Fumitremorgin C

• CAT Number: R040880
• CAS Number: 118974-02-0
• Molecular Formula: C22H25N3O3
• Molecular Weight: 379.5
• Purity: ≥95%
• Synonyms: (5aS,12S,14aS)-1,2,3,5a,6,11,12,14a-Octahydro-9-methoxy-12-(2-methyl-1-propen-1-yl)-5H,14H-pyrrolo[1’’,2’’:4’,5’]pyrazino[1’,2’:1,6]pyrido[3,4-b]indole-5,14-dione
• Target: Multidrug Transporters
• Solubility: Soluble in DMSO > 10 mM
• Storage: Store at +4C
• IUPAC Name: (1S,12S,15S)-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione
• InChI: InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
• InChIKey: DBEYVIGIPJSTOR-FHWLQOOXSA-N
• SMILES: CC(=CC1C2=C(CC3N1C(=O)C4CCCN4C3=O)C5=C(N2)C=C(C=C5)OC)C

Fumitremorgin C(CAS118974-02-0) is a tremorgenic mycotoxin isolated from Aspergillus fumigatus. Recent research has recognized Fumitremorgin C as a potent and specific inhibitor of the breast cancer resistance protein (BCRP/ABCG2) multidrug transporter. It reverses multidrug resistance mediated by BCRP and increases cytotoxicity of several anticancer agents in vitro.

Reference

1.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. Allen J.D. et al. Mol. Cancer Ther. 2002, 1, 417.

2.Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Rabindran S.K. et al. Cancer Res. 2000, 60, 47.

3.Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties. Cui C.B. et al. J. Antibiot. 1996, 49, 527.

4.Mycotoxins produced by Aspergillus fumigatus species isolated from molded silage. Cole R.J. et al. J. Agric. Food Chem. 1977, 25, 826.