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Meleagrin is a novel indole alkaloid with a heterotetracyclic skeleton, biosynthesized via the roquefortine branched biosynthetic pathway. It is an alkaloid derived from various species of Penicillium and is known for its antitumor and antibiotic properties. Meleagrin is also a common taxonomic marker for fungal contamination of foodstuffs. It displays excellent ATP-competitive c-MET inhibition, which helps in inhibiting the growth, migration, and invasion of numerous breast cancer cell lines. Additionally, Meleagrin has been shown to inhibit the bacterial enoyl-acyl carrier protein reductase (Fabl) with IC50s in the 33-40 mM range.

71751-77-4

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71751-77-4 Usage

Uses

Used in Anticancer Applications:
Meleagrin is used as an antitumor agent for its ATP-competitive c-MET inhibition, which helps in inhibiting the growth, migration, and invasion of various breast cancer cell lines.
Used in Antibiotic Applications:
Meleagrin is used as an antibiotic derived from the deep ocean, acting as an inhibitor of the bacterial enoyl-acyl carrier protein reductase (Fabl). It effectively inhibits the growth of S. aureus, E. coli, and S. pneumoniae.
Used in Food Industry:
Meleagrin is used as a taxonomic marker for detecting fungal contamination in the food industry, ensuring the safety and quality of food products.

in vitro

it was found that consistent with their selective inhibition of staphylococcus aureus fabi, meleagrin and its more active derivatives could directly bind to s. aureus fabi that was measured in a fluorescence quenching assay, inhibit intracellular fatty acid biosynthesis and growth of s. aureus, and increase the minimum inhibitory concentration (mic) for fabi-overexpressing s. aureus. the compounds that were not effective against the fabk isoform, however, were able to inhibit the growth of streptococcus pneumoniae containing only the fabk isoform. in addition, no resistant mutant to these compounds was obtained. notely, fabk-overexpressing escherichia coli was found to be not resistant to these compounds, but was resistant to triclosan [1]. another study found that meleagrin was able to inhibit the growth of the human breast cancer cell lines, while similar treatment doses had no effect on the growth and viability of the non-tumorigenic human mammary epithelial cells mcf10a. meleagrin also displayed good atp competitive c-met inhibitory activity in z-lyte assay [2].

References

1) Ries et al. (2013), Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway; J. Biol. Chem., 288 37289 2) Newmister et al. (2016), OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30l; J. Am. Chem. Soc., 138 11176 3) Mady et al. (2016), 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, migrations and invasion; Bioorg. Med. Chem., 24 113 4) Zheng et al. (2013), Meleagrin, a new Fabl inhibitor from Penicillium chryosogenum with at least one additional mode of action; PLoS One, 8(11) e78922

Check Digit Verification of cas no

The CAS Registry Mumber 71751-77-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,7,5 and 1 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 71751-77:
(7*7)+(6*1)+(5*7)+(4*5)+(3*1)+(2*7)+(1*7)=134
134 % 10 = 4
So 71751-77-4 is a valid CAS Registry Number.

71751-77-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name meleagrine

1.2 Other means of identification

Product number -
Other names [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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71751-77-4 SDS

71751-77-4Downstream Products

71751-77-4Relevant articles and documents

Oxaline and Neoxaline

Konda, Yaeko,Onda, Masayuki,Hirano, Atsushi,Omura, Satoshi

, p. 2987 - 2993 (2007/10/02)

Oxaline (1) has been isolated from Penicillium species Fg-234 and the structure of the compound (2) obtained by treatment of 1 with hydrochloric acid is deduced on the basis of spectral data.Neoxaline (9) isolated from Aspergillus japonicus Fg-551 has a structural framework similar to that of 1.

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