Rapanone
(Synonyms: 拉帕酮) 目录号 : GC63860
Rapanone是一种天然存在的具有优势螯合结构的羟基苯醌，具有广泛的生物活性，特别是其抗炎、驱虫和细胞毒性活性。
Cas No.:573-40-0
Sample solution is provided at 25 µL, 10mM.
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Rapanone naturally occurring hydroxyl-benzoquinone with a privileged chelating structure, having a broad spectrum of biological actions, highlighting its anti-inflammatory, anthelmintic, and cytotoxic activities[1]. Rapanone exhibits antioxidant potential by oxidizing Fe(II) and O2⁻ radicals, thereby inhibiting Fenton-Haber-Weiss reactions. Rapanone’s antioxidant capacity is enhanced upon interaction with Fe(II) or mitochondria, and it prevents iron or free radical-induced mitochondrial damage through multiple mechanisms[1-2].
In vitro, Rapanone (25 and 50μM) induces apoptosis in the MCF-7 cell line after 24 hours of treatment[3]. In the hepatic carcinoma (HepG2), 24 hours of Rapanone (20-40μM) treatment induced a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and phosphatidyl serine externalization[4].
In vivo, oral administration of Rapanone to female albino mice at doses of 60mg/kg and 120mg/kg induced uterine alterations in both the first and second gestation periods and decreased the pregnancy rate in a dose-dependent manner[5]. In female Swiss mice, treatment with Rapanone (2.5, 5, 10mg/kg; i. p.) significantly inhibited the formation of oedema as well as the content of elastase and Prostaglandin E2 (PGE2) in a dose-dependent manner[6]. After exposing zebrafish embryos to Rapanone (160μM) for 96 hours, the embryo survival rate was 90-98%, and Rapanone showed low toxicity[7].
References:
[1] de la Vega-Hernández K, Antuch M, Cuesta-Rubio O, Núñez-Figueredo Y, Pardo-Andreu GL. Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities. J Inorg Biochem. 2017;170:134-147.
[2] Wróbel-Biedrawa D, Grabowska K, Galanty A, Sobolewska D, Żmudzki P, Podolak I. Anti-melanoma potential of two benzoquinone homologues embelin and rapanone - a comparative in vitro study. Toxicol In Vitro. 2020;65:104826.
[3] Arunachalam A, Sankar M, Pandi B, Paul S, Thilagar S. Evaluation of Rapanone and Nectandrin B as novel inhibitors for targeting the metastatic regulator protein BACH1 using breast cancer cell line Mcf-7. J Biomol Struct Dyn. 2024;42(20):11185-11200.
[4] Pardo Andreu GL, Reis FZD, González-Durruthy M, et al. Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death. Toxicol In Vitro. 2020;63:104737.
[5] Calle J, Olarte J, Pinzon R, Ospina LF, Mendoza MC, Orozco MJ. Alterations in the reproduction of mice induced by rapanone. J Ethnopharmacol. 2000;71(3):521-525.
[6] Ospina LF, Calle J, Arteaga L, Pinzón R, Alcaraz MJ, Payá M. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta Med. 2001;67(9):791-795.
[7] Mariyappan V, Munuswamy-Ramanujam G, Ramasamy M. Synthesis of novel rapanone derivatives via organocatalytic reductive C-alkylation: biological evaluation of antioxidant properties, in vivo zebrafish embryo toxicity, and docking studies. RSC Med Chem. 2023;15(2):623-635.
Rapanone是一种天然存在的具有优势螯合结构的羟基苯醌，具有广泛的生物活性，特别是其抗炎、驱虫和细胞毒性活性[1]。Rapanone通过氧化Fe(Ⅱ)和O2⁻自由基，抑制芬顿-哈伯-魏斯反应，从而显示出抗氧化潜力。Rapanone的抗氧化能力在与Fe(Ⅱ)或线粒体相互作用时得到增强，并且通过多种机制防止铁或自由基诱导的线粒体损伤[1-2]。
在体外，Rapanone（25和50μM）在处理24小时后可诱导MCF-7细胞系发生凋亡[3]。在肝癌（HepG2）细胞中，24小时的Rapanone（20-40μM）处理诱导了线粒体膜电位的浓度依赖性耗散、ATP耗竭、过氧化氢生成以及磷脂酰丝氨酸外翻[4]。
在体内，对雌性白化小鼠口服给予Rapanone，剂量分别为60mg/kg和120mg/kg，可在第一和第二个妊娠期诱导子宫发生改变，并以剂量依赖性方式降低怀孕率[5]。在瑞士雌性小鼠中，用Rapanone（2.5、5、10mg/kg；腹腔注射）处理显著抑制了水肿的形成以及弹性蛋白酶和前列腺素E2（PGE2）含量，且呈剂量依赖性[6]。将斑马鱼胚胎暴露于Rapanone（160μM）96小时后，胚胎存活率为90-98%，且Rapanone显示低毒性[7]。
| Cell experiment [1]: | |
Cell lines | MCF-7 cells |
Preparation Method | MCF-7 cells were seeded in a 6-well plate (1×106/well) and incubated at 37°C for 24h. The medium was then removed and replaced with (0.25, 5, 25, 50 and 100µM) of Rapanone, which was suspended in a serum-free medium. The cells were incubated for 24h, followed by washing with Phosphate Buffered Saline (PBS) 3 times. The cells were then stained with acridine orange and propidium iodide. |
Reaction Conditions | 0.25, 5, 25, 50 and 100µM; 24h |
Applications | Rapanone induces apoptosis in MCF-7 cell line at a concentration of 25 and 50μM. |
| Animal experiment [2]: | |
Animal models | Female Swiss mice |
Preparation Method | Inflammatory response was induced by injection of carrageenan (0.05ml; 3%w/v in saline) into the subplantar area of the right hind paws of groups of six animals. Rapanone was administered i. p. (propylene glycol/glycerol/distilled water, 40:10:50, v/v/v) at the doses of 2.5, 5, and 10mg/kg 1h before injection of carrageenan. Paw volumes were measured using a plethysmometer. Mice were sacrificed by cervical dislocation 5h after carrageenan administration, and hind paws were homogenized in saline. Prostaglandin E2 (PGE2) and elastase activity content in paw homogenates were determined. |
Dosage form | 2.5, 5, 10mg/kg; i.p. |
Applications | Intraperitoneal administration of Rapanone significantly inhibited the formation of oedema, as well as elastase and PGE2 content in a dose-dependent manner. |
References: | |
| Cas No. | 573-40-0 | SDF | Download SDF |
| 别名 | 拉帕酮 | ||
| 分子式 | C19H30O4 | 分子量 | 322.44 |
| 溶解度 | DMSO : 25 mg/mL (77.53 mM; ultrasonic and warming and heat to 60°C) | 储存条件 | Store at -20°C,protect from light |
| 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 | 3.1014 mL | 15.5068 mL | 31.0135 mL |
| 5 mM | 0.6203 mL | 3.1014 mL | 6.2027 mL |
| 10 mM | 0.3101 mL | 1.5507 mL | 3.1014 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: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
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