L-Mimosine

• CAT Number: R061202
• CAS Number: 500-44-7
• Molecular Formula: C8H10N2O4
• Molecular Weight: 198.178
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
• InChI: 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)/t5-/m0/s1
• InChIKey: WZNJWVWKTVETCG-YFKPBYRVSA-N
• SMILES: C1=CN(C=C(C1=O)O)CC(C(=O)O)N

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.

Reference

1:Expression of circadian core clock genes in fibroblasts of human gingiva and periodontal ligament is modulated by L-Mimosine and hypoxia in monolayer and spheroid cultures. Janjić K, Kurzmann C, Moritz A, Agis H.Arch Oral Biol. 2017 Jul;79:95-99. doi: 10.1016/j.archoralbio.2017.03.007. Epub 2017 Mar 14. PMID: 28350992 2:Effects of Prolyl Hydroxylase Inhibitor L-mimosine on Dental Pulp in the Presence of Advanced Glycation End Products. Müller HD, Cvikl B, Janjić K, Nürnberger S, Moritz A, Gruber R, Agis H.J Endod. 2015 Nov;41(11):1852-61. doi: 10.1016/j.joen.2015.08.002. Epub 2015 Sep 26. PMID: 26395911 3:Inhibitory effect of l-mimosine on bleomycin-induced pulmonary fibrosis in rats: Role of eIF3a and p27. Li XW, Hu CP, Li YJ, Gao YX, Wang XM, Yang JR.Int Immunopharmacol. 2015 Jul;27(1):53-64. doi: 10.1016/j.intimp.2015.04.048. Epub 2015 May 5. PMID: 25957199 4:In vitro release of dimethyloxaloylglycine and l-mimosine from bovine bone mineral. Agis H, Hueber L, Pour Sadeghian N, Pensch M, Gruber R.Arch Oral Biol. 2014 Oct;59(10):1024-31. doi: 10.1016/j.archoralbio.2014.05.027. Epub 2014 Jun 10. PMID: 24960117 5:L-mimosine increases the production of vascular endothelial growth factor in human tooth slice organ culture model. Trimmel K, Cvikl B, Müller HD, Nürnberger S, Gruber R, Moritz A, Agis H.Int Endod J. 2015 Mar;48(3):252-60. doi: 10.1111/iej.12307. Epub 2014 Jun 28. PMID: 24786562 6:L-mimosine and dimethyloxaloylglycine decrease plasminogen activation in periodontal fibroblasts. Wehner C, Gruber R, Agis H.J Periodontol. 2014 Apr;85(4):627-35. doi: 10.1902/jop.2013.120703. Epub 2013 Jul 4. PMID: 23826644 7: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. Negi VS, Bingham JP, Li QX, Borthakur D.Amino Acids. 2013 Jun;44(6):1537-47. doi: 10.1007/s00726-013-1479-z. Epub 2013 Mar 6. PMID: 23462928 8:L-Mimosine blocks cell proliferation via upregulation of B-cell translocation gene 2 and N-myc downstream regulated gene 1 in prostate carcinoma cells. Chung LC, Tsui KH, Feng TH, Lee SL, Chang PL, Juang HH.Am J Physiol Cell Physiol. 2012 Feb 15;302(4):C676-85. doi: 10.1152/ajpcell.00180.2011. Epub 2011 Nov 23. PMID: 22116304 Free Article9:Transient hypoxia-inducible factor activation in rat renal ablation and reduced fibrosis with L-mimosine. Yu X, Fang Y, Ding X, Liu H, Zhu J, Zou J, Xu X, Zhong Y.Nephrology (Carlton). 2012 Jan;17(1):58-67. doi: 10.1111/j.1440-1797.2011.01498.x. PMID: 21777345 10:Inhibition of MCP-1 and MIP-2 chemokines in murine trichinellosis: effect of the anti-inflammatory compound L-mimosine. Frydas S, Papaioannou N, Papazahariadou M, Hatzistilianou M, Karagouni E, Trakatelli M, Brellou G, Petrarca C, Castellani ML, Conti P, Riccioni G, Patruno A, Grilli A.Int J Immunopathol Pharmacol. 2005 Jan-Mar;18(1):85-94. PMID: 15698514