(S)-α-Amino-3-hydroxy-4-oxo-1(4H)-pyridylpropionsure

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

L-MIMOSINE Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Beschreibung

  This alkaloid was isolated by Renz from Mimosia pudica L. and also from Leucaena glauca Benth. It is laevorotatory with [α]²²_D - 21 ° (H20) and yields a blue, crystalline copper salt. On heating the chloride under pressure, a sublimate is formed which has been shown, by comparison with a synthetic specimen, to be N-methyl-3-hydroxypyrid-4-one, m.p. 224°C. The alkaloid is toxic and in horses produces loss of hair when administered in large doses.

• Chemische Eigenschaften

  light tan to pink crystalline powder

• Verwenden

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

• Definition

  ChEBI: An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.

• Allgemeine Beschreibung

  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.

• 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.

• Einzelnachweise

  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)

(S)-α-Amino-3-hydroxy-4-oxo-1(4H)-pyridylpropionsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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