Meleagrin

• CAT Number: R028312
• CAS Number: 71751-77-4
• Molecular Formula: C23H23N5O4
• Molecular Weight: 433.46
• Purity: ≥95%
• Synonyms: (1S,9R,14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7,10-tetraene-12,15-dione
• InChI: InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1
• InChIKey: JTJJJLSLKZFEPJ-ZAYCRUKZSA-N
• SMILES: CC(C)(C=C)C12C=C(C(=O)N3C1(NC(=O)C3=CC4=CN=CN4)N(C5=CC=CC=C25)OC)O

Meleagrin is a roquefortine C-derived alkaloid produced by fungi of the genus Penicillium and has antimicrobial and anti-proliferative activities. Meleagrin is a class of FabI inhibitor. Meleagrin is a lead c-Met inhibitory entity useful for the control of c-Met-dependent metastatic and invasive breast malignancies[1][2][3].
Meleagrin inhibits the growth of the human breast cancer cell lines MDA-MB-231, MDA-468, BT-474, SK BR-3, MCF7 and MCF7-dox[3].
Meleagrin causes a dose-dependent inhibition of HGF-induced cell migration, and invasion of breast cancer cell lines[3].
Meleagrin potently suppresses the invasive triple negative breast tumor cell growth in an orthotopic athymic nude mice model[3].

Reference

[1]. Newmister SA, et al. Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosyntheticpathway. Org Biomol Chem. 2018 Sep 11;16(35):6450-6459.
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[2]. Zheng CJ, et al. Meleagrin, a new FabI inhibitor from Penicillium chryosogenum with at least one additional mode of action. PLoS One. 2013 Nov 28;8(11):e78922.
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[3]. Mady MS, et al. The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion. Bioorg Med Chem. 2016 Jan 15;24(2):113-22.
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