Tulipalin A

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Chemical Structure| 547-65-9 同义名 : α-亚甲基-γ-丁内酯 ;α-Methylene butyrolactone; MBL; α-methylene-γ-butyrolactone; 2-Methylenebutyrolactone
CAS号 : 547-65-9
货号 : A309252
分子式 : C5H6O2
纯度 : 95% (stabilized with 2% 2,6-Di-tert-butyl-p-cresol)
分子量 : 98.1
MDL号 : MFCD00005407
存储条件:

Pure form Keep in dark place, inert atmosphere, 2-8°C

In solvent -20°C:3-6个月-80°C:12个月

溶解度 :

DMSO: 105 mg/mL(1070.34 mM),注意:DMSO长时间开封后,会吸水并导致溶解能力下降,请避免使用长期开封的DMSO

动物实验配方:
生物活性
描述 After exposure of Jurkat T cells to 2-Methylenebutyrolactone (Tulipalin A , TUPA) for 72 h, a dose dependent toxicity is detected. Concentrations higher than 20 μM lead to a significant reduction of viable cells. Compared to vehicle-treated control cells, concentrations of 47.6 and 26.8 μM decrease the cell viability significantly by 50% (IC50) and 10% (IC10), respectively. In contrast, THP-1 cells are less sensitive toward TUPA. Concentrations >41 μM lead to a significant reduction of viable cells. IC10 is calculated with 50 μM, whereas a concentration of 83 μM is necessary to decrease the cell viability to 50% (IC50). In Jurkat T cells, four proteins responsible for the de novo purine synthesis, namely phosphoribosylformylglycinamidine synthase (PFAS), GMP synthase (GMPS), and ribosephosphate pyrophosphokinases 1 and 2 (PRPS1/2) are increased through TUPA treatment. Glutamine is also increased after TUPA treatment. In addition to the proteins belonging to the purine synthesis pathway, the abundances of proteins for DNA synthesis and repair (XRCC5, XRCC6, MCM3, MCM6, MCM7, TRA1) are also increased/induced during the treatment. While in THP-1 cells, no indication for higher purine synthesis induced by TUPA in subtoxic concentrations is discovered. TUPA induces the expression of proteins in Jurkat T cells responsible for cell stress, drug response, and protein folding: HYOU1, PDIA3, and DNAJB11. Additionally, the treatment with TUPA leads to the induction of three heat shock proteins (HSP90AA1, HSP90AB1, and HSP90B1) and three proteins belonging to the TRiC complex (CCT3,6,8) that are also responsible for proper protein folding. Treatment with TUPA leads to the induction of ROS that have adverse effects on Jurkat T cells and evokes slight cell stress responses in THP-1 cells. TUPA has influence on proteins in Jurkat T cells that contribute to different immune-specific, especially immunostimulating, reactions as allergic contact dermatitis. In THP-1 cells, no proteins regarding immune-specific reactions are up- or downregulated due to TUPA treatment.
实验方案
1mg 5mg 10mg

1 mM

5 mM

10 mM

10.19mL

2.04mL

1.02mL

50.97mL

10.19mL

5.10mL

101.94mL

20.39mL

10.19mL