Juglone
(Synonyms: 胡桃醌; 5-Hydroxy-1,4-naphthalenedione) 目录号 : GC43933
Juglone是一种存在于核桃中的酚类化合物，可抑制胱硫醚γ-合成酶（HpCGS）、丙二酰辅酶A：酰基载体蛋白转酰基酶（HpFabD）和β-羟基酰基ACP脱水酶（HpFabZ），IC50值分别为7.0±0.7µM、20±1µM和30±4µM。
Cas No.:481-39-0
Sample solution is provided at 25 µL, 10mM.
Juglone, a phenolic compound found in walnuts, inhibits cystathionine γ-synthase (HpCGS), malonyl-CoA:acylcarrier protein transacylase (HpFabD), and β-hydroxyacylACP dehydratase (HpFabZ) with IC50 values of 7.0±0.7, 20±1, and 30±4µM, respectively[1]. Juglone contains an intramolecular hydrogen bond between hydroxyl and keto groups and is active in donating the hydrogen-atom, which combats oxidative stress[2]. Juglone, a potent urease inactivator, produces irreversible inhibition by covalent modification of protein thiol, which is widely used in antibacterial and antifungal research[3].
In vitro, Juglone treatment for 24h inhibited cell viability of BxPC-3 cells and PANC-1 cells with IC50 values of 21.05 and 21.25μM, respectively[4]. Juglone treatment for 24 hours inhibited the viability of A549 cells with an IC50 value of 9.47μM, arrested the cell cycle and induced apoptosis[5]. Treatment of human fibroblasts with 5μM Juglone for 30min rapidly induced DNA damage, which triggered a stress response leading to H2AX phosphorylation[6].
In vivo, Intraperitoneal injection of Juglone (4mg/kg) to mice every other day for 20 days significantly inhibited the growth of transplanted tumors, resulting in partial degeneration and necrosis of tumor cells [7]. Intraperitoneal injection of Juglone (1mg/kg) every 3 days for 40 days delayed the growth of glioma in mice and prolonged the survival time of glioma-bearing mice [8].
References:
[1] Kong YunHua K Y H, Zhang Liang Z L, Yang ZhengYi Y Z Y, et al. Natural product juglone targets three key enzymes from Helicobacter pylori: inhibition assay with crystal structure characterization[J]. 2008.
[2] Ahmad T, Suzuki Y J. Juglone in oxidative stress and cell signaling[J]. Antioxidants, 2019, 8(4): 91.
[3] Islam A K M M, Widhalm J R. Agricultural uses of juglone: Opportunities and challenges[J]. Agronomy, 2020, 10(10): 1500.
[4] Avcı E, Arıkoğlu H, Kaya D E. Investigation of juglone effects on metastasis and angiogenesis in pancreatic cancer cells[J]. Gene, 2016, 588(1): 74-78.
[5] Zhong J, Hua Y, Zou S, et al. Juglone triggers apoptosis of non-small cell lung cancer through the reactive oxygen species-mediated PI3K/Akt pathway[J]. Plos one, 2024, 19(5): e0299921.
[6] Paulsen M T, Ljungman M. The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts[J]. Toxicology and applied pharmacology, 2005, 209(1): 1-9.
[7] Wang P, Zhang S D, Jiao J, et al. ROS-mediated p53 activation by juglone enhances apoptosis and autophagy in vivo and in vitro[J]. Toxicology and Applied Pharmacology, 2019, 379: 114647.
[8] Wu J, Zhang H, Xu Y, et al. Juglone induces apoptosis of tumor stem-like cells through ROS-p38 pathway in glioblastoma[J]. BMC neurology, 2017, 17(1): 70.
Juglone是一种存在于核桃中的酚类化合物，可抑制胱硫醚γ-合成酶（HpCGS）、丙二酰辅酶A：酰基载体蛋白转酰基酶（HpFabD）和β-羟基酰基ACP脱水酶（HpFabZ），IC50值分别为7.0±0.7µM、20±1µM和30±4µM[1]。Juglone通过羟基与酮基形成分子内氢键，具有提供氢原子抵抗氧化应激的活性[2]。作为强效脲酶灭活剂，Juglone通过共价修饰蛋白巯基产生不可逆抑制，被广泛用于抗菌和抗真菌研究[3]。
在体外，Juglone处理24小时可抑制BxPC-3和PANC-1细胞活力，IC50值分别为21.05μM和21.25μM[4]。Juglone处理A549细胞24小时的IC50值为9.47μM，可诱导细胞周期阻滞和凋亡[5]。5μM的Juglone处理人成纤维细胞30分钟能快速诱导DNA损伤，触发应激反应导致H2AX磷酸化[6]。
在体内，小鼠隔日腹腔注射Juglone（4mg/kg；持续20天）可显著抑制移植瘤生长，导致肿瘤细胞部分变性和坏死[7]。每3天腹腔注射1mg/kg剂量的Juglone（持续40天）能延缓小鼠神经胶质瘤生长并延长荷瘤鼠生存时间[8]。
| Cell experiment [1]: | |
Cell lines | A549 cells |
Preparation Method | A549 cells were cultured in high-glucose DMEM medium supplemented with 10% fetal bovine serum (FBS), 100U/ml penicillin and 100μg/ml streptomycin, and cultured at 37℃ in a humidified environment with 5% CO2. The solution was changed once a day and digested with 0.25% trypsin every 3 days. A549 cells were seeded in 96-well plates (5×103 cells/well) overnight. After adherence, cells were treated with different concentrations of Juglone (1, 2, 4, 8, 16, and 32μM) for 24 hours. Then, 50μL MTT solution was added to each well and incubated for 4 hours. The supernatant was discarded and 100μL DMSO was added to dissolve formazan crystals and the absorbance at 490nm was measured. |
Reaction Conditions | 1, 2, 4, 8, 16, and 32μM; 24h |
Applications | Juglone inhibited cell viability in a concentration-dependent manner within A549 cells. |
| Animal experiment [2]: | |
Animal models | BALB/c nude mice |
Preparation Method | Four-week-old female BALB/c nude mice were cultured and acclimated to the standard environment for one week, and 1 × 107 HepG2 cells were suspended in 100μl cold PBS and injected into the right forelimb socket. When the tumor reached 50mm3 in size, the mice were randomly divided into two groups: the control group and Juglone group (five mice per group). The control group was intraperitoneally injected with 10% DMSO+90% normal saline, and the Juglone group was intraperitoneally injected with 4mg/kg Juglone every other day for 20 days. Mouse body weight and tumor size were measured every 3 days for 4 weeks, and tumor volume was calculated using the following formula: length × width2/2. After treatment, mice were sacrificed, and tumors were removed, weighed, and fixed for immunohistochemical experiments. |
Dosage form | 4mg/kg every other day for 20 days; i.p. |
Applications | Juglone treatment resulted in the reduction of tumor volume in mice, partial degeneration and necrosis of tumor cells, and high expression of cleaved caspase-3. |
References: | |
| Cas No. | 481-39-0 | SDF | |
| 别名 | 胡桃醌; 5-Hydroxy-1,4-naphthalenedione | ||
| Canonical SMILES | O=C1C=CC(C2=CC=CC(O)=C21)=O | ||
| 分子式 | C10H6O3 | 分子量 | 174.2 |
| 溶解度 | Ethanol: 10 mg/ml（DMSO can inactivate Juglone's activity）（The solution is unstable, it is recommended to prepare it before use） | 储存条件 | 4°C, protect from light ,unstable in solution, ready to use. |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.7405 mL | 28.7026 mL | 57.4053 mL |
| 5 mM | 1.1481 mL | 5.7405 mL | 11.4811 mL |
| 10 mM | 574.1 μL | 2.8703 mL | 5.7405 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
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- Purity: >97.00%
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