Nicotianamine
Nicotianamine is an orally active ACE inhibitor with an IC50 of 76 nM for rhACE2 and an IC50 of 59 nM for rhACE. Nicotianamine is also a metal chelator with high affinity for ferrous ions and other divalent metal cations. Nicotianamine is isolated from soybean. Nicotianamine reduces systolic blood pressure in spontaneously hypertensive rats. Nicotianamine chelates iron and zinc, promotes iron transport, enhances iron bioavailability through stable Fe2+-NA complexes and intestinal Fe2+ uptake, and promotes phloem-to-sink Fe mobilization, long-distance transport of Zn to leaves and flowers, and pollen development. Nicotianamine is a biosynthetic precursor of plant phytosiderophores, reverses chlorosis, and rescues sterility in NA-free mutants. Nicotianamine is used in research on hypertension, chlorosis, and iron deficiency anemia.
For research use only. We do not sell to patients.
- CAS No.: 34441-14-0
- Formula: C12H21N3O6
- Molecular Weight:303.31
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Storage:
-20°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
IC50 & Target
[1]|
ACE 59 nM (IC50) |
In Vitro
Nicotianamine inhibits rhACE2 activity with an IC50 of 76 nM[1].
Nicotianamine inhibits rhACE activity with an IC50 of 59 nM[1].
Nicotianamine inhibits ACE with an IC50 of 0.26 µM[2].
Nicotianamine (1 h) inhibits rabbit lung ACE activity with an IC50 of 0.69 μM in a cell-free enzymatic assay[3].
Synthetic Nicotianamine (30 µM; daily for seven days) reverts the chlorotic phenotype and restores normal growth in the NA-free tomato mutant chloronerva[4].
Nicotianamine (5 µM; daily) application rescues sterility in Arabidopsis thaliana nas4x-2 mutant plants[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Nicotianamine (0.9-9.0 mg/kg; p.o.; single dose) significantly reduces systolic blood pressure at 1 h after administration in SHR rats, with the effect returning to control levels at 3 h[3].
Nicotianamine (9.0 mg/kg; p.o.; daily; 8 weeks) produces a sustained antihypertensive effect in SHR, maintaining a 23.4 mmHg reduction in SBP throughout the 8-week feeding period, which correlates with a serum NA concentration of 32.6 μg/dL[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Spontaneously hypertensive rats (SHR)[2]
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Dosage:20 mg/kg
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Administration:single administration
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Result:Decreased blood pressure by 24 mmHg at 1 h.
Decreased blood pressure by 20 mmHg at 4 h.
Decreased blood pressure by 19 mmHg at 8 h.
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Animal Model:Sprague-Dawley-derived SHR (male, 20 weeks old)[3]
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Dosage:0.9, 4.5, and 9.0 mg/kg body weight
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Administration:p.o.; single dose
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Result:Significantly lowered systolic blood pressure at 1 h after administration at 4.5 mg/kg and 9.0 mg/kg body weight compared to control.
Returned systolic blood pressure to control level at 3 h after administration.
Did not produce a significant reduction in systolic blood pressure at 0.9 mg/kg single dose.
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Animal Model:Sprague-Dawley-derived SHR (male, 22 weeks old)[3]
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Dosage:0.9, 4.5, and 9.0 mg/kg body weight
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Administration:p.o.; daily; 8 weeks, followed by 2-week withdrawal
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Result:Significantly lowered systolic blood pressure for 2-4 weeks after administration initiation at 0.9, 4.5, and 9.0 mg/kg.
Gradually returned systolic blood pressure to control level 6 to 8 weeks after administration initiation at 0.9 and 4.5 mg/kg.
Significantly lowered systolic blood pressure with a 23.4 mmHg decrease for the full 8 weeks of the test feeding period at 9.0 mg/kg.
Detected serum NA content of 32.6 μg/dL (n=6) at 8 weeks after administration at 9.0 mg/kg.
Did not detect serum NA content at 8 weeks after administration at 0.9 mg/kg and 4.5 mg/kg.
Did not detect nicotianamine in the serum at 2 weeks after withdrawal from the test diet.
Chemical Information
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CAS No. 34441-14-0
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Appearance Solid
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Molecular Weight 303.31
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Formula C12H21N3O6
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Color White to off-white
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SMILES
OC([C@@H](N)CCN[C@H](C(O)=O)CCN1[C@@H](CC1)C(O)=O)=O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
-20°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Purity & Documentation
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Data Sheet (286 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
[1]. Takahashi S, et al. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soybean. Biomedical research (Tokyo, Japan). 2015;36(3):219-24. [Content Brief]
[4]. Bouazaoui M, et al. Synthesis and biological activity of nicotianamine and analogues. Adv Exp Med Biol. 2009;611:555-7. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Nicotianamine Related Classifications
HY-121858 Related Classifications
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