Meleagrin

Modify Date: 2024-01-03 10:50:56

Meleagrin Structure
Meleagrin structure
Common Name Meleagrin
CAS Number 71751-77-4 Molecular Weight 433.46000
Density 1.47g/cm3 Boiling Point N/A
Molecular Formula C23H23N5O4 Melting Point N/A
MSDS Chinese USA Flash Point N/A

 Use of Meleagrin


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].

 Names

Name meleagrine
Synonym More Synonyms

 Meleagrin Biological Activity

Description 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].
Related Catalog
In Vitro 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].
In Vivo Meleagrin potently suppresses the invasive triple negative breast tumor cell growth in an orthotopic athymic nude mice model[3].
References

[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.

[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.

[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.

 Chemical & Physical Properties

Density 1.47g/cm3
Molecular Formula C23H23N5O4
Molecular Weight 433.46000
Exact Mass 433.17500
PSA 110.79000
LogP 2.68160
Index of Refraction 1.717

 Safety Information

Hazard Codes Xi
RIDADR NONH for all modes of transport

 Precursor & DownStream

Precursor  1

DownStream  0

 Articles4

More Articles
[The biosynthesis of low-molecular-weight nitrogen-containing secondary metabolite-alkaloids by the resident strains of Penicillium chrysogenum and Penicillium expansum isolated on the board of the Mir space station ].

Mikrobiologiia 71(6) , 773-7, (2002)

The analysis of the absorption spectra of the low-molecular-weight nitrogen-containing secondary metabolites--alkaloids--of 4 Penicillium chrysogenum strains and 6 Penicillium expansum strains isolate...

A single cluster of coregulated genes encodes the biosynthesis of the mycotoxins roquefortine C and meleagrin in Penicillium chrysogenum.

Chem. Biol. 18(11) , 1499-512, (2011)

A single gene cluster of Penicillium chrysogenum contains genes involved in the biosynthesis and secretion of the mycotoxins roquefortine C and meleagrin. Five of these genes have been silenced by RNA...

Roquefortine/oxaline biosynthesis pathway metabolites in Penicillium ser. Corymbifera: in planta production and implications for competitive fitness.

J. Chem. Ecol. 31(10) , 2373-90, (2005)

Three strains of each of the seven taxa comprising the Penicillium series Corymbifera were surveyed by direct injection mass spectrometry (MS) and liquid chromatography-MS for the production of terres...

 Synonyms

[3E,7aR,12aS,(-)]-7a-(1,1-Dimethyl-2-propenyl)-7a,12-dihydro-6-hydroxy-3-(1H-imidazole-4-ylmethylene)-12-methoxy-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2(3H),5-dione
8,9-dehydroneoxaline
MELEAGRIN
Meleagrine