Nicotianamine |
| Katalog-Nr.GC18766 |
Nicotianamine is a secondary metabolite synthesized by plants that plays a central role in maintaining metal ion homeostasis.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 34441-14-0
Sample solution is provided at 25 µL, 10mM.
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Nicotianamine is a secondary metabolite synthesized by plants that plays a central role in maintaining metal ion homeostasis[1]. Nicotianamine can form stable chelates with various metal ions, for example, iron, zinc, copper, and manganese, thereby promoting their transport and distribution within plants[2]. Nicotianamine is essential for metal nutrition and metal homeostasis in flowering plants, and its deficiency leads to growth abnormalities and imbalances in metal ion distribution[3]. Additionally, Nicotianamine exhibits inhibitory activity against angiotensin-converting enzyme (ACE), with IC₅₀ values of 76nM (against rhACE2) and 59nM (against rhACE)[4].
In vitro, treatment of Caco-2 cells with Nicotianamine (10μM) together with an iron-containing solution significantly increased cellular ferritin synthesis levels, enhancing iron bioavailability[5]. When supplemented (100 μM) into airway mucosal secretions (AMS) and used to pretreat Pseudomonas aeruginosa (PAO1) and ΔPA4834 mutant strain for 16 hours, Nicotianamine maintained the growth capacity of both PAO1 and the ΔPA4834 mutant in AMS and significantly improved bacterial iron acquisition efficiency[6].
In vivo, oral administration of a Nicotianamine (33mM) and ferrous iron (3.3mM) chelate via gastric gavage to 8-week-old ICR mice significantly promoted iron absorption in the proximal jejunum and increased iron content in the kidneys and spleen within 5 hours[7]. In ovo injection of Nicotianamine (1.6mM) into 17-day-old chicken embryos significantly elevated serum iron concentration in the chickens and suppressed the expression of iron homeostasis genes such as DcytB and DMT1 in the duodenum[8].
References:
[1] Bouazaoui M, Mari S, Czernic P, et al. Synthesis and biological activity of nicotianamine and analogues. Adv Exp Med Biol. 2009;611:555-7.
[2] Trampczynska A, Küpper H, Meyer-Klaucke W, et al. Nicotianamine forms complexes with Zn(II) in vivo. Metallomics. 2010 Jan;2(1):57-66.
[3] Clemens S, Deinlein U, Ahmadi H, et al. Nicotianamine is a major player in plant Zn homeostasis. Biometals. 2013 Aug;26(4):623-32.
[4] Takahashi S, Yoshiya T, Yoshizawa-Kumagaye K, et al. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soybean. Biomed Res. 2015;36(3):219-24.
[5] Zheng L, Cheng Z, Ai C, et al. Nicotianamine, a novel enhancer of rice iron bioavailability to humans. PLoS One. 2010 Apr 16;5(4):e10190.
[6] Gi M, Lee KM, Kim SC, et al. A novel siderophore system is essential for the growth of Pseudomonas aeruginosa in airway mucus. Sci Rep. 2015 Oct 8;5:14644.
[7] Murata Y, Yoshida M, Sakamoto N, et al. Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine. J Biol Chem. 2021 Jan-Jun;296:100195.
[8] Beasley JT, Johnson AAT, Kolba N, et al. Nicotianamine-chelated iron positively affects iron status, intestinal morphology and microbial populations in vivo (Gallus gallus). Sci Rep. 2020 Feb 10;10(1):2297.
| Cell experiment [1]: | |
Cell lines | Caco-2 cells (human epithelial colorectal adenocarcinoma cell line) |
Preparation Method | Caco-2 cell monolayers were cultured in high-glucose Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% fetal bovine serum and 1% penicillin/streptomycin at 37°C in a 5% CO₂ atmosphere. Cells were incubated with in vitro digested milled rice samples containing varying Nicotianamine (10μM) concentrations for measurement of iron bioavailability. |
Reaction Conditions | 10μM; 30min |
Applications | Nicotianamine significantly enhanced iron bioavailability in Caco-2 cells. |
| Animal experiment [2]: | |
Animal models | ICR mice |
Preparation Method | Mice were fed synthetic AIN-93M diet for 1 week to eliminate dietary NA effects, fasted for 16 hours, then orally administered NA-Fe(II) complex [Nicotianamine (33mM) /Fe (3.3mM) molar ratio=10:1] or free Fe(II) via intragastric gavage (200μL). Blood, spleen, liver, kidney, and small intestine tissues were collected at 0.5, 2, and 5 hours post-administration for isotope analysis. |
Dosage form | 33mM; oral gavage |
Applications | Nicotianamine -Fe(II) complex administration resulted in significantly higher Fe accumulation in kidney and spleen tissues compared to free Fe(II) at 5 hours post-administration. Nicotianamine-Fe(II) also induced a slight increase in hemoglobin concentration, while free Fe(II) caused a decrease due to fasting effects. |
References: | |
| Cas No. | 34441-14-0 | SDF | |
| Chemical Name | αS-[[(3S)-3-amino-3-carboxypropyl]amino]-2S-carboxy-1-azetidinebutanoic acid | ||
| Canonical SMILES | OC([C@@H](NCC[C@H](N)C(O)=O)CCN1[C@H](C(O)=O)CC1)=O | ||
| Formula | C12H21N3O6 | M.Wt | 303.3 |
| Löslichkeit | Slightly soluble in Methanol & Water | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
||
| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 3.2971 mL | 16.4853 mL | 32.9707 mL |
| 5 mM | 659.4 μL | 3.2971 mL | 6.5941 mL |
| 10 mM | 329.7 μL | 1.6485 mL | 3.2971 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 39 reference(s) in Google Scholar.)
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