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| | Pifithrin-α, p-nitro, cyclic Basic information |
| Product Name: | Pifithrin-α, p-nitro, cyclic | | Synonyms: | Pifithrin-α, p-nitro, cyclic;p-nitro-Cyclic Pifithrin-α;Pifithrin-alpha, p-Nitro, Cyclic;2-(4-Nitro-phenyl)-5,6,7,8-tetrahydro-benzo[d]imidazo[2,1-b]thiazole;p-nitro Cyclic Pifithrin-.alpha.;Cyclic pifithrin-α-p-nitro;Pifithrin-α, p-Nitro, Cyclic - CAS 60477-38-5 - Calbiochem;p-Nitro-Cyclic Pifithrin-a | | CAS: | 60477-38-5 | | MF: | C15H13N3O2S | | MW: | 299.35 | | EINECS: | | | Product Categories: | | | Mol File: | 60477-38-5.mol |  |
| | Pifithrin-α, p-nitro, cyclic Chemical Properties |
| Melting point | 233-234 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5)) | | density | 1.53±0.1 g/cm3(Predicted) | | storage temp. | -20C | | solubility | ≤1mg/ml in dimethyl formamide | | pka | 6.14±0.20(Predicted) | | form | Yellow solid | | color | Light yellow to yellow | | InChI | 1S/C15H13N3O2S/c19-18(20)11-7-5-10(6-8-11)12-9-17-13-3-1-2-4-14(13)21-15(17)16-12/h5-9H,1-4H2 | | InChIKey | XMFNSEDROOHGBY-UHFFFAOYSA-N | | SMILES | [s]1c2[n](c4c1CCCC4)cc(n2)c3ccc(cc3)[N+](=O)[O-] |
| WGK Germany | WGK 1 | | Storage Class | 11 - Combustible Solids |
| | Pifithrin-α, p-nitro, cyclic Usage And Synthesis |
| Uses | p-nitro-Cyclic Pifithrin-α is an inactivator of p53 that blocks p53-dependent transcriptional activation and apoptisis. Anti-cancer agent. | | General Description | A cell-permeable p53 inhibitor that exhibits 10-fold higher potency (ED50 = 30 nM in protecting etoposide-induced cortical neuron death) and 50% longer half-life (t1/2 = 6h in neuron culture medium at 37°C) than Pifithrin-α (Cat. No. 506132). However, despite its in vitro efficacy, this inhibitor is not effective when adminstered in rats in vivo. For in vivo applications, please consider Pifithrin-α, p-Nitro (Cat. No. 506152). | | Biological Activity | p-nitro-cyclic pifithrin-α is an inactivator of p53.the activation of the tumor suppressor gene p53 plays a key role in regulating the in-vitro death of neurons, following apoptotic stimuli molecules including glutamate and dna-damaging agents. thus, p53 inhibitors may prove effective in suppressing the degenerative processes in neurodegenerative disorders. | | Biochem/physiol Actions | Cell permeable: yes | | in vitro | pifithrin-α (pft-α) was identified as an inactivator of p53 blocking p53-dependent transcriptional activation and apoptosis. cyclic pft-α was a stable analog of pft-α. p-nitro-cyclic pft-α, a cell-permeable form of cyclic pft-α, was found to be one order of magnitude more active than pft-α in protecting cortical neurons exposed to etoposide. p-nitro-cyclic pft-α acted in a p53-dependently but did not block phosphorylation of p53 on ser15 in response to etoposide treatment, although it prevented p53 posttranscriptional activity [1]. | | in vivo | in a previou study, c57bl/6 mice were fed a high-fat (hfd) or control diet for 8 weeks; pft was administered three times per week. results showed that pft administration could suppress hfd-induced weight gain, steatosis, oxidative stress, alt elevation, and apoptosis. pft treatment also able to blunt the hfd-induced upregulation of mirna34a and increase sirt1 expression. in the livers of hfd-fed, pft-treated mice, activation of the sirt1/pgc1α/pparα axis increased the expression of malonyl-coa decarboxylase [2]. | | references | [1] . pietrancosta, n.,moumen, a.,dono, r., et al. imino-tetrahydro-benzothiazole derivatives as p53 inhibitors: discovery of a highly potent in vivo inhibitor and its action mechanism. journal of medicinal chemistry 49(12), 3645-3652 (2006).
[2] derdak z, villegas ka, harb r, wu am, sousa a, wands jr. inhibition of p53 attenuates steatosis and liver injury in a mouse model of non-alcoholic fatty liver disease. j hepatol. 2013 apr;58(4):785-91. |
| | Pifithrin-α, p-nitro, cyclic Preparation Products And Raw materials |
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