118974-02-0,MFCD08702652
Catalog No.:AA008XZ6

118974-02-0 | FUMITREMORGIN C

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Purity
Availability
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1mg
95%
in stock  
$563.00   $394.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA008XZ6
Chemical Name:
FUMITREMORGIN C
CAS Number:
118974-02-0
Molecular Formula:
C22H25N3O3
Molecular Weight:
379.4522
MDL Number:
MFCD08702652
SMILES:
COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
NSC Number:
719655
Properties
Computed Properties
 
Complexity:
703  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
3  

Literature

Title: Breast cancer resistance protein (BCRP/ABCG2) localises to the nucleus in glioblastoma multiforme cells.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20120801

Title: Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus.

Journal: Journal of natural products 20120427

Title: Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.

Journal: Journal of agricultural and food chemistry 20120404

Title: Serum-dependent export of protoporphyrin IX by ATP-binding cassette transporter G2 in T24 cells.

Journal: Molecular and cellular biochemistry 20111201

Title: Specific inhibition of the ABCG2 transporter could improve the efficacy of photodynamic therapy.

Journal: Journal of photochemistry and photobiology. B, Biology 20111103

Title: Inhibition of c-Kit, VEGFR-2 (KDR), and ABCG2 by analogues of OSI-930.

Journal: Bioorganic & medicinal chemistry letters 20111101

Title: Fungal indole alkaloid biosynthesis: genetic and biochemical investigation of the tryptoquialanine pathway in Penicillium aethiopicum.

Journal: Journal of the American Chemical Society 20110302

Title: Differential inhibition of murine Bcrp1/Abcg2 and human BCRP/ABCG2 by the mycotoxin fumitremorgin C.

Journal: European journal of pharmacology 20101010

Title: Specific inhibitors of the breast cancer resistance protein (BCRP).

Journal: ChemMedChem 20100903

Title: BCRP/ABCG2 confers anticancer drug resistance without covalent dimerization.

Journal: Cancer science 20100801

Title: Doxorubicin fails to eradicate cancer stem cells derived from anaplastic thyroid carcinoma cells: characterization of resistant cells.

Journal: International journal of oncology 20100801

Title: Novel structure-activity relationships and selectivity profiling of cage dimeric 1,4-dihydropyridines as multidrug resistance (MDR) modulators.

Journal: Bioorganic & medicinal chemistry 20100715

Title: Breast cancer resistance protein (BCRP)-mediated glyburide transport: effect of the C421A/Q141K BCRP single-nucleotide polymorphism.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100501

Title: Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of p-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091001

Title: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties.

Journal: British journal of pharmacology 20091001

Title: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20090801

Title: Bioactive alkaloids from endophytic Aspergillus fumigatus.

Journal: Journal of natural products 20090401

Title: Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus.

Journal: Chembiochem : a European journal of chemical biology 20090323

Title: Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar.

Journal: Journal of medicinal chemistry 20090226

Title: ABCG2 is expressed in late spermatogenesis and is associated with the acrosome.

Journal: Biochemical and biophysical research communications 20090109

Title: Molecular expression and functional evidence of a drug efflux pump (BCRP) in human corneal epithelial cells.

Journal: Current eye research 20090101

Title: Application and limitation of inhibitors in drug-transporter interactions studies.

Journal: International journal of pharmaceutics 20080522

Title: Constitutive overexpression of P-glycoprotein, rather than breast cancer resistance protein or organic cation transporter 1, contributes to acquisition of imatinib-resistance in K562 cells.

Journal: Pharmaceutical research 20080401

Title: The breast cancer resistance protein (Bcrp1/Abcg2) limits fetal distribution of glyburide in the pregnant mouse: an Obstetric-Fetal Pharmacology Research Unit Network and University of Washington Specialized Center of Research Study.

Journal: Molecular pharmacology 20080301

Title: Functionalized chalcones as selective inhibitors of P-glycoprotein and breast cancer resistance protein.

Journal: Bioorganic & medicinal chemistry 20080101

Title: Porphyrin homeostasis maintained by ABCG2 regulates self-renewal of embryonic stem cells.

Journal: PloS one 20080101

Title: Expression of the ATP-binding cassette membrane transporter, ABCG2, in human and rodent brain microvessel endothelial and glial cell culture systems.

Journal: Pharmaceutical research 20070701

Title: C421 allele-specific ABCG2 gene amplification confers resistance to the antitumor triazoloacridone C-1305 in human lung cancer cells.

Journal: Biochemical pharmacology 20070630

Title: Energy transfer to analyse membrane-integrated mitoxantrone in BCRP-overexpressed cells.

Journal: Journal of photochemistry and photobiology. B, Biology 20070525

Title: Progesterone inhibits folic acid transport in human trophoblasts.

Journal: The Journal of membrane biology 20070401

Title: Zebrafish kidney marrow contains ABCG2-dependent side population cells exhibiting hematopoietic stem cell properties.

Journal: Differentiation; research in biological diversity 20070301

Title: Absorption of folate by Caco-2 cells is not affected by high glucose concentration.

Journal: European journal of pharmacology 20061203

Title: Complex interaction of BCRP/ABCG2 and imatinib in BCR-ABL-expressing cells: BCRP-mediated resistance to imatinib is attenuated by imatinib-induced reduction of BCRP expression.

Journal: Blood 20060715

Title: Expression and functional activity of breast cancer resistance protein (BCRP, ABCG2) transporter in the human choriocarcinoma cell line BeWo.

Journal: Clinical and experimental pharmacology & physiology 20060101

Title: Piperazinobenzopyranones and phenalkylaminobenzopyranones: potent inhibitors of breast cancer resistance protein (ABCG2).

Journal: Journal of medicinal chemistry 20051117

Title: Breast cancer resistance protein-mediated efflux of androgen in putative benign and malignant prostate stem cells.

Journal: Cancer research 20050801

Title: ABCG2-mediated transport of photosensitizers: potential impact on photodynamic therapy.

Journal: Cancer biology & therapy 20050201

Title: An improved definition of mouse mammary epithelial side population cells.

Journal: Cytotherapy 20050101

Title: Polyphasic taxonomy of Aspergillus fumigatus and related species.

Journal: Mycologia 20050101

Title: Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites.

Journal: Journal of biotechnology 20041109

Title: Liquid chromatography method for the quantitation of the breast cancer resistance protein ABCG2 inhibitor fumitremorgin C and its chemical analogues in mouse plasma and tissues.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040805

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

Journal: Journal of natural products 20040801

Title: Broad-spectrum modulation of ATP-binding cassette transport proteins by the taxane derivatives ortataxel (IDN-5109, BAY 59-8862) and tRA96023.

Journal: Cancer chemotherapy and pharmacology 20040501

Title: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport.

Journal: Molecular pharmacology 20040501

Title: Single amino acid substitutions in the transmembrane domains of breast cancer resistance protein (BCRP) alter cross resistance patterns in transfectants.

Journal: International journal of cancer 20031210

Title: The role of breast cancer resistance protein in acute lymphoblastic leukemia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031101

Title: Breast cancer resistance protein exports sulfated estrogens but not free estrogens.

Journal: Molecular pharmacology 20030901

Title: Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter.

Journal: Cancer research 20030901

Title: Transport of methotrexate, methotrexate polyglutamates, and 17beta-estradiol 17-(beta-D-glucuronide) by ABCG2: effects of acquired mutations at R482 on methotrexate transport.

Journal: Cancer research 20030715

Title: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors.

Journal: Molecular pharmacology 20030101

Title: Isolation and toxigenicity of Aspergillus fumigatus from moldy silage.

Journal: Mycopathologia 20030101

Title: Penicillium digitatum metabolites on synthetic media and citrus fruits.

Journal: Journal of agricultural and food chemistry 20021023

Title: Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C.

Journal: Molecular cancer therapeutics 20020401

Title: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells.

Journal: Biochemical and biophysical research communications 20010706

Title: Inhibition of BCRP-mediated drug efflux by fumitremorgin-type indolyl diketopiperazines.

Journal: Bioorganic & medicinal chemistry letters 20010108

Title: Overexpression of the ATP-binding cassette half-transporter, ABCG2 (Mxr/BCrp/ABCP1), in flavopiridol-resistant human breast cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20010101

Title: Rabindran SK, et al. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res. 1998 Dec 15;58(24):5850-8.

Title: Rabindran SK, et al. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 2000 Jan 1;60(1):47-50.

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SDS
Tags:118974-02-0 Molecular Formula|118974-02-0 MDL|118974-02-0 SMILES|118974-02-0 FUMITREMORGIN C
Catalog No.: AA008XZ6
118974-02-0,MFCD08702652
118974-02-0 | FUMITREMORGIN C
Pack Size: 1mg
Purity: 95%
in stock
$563.00 $394.00
Quantity
- +
Add to Card
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bulk Quotation Request
Technical Information
Catalog Number: AA008XZ6
Chemical Name: FUMITREMORGIN C
CAS Number: 118974-02-0
Molecular Formula: C22H25N3O3
Molecular Weight: 379.4522
MDL Number: MFCD08702652
SMILES: COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
NSC Number: 719655
Properties
Complexity: 703  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 3  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 28  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 2  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 3  
Literature fold

Title: Breast cancer resistance protein (BCRP/ABCG2) localises to the nucleus in glioblastoma multiforme cells.

Journal: Xenobiotica; the fate of foreign compounds in biological systems20120801

Title: Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus.

Journal: Journal of natural products20120427

Title: Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.

Journal: Journal of agricultural and food chemistry20120404

Title: Serum-dependent export of protoporphyrin IX by ATP-binding cassette transporter G2 in T24 cells.

Journal: Molecular and cellular biochemistry20111201

Title: Specific inhibition of the ABCG2 transporter could improve the efficacy of photodynamic therapy.

Journal: Journal of photochemistry and photobiology. B, Biology20111103

Title: Inhibition of c-Kit, VEGFR-2 (KDR), and ABCG2 by analogues of OSI-930.

Journal: Bioorganic & medicinal chemistry letters20111101

Title: Fungal indole alkaloid biosynthesis: genetic and biochemical investigation of the tryptoquialanine pathway in Penicillium aethiopicum.

Journal: Journal of the American Chemical Society20110302

Title: Differential inhibition of murine Bcrp1/Abcg2 and human BCRP/ABCG2 by the mycotoxin fumitremorgin C.

Journal: European journal of pharmacology20101010

Title: Specific inhibitors of the breast cancer resistance protein (BCRP).

Journal: ChemMedChem20100903

Title: BCRP/ABCG2 confers anticancer drug resistance without covalent dimerization.

Journal: Cancer science20100801

Title: Doxorubicin fails to eradicate cancer stem cells derived from anaplastic thyroid carcinoma cells: characterization of resistant cells.

Journal: International journal of oncology20100801

Title: Novel structure-activity relationships and selectivity profiling of cage dimeric 1,4-dihydropyridines as multidrug resistance (MDR) modulators.

Journal: Bioorganic & medicinal chemistry20100715

Title: Breast cancer resistance protein (BCRP)-mediated glyburide transport: effect of the C421A/Q141K BCRP single-nucleotide polymorphism.

Journal: Drug metabolism and disposition: the biological fate of chemicals20100501

Title: Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of p-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine.

Journal: Drug metabolism and disposition: the biological fate of chemicals20091001

Title: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties.

Journal: British journal of pharmacology20091001

Title: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting.

Journal: American journal of physiology. Gastrointestinal and liver physiology20090801

Title: Bioactive alkaloids from endophytic Aspergillus fumigatus.

Journal: Journal of natural products20090401

Title: Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus.

Journal: Chembiochem : a European journal of chemical biology20090323

Title: Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar.

Journal: Journal of medicinal chemistry20090226

Title: ABCG2 is expressed in late spermatogenesis and is associated with the acrosome.

Journal: Biochemical and biophysical research communications20090109

Title: Molecular expression and functional evidence of a drug efflux pump (BCRP) in human corneal epithelial cells.

Journal: Current eye research20090101

Title: Application and limitation of inhibitors in drug-transporter interactions studies.

Journal: International journal of pharmaceutics20080522

Title: Constitutive overexpression of P-glycoprotein, rather than breast cancer resistance protein or organic cation transporter 1, contributes to acquisition of imatinib-resistance in K562 cells.

Journal: Pharmaceutical research20080401

Title: The breast cancer resistance protein (Bcrp1/Abcg2) limits fetal distribution of glyburide in the pregnant mouse: an Obstetric-Fetal Pharmacology Research Unit Network and University of Washington Specialized Center of Research Study.

Journal: Molecular pharmacology20080301

Title: Functionalized chalcones as selective inhibitors of P-glycoprotein and breast cancer resistance protein.

Journal: Bioorganic & medicinal chemistry20080101

Title: Porphyrin homeostasis maintained by ABCG2 regulates self-renewal of embryonic stem cells.

Journal: PloS one20080101

Title: Expression of the ATP-binding cassette membrane transporter, ABCG2, in human and rodent brain microvessel endothelial and glial cell culture systems.

Journal: Pharmaceutical research20070701

Title: C421 allele-specific ABCG2 gene amplification confers resistance to the antitumor triazoloacridone C-1305 in human lung cancer cells.

Journal: Biochemical pharmacology20070630

Title: Energy transfer to analyse membrane-integrated mitoxantrone in BCRP-overexpressed cells.

Journal: Journal of photochemistry and photobiology. B, Biology20070525

Title: Progesterone inhibits folic acid transport in human trophoblasts.

Journal: The Journal of membrane biology20070401

Title: Zebrafish kidney marrow contains ABCG2-dependent side population cells exhibiting hematopoietic stem cell properties.

Journal: Differentiation; research in biological diversity20070301

Title: Absorption of folate by Caco-2 cells is not affected by high glucose concentration.

Journal: European journal of pharmacology20061203

Title: Complex interaction of BCRP/ABCG2 and imatinib in BCR-ABL-expressing cells: BCRP-mediated resistance to imatinib is attenuated by imatinib-induced reduction of BCRP expression.

Journal: Blood20060715

Title: Expression and functional activity of breast cancer resistance protein (BCRP, ABCG2) transporter in the human choriocarcinoma cell line BeWo.

Journal: Clinical and experimental pharmacology & physiology20060101

Title: Piperazinobenzopyranones and phenalkylaminobenzopyranones: potent inhibitors of breast cancer resistance protein (ABCG2).

Journal: Journal of medicinal chemistry20051117

Title: Breast cancer resistance protein-mediated efflux of androgen in putative benign and malignant prostate stem cells.

Journal: Cancer research20050801

Title: ABCG2-mediated transport of photosensitizers: potential impact on photodynamic therapy.

Journal: Cancer biology & therapy20050201

Title: An improved definition of mouse mammary epithelial side population cells.

Journal: Cytotherapy20050101

Title: Polyphasic taxonomy of Aspergillus fumigatus and related species.

Journal: Mycologia20050101

Title: Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites.

Journal: Journal of biotechnology20041109

Title: Liquid chromatography method for the quantitation of the breast cancer resistance protein ABCG2 inhibitor fumitremorgin C and its chemical analogues in mouse plasma and tissues.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20040805

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

Journal: Journal of natural products20040801

Title: Broad-spectrum modulation of ATP-binding cassette transport proteins by the taxane derivatives ortataxel (IDN-5109, BAY 59-8862) and tRA96023.

Journal: Cancer chemotherapy and pharmacology20040501

Title: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport.

Journal: Molecular pharmacology20040501

Title: Single amino acid substitutions in the transmembrane domains of breast cancer resistance protein (BCRP) alter cross resistance patterns in transfectants.

Journal: International journal of cancer20031210

Title: The role of breast cancer resistance protein in acute lymphoblastic leukemia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20031101

Title: Breast cancer resistance protein exports sulfated estrogens but not free estrogens.

Journal: Molecular pharmacology20030901

Title: Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter.

Journal: Cancer research20030901

Title: Transport of methotrexate, methotrexate polyglutamates, and 17beta-estradiol 17-(beta-D-glucuronide) by ABCG2: effects of acquired mutations at R482 on methotrexate transport.

Journal: Cancer research20030715

Title: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors.

Journal: Molecular pharmacology20030101

Title: Isolation and toxigenicity of Aspergillus fumigatus from moldy silage.

Journal: Mycopathologia20030101

Title: Penicillium digitatum metabolites on synthetic media and citrus fruits.

Journal: Journal of agricultural and food chemistry20021023

Title: Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C.

Journal: Molecular cancer therapeutics20020401

Title: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells.

Journal: Biochemical and biophysical research communications20010706

Title: Inhibition of BCRP-mediated drug efflux by fumitremorgin-type indolyl diketopiperazines.

Journal: Bioorganic & medicinal chemistry letters20010108

Title: Overexpression of the ATP-binding cassette half-transporter, ABCG2 (Mxr/BCrp/ABCP1), in flavopiridol-resistant human breast cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20010101

Title: Rabindran SK, et al. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res. 1998 Dec 15;58(24):5850-8.

Title: Rabindran SK, et al. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 2000 Jan 1;60(1):47-50.

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