M0253
L-Mimosine from Koa hoale seeds
≥98%
Sinónimos:
(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid, Leucenol
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About This Item
Fórmula empírica (notación de Hill):
C8H10N2O4
Número de CAS:
Peso molecular:
198.18
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de la sustancia en PubChem:
NACRES:
NA.77
Productos recomendados
Nivel de calidad
Ensayo
≥98%
cadena SMILES
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
Clave InChI
WZNJWVWKTVETCG-YFKPBYRVSA-N
Descripción general
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.
Aplicación
L-Mimosine from Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).
Acciones bioquímicas o fisiológicas
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.
Palabra de señalización
Warning
Frases de peligro
Consejos de prudencia
Clasificaciones de peligro
Acute Tox. 4 Oral
Código de clase de almacenamiento
11 - Combustible Solids
Clase de riesgo para el agua (WGK)
WGK 3
Punto de inflamabilidad (°F)
Not applicable
Punto de inflamabilidad (°C)
Not applicable
Equipo de protección personal
dust mask type N95 (US), Eyeshields, Gloves
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H Agis et al.
Journal of periodontal research, 47(2), 165-173 (2011-10-01)
Pharmacological inhibitors of prolyl hydroxylases (PHDs) can induce a proangiogenic response that favors wound healing and bone regeneration. However, the response of periodontal cells to PHD inhibitors is unknown. To determine the effects of PHD inhibitors on periodontal cells, we
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Mimosine blocks cell cycle progression by chelating iron in asynchronous human breast cancer cells.
Kulp KS and Vulliet PR.
Toxicology and Applied Pharmacology, 139(2), 356-364 (1996)
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