| Identification | Back Directory | [Name]
Pifithrin-α, p-Nitro | [CAS]
389850-21-9 | [Synonyms]
p-nitro-Pifithrin-α
Pifithrin-α, p-Nitro
Pifithrin-α, p-Nitro
p-nitro-Pifithrin-.alpha.
Pifithrin-alpha, p-Nitro hydrobromide,
2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3-yl)-1-(4-nitrophenyl)ethanone
2-(2-IMINO-4,5,6,7-TETRAHYDROBENZO[D]THIAZOL-3(2H)-YL)-1-(4-NITROPHENYL)ETHANONE HBR | [Molecular Formula]
C15H16BrN3O3S | [MDL Number]
MFCD00398180 | [MOL File]
389850-21-9.mol | [Molecular Weight]
398.275 |
| Chemical Properties | Back Directory | [Melting point ]
239-240 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6)) | [storage temp. ]
Store at -20°C, protect from light | [solubility ]
Soluble in DMSO or ethanol | [form ]
Solid | [color ]
White to light yellow | [Sensitive ]
Light Sensitive & Hygroscopic |
| Hazard Information | Back Directory | [Uses]
A cell-permeable p53 inhibitor | [Biological Activity]
p-nitro-pifithrin-α, a cell-permeable cyclic analog of pifithrin-α, is an inhibitor of p53 activity [1].the p53 tumor suppressor gene product can induce apoptotic cell death and plays a dominant role in apoptosis, genomic stability, and inhibition of angiogenesis. the p53 has been considered to be an oncogene and the wild-type gene product actually functions as a tumour suppressor gene. p53 mutations play an important role in the development of many common human malignancies [2].in human proximal tubular cells, p-nitro-pifithrin-α (10 μm) suppressed p53-mediated tgf-β1 expression [3]. | [in vitro]
in p53-/- cortical neuron, p-nitro-pifithrin-α exihibited a p53 inhibitory activity in preventing p53-induced death[1]. p-nitro-pifithrin-α did not prevent cortical neuronal death induced by p40met, showing the remarkable specificity in the inhibitory action of p-nitro-pifithrin-α on p53. p-nitro-pifithrin-α (300 nm) prevented p53-triggered increase in protein levels of p21/waf1, indicating that p-nitro-pifithrin-α behaved as p53 posttranscriptional activity inhibitors. p-nitro-pifithrin-α at a dose of 30 nm was sufficient to prevent the increase of p21/waf1 levels [1]. p-nitro-pifithrin-α was slowly converted into a more potent cyclized form, p-nitro cyclic pifithrin-α, when incubated in biological media (t1/2= 8 h) | [in vivo]
in a mouse model of non-alcoholic fatty liver disease, p-nitro-pifithrin-α attenuated steatosis and liver injury in mice fed a high-fat diet [4]. | [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[j]. journal of medicinal chemistry, 2006, 49(12): 3645-3652.
[2] nigro j m, baker s j, preisinger a c, et al. mutations in the p53 gene occur in diverse human tumour types[j]. nature, 1989, 342(6250): 705-708.
[3] shimizu h, yisireyili m, nishijima f, et al. indoxyl sulfate enhances p53-tgf-β1-smad3 pathway in proximal tubular cells[j]. american journal of nephrology, 2013, 37(2): 97-103.
[4] derdak z, villegas k a, harb r, et al. inhibition of p53 attenuates steatosis and liver injury in a mouse model of non-alcoholic fatty liver disease[j]. journal of hepatology, 2013, 58(4): 785-791. |
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