: Archives of medical research 20010101

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Journal: Anticancer research 20010101

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Related Products of 23110-15-8
Tags:23110-15-8 Molecular Formula|23110-15-8 MDL|23110-15-8 SMILES|23110-15-8 Fumagillin
Catalog No.: AA006YF7
23110-15-8,MFCD00864660
23110-15-8 | Fumagillin
Pack Size: 1mg
Purity: ≥95%
in stock
$138.00 $96.00
Pack Size: 10mg
Purity:
in stock
$170.00 $119.00
Pack Size: 25mg
Purity:
in stock
$294.00 $206.00
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Technical Information
Catalog Number: AA006YF7
Chemical Name: Fumagillin
CAS Number: 23110-15-8
Molecular Formula: C26H34O7
Molecular Weight: 458.5440
MDL Number: MFCD00864660
SMILES: COC1C(CCC2(C1C1(C)OC1CC=C(C)C)CO2)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O
Properties
Complexity: 879  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 6  
Defined Bond Stereocenter Count: 4  
Formal Charge: 0  
Heavy Atom Count: 33  
Hydrogen Bond Acceptor Count: 7  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 11  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 4  
Downstream Synthesis Route
fumagillol 
 
(2E,4E,6E,8E)-Deca-2,4,6,8-tetraenedioyldichloride 
  23110-15-8 

[1]Taber,DouglassF.;Christos,ThomasE.;Rheingold,ArnoldL.;Guzei,IliaA.[JournaloftheAmericanChemicalSociety,1999,vol.121,#23,p.5589-5590]

23110-15-8   
(2E,4E,6E,8E)-Deca-2,4,6,8-tetraenedioicacidmono-{(3R,4S,5S,6R)-4-(2R,3R)-3-(3,3-dimethyl-oxiranylmethyl)-2-methyl-oxiranyl-5-methoxy-1-oxa-spiro2.5oct-6-yl}ester 

[1]Halász,Judit;Podányi,Benjamin;Vasvári-Debreczy,Lelle;Szabó,Anna;Hajdú,Félix;Böcskei,Zsolt;Hegedus-Vajda,Judit;Gyorbíró,Andrea;Hermecz,István[Tetrahedron,2000,vol.56,#51,p.10081-10085]

23110-15-8   
fumagillol 

[1]Grenning,AlexanderJ.;Snyder,JohnK.;Porco,JohnA.[OrganicLetters,2014,vol.16,#3,p.792-795]

[2]Locationinpatent:experimentalpartLee,HongWoo;Kang,SungKwon;Yoo,ChoongLeol;Lee,SeungUk[Heterocycles,2009,vol.78,#7,p.1837-1846]

[3]Asami,Yukihiro;Kakeya,Hideaki;Onose,Rie;Chang,Yie-Hwa;Toi,Masakazu;Osada,Hiroyuki[Tetrahedron,2004,vol.60,#33,p.7085-7091]

[4]Vansteelandt,Marieke;Blanchet,Elodie;Egorov,Maxim;Petit,Fabien;Toupet,Loic;Bondon,Arnaud;Monteau,Fabrice;Bizec,Bruno;Thomas,OlivierP.;Pouchus,YvesFrancois;Bot,RonanLe;Grovel,Olivier[JournalofNaturalProducts,2013,vol.76,#2,p.297-301]

[5]Blanchet,Elodie;Vansteelandt,Marieke;LeBot,Ronan;Egorov,Maxim;Guitton,Yann;Pouchus,YvesFrançois;Grovel,Olivier[EuropeanJournalofMedicinalChemistry,2014,vol.79,p.244-250]

23110-15-8    132746-88-4 

[1]Asami,Yukihiro;Kakeya,Hideaki;Onose,Rie;Chang,Yie-Hwa;Toi,Masakazu;Osada,Hiroyuki[Tetrahedron,2004,vol.60,#33,p.7085-7091]

23110-15-8   
N-methyl-N'-nitrosoguanidine 
  1399360-30-5 

[1]CurrentPatentAssignee:LARIMARTHERAPEUTICSINC-WO2012/122264,2012,A1Locationinpatent:Page/Pagecolumn54

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

Journal: Bioorganic & medicinal chemistry20121115

Title: Suppression of inflammation in a mouse model of rheumatoid arthritis using targeted lipase-labile fumagillin prodrug nanoparticles.

Journal: Biomaterials20121101

Title: Impact of Nosema (Microsporidia) infection and fumagillin treatment on Lygus lineolaris (Hemiptera: Miridae).

Journal: Journal of invertebrate pathology20121001

Title: The effect of induced queen replacement on Nosema spp. infection in honey bee (Apis mellifera iberiensis) colonies.

Journal: Environmental microbiology20120401

Title: The development of MetAP-2 inhibitors in cancer treatment.

Journal: Current medicinal chemistry20120101

Title: Early treatment with fumagillin, an inhibitor of methionine aminopeptidase-2, prevents Pulmonary Hypertension in monocrotaline-injured rats.

Journal: PloS one20120101

Title: Anti-angiogenic treatment strategies for the therapy of endometriosis.

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Title: Methionine aminopeptidase 2 is required for HSC initiation and proliferation.

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Title: Disruption of Wnt planar cell polarity signaling by aberrant accumulation of the MetAP-2 substrate Rab37.

Journal: Chemistry & biology20111028

Title: Local inhibition of angiogenesis results in an atrophic non-union in a rat osteotomy model.

Journal: European cells & materials20110706

Title: The Aspergillus fumigatus toxin fumagillin suppresses the immune response of Galleria mellonella larvae by inhibiting the action of haemocytes.

Journal: Microbiology (Reading, England)20110501

Title: Identification, structural properties and chelating capacity of miltipolone as a broad-spectrum inhibitor to cancer cells.

Journal: European journal of medicinal chemistry20110401

Title: Rapid determination of fumagillin residues in honey by liquid chromatography-tandem mass spectrometry using the QuEChERS method.

Journal: Journal of AOAC International20110101

Title: Fumagillin reduces adipose tissue formation in murine models of nutritionally induced obesity.

Journal: Obesity (Silver Spring, Md.)20101201

Title: Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines.

Journal: European journal of medicinal chemistry20101201

Title: p67/MetAP2 suppresses K-RasV12-mediated transformation of NIH3T3 mouse fibroblasts in culture and in athymic mice.

Journal: Biochemistry20101130

Title: Concise synthesis and antiangiogenic activity of artemisinin-glycolipid hybrids on chorioallantoic membranes.

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Title: Methionine aminopeptidases as potential targets for treatment of gastrointestinal cancers and other tumours.

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Title: Fumagillin for treatment of intestinal microsporidiosis in renal transplant recipients.

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Title: A novel angiogenesis model for screening anti-angiogenic compounds: the chorioallantoic membrane/feather bud assay.

Journal: International journal of oncology20100701

Title: Inhibition of neutrophil function following exposure to the Aspergillus fumigatus toxin fumagillin.

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Title: Syntheses of fumagillin and ovalicin.

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Title: Effect of fumagillin on adipocyte differentiation and adipogenesis.

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Title: Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

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Title: Carbamate analogues of fumagillin as potent, targeted inhibitors of methionine aminopeptidase-2.

Journal: Journal of medicinal chemistry20091224

Title: Structure of a microsporidian methionine aminopeptidase type 2 complexed with fumagillin and TNP-470.

Journal: Molecular and biochemical parasitology20091201

Title: Roles of P67/MetAP2 as a tumor suppressor.

Journal: Biochimica et biophysica acta20091201

Title: Emerging prevalence of microsporidial keratitis in Singapore: epidemiology, clinical features, and management.

Journal: Ophthalmology20091201

Title: Paracrine induction of endothelium by tumor exosomes.

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Title: Alphavbeta3-targeted nanotherapy suppresses inflammatory arthritis in mice.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20090901

Title: Antiparasitic activities of novel, orally available fumagillin analogs.

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Title: Fumagillin inhibits colorectal cancer growth and metastasis in mice: in vivo and in vitro study of anti-angiogenesis.

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Title: Fumagillin and fumarranol interact with P. falciparum methionine aminopeptidase 2 and inhibit malaria parasite growth in vitro and in vivo.

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Title: Microsporidiosis in solid organ transplant recipients: two Enterocytozoon bieneusi cases and review.

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Title: Testing intra-hemocelic injection of antimicrobials against Encephalitozoon sp. (Microsporidia) in an insect host.

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Title: Three-dimensional MR mapping of angiogenesis with alpha5beta1(alpha nu beta3)-targeted theranostic nanoparticles in the MDA-MB-435 xenograft mouse model.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20081201

Title: Magnetic circular dichroism study of a dicobalt(II) methionine aminopeptidase/fumagillin complex and dicobalt II-II and II-III model complexes.

Journal: Inorganic chemistry20081117

Title: Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

Journal: Journal of medicinal chemistry20081113

Title: Does fumagillin control the recently detected invasive parasite Nosema ceranae in western honey bees (Apis mellifera)?

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Title: In vitro evaluation of the clastogenicity of fumagillin.

Journal: Environmental and molecular mutagenesis20081001

Title: How natural infection by Nosema ceranae causes honeybee colony collapse.

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Title: Effect of four antimicrobials against an Encephalitozoon sp. (Microsporidia) in a grasshopper host.

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Title: Antiangiogenic synergism of integrin-targeted fumagillin nanoparticles and atorvastatin in atherosclerosis.

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Title: Theranostic strategy against plaque angiogenesis.

Journal: JACC. Cardiovascular imaging20080901

Title: Minute dosages of alpha(nu)beta3-targeted fumagillin nanoparticles impair Vx-2 tumor angiogenesis and development in rabbits.

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Title: Trace analysis of fumagillin in honey by liquid chromatography-diode array-electrospray ionization mass spectrometry.

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Title: New insect system for testing antibiotics.

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Title: FGFR1/PI3K/AKT signaling pathway is a novel target for antiangiogenic effects of the cancer drug fumagillin (TNP-470).

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Title: Methionine aminopeptidase-2 as a selective target of myofibroblasts in pulmonary fibrosis.

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Title: Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors.

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Title: Design, synthesis, and antiangiogenic effects of a series of potent novel fumagillin analogues.

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Title: Evaluation of genotoxic effects of fumagillin by cytogenetic tests in vivo.

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Title: Stromelysin-1 expression is activated in vivo by Ets-1 through palindromic head-to-head Ets binding sites present in the promoter.

Journal: Oncogene20060921

Title: Fumarranol, a rearranged fumagillin analogue that inhibits angiogenesis in vivo.

Journal: Journal of medicinal chemistry20060921

Title: Endothelial alpha(v)beta3 integrin-targeted fumagillin nanoparticles inhibit angiogenesis in atherosclerosis.

Journal: Arteriosclerosis, thrombosis, and vascular biology20060901

Title: A noncanonical path to mechanism of action.

Journal: Chemistry & biology20060901

Title: A chemical and genetic approach to the mode of action of fumagillin.

Journal: Chemistry & biology20060901

Title: Fumagillin suppresses HIV-1 infection of macrophages through the inhibition of Vpr activity.

Journal: FEBS letters20060515

Title: Antiangiogenic activity of deoxoartemisinin derivatives on chorioallantoic membrane.

Journal: Bioorganic & medicinal chemistry letters20060301

Title: Interaction between tacrolimus and fumagillin in two kidney transplant recipients.

Journal: Transplantation20060115

Title: Advances in understanding angiogenesis through molecular studies.

Journal: International journal of radiation oncology, biology, physics20060101

Title: Antiparasitic and immunomodulatory effect of innovative treatments against Myxobolus sp. infection in Diplodus puntazzo.

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Title: Cerebrospinal fluid proteomic analysis reveals dysregulation of methionine aminopeptidase-2 expression in human and mouse neurofibromatosis 1-associated glioma.

Journal: Cancer research20051101

Title: Keratitis caused by Trachipleistophora anthropopthera.

Journal: The Journal of infection20051101

Title: 4-Aryl-1,2,3-triazole: a novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo.

Journal: Journal of medicinal chemistry20050908

Title: Oxocarbenium ion cyclizations for C-branched cyclitols: synthesis of a relay intermediate for fumagillin analogues.

Journal: The Journal of organic chemistry20050819

Title: Methionine aminopeptidases type I and type II are essential to control cell proliferation.

Journal: Journal of cellular biochemistry20050815

Title: Total synthesis and antiangiogenic activity of cyclopentane analogues of fumagillol.

Journal: Bioorganic & medicinal chemistry letters20050801

Title: Synthesis and biological evaluation of novel fumagillin and ovalicin analogues.

Journal: Organic & biomolecular chemistry20050607

Title: Phylogenetic relationships of methionine aminopeptidase 2 among Encephalitozoon species and genotypes of microsporidia.

Journal: Molecular and biochemical parasitology20050401

Title: Microsporidiosis: an emerging and opportunistic infection in humans and animals.

Journal: Acta tropica20050401

Title: Enantioselective approaches to potential MetAP-2 reversible inhibitors.

Journal: The Journal of organic chemistry20050318

Title: Novel inhibitors targeted to methionine aminopeptidase 2 (MetAP2) strongly inhibit the growth of cancers in xenografted nude model.

Journal: International journal of cancer20050310

Title: Fumagillin treatment of hepatocellular carcinoma in rats: an in vivo study of antiangiogenesis.

Journal: World journal of gastroenterology20050214

Title: Characterization of the active site and insight into the binding mode of the anti-angiogenesis agent fumagillin to the manganese(II)-loaded methionyl aminopeptidase from Escherichia coli.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry20050101

Title: Octosporea bayeri: fumidil B inhibits vertical transmission in Daphnia magna.

Journal: Experimental parasitology20050101

Title: The parasitophorous vacuole membrane of Encephalitozoon cuniculi lacks host cell membrane proteins immediately after invasion.

Journal: Eukaryotic cell20050101

Title: Antiangiogenic agents: studies on fumagillin and curcumin analogs.

Journal: Current pharmaceutical design20050101

Title: Treatment of cells with the angiogenic inhibitor fumagillin results in increased stability of eukaryotic initiation factor 2-associated glycoprotein, p67, and reduced phosphorylation of extracellular signal-regulated kinases.

Journal: Biochemistry20041123

Title: The C. elegans methionine aminopeptidase 2 analog map-2 is required for germ cell proliferation.

Journal: FEBS letters20041008

Title: Occurrence of Cystosporogenes sp. (Protozoa, Microsporidia) in a multi-species insect production facility and its elimination from a colony of the eastern spruce budworm, Choristoneura fumiferana (Clem.) (Lepidoptera: Tortricidae).

Journal: Journal of invertebrate pathology20040901

Title: Early genetic mechanisms underlying the inhibitory effects of endostatin and fumagillin on human endothelial cells.

Journal: Genome research20040801

Title: Fumagiringillin, a new fumagillin derivative from a strain of the fungus Aspergillus fumigatus.

Journal: Journal of natural products20040801

Title: Depletion of methionine aminopeptidase 2 does not alter cell response to fumagillin or bengamides.

Journal: Cancer research20040501

Title: Inhibitory effects of 9-(4-thio-beta-D-ribo-pentofuranosyl)guanine on tumor growth and angiogenesis.

Journal: Biological & pharmaceutical bulletin20040401

Title: Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs.

Journal: Archives of pharmacal research20040201

Title: MetAP-2 inhibitors based on the fumagillin structure. Side-chain modification and ring-substituted analogues.

Journal: The Journal of organic chemistry20040123

Title: Investigation of novel fumagillin analogues as angiogenesis inhibitors.

Journal: Bioorganic & medicinal chemistry letters20040105

Title: Small molecule inhibitors of methionine aminopeptidase type 2 (MetAP-2).

Journal: Angiogenesis20040101

Title: Proteomics-based target identification: bengamides as a new class of methionine aminopeptidase inhibitors.

Journal: The Journal of biological chemistry20031226

Title: Protonation states of methionine aminopeptidase and their relevance for inhibitor binding and catalytic activity.

Journal: The Journal of biological chemistry20031128

Title: Design, synthesis and evaluation of a series of novel fumagillin analogues.

Journal: Bioorganic & medicinal chemistry20031117

Title: Angiogenesis inhibitors target the endothelial cell cytoskeleton through altered regulation of heat shock protein 27 and cofilin.

Journal: Cancer research20031001

Title: Effects of Nosema bombi and its treatment fumagillin on bumble bee (Bombus occidentalis) colonies.

Journal: Journal of invertebrate pathology20030901

Title: Homology modeling and calculation of the cobalt cluster charges of the Encephazlitozoon cuniculi methionine aminopeptidase, a potential target for drug design.

Journal: Biophysical chemistry20030801

Title: Fumagalone, a reversible inhibitor of type 2 methionine aminopeptidase and angiogenesis.

Journal: Journal of medicinal chemistry20030731

Title: Microsporidial keratoconjunctivitis in healthy individuals: a case series.

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Title: Discovery and structural modification of inhibitors of methionine aminopeptidases from Escherichia coli and Saccharomyces cerevisiae.

Journal: Journal of medicinal chemistry20030619

Title: Development of a real-time polymerase-chain-reaction assay for quantitative detection of Enterocytozoon bieneusi DNA in stool specimens from immunocompromised patients with intestinal microsporidiosis.

Journal: The Journal of infectious diseases20030501

Title: Bilateral microsporidial keratoconjunctivitis in an immunocompetent non-contact lens wearer.

Journal: Cornea20030501

Title: Microsporidial keratoconjunctivitis in a healthy patient with a history of LASIK surgery.

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Title: Carbon and nitrogen source nutrition of fumagillin biosynthesis by Aspergillus fumigatus.

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Title: Electrochemical desorption of self-assembled monolayers noninvasively releases patterned cells from geometrical confinements.

Journal: Journal of the American Chemical Society20030305

Title: A novel early chorioallantoic membrane assay demonstrates quantitative and qualitative changes caused by antiangiogenic substances.

Journal: The Journal of laboratory and clinical medicine20030301

Title: Concise stereocontrolled routes to fumagillol, fumagillin, and TNP-470.

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Title: Effects of carboxymethylcellulose and carboxypolymethylene on morphology of Aspergillus fumigatus NRRL 2346 and fumagillin production.

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Title: [Light- and temperature-induced degradation of fumagillin].

Journal: Acta pharmaceutica Hungarica20030101

Title: Understanding the selectivity of fumagillin for the methionine aminopeptidase type II.

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Title: Methionine aminopeptidase 2 is a new target for the metastasis-associated protein, S100A4.

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Title: Fumagillin treatment of intestinal microsporidiosis.

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Title: Novel bicyclic oxazolone derivatives as anti-angiogenic agents.

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Title: Angiogenesis inhibitors specific for methionine aminopeptidase 2 as drugs for malaria and leishmaniasis.

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Title: Effect of vaginally administered fumagillin on immunohistochemical distribution of leukemia inhibitory factor, interleukin 6, transforming growth factor beta and vascular endothelial growth factor in implantation stage endometrium of the rhesus monkey.

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