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L-Mimosine

In stock
Catalog No.
B4751
iron chelator and prolyl 4-hydroxylase inhibitor
Grouped product items
SizePriceStock Qty
200mg
$80.00
In stock
500mg
$150.00
In stock

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L-mimosine is a prolyl 4-hydroxylase inhibitor and acts as an iron chelator [1]. In rats, it interfered with the reconstitution of the active human prolyl 4-hydroxylase with an IC50 value of 120 µM [2].

Prolyl 4-hydroxylase (EC 1.14.11.2) is an α2β2 tetramer. It catalyses the formation of 4-hydroxyproline in coliagen via the hydroxylation of proline residues in the peptide linkage [3]. Prolyl-4-hydroxylase domain-containing protein (PHD) regulates HIF-1α levels in renal medulla and participates in controlling renal Na+ excretion [4].

L-mimosine acted as an inhibitor for prolyl 4-hydroxylase in cultured vascular cells. L-mimosine dose-dependently inhibited the activity of prolyl hydroxylase in rat and human smooth muscle cells (SMC) and at concentrations of 400-500 µM decreased hydroxyprolyl generation by 80-90%. At that concentration, [3H]proline incorporation was decreased by < 20% in human SMC and was increased by 20% in rat SMC. These results indicated that L-mimosine quite specifically inhibited prolyl hydroxylation [2].

In rats, the pretreatment with L-mimosine for 2 weeks significantly reduced the PHD activity in kidneys. This inhibition was greater in renal medulla than in renal cortex. Western blot analysis data demonstrated that L-mimosine significantly increased protein levels of HIF-1α in the kidneys from L-mimosine-treated rats, compared with vehicle-treated rats. In animals, the pretreatment with L-mimosine substantially increased HIF-1α levels in medulla and renal cortex, but the effect in the medulla was much greater than that in the cortex. Inhibitory effects on PHD activity and HIF-1α decoyed on HIF-1α transcriptional activities in renal medulla [4]

References:
[1].  Chung LC, Tsui KH, Feng TH, et al. L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. American Journal of Physiology-Cell Physiology, 2012, 302(4): C676-C685.
[2].  McCaffrey TA, Pomerantz KB, Sanborn TA, et al. Specific inhibition of eIF-5A and collagen hydroxylation by a single agent. Antiproliferative and fibrosuppressive effects on smooth muscle cells from human coronary arteries. Journal of Clinical Investigation, 1995, 95(2): 446.
[3].  Pihlajaniemi T, Helaakoski T, Tasanen K, et al. Molecular cloning of the beta-subunit of human prolyl 4-hydroxylase. This subunit and protein disulphide isomerase are products of the same gene. The EMBO Journal, 1987, 6(3): 643.
[4].  Li N, Yi F, Sundy CM, et al. Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. American Journal of Physiology-Renal Physiology, 2007, 292(1): F207-F216.

Chemical Properties

StorageDesiccate at -20°C
M.Wt198.18
Cas No.500-44-7
FormulaC8H10N2O4
Solubility<1.98mg/mL in DMSO, ≥1.98mg/mL in H2O with ultrasonic and warming
Chemical Name(S)-2-amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid
SDFDownload SDF
Canonical SMILESN[[email protected]@](C(O)=O)([H])CN(C=C1O)C=CC1=O
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

LNCaP and PC-3 cell lines

Preparation method

The solubility of this compound in DMSO is limited. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

0–800 μM for 48h

Applications

In [3H]thymidine incorporation assay, inhibition of PC-3 cell growth occurred initially at 50 μM of L-mimosine, increasing as the dose increased. The 400 μM of L-mimosine significantly blocked 97% of [3H]thymidine incorporation in PC-3 cells after treatment with L-mimosine for 48 h.

Animal experiment [2]:

Animal models

Sprague-Dawley rats

Dosage form

50 mg/kg/day, i.p. for 2 wk

Application

In rat, the PHD inhibitor L-mimosine upregulated HIF-1α expression in the kidneys, especially in the renal medulla, and remarkably enhanced the natriuretic response to renal perfusion pressure.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1] Chung LC, Tsui KH, Feng TH, et al. L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. American Journal of Physiology-Cell Physiology, 2012, 302(4): C676-C685.

[2] Li N, Yi F, Sundy CM, et al. Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. American Journal of Physiology-Renal Physiology, 2007, 292(1): F207-F216.

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