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M0253 Sigma-Aldrich

L-Mimosine from Koa hoale seeds

≥98%

Synonym: (S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid, Leucenol

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Properties

Related Categories Aerobic Glycolysis (the Warburg Effect), Apoptosis and Cell Cycle, Cancer Metabolism, Cancer Research, Cell Biology,
Quality Level   200
assay   ≥98%
SMILES string   N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O
InChI   1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
InChI key   WZNJWVWKTVETCG-YFKPBYRVSA-N

Description

General description

L-mimosine [β-N (3-hydroxy-4-pyridone)-α-amino propionic acid] is a non-protein amino acid and is a vital component of tropical legumes, such as Leucaena glauca and other legumes belonging to Mimosa spp. Structurally L-mimosine resembles dihydroxyphenylalanine except 3,4-dihydroxy-phenyl ring replaced by 3-hydroxy-4-pyridone ring.

Application

L-Mimosine from Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).

Packaging

1 g in glass bottle

100, 500 mg in glass bottle

25 mg in poly bottle

Biochem/physiol Actions

L-Mimosine is a plant amino acid and potential inhibitor of the cell cycle giving rise to growth arrest in G1-phase. It is an iron chelator that inhibits DNA replication in mammalian cells. L-Mimosine has been shown to promote apoptosis in xenotransplanted human pancreatic cancer. L-Mimosine stabilizes hypoxia inducible factor 1 (HIF-1) and stimulates the expression of B-cell translocation gene 2 (Btg2) and N-myc downstream regulated gene 1 (Ndrg1) at the transcriptional level, which reduce cell proliferation of prostate carcinoma cells in vitro. L-Mimosine stabilizes HIF-1 through the inhibition of prolyl hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity. Mimosine inhibits cell cycle progression via iron chelation in MDA-MB-453 human breast cancer cells. Mimosine, hinder folate metabolism in cell-specific manner.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Oncogenes and Tumor Suppressors Reprogram Metabolism

Proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication. This requires a reprogramming of the metabolic pathways to ensure nutrients s...
BioFiles v7 n4
Keywords: Aerobic, Antitumor agents, Apoptosis, Cancer, Citric Acid Cycle, Degradations, Environmental, Gene expression, Glycolysis, Growth factors, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, Pentose phosphate pathway, Phosphorylations

Peer-Reviewed Papers
15

References

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