A1393

5-Aminoimidazol-4-carboxamid-1-β-D-ribofuranosyl 5′-Monophosphat

≥93%

• Synonym(e): AICAR-monophosphat, N¹-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazol-4-carboxamid, NSC 283955, NSC 292227, ZMP
• Empirische Formel (Hill-System): C₉H₁₅N₄O₈P
• CAS-Nummer: 3031-94-5
• Molekulargewicht: 338.21
• EG-Nummer: 221-212-1
• UNSPSC-Code: 41106305
• PubChem Substanz-ID: 24890538
• NACRES: NA.51

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥93%
• Form: powder
• Mol-Gew.: 338.21 g/mol
• Lagertemp.: −20°C
• SMILES String: O[C@H]1[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O[C@@H]1COP(O)(O)=O
• InChI: 1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
• InChIKey: NOTGFIUVDGNKRI-UUOKFMHZSA-N

Beschreibung

Allgemeine Beschreibung

5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5′-monophosphate (AICAR), a natural metabolic intermediate of purine biosynthesis, is usually found in all organisms. It is produced from succinyl-AICAR (SAICAR) with the help of adenylosuccinate lyase (ASL) enzyme.

Anwendung

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate has been used in the study to explore the anticancer effect of nine statins in breast cancer and glioblastoma.

AICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.

Biochem./physiol. Wirkung

A 5′-phosphorylated analog of cell permeable AICAR that mimics adenosine monophosphate (AMP). It is an AMP-activated protein kinase (AMPK) activator.
In humans, 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR) is found to be accumulated in numerous metabolic diseases. It can increase the endurance of sedentary mice. AICAR exhibits antiproliferative effects. It can induce apoptosis of aneuploid cells.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)