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Patulin

(Synonyms: 棒曲霉素; Terinin) 目录号 : GC40483

Patulin是一种有毒的多酚类乳内酯。

Patulin Chemical Structure

Cas No.:149-29-1

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5mg
¥965.00
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10mg
¥1,829.00
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Description

Patulin is a toxic polyphenolic lactolactone [1]. Patulin reacts with protein sulfhydryl groups, triggering cellular oxidative stress and p53-mediated DNA damage, which damages the intestinal epithelial barrier [2]. Patulin has teratogenic, genotoxic, and neurotoxic properties [3-4].

In HL-60 cells, after Patulin (0-10μM; 6h) significantly decreased cell viability [5]. In HepG2 cells, Patulin (0.5-2μM; 24h) induces autophagy in cells via the ROS-Akt1-MTOR pathway [6].

In CF-1 mice, Patulin (1.0-3.75mg/kg; ip; single injection) induced DNA strand breaks, decreased GSH levels, and increased lipid peroxidation in the brain, liver, and kidney [7]. In B16F10 cell xenograft mouse model, Patulin (5-50μg/kg; ip; 20d) significantly induced tumor regression [8].

References:
[1]. Puel O, Galtier P, Oswald I P. Biosynthesis and toxicological effects of patulin[J]. Toxins, 2010, 2(4): 613-631.
[2]. Saxena N, Ansari K M, Kumar R, et al. Patulin causes DNA damage leading to cell cycle arrest and apoptosis through modulation of Bax, p53 and p21/WAF1 proteins in skin of mice[J]. Toxicology and applied pharmacology, 2009, 234(2): 192-201.
[3]. Glaser N, Stopper H. Patulin: Mechanism of genotoxicity[J]. Food and Chemical Toxicology, 2012, 50(5): 1796-1801.
[4]. Lei W L, Li Y Y, Hou Y, et al. Toxic effects of patulin on mouse oocytes and its possible mechanisms[J]. Toxicology, 2021, 464: 153013.
[5]. Wu T S, Liao Y C, Yu F Y, et al. Mechanism of patulin-induced apoptosis in human leukemia cells (HL-60)[J]. Toxicology letters, 2008, 183(1-3): 105-111.
[6]. Yang G, Bai Y, Wu X, et al. Patulin induced ROS-dependent autophagic cell death in Human Hepatoma G2 cells[J]. Chemico-Biological Interactions, 2018, 288: 24-31.
[7]. de Melo F T, de Oliveira I M, Greggio S, et al. DNA damage in organs of mice treated acutely with patulin, a known mycotoxin[J]. Food and Chemical Toxicology, 2012, 50(10): 3548-3555.
[8]. Boussabbeh M, Ben Salem I, Rjiba-Touati K, et al. The potential effect of patulin on mice bearing melanoma cells: an anti-tumour or carcinogenic effect?[J]. Tumor Biology, 2016, 37(5): 6285-6295.

Patulin是一种有毒的多酚类乳内酯 [1]。Patulin可与蛋白质巯基发生反应,引发细胞氧化应激和p53介导的DNA损伤,从而破坏肠道上皮屏障 [2]。Patulin具有致畸、遗传毒性和神经毒性 [3-4]

在HL-60细胞中,Patulin(0-10μM;6h)治疗后细胞活力显著下降 [5]。在HepG2细胞中,Patulin(0.5-2μM;24h)通过ROS-Akt1-MTOR通路诱导细胞自噬 [6]

在CF-1小鼠中,Patulin(1.0-3.75mg/kg;ip;单次注射)诱导DNA链断裂,降低谷胱甘肽(GSH)水平,并增加脑、肝和肾中的脂质过氧化 [7]。在B16F10细胞异种移植小鼠模型中,Patulin(5-50μg/kg;ip;20d)显著诱导肿瘤消退 [8]

实验参考方法

Cell experiment [1]:

Cell lines

HL-60 cells

Preparation Method

HL-60 (1 × 105 cells) were seeded in 96-well plates, treated with vehicle (15% ethanol in 0.01M PBS) alone or various concentrations (final concentration 0-10μM) of Patulin at the designated time.

Reaction Conditions

0-10μM; 6h

Applications

Patulin treatment significantly decreased cell viability.
Animal experiment [2]:

Animal models

CF-1 mice

Preparation Method

The experimental design involved nine groups of 10 mice, housed individually in cages. Mice received a single intraperitoneal (i.p.) dose of 1.0, 2.5, or 3.75mg/kg body weight (BW) of Patulin. Patulin stock solution was dissolved in DMSO and then diluted with saline to a final DMSO concentration below 0.1%. Mice were divided into the following groups: Group 1: Control group, administered with 0.1% DMSO in saline (5mL/kg BW). Group 2: Positive control group, administered with MMS (40mg/kg BW). Groups 3-5: Patulin was administered intraperitoneally at the following doses: Group 3, 1.0mg/kg BW; Group 4, 2.5mg/kg BW; Group 5, 3.75mg/kg BW. Group 6: N-ac (1840μmol/kg BW) was administered 3 hours prior to administration of 0.1% DMSO (5mL/kg BW). Groups 7-9 were intraperitoneally injected with Patulin at the following doses: 1.0mg/kg body weight for Group 7; 2.5mg/kg body weight for Group 8; and 3.75mg/kg body weight for Group 9. All animals in Groups 7-9 were given 300mg/kg of N-ac 3 hours before Patulin.

Dosage form

1.0-3.75mg/kg; ip; single injection

Applications

Patulin induced DNA strand breaks, decreased GSH levels, and increased lipid peroxidation in the brain, liver, and kidney.

References:
[1]. Wu T S, Liao Y C, Yu F Y, et al. Mechanism of patulin-induced apoptosis in human leukemia cells (HL-60)[J]. Toxicology letters, 2008, 183(1-3): 105-111.
[2]. de Melo F T, de Oliveira I M, Greggio S, et al. DNA damage in organs of mice treated acutely with patulin, a known mycotoxin[J]. Food and Chemical Toxicology, 2012, 50(10): 3548-3555.

化学性质

Cas No. 149-29-1 SDF
别名 棒曲霉素; Terinin
化学名 4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Canonical SMILES O=C1OC2=CCOC(O)C2=C1
分子式 C7H6O4 分子量 154.1
溶解度 13mg/mL in ethanol, 10mg/mL in DMSO, 20mg/mL in DMF 储存条件 -20°C, protect from light
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1 mM 6.4893 mL 32.4465 mL 64.8929 mL
5 mM 1.2979 mL 6.4893 mL 12.9786 mL
10 mM 0.6489 mL 3.2446 mL 6.4893 mL
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