IUPAC/Chemical Name
(S)-1-((S)-3-(((S)-3-amino-3-carboxypropyl)amino)-3-carboxypropyl)azetidine-2-carboxylic acid
InChi Key
KRGPXXHMOXVMMM-CIUDSAMLSA-N
InChi Code
InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1
SMILES Code
OC([C@@H](NCC[C@H](N)C(O)=O)CCN1[C@H](C(O)=O)CC1)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Nicotianamine is an iron chelating amino acid that promotes uptake of iron from soil.
In vitro activity:
The purpose of this study is to prove that NA (nicotianamine) contributes to the suppression of hypertension by preferential inhibition of ACE. On comparison with EDTA-a chelator-this study found that the inhibition pattern of NA for ACE is that of mixed inhibition and that NA exhibits weak chelation effects for zinc, copper, and cobalt ions.
Reference: J Nutr Sci Vitaminol (Tokyo). 2007 Aug;53(4):331-6. https://pubmed.ncbi.nlm.nih.gov/17934238/
In vivo activity:
The rate of 59Fe absorption in the spleen, liver, and kidney was higher when mice were orally administered NA (nicotianamine)-59Fe (II) compared with free 59Fe (II). The profile of site-specific PAT1 expression in the mouse intestine coincided with those of NA and iron contents, which were the highest in the proximal jejunum. Orally administered NA-59Fe (II) complex in mice was detected in the proximal jejunum by thin layer chromatography.
Reference: J Biol Chem. 2021 Jan-Jun;296:100195. https://pubmed.ncbi.nlm.nih.gov/33334885/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
303.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hayashi A, Kimoto K. Nicotianamine preferentially inhibits Angiotensin I-converting enzyme. J Nutr Sci Vitaminol (Tokyo). 2007 Aug;53(4):331-6. doi: 10.3177/jnsv.53.331. PMID: 17934238.
2. von Wiren N, Klair S, Bansal S, Briat JF, Khodr H, Shioiri T, Leigh RA, Hider RC. Nicotianamine chelates both FeIII and FeII. Implications for metal transport in plants. Plant Physiol. 1999 Mar;119(3):1107-14. doi: 10.1104/pp.119.3.1107. PMID: 10069850; PMCID: PMC32093.
3. Murata Y, Yoshida M, Sakamoto N, Morimoto S, Watanabe T, Namba K. Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine. J Biol Chem. 2021 Jan-Jun;296:100195. doi: 10.1074/jbc.RA120.015861. Epub 2020 Dec 25. PMID: 33334885; PMCID: PMC7948497.
In vitro protocol:
1. Hayashi A, Kimoto K. Nicotianamine preferentially inhibits Angiotensin I-converting enzyme. J Nutr Sci Vitaminol (Tokyo). 2007 Aug;53(4):331-6. doi: 10.3177/jnsv.53.331. PMID: 17934238.
2. von Wiren N, Klair S, Bansal S, Briat JF, Khodr H, Shioiri T, Leigh RA, Hider RC. Nicotianamine chelates both FeIII and FeII. Implications for metal transport in plants. Plant Physiol. 1999 Mar;119(3):1107-14. doi: 10.1104/pp.119.3.1107. PMID: 10069850; PMCID: PMC32093.
In vivo protocol:
1. Murata Y, Yoshida M, Sakamoto N, Morimoto S, Watanabe T, Namba K. Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine. J Biol Chem. 2021 Jan-Jun;296:100195. doi: 10.1074/jbc.RA120.015861. Epub 2020 Dec 25. PMID: 33334885; PMCID: PMC7948497.
1. Curie, C., Cassin, G., Couch, D., et al. Metal movement within the plant: Contribution of nicotianamine and yellow stripe 1-like transporters. Ann. Bot. 103(1), 1-11 (2009).
2. Zhao, L., Ortiz, C., Adeleye, A.S., et al. Metabolomics to detect response of lettuce (Lactuca sativa) to Cu(OH)2 nanopesticides: Oxidative stress response and detoxification mechanisms. Environ. Sci. Technol. 50(17), 9697-9707 (2016).
3. Kinoshita, E., J., Y., and Kikuchi, M. Purification and identification of an angiotensin I-converting enzyme inhibitor from soy sauce. Biosci. Biotech. Biochem. 57(7), 1107-1110 (1993).
4. Takahashi, S., Yoshiya, T., Yoshizawa-Kumagaye, K., et al. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soy-bean. Biomed. Res. (Tokyo) 36(3), 219-224 (2015).
