Tranylcypromine hydrochlorideIrreversible inhibitor of MAO-A, MAO-B and LSD1 CAS# 1986-47-6 |
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Quality Control & MSDS
3D structure
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| Cas No. | 1986-47-6 | SDF | Download SDF |
| PubChem ID | 6419961 | Appearance | Powder |
| Formula | C9H12ClN | M.Wt | 169.65 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | 2-PCPA;4548-34-9 | ||
| Solubility | Soluble to 100 mM in water and to 100 mM in DMSO | ||
| Chemical Name | (1S,2R)-2-phenylcyclopropan-1-amine;hydrochloride | ||
| SMILES | C1C(C1N)C2=CC=CC=C2.Cl | ||
| Standard InChIKey | ZPEFMSTTZXJOTM-RJUBDTSPSA-N | ||
| Standard InChI | InChI=1S/C9H11N.ClH/c10-9-6-8(9)7-4-2-1-3-5-7;/h1-5,8-9H,6,10H2;1H/t8-,9+;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Irreversible inhibitor of lysine-specific demethylase 1 (LSD1/BHC110) and monoamine oxidase (MAO). Inhibits histone demethylation. In combination with CHIR 99021, enables reprogramming of mouse embryonic fibroblasts transduced by only two factors, Oct4 and Klf4, into induced pluripotent stem (iPS) cells. |
Tranylcypromine hydrochloride Dilution Calculator
Tranylcypromine hydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.8945 mL | 29.4724 mL | 58.9449 mL | 117.8898 mL | 147.3622 mL |
| 5 mM | 1.1789 mL | 5.8945 mL | 11.789 mL | 23.578 mL | 29.4724 mL |
| 10 mM | 0.5894 mL | 2.9472 mL | 5.8945 mL | 11.789 mL | 14.7362 mL |
| 50 mM | 0.1179 mL | 0.5894 mL | 1.1789 mL | 2.3578 mL | 2.9472 mL |
| 100 mM | 0.0589 mL | 0.2947 mL | 0.5894 mL | 1.1789 mL | 1.4736 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Tranylcypromine, also known as 2-PCPA, is a monoamine oxidase inhibitor (MAOI) that irreversibly inhibits MAO A and MAO B with the inhibition constant Ki values of 101.9 μM and 16 μM and the half maximal inhibition concentration IC50 values of 2.3 μM and 0.95 μM respectively [1].
Tranylcypromine has also been found to potently and irreversibly inhibit histone demethylase lysine-specific demethylase 1 (LSD1), which is an amine oxidase homologue of MAO sharing similarities in the catalytic site with MAO A and B, in a time dependent and mechanism based manner with Ki and IC50 values of 242 μM and 20.7 μM respectively [1].
Reference
References:
[1] Schmidt DM, McCafferty DG. trans-2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1. Biochemistry. 2007 Apr 10;46(14):4408-16. Epub 2007 Mar 17.
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Generation of human-induced pluripotent stem cells in the absence of exogenous Sox2.[Pubmed:19839055]
Stem Cells. 2009 Dec;27(12):2992-3000.
Induced pluripotent stem cell technology has attracted enormous interest for potential application in regenerative medicine. Here, we report that a specific glycogen synthase kinase 3 (GSK-3) inhibitor, CHIR99021, can induce the reprogramming of mouse embryonic fibroblasts transduced by only two factors, Oct4 and Klf4. When combined with Parnate (also named tranylcypromine), an inhibitor of lysine-specific demethylase 1, CHIR99021 can cause the reprogramming of human primary keratinocyte transduced with the two factors, Oct4 and Klf4. To our knowledge, this is the first time that human iPS cells have been generated from somatic cells without exogenous Sox2 expression. Our studies suggest that the GSK-3 inhibitor might have a general application to replace transcription factors in both mouse and human reprogramming.
trans-2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1.[Pubmed:17367163]
Biochemistry. 2007 Apr 10;46(14):4408-16.
The catalytic domain of the flavin-dependent human histone demethylase lysine-specific demethylase 1 (LSD1) belongs to the family of amine oxidases including polyamine oxidase and monoamine oxidase (MAO). We previously assessed monoamine oxidase inhibitors (MAOIs) for their ability to inhibit the reaction catalyzed by LSD1 [Lee, M. G., et al. (2006) Chem. Biol. 13, 563-567], demonstrating that trans-2-phenylcyclopropylamine (2-PCPA, tranylcypromine, Parnate) was the most potent with respect to LSD1. Here we show that 2-PCPA is a time-dependent, mechanism-based irreversible inhibitor of LSD1 with a KI of 242 microM and a kinact of 0.0106 s-1. 2-PCPA shows limited selectivity for human MAOs versus LSD1, with kinact/KI values only 16-fold and 2.4-fold higher for MAO B and MAO A, respectively. Profiles of LSD1 activity and inactivation by 2-PCPA as a function of pH are consistent with a mechanism of inactivation dependent upon enzyme catalysis. Mass spectrometry supports a role for FAD as the site of covalent modification by 2-PCPA. These results will provide a foundation for the design of cyclopropylamine-based inhibitors that are selective for LSD1 to probe its role in vivo.
Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications.[Pubmed:16793513]
Chem Biol. 2006 Jun;13(6):563-7.
Demethylation of histone H3 lysine 4 is carried out by BHC110/LSD1, an enzyme with close homology to monoamine oxidases (MAO). Monoamine oxidase A or B are frequent targets of selective and nonselective small molecular inhibitors used for treatment of depression. Here we show that in contrast to selective monoamine oxidase inhibitors such as pargyline, nonselective monoamine oxidase inhibitors potently inhibit nucleosomal demethylation of histone H3 lysine 4. Tranylcypromine (brand name Parnate) displayed the best inhibitory activity with an IC50 of less than 2 microM. Treatment of P19 embryonal carcinoma cells with tranylcypromine resulted in global increase in H3K4 methylation as well as transcriptional derepression of two BHC110 target genes, Egr1 and the pluripotent stem cell marker Oct4. These results attest to the effectiveness of tranylcypromine as a small molecular inhibitor of histone demethylation.
