500-44-7 Usage
Description
L-MIMOSINE, also known as β-N(3-hydroxy-4-pyridone)-α-amino propionic acid, is a non-protein amino acid derived from tropical legumes such as Leucaena glauca and other legumes belonging to the Mimosa spp. It is structurally similar to dihydroxyphenylalanine, with a 3-hydroxy-4-pyridone ring replacing the 3,4-dihydroxy-phenyl ring. L-MIMOSINE is a light tan to pink crystalline powder and is toxic, causing hair loss in horses when administered in large doses.
Uses
Used in Pharmaceutical Industry:
L-MIMOSINE is used as a pharmaceutical compound for its potential anti-inflammatory effects. It has been studied for its impact on chronic inflammatory responses, such as those induced by potassium permanganate in chronic granuloma.
Used in Research and Development:
L-MIMOSINE serves as a valuable compound in research and development, particularly in the study of its chemical properties, structural similarities to other compounds, and potential applications in various fields, including pharmaceuticals and agriculture.
Used in Toxicology Studies:
Due to its toxic nature, L-MIMOSINE is utilized in toxicology studies to understand its effects on living organisms and to develop potential antidotes or treatments for its toxic effects.
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.
References
Renz., Zeit. physiol. Chem., 244, 153 (1936)Nienburg, Taubock., ibid, 250,80 (1937)Kostermanns., Rec. trav. Chim. Pays-Bas, 65, 319 (1946)Kostermann., ibid, 66,93 (1947)
Check Digit Verification of cas no
The CAS Registry Mumber 500-44-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 500-44:
(5*5)+(4*0)+(3*0)+(2*4)+(1*4)=37
37 % 10 = 7
So 500-44-7 is a valid CAS Registry Number.
InChI:InChI=1/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-/m1/s1
500-44-7Relevant articles and documents
BIOSYNTHESIS OF β-(1,2,4-TRIAZOL-1-YL)ALANINE IN HIGHER PLANTS
Ikegami, Fumio,Komada, Yumiko,Kobori, Masuko,Hawkins, Douglas R.,Murakoshi, Isamu
, p. 2507 - 2508 (2007/10/02)
β-(1,2,4-triazol-1-yl)Alanine, an important metabolite of the triazole-based fungicide Myclobutanil, was shown to be derived from O-acetyl-L-serine and 1,2,4-triazole by cysteine synthase in higher plants.Some properties of this enzyme in the biosynthesis of β-(1,2,4-triazol-1-yl)alanine are described.
BIOSYNTHESIS AND BIOMIMETIC SYNTHESIS OF HETEROCYCLIC β-SUBSTITUTED ALANINES IN HIGHER PLANTS
Murakoshi, Isamu,Ikegami, Fumio,Koide, Chiharu
, p. 705 (2007/10/02)
-