Mimosine

Names

[ CAS No. ]:
500-44-7

[ Name ]:
Mimosine

[Synonym ]:
Mimosine
(S)-2-amino-3-(3-hydroxy-4-oxo-4H-[1]pyridyl)-propionic acid
EINECS 207-905-1
leucenine
(S)-2-Amino-3-(3-hydroxy-4-oxo-4H-[1]pyridyl)-propionsaeure
(s)-1(4h)-pyridinepropanoicaci
MimosineLeucenol
MFCD00075909
L-Mimosine from Koa hoale seeds
L-LEUCININE
L(-)-MIMOSINE
LEUCENOL

Biological Activity

[Description]:

Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

Mimosine, a known chelator of Fe(III), may facilitate Fe(III) uptake in leucaena by serving as a phytosiderophore[2]. Mimosine, a bidentate iron-binding ligand, may also play a role in cellular translocation of iron within leucaena[2]. Mimosine is a toxic nonprotein amino acid that is a major constituent of the tropical legumesLeucaenaandMimosa[4]. Mimosine (400 μM), through iron chelation, reversibly blocks cell cycle progression in MDA-MB-453 human breast cancer cells[4]. Mimosine (400 μM) reduces DNA synthesis by greater than 90% of control within 4 hr of treatment, and suppresses total proline-directed protein kinase activity to less than 10% of control after 16 hr treatment[4].

[In Vivo]

Mimosine (30, and 60 mg/kg) decreases sperm concentration[5]. Animal Model: ICR male mice (6-8 weeks)[5] Dosage: 15, 30, or 60 mg/kg Administration: Injected (i.p.) for 7 consecutive days Result: Could significantly reduce sperm concentration as compared to the control or low dose mimosine group (15 mg/kg) at doses of 30 and 60 mg/kg.

[References]

[1]. Keiko Murakami, et al. Generation of reactive oxygen species by hydroxypyridone compound/iron complexes. Redox Rep. 2020 Dec;25(1):59-63.

[2]. Michael D H Honda, et al. Mimosine facilitates metallic cation uptake by plants through formation of mimosine-cation complexes.Plant Mol Biol. 2020 Mar;102(4-5):431-445.

[3]. MaherHallakMSc, et al. Mimosine Induces Apoptosis through Metal Ion Chelation, Mitochondrial Activation and Reactive Oxygen Species Production in Human Leukemic Cells. Blood.2004, Nov 16, 104 (11): 4481.

[4]. K S Kulp, et al. Mimosine blocks cell cycle progression by chelating iron in asynchronous human breast cancer cells. Toxicol Appl Pharmacol. 1996 Aug;139(2):356-64.

[5]. Pipatpong Kanla, et al. Acute Effects of Mimosine Purified from Leucaena leucocephala on Male Reproductive System of Adult Mice. Int. J. Morphol., 36(2):507-512, 2018.

Chemical & Physical Properties

[ Density]:
1.544g/cm3

[ Boiling Point ]:
428.6ºC at 760mmHg

[ Melting Point ]:
224-228 °C

[ Molecular Formula ]:
C₈H₁₀N₂O₄

[ Molecular Weight ]:
198.18

[ Flash Point ]:
213ºC

[ Exact Mass ]:
198.06400

[ PSA ]:
105.55000

[ Index of Refraction ]:
1.645

[ Storage condition ]:
2-8C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933399090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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