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IPPD-Q

(Synonyms: N-Isopropyl-N'-phenyl-p-phenylenediamine-quinone) 目录号 : GC91672

IPPD-Q是N,N'-取代对苯二胺类化合物(PPD)的氧化产物,消耗二硫苏糖醇(DTT)的氧化潜势值为0.93μM min–1μM–1

IPPD-Q Chemical Structure

Cas No.:68054-73-9

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1 mg
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5 mg
¥3,276.00
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10 mg
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25 mg
¥12,740.00
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Sample solution is provided at 25 µL, 10mM.

Description

IPPD-Q is the oxidation products of N,N'-Substituted p-phenylenediamines (PPD), with oxidative potential values of 0.93μM min–1μM–1for dithiothreitol (DTT) consumption rate[1-2]. IPPD-Q has been used in air pollution research and pollutant diagnosis research[3].

In vitro, IPPD-Q exhibits EC50 values of 2.97mg/L (30min) for Aquatic bacterium Vibrio fischeri[4]. IPPD-Q treatment (2.97mg/L) for 30min resulted in a significant decrease in metabolic activity and esterase activity and an increase in the degree of membranocyte damage and oxidative stress in Vibrio fischeri[4]. Treatment of hCMEC-D3 cells with 1.00μM IPPD-Q for 24 hours induced cell apoptosis, endothelial-mesenchymal transition, upregulated Plasminogen activator inhibitor-1 (PAI-1) expression, and triggered blood-brain barrier dysfunction[5].

References:
[1] Wang W, Cao G, Zhang J, et al. p-Phenylenediamine-derived quinones as new contributors to the oxidative potential of fine particulate matter[J]. Environmental Science & Technology Letters, 2022, 9(9): 712-717.
[2] Wang W, Cao G, Zhang J, et al. Beyond substituted p-Phenylenediamine antioxidants: Prevalence of their quinone derivatives in PM2. 5[J]. Environmental Science & Technology, 2022, 56(15): 10629-10637.
[3] Mao T, Liu W, Deng J, et al. p-Phenylenediamines and p-phenylenediamine quinone derivatives in rubber consumer products and typical urban dust: Sources, transformation profiles, and health risks[J]. Environment International, 2024, 192: 109042.
[4] Wang W, Chen Y, Fang J, et al. Toxicity of substituted p-phenylenediamine antioxidants and their derived novel quinones on aquatic bacterium: Acute effects and mechanistic insights[J]. Journal of Hazardous Materials, 2024, 469: 133900.
[5] Han M, Xia K, Xue Y, et al. Emergence of More Potent PPD-Qs beyond 6PPD-Q in Human Blood and Cerebrospinal Fluid[J]. Environmental Science & Technology Letters, 2025.

IPPD-Q是N,N'-取代对苯二胺类化合物(PPD)的氧化产物,消耗二硫苏糖醇(DTT)的氧化潜势值为0.93μM min–1μM–1[1-2]。IPPD-Q已被应用于大气污染研究和污染物溯源诊断研究[3]

在体外,IPPD-Q对水生细菌费氏弧菌的EC50值(30分钟)为2.97mg/L[4]。IPPD-Q处理(2.97mg/L)30分钟会显著降低费氏弧菌的代谢活性和酯酶活性,同时增加细胞膜损伤程度和氧化应激水平[4]。在人脑血管内皮细胞(hCMEC-D3)中,1.00μM浓度的IPPD-Q处理24小时可诱导细胞凋亡和内皮-间质转化,上调纤溶酶原激活物抑制因子-1(PAI-1)的表达,并引发血脑屏障功能障碍[5]

实验参考方法

Cell experiment [1]:

Cell lines

hCMEC-D3 cell

Preparation Method

hCMEC-D3 cells were grown in endothelial cell medium (ECM) which included 5% fetal bovine serum (FBS) and 1% endothelial cell growth supplement along with 1% penicillin/streptomycin solution. Under 37 °C conditions with 5% CO2 humidified atmosphere the cell culture medium was changed every two days until cells reached 90% confluency. For 24 hours cells underwent treatment with different concentrations of IPPD-Q including 0, 0.01, 0.10, and 1.00μM. Collect cells from various exposure groups for protein expression analysis using Western blotting assays. Assess whether atorvastatin at a concentration of 0.30μM could modify the cellular effects of IPPD-Q when cells received both treatments simultaneously. The vehicle control that consisted of 0.1% DMSO (v/v) showed negligible effects after its evaluation process and thus became the designated exposure group 0.

Reaction Conditions

0, 0.01, 0.10, and 1.00μM; 24h

Applications

IPPD-Q can increase the level of TNF-α, induce cell apoptosis, up-regulate PAI-1 and lead to endothelial-to-mesenchymal transition of hCMEC-D3 cells, resulting in endothelial cell dysfunction.

References:
[1] Han M, Xia K, Xue Y, et al. Emergence of More Potent PPD-Qs beyond 6PPD-Q in Human Blood and Cerebrospinal Fluid[J]. Environmental Science & Technology Letters, 2025.

化学性质

Cas No. 68054-73-9 SDF Download SDF
别名 N-Isopropyl-N'-phenyl-p-phenylenediamine-quinone
分子式 C15H16N2O2 分子量 256.3
溶解度 Acetonitrile: Slightly soluble: 0.1-1 mg/ml,DMSO: Sparingly soluble: 1- 10 mg/ml 储存条件 -20°C
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1 mM 3.9017 mL 19.5084 mL 39.0168 mL
5 mM 0.7803 mL 3.9017 mL 7.8034 mL
10 mM 0.3902 mL 1.9508 mL 3.9017 mL
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