This product can be solubilized at 50 mg/ml of 1M ammonium hydroxide. This product can also be
solubilized in water at 2mg/ml forming a clear to slightly hazy colorless solution. Solubility may be increased to at least 10mg/ml by solubilizing in either dilute acid or base. It is probably preferable to prepare a slightly acidic solution since this would maintain the amine group as a quaternary amine, which is less prone to oxidation. These solutions may be stored short term in the refrigerator or long term as frozen aliquots. Specifics around in vivo and/or in vitro applications have not been determined for this product. Consult the scientific literature for further information around the use of this product in these applications. You can find "Peer Reviewed Papers" near the bottom of this product's webpage for help in your search for more information.
M0253
L-Mimosine from Koa hoale seeds
≥98%
Synonym(s):
(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid, Leucenol
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About This Item
Empirical Formula (Hill Notation):
C8H10N2O4
CAS Number:
Molecular Weight:
198.18
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
207-905-1
MDL number:
Pricing and availability is not currently available.
Quality Segment
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
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).
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.[1] 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.[1] 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.
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This Item | |||
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| assay ≥98% | assay 99% | assay ≥99% (TLC) | assay 99% |
| Quality Level 200 | Quality Level 300 | Quality Level 200 | Quality Level 300, 400 |
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Dear Sigma, We would like to know what solvent can be used to dissolve M0253 L-Mimosine into solution? What working concentrations are recommended to use in vivo and in cells respectively? What maximal concentrations have been used without toxicity ?
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