Мимозин

What is this

Mimosine is a non-proteinogenic amino acid of plant origin, (S)-α-amino-3-hydroxy-4-oxo-1(4H)-pyridinepropanoic acid. Instead of the benzene ring of tyrosine, the molecule contains 3-hydroxy-4-pyridone, linked to the side chain through a nitrogen atom. Synonyms: L-mimosine, leukaenin, leukaenol, leucenol, leucenin, NSC 69188. Produced by legumes of the genera Leucaena and Mimosa, it serves as their protective secondary metabolite.

Basic Attributes

• CAS No.: 500-44-7; additional registration number 27678-82-6
• Chemical formula: C8H10N2O4
• Molecular Weight: 198.18
• Exact weight: 198.18
• EU number: 207-905-1
• UNII: Z46B1LUI5N
• HS code: 29333990
• PSA Specifications: 104
• XLogP3: −2.5

Physico-chemical characteristics

• Appearance: solid; crystallizes from water in the form of crystals and plates
• Density: 1.544 g/cm³
• Melting point: 225 °C
• Boiling point: 428.6 °C at 760 mm Hg. Art.
• Flash point: 213 °C
• Refractive index: 1.645
• Solubility in water: 13.1 g/l
• Specific optical rotation: −21° at 22 °C, line D, water, C = 0.5
• Absorption maxima in water: 215 nm (log ε = 4.6) and 280 nm (log ε = 4.6)
• Impact cross section: 143.47 Ų [M+H]⁺, CCS type: DT, step field method

Mechanism of action

Mimosine is structurally close to tyrosine and for this reason inhibits tyrosinase. The second key property is iron chelation: by binding a metal ion, the substance turns off iron-dependent ribonucleotide reductase, disrupts the exchange of deoxyribonucleotides and stops DNA elongation at the G1/S transition. Hence the main laboratory application: the compound synchronizes cell cultures in the late G1 phase, blocking entry into S-phase, while the involvement of the ATM gene and the accumulation of the cyclin-dependent kinase inhibitor p27(Kip1) are described. Publications in recent years have examined the antitumor potential of the substance on different types of malignant cells.

Application

• cell biology reagent for synchronizing cultures at the G1/S boundary
• research tool for iron-dependent enzymes and chelation therapy
• object of work on inhibition of tyrosinase and melanogenesis
• analytical standard for the control of feed raw materials from leucaena: the mimosine content limits the share of this plant in the animal diet

Safety Information

• Hazard statements: H302, H312, H332
• Precautionary statements: P280
• Hazard class code according to the previous system: 20/21/22
• Safety instructions: 22-36
• Tags: Xn
• WGK Germany: 3
• Transport codes: NONH for all modes of transport

Storage and handling

Keep in a tightly closed container in a dry place, protected from light: the hydroxypyridone fragment is prone to oxidation and forms colored complexes with iron ions. Work with the powder is carried out with gloves, safety glasses and respiratory protection; inhalation of dust and contact with skin is excluded.