Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H10N2O4 |
Molecular Weight | 198.176 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O
InChI
InChIKey=WZNJWVWKTVETCG-YFKPBYRVSA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27213712Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26610453 |
https://www.ncbi.nlm.nih.gov/pubmed/10047457 |
https://www.ncbi.nlm.nih.gov/pubmed/25957199
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27213712
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26610453 |
https://www.ncbi.nlm.nih.gov/pubmed/10047457 |
https://www.ncbi.nlm.nih.gov/pubmed/25957199
Mimosine or leucenol is an alkaloid, beta-3-hydroxy-4 pyridone amino acid. Mimosine is an effective inhibitor of DNA replication in mammalian cells. It blocks entry into S phase (late G1 phase), and suppress elongation of DNA replication (S phase). The chelation of iron seems to be one of the main modes of action of mimosine for cell cycle arrest. As an iron-chelating and cell cycle stopping agent, mimosine was tested in preclinical models of cancer, pulmonary fibrosis and iron overload.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006879 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27213712 |
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Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15577244 |
3.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Anatomy of the primase-alpha DNA polymerase reaction accomplished by nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. | 2001 Apr |
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Partial purification, characterization, and histochemical localization of fully latent desert truffle (Terfezia claveryi Chatin) polyphenol oxidase. | 2001 Apr |
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Lymphoblasts already in the DNA synthesis phase of the cell cycle can be reversibly arrested at the R/G transition. | 2001 Dec |
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MCM3AP, a novel acetyltransferase that acetylates replication protein MCM3. | 2001 Feb |
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Prevention of entrance into G2 cell cycle phase by mimosine decreases locomotion of cells from the tumor cell line SW480. | 2001 Jan |
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Kinetic analyses of mitochondrial 75selenium uptake in Trigonella foenum-graecum seedlings exposed to selenium and mimosine. | 2001 Mar |
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Survivin exists in immunochemically distinct subcellular pools and is involved in spindle microtubule function. | 2002 Feb 1 |
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Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53. | 2002 Jan 17 |
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Inhibition of ultraviolet B (UVB) induced apoptosis in A431 cells by mimosine is not dependent on cell cycle arrest. | 2002 Jul |
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Tuning up or down the UV-induced apoptosis in Chinese hamster ovary cells with cell cycle inhibitors. | 2002 Jun |
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Ultraviolet-B-induced G1 arrest is mediated by downregulation of cyclin-dependent kinase 4 in transformed keratinocytes lacking functional p53. | 2002 May |
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Ultraviolet light-induced apoptosis is associated with S-phase in primary human fibroblasts. | 2002 Oct 1 |
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Engineering bacterial competitiveness and persistence in the phytosphere. | 2002 Sep |
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The mid genes of Rhizobium sp strain TAL1145 are required for degradation of mimosine into 3-hydroxy-4-pyridone and are inducible by mimosine. | 2003 Feb |
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Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells. | 2003 Feb 7 |
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Latent HIV-1 reactivation in transgenic mice requires cell cycle -dependent demethylation of CREB/ATF sites in the LTR. | 2003 Jan 24 |
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Asynchronous replication timing of imprinted loci is independent of DNA methylation, but consistent with differential subnuclear localization. | 2003 Mar 15 |
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Progesterone receptor and the cell cycle modulate apoptosis in granulosa cells. | 2004 Nov |
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Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. | 2005 Jan 7 |
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Modulation of differentiation-related gene 1 expression by cell cycle blocker mimosine, revealed by proteomic analysis. | 2005 Jul |
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Immediate transfection of patient-derived leukemia: a novel source for generating cell-based vaccines. | 2005 Jun 21 |
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Piperidones with activity against Plasmodium falciparum. | 2006 Aug |
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Activation of the human FP prostanoid receptor disrupts mitosis progression and generates aneuploidy and polyploidy. | 2006 Jan |
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Selective determination of mimosine and its dihydroxypyridinyl derivative in plant systems. | 2006 Oct |
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The mitotic manipulation of cytotrophoblast differentiation in vitro. | 2007 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25957199
In model of pulmonary fibrosis mimosine was administed at doses 25 and 50 mg/kg. Pulmonary fibrosis was induced by tracheal instillation of 5 mg/kg bleomycin. Mimosine was first dissolved in Tris-buffer at pH 8.9, and then pH was adjusted to 7.2 with 1 N HCl. Before administration, this solution was freshly diluted by 0.9% physiologic saline to achieve the required concentration. L-Mimosine was administered via subcutaneous injection once daily from day 1 to day 28 after BLM or saline treatment.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10047457
The effect of mimosine on asynchronously proliferating HeLa cells was analyzed by flow cytometry. HeLa-S3 cells were cultured as proliferating monolayers on 145-mm plates in DMEM, supplemented with 10% FCS, 10 U/ml penicillin, and 0.1 mg/ml streptomycin. Mimosine stock solution was prepared at 10 mM in DMEM and filtered through 20-mm filters. Synchronization of HeLa cells by mimosine was achieved by adding mimosine from the stock solution directly to the cells at the concentrations specified. Cell synchronization was determined by flow cytometry of isolated nuclei. One million nuclei were directly stained with propidium iodide (5 mg/ml in PBS containing 0.4% Triton X-100) and analyzed by FACScan (Becton Dickinson) using the Lysis II-software.
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SUBSTANCE RECORD