2,3-Dimethoxy-5-methyl-p-benzoquinone
(Synonyms: 2,3-二甲氧基-5-甲基-1,4-苯醌,CoQ0) 目录号 : GC40947
An intermediate in the synthesis of ubiquinones that has anticancer activity
Cas No.:605-94-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2,3-Dimethoxy-5-methyl-p-benzoquinone, also known as coenzyme Q0, is a key intermediate in the synthesis of coenzyme Q, coenzyme Q10, other ubiquinones, and vitamin E. It inhibits the growth of SKOV-3, A2780, and A2870/CP70 human ovarian carcinoma cells (IC50s = 26.6, 27.3, and 28.4 µM, respectively) with a cytotoxic concentration of greater than 40 µM for non-cancerous ovarian surface epithelial cells. It halts the cell cycle at the G2/M phase, increases the production of reactive oxygen species (ROS), and induces autophagy and apoptosis in SKOV-3 cells. 2,3-Dimethoxy-5-methyl-p-benzoquinone downregulates the protooncogene HER-2 and decreases the protein levels of phosphorylated AKT and mTOR in SKOV-3 cells. It also decreases the incidence of tumors and tumor burden in a SKOV-3 human ovarian carcinoma mouse xenograft model when administered at a dose of 2.5 mg/kg every four days.
| Cas No. | 605-94-7 | SDF | |
| 别名 | 2,3-二甲氧基-5-甲基-1,4-苯醌,CoQ0 | ||
| Canonical SMILES | O=C(C(C)=C1)C(OC)=C(OC)C1=O | ||
| 分子式 | C9H10O4 | 分子量 | 182.2 |
| 溶解度 | DMF: 100 mg/ml,DMSO: 100 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): 0.2 mg/ml | 储存条件 | Store at -20°C |
| 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 | 5.4885 mL | 27.4424 mL | 54.8847 mL |
| 5 mM | 1.0977 mL | 5.4885 mL | 10.9769 mL |
| 10 mM | 0.5488 mL | 2.7442 mL | 5.4885 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。
2,3-Dimethoxy-5-methyl-p-benzoquinone (Coenzyme Q0) Disrupts Carbohydrate Metabolism of HeLa Cells by Adduct Formation with Intracellular Free Sulfhydryl-Groups, and Induces ATP Depletion and Necrosis
Biol Pharm Bull 2018;41(12):1809-1817.PMID:30504682DOI:10.1248/bpb.b18-00497.
2,3-Dimethoxy-5-methyl-p-benzoquinone is a common chemical structure of coenzyme Q (CoQ) that conjugates different lengths of an isoprenoid side chain at the 6-position of the p-benzoquinone ring. In a series of studies to explore the cytotoxic mechanism of CoQ homologues with a short isoprenoid side chain, we found that a CoQ analogue without an isoprenoid side chain, CoQ0, showed marked toxicity against HeLa cells in comparison with cytotoxic homologues. Therefore, we examined the cytotoxic mechanism of CoQ0. Different from the cytotoxic CoQ homologues that induced apoptosis, 100 µM CoQ0 induced necrosis of HeLa cells. The CoQ0-induced cell death was accompanied by a decrease in endogenous non-protein and protein-associated sulfhydryl (SH)-groups, but this improved with the concomitant addition of compounds with SH-groups but not antioxidants without SH-groups. In addition, UV-spectrum analysis suggested that CoQ0 could rapidly form S-conjugated adducts with compounds with SH-groups by Michael addition. On the other hand, enzyme activities of both glyceraldehyde-3-phosphate dehydrogenase, which has a Cys residue in the active site, and α-ketoglutarate dehydrogenase complex, which requires cofactors with SH-groups, CoA and protein-bound α-lipoic acid, and CoA and ATP contents in the cells were significantly decreased by the addition of CoQ0 but not CoQ1. Furthermore, the decrease of an endogenous antioxidant, glutathione (GSH), by CoQ0 treatment was much greater than the predicted increase of endogenous GSH disulfide. These results suggest that CoQ0 rapidly forms S-conjugate adducts with these endogenous non-protein and protein-associated SH-groups of HeLa cells, which disrupts carbohydrate metabolism followed by intracellular ATP depletion and necrotic cell death.
Constituents from solid-cultured Antrodia camphorata
Nat Prod Res 2017 Nov;31(21):2564-2567.PMID:28768421DOI:10.1080/14786419.2017.1320785.
Antrodia camphorata is a rare and precious traditional food and medicine for improving health-related conditions in Taiwan. The phytochemical research of the mushroom led to the isolation of a new naphthalenecarboxaldehyde, named as 1-Naphthalenecarboxaldehyde,3,4,4a,5,6,7,8,8a-octahydro-2-(hydroxymethyl)-5,5,8a-trimethyl (1). Meanwhile, seven other known compounds of nerolidol (2), cadinol (3), herbarulide (4), 3β-Hydroxy-5a,8a-epidioxyergosta-6,22-diene (5), ergosta-7,22-diene-3,6-dione (6) 2,3-Dimethoxy-5-methyl-p-benzoquinone (7) and β-sitosterol (8) were also obtained from A. camphorata for the first time except compound (8). The new compound was elucidated by 2D NMR techniques (COSY, HMBC, HSQC, NOESY) and HRMS while those known compounds deduced by comparing 1H NMR and 13C NMR data with other literatures. Then, the hepG2 cell toxicity screening was conducted and the results demonstrated that only compound 7 and 8 exhibited significant toxicity to hepG2 cell at the concentration of 50 μg/mL.
Photo-oxidation and Photoreduction of Catechols by Chlorophyll Metabolites and Methylene Blue
Chem Res Toxicol 2022 Oct 17;35(10):1851-1862.PMID:36044382DOI:10.1021/acs.chemrestox.2c00142.
While plant-derived oxidants can protect cells from oxidative damage, limited research has examined the role of dietary chlorophyll. Photoreduction of ubiquinone by chlorophyll metabolites and red light has been reported in vitro and in animal models. Herein we examined photo-oxidation and photoreduction reactions of catechols, dopamine and hydrocaffeic acid. Photo-oxidation of dopamine by methylene blue and the chlorophyll metabolites pheophorbide A, chlorin e6 and sodium copper chlorophyllin was studied by monitoring aminochrome, the cyclized product of the dopamine o-quinone with its amine. Singlet oxygen scavengers including sodium azide, ascorbate and glutathione decreased aminochrome formation by methylene blue and pheophorbide A. Addition of EDTA, a tertiary amine electron donor, to the reaction of dopamine, photosensitizer and red light decreased aminochrome formation. Photoreduction of the dopamine o-quinone produced by mushroom tyrosinase was achieved by both methylene blue and pheophorbide A only when an electron donor was included. Due to limited solubility, photo-oxidation and photoreduction reactions by pheophorbide A required 5-7.5% dimethylformamide for optimal reactivity. Catalytic photoreduction of 2,3-Dimethoxy-5-methyl-p-benzoquinone by methylene blue or pheophorbide A and tertiary amine electron donors was observed. Among the chlorophyll metabolites, pheophorbide A was more effective than chlorin e6 or sodium copper chlorophyllin in photo-oxidation of dopamine and photoreduction reactions. Singlet oxygen inhibited lactate dehydrogenase A activity, and higher molecular weight protein cross-links were observed on SDS-PAGE. Hydrocaffeic acid competed with lactate dehydrogenase A for reaction with singlet oxygen produced by methylene blue; however, no protection by hydrocaffeic acid (HCA) was observed when pheophorbide A was used. Cysteine modification of lactate dehydrogenase A by the o-quinone of hydrocaffeic acid was detected using a redox cycling stain. Inclusion of an electron donor decreased protein labeling.