Mimosine | CAS#500-44-7

MedKoo Cat#: 318275 | Name: Mimosine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mimosine is an alkaloid, β-3-hydroxy-4 pyridone amino acid. It is a toxic non-protein free amino acid otherwise chemically similar to tyrosine, and was first isolated from Mimosa pudica.

Chemical Structure

Mimosine

CAS#500-44-7

Theoretical Analysis

MedKoo Cat#: 318275

Name: Mimosine

CAS#: 500-44-7

Chemical Formula: C8H10N2O4

Exact Mass: 198.0641

Molecular Weight: 198.18

Elemental Analysis: C, 48.48; H, 5.09; N, 14.14; O, 32.29

Price and Availability

Size	Price	Availability
100mg	USD 285.00	2 weeks
250mg	USD 550.00	2 weeks
500mg	USD 850.00	2 weeks

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Related CAS #

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Synonym

Mimosine, Leucenol, Leucaenine

IUPAC/Chemical Name

2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid

InChi Key

WZNJWVWKTVETCG-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)

SMILES Code

O=C(O)C(N)CN(C=C1O)C=CC1=O

Appearance

Solid powder

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, not in water

Shelf Life

>2 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mimosine, a tyrosine analog, can act as an antioxidant by its potent iron-binding activity. Mimosine is a known chelator of Fe(III).

In vitro activity:

The effect of L-mimosine on cell proliferation of prostate carcinoma cells was determined by the [3H]thymidine incorporation and flow cytometry assays. L-Mimosine arrested the cell cycle at the G1 phase in PC-3 cells and at the S phase in LNCaP cells, thus attenuating cell proliferation. Reference: Am J Physiol Cell Physiol. 2012 Feb 15;302(4):C676-85. https://pubmed.ncbi.nlm.nih.gov/22116304/

In vivo activity:

Functionally, the PHD inhibitor l-mimosine (l-Mim, 50 mg x kg(-1) x day(-1) i.p. for 2 wk) substantially upregulated HIF-1alpha expression in the kidneys, especially in the renal medulla, and remarkably enhanced (by >80%) the natriuretic response to renal perfusion pressure in Sprague-Dawley rats. Reference: Am J Physiol Renal Physiol. 2007 Jan;292(1):F207-16. https://pubmed.ncbi.nlm.nih.gov/16885149/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.05
	Water	5.0	25.23

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 198.18 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. Chung LC, Tsui KH, Feng TH, Lee SL, Chang PL, Juang HH. L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. Am J Physiol Cell Physiol. 2012 Feb 15;302(4):C676-85. doi: 10.1152/ajpcell.00180.2011. Epub 2011 Nov 23. PMID: 22116304. 2. Kulp KS, Vulliet PR. Mimosine blocks cell cycle progression by chelating iron in asynchronous human breast cancer cells. Toxicol Appl Pharmacol. 1996 Aug;139(2):356-64. doi: 10.1006/taap.1996.0176. PMID: 8806853. 3. Fang Y, Zhang H, Zhong Y, Ding X. Prolyl hydroxylase 2 (PHD2) inhibition protects human renal epithelial cells and mice kidney from hypoxia injury. Oncotarget. 2016 Aug 23;7(34):54317-54328. doi: 10.18632/oncotarget.11104. PMID: 27527871; PMCID: PMC5342344. 4. Li N, Yi F, Sundy CM, Chen L, Hilliker ML, Donley DK, Muldoon DB, Li PL. Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. Am J Physiol Renal Physiol. 2007 Jan;292(1):F207-16. doi: 10.1152/ajprenal.00457.2005. Epub 2006 Aug 1. PMID: 16885149.

In vitro protocol:

In vivo protocol:

1. Fang Y, Zhang H, Zhong Y, Ding X. Prolyl hydroxylase 2 (PHD2) inhibition protects human renal epithelial cells and mice kidney from hypoxia injury. Oncotarget. 2016 Aug 23;7(34):54317-54328. doi: 10.18632/oncotarget.11104. PMID: 27527871; PMCID: PMC5342344. 2. Li N, Yi F, Sundy CM, Chen L, Hilliker ML, Donley DK, Muldoon DB, Li PL. Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. Am J Physiol Renal Physiol. 2007 Jan;292(1):F207-16. doi: 10.1152/ajprenal.00457.2005. Epub 2006 Aug 1. PMID: 16885149.

1: Kuroyanagi G, Otsuka T, Yamamoto N, Kainuma S, Ohguchi R, Fujita K, Matsushima-Nishiwaki R, Kozawa O, Tokuda H. Mimosine suppresses the PGF2α-induced synthesis of osteoprotegerin but not interleukin-6 in osteoblasts. Int J Mol Med. 2016 Feb;37(2):533-41. doi: 10.3892/ijmm.2016.2452. Epub 2016 Jan 7. PubMed PMID: 26744072. 2: Derakhshani H, Corley SW, Al Jassim R. Isolation and characterization of mimosine, 3, 4 DHP and 2, 3 DHP degrading bacteria from a commercial rumen inoculum. J Basic Microbiol. 2016 Jan 15. doi: 10.1002/jobm.201500590. [Epub ahead of print] PubMed PMID: 26773324. 3: Nguyen BC, Tawata S. Mimosine Dipeptide Enantiomsers: Improved Inhibitors against Melanogenesis and Cyclooxygenase. Molecules. 2015 Aug 6;20(8):14334-47. doi: 10.3390/molecules200814334. PubMed PMID: 26287130. 4: Müller HD, Cvikl B, Janjić K, Nürnberger S, Moritz A, Gruber R, Agis H. Effects of Prolyl Hydroxylase Inhibitor L-mimosine on Dental Pulp in the Presence of Advanced Glycation End Products. J Endod. 2015 Nov;41(11):1852-61. doi: 10.1016/j.joen.2015.08.002. Epub 2015 Sep 26. PubMed PMID: 26395911. 5: Fallon AM. Effects of mimosine on Wolbachia in mosquito cells: cell cycle suppression reduces bacterial abundance. In Vitro Cell Dev Biol Anim. 2015 Oct;51(9):958-63. doi: 10.1007/s11626-015-9918-7. Epub 2015 May 28. PubMed PMID: 26019119. 6: Nguyen BC, Chompoo J, Tawata S. Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives. Molecules. 2015 Sep 14;20(9):16741-56. doi: 10.3390/molecules200916741. PubMed PMID: 26389870. 7: Li XW, Hu CP, Li YJ, Gao YX, Wang XM, Yang JR. Inhibitory effect of l-mimosine on bleomycin-induced pulmonary fibrosis in rats: Role of eIF3a and p27. Int Immunopharmacol. 2015 Jul;27(1):53-64. doi: 10.1016/j.intimp.2015.04.048. Epub 2015 May 5. PubMed PMID: 25957199. 8: Pluchino LA, Liu AK, Wang HC. Reactive oxygen species-mediated breast cell carcinogenesis enhanced by multiple carcinogens and intervened by dietary ergosterol and mimosine. Free Radic Biol Med. 2015 Mar;80:12-26. doi: 10.1016/j.freeradbiomed.2014.12.015. Epub 2014 Dec 20. PubMed PMID: 25535943. 9: Trimmel K, Cvikl B, Müller HD, Nürnberger S, Gruber R, Moritz A, Agis H. L-mimosine increases the production of vascular endothelial growth factor in human tooth slice organ culture model. Int Endod J. 2015 Mar;48(3):252-60. doi: 10.1111/iej.12307. Epub 2014 Jun 28. PubMed PMID: 24786562. 10: Agis H, Hueber L, Pour Sadeghian N, Pensch M, Gruber R. In vitro release of dimethyloxaloylglycine and l-mimosine from bovine bone mineral. Arch Oral Biol. 2014 Oct;59(10):1024-31. doi: 10.1016/j.archoralbio.2014.05.027. Epub 2014 Jun 10. PubMed PMID: 24960117. 11: Yafuso JT, Negi VS, Bingham JP, Borthakur D. An O-acetylserine (thiol) lyase from Leucaena leucocephala is a cysteine synthase but not a mimosine synthase. Appl Biochem Biotechnol. 2014 Jul;173(5):1157-68. doi: 10.1007/s12010-014-0917-z. Epub 2014 Apr 29. PubMed PMID: 24777760. 12: Wehner C, Gruber R, Agis H. L-mimosine and dimethyloxaloylglycine decrease plasminogen activation in periodontal fibroblasts. J Periodontol. 2014 Apr;85(4):627-35. doi: 10.1902/jop.2013.120703. Epub 2013 Jul 4. PubMed PMID: 23826644. 13: Ogita S, Kato M, Watanabe S, Ashihara H. The co-occurrence of two pyridine alkaloids, mimosine and trigonelline, in Leucaena leucocephala. Z Naturforsch C. 2014 Mar-Apr;69(3-4):124-32. PubMed PMID: 24873033. 14: Kubota S, Fukumoto Y, Ishibashi K, Soeda S, Kubota S, Yuki R, Nakayama Y, Aoyama K, Yamaguchi N, Yamaguchi N. Activation of the prereplication complex is blocked by mimosine through reactive oxygen species-activated ataxia telangiectasia mutated (ATM) protein without DNA damage. J Biol Chem. 2014 Feb 28;289(9):5730-46. doi: 10.1074/jbc.M113.546655. Epub 2014 Jan 13. PubMed PMID: 24421316; PubMed Central PMCID: PMC3937646. 15: Negi VS, Bingham JP, Li QX, Borthakur D. A carbon-nitrogen lyase from Leucaena leucocephala catalyzes the first step of mimosine degradation. Plant Physiol. 2014 Feb;164(2):922-34. doi: 10.1104/pp.113.230870. Epub 2013 Dec 18. PubMed PMID: 24351687; PubMed Central PMCID: PMC3912116. 16: Soltan YA, Morsy AS, Sallam SM, Lucas RC, Louvandini H, Kreuzer M, Abdalla AL. Contribution of condensed tannins and mimosine to the methane mitigation caused by feeding Leucaena leucocephala. Arch Anim Nutr. 2013 Jun;67(3):169-84. doi: 10.1080/1745039X.2013.801139. PubMed PMID: 23742642. 17: Negi VS, Bingham JP, Li QX, Borthakur D. midD-encoded 'rhizomimosinase' from Rhizobium sp. strain TAL1145 is a C-N lyase that catabolizes L-mimosine into 3-hydroxy-4-pyridone, pyruvate and ammonia. Amino Acids. 2013 Jun;44(6):1537-47. doi: 10.1007/s00726-013-1479-z. Epub 2013 Mar 6. PubMed PMID: 23462928. 18: Barros-Rodríguez M, Solorio-Sánchez J, Ku-Vera J, Ayala-Burgos A, Sandoval-Castro C, Solís-Pérez G. Productive performance and urinary excretion of mimosine metabolites by hair sheep grazing in a silvopastoral system with high densities of Leucaena leucocephala. Trop Anim Health Prod. 2012 Dec;44(8):1873-8. doi: 10.1007/s11250-012-0150-0. Epub 2012 Apr 19. PubMed PMID: 22528536. 19: Nokihara K, Hirata A, Sogon T, Ohyama T. Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid. Amino Acids. 2012 Jul;43(1):475-82. doi: 10.1007/s00726-011-1104-y. Epub 2011 Oct 13. PubMed PMID: 21993536. 20: Jetana T, Thongruay S, Uswang S, Hengtrakulsin R. A comparative study on mimosine, 3,4-dihydroxy pyridone (3,4-DHP) and 2,3-dihydroxy pyridone (2,3-DHP), purine derivatives (PD) excretion in the urine, thyroid hormone and blood metabolites profiles of Thai swamp buffalo (Bubalus bubalis) and Murrah buffalo (Bubalus bubalis). Trop Anim Health Prod. 2012 Apr;44(4):887-97. doi: 10.1007/s11250-011-9983-1. Epub 2011 Sep 18. PubMed PMID: 21928129.