Anthraquinone-2-carboxylic acid
(Synonyms: 蒽醌-2-羧酸) 目录号 : GC39598
Anthraquinone-2-carboxylic Acid is a novel electron shuttling mediator, showing potent anti-inflammatory and antinociceptive activities in vivo.
Cas No.:117-78-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Anthraquinone-2-carboxylic Acid is a novel electron shuttling mediator, showing potent anti-inflammatory and antinociceptive activities in vivo.
| Cas No. | 117-78-2 | SDF | |
| 别名 | 蒽醌-2-羧酸 | ||
| Canonical SMILES | O=C(C1=C2C=CC=C1)C(C=C3C(O)=O)=C(C=C3)C2=O | ||
| 分子式 | C15H8O4 | 分子量 | 252.22 |
| 溶解度 | DMSO: 25 mg/mL (99.12 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 3.9648 mL | 19.824 mL | 39.6479 mL |
| 5 mM | 0.793 mL | 3.9648 mL | 7.9296 mL |
| 10 mM | 0.3965 mL | 1.9824 mL | 3.9648 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。
Anti-Inflammatory and Antinociceptive Activities of Anthraquinone-2-carboxylic acid
Mediators Inflamm 2016;2016:1903849.PMID:27057092DOI:10.1155/2016/1903849.
Anthraquinone compounds are one of the abundant polyphenols found in fruits, vegetables, and herbs. However, the in vivo anti-inflammatory activity and molecular mechanisms of anthraquinones have not been fully elucidated. We investigated the activity of anthraquinones using acute inflammatory and nociceptive experimental conditions. Anthraquinone-2-carboxylic acid (9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid, AQCA), one of the major anthraquinones identified from Brazilian taheebo, ameliorated various inflammatory and algesic symptoms in EtOH/HCl- and acetylsalicylic acid- (ASA-) induced gastritis, arachidonic acid-induced edema, and acetic acid-induced abdominal writhing without displaying toxic profiles in body and organ weight, gastric irritation, or serum parameters. In addition, AQCA suppressed the expression of inflammatory genes such as cyclooxygenase- (COX-) 2 in stomach tissues and lipopolysaccharide- (LPS-) treated RAW264.7 cells. According to reporter gene assay and immunoblotting analyses, AQCA inhibited activation of the nuclear factor- (NF-) κB and activator protein- (AP-) 1 pathways by suppression of upstream signaling involving interleukin-1 receptor-associated kinase 4 (IRAK1), p38, Src, and spleen tyrosine kinase (Syk). Our data strongly suggest that anthraquinones such as AQCA act as potent anti-inflammatory and antinociceptive components in vivo, thus contributing to the immune regulatory role of fruits and herbs.
Dual-ratiometric electrochemical aptasensor based on carbon nanohorns/Anthraquinone-2-carboxylic acid/Au nanoparticles for simultaneous detection of malathion and omethoate
Talanta 2023 Feb 1;253:123966.PMID:36182706DOI:10.1016/j.talanta.2022.123966.
Organophosphorus pesticides (OPs) are one of the most frequently used pesticides in agriculture, and their residues in environment have caused serious human health and environmental concerns. In this work, we reported a dual-ratiometric electrochemical aptasensor based on carbon nanohorns/Anthraquinone-2-carboxylic acid/Au nanoparticles (CNHs/AQ/AuNPs) for simultaneous detection of malathion (MAL) and omethoate (OMT). Here, CNHs/AQ/AuNPs composites were synthesized by a simple room temperature method, and used as a substrate to generate a reference signal (IAQ) and enlarge response signals. Hairpin DNA was then immobilized, offering independent and specific binding sites to further adsorb MB-labelled MAL aptamer (MB-Apt1) and Fc-labelled OMT aptamer (Fc-Apt2). Upon the addition of MAL or OMT, the formation of aptamer-target complex caused the release of MB-Apt1 or Fc-Apt2 from the electrode, resulting in a decrease in IMB or IFc, while IAQ kept unchanged. Based on this principle, the ratiometric signals of IMB/IAQ and IFc/IAQ were used to simultaneously detect MAL and OMT, offering a linear range of 3 pg mL-1 to 3 ng mL-1 for MAL and 10 pg mL-1 to 10 ng mL-1 for OMT, and no significant cross-reactivity existed. By taking advantage of the excellent conductivity and large specific area of CNHs/AQ/AuNPs and the stable two-dimensional structure of hairpin DNA, the aptasensor exhibited high sensitivity, selectivity and reliability. Our work has offered a novel way for simultaneous detection of multiple OPs.
Adsorption state and morphology of Anthraquinone-2-carboxylic acid deposited from solution onto the atomically-smooth native oxide surface of Al(111) films studied by infrared reflection absorption spectroscopy, X-ray photoelectron spectroscopy, and atomic force microscopy
Anal Sci 2008 Mar;24(3):313-20.PMID:18332536DOI:10.2116/analsci.24.313.
The adsorption state and morphology of Anthraquinone-2-carboxylic acid (AQ-2-COOH) deposited from acetone solutions (0.02 - 1.00 mg ml(-1)) onto atomically-smooth native oxide surfaces of Al(111) films were investigated by infrared reflection absorption spectroscopy, X-ray photoelectron spectroscopy, and atomic force microscopy. The atomically-smooth oxide surfaces were prepared by vacuum evaporation of Al on mica substrates at 350 degrees C, followed by oxidation in an oxygen-dc glow discharge at room temperature. It was found that AQ-2-COOH is adsorbed on the film surfaces in both the neutral and ionized state, where the amount of the neutral molecules increases with increasing concentration. This molecule is adsorbed as both a uniform nanometer-scale film, and as micrometer-sized particles with heights ranging from 10 to 200 nm above the film surface. The volumes of the particles of deposited AQ-2-COOH increased with increasing concentration. It is concluded that the particles are microcrystallites of neutral AQ-2-COOH and that the thin uniform film results from AQ-2-COOH anion formation on the film surfaces. A comparison of the results obtained by use of these surface analytical techniques clearly shows the features and advantages of these tools.
L-proline analogues of Anthraquinone-2-carboxylic acid: cytotoxic activity in breast cancer MCF-7 cells and inhibitory activity against topoisomerase I and II
Pol J Pharmacol 2001 May-Jun;53(3):283-7.PMID:11785929doi
A series of proline analogues of Anthraquinone-2-carboxylic acid (1-3) were synthesized and evaluated for cytotoxic activity in the cultured breast cancer MCF-7 cells. The concentrations of 1, 2 and 3 needed to inhibit [3H]thymidine incorporation into DNA by 50% (IC50) were found to be 107 +/- 6 microM, 185 +/- 5 microM and 87 +/- 6 microM, respectively. To test whether cytotoxic properties were related to topoisomerase action, the most potent compounds 1 and 3 were evaluated in a cell-free system. Compound 3, which contains a basic substituent at C terminus of the amino acid such as (dimethylamino)propyl inhibited the catalytic activity of both topoisomerases I and II at a concentration of 30 and 60 microM, respectively. However, compound 1 containing an electrostatically neutral moiety, such as methyl ester did not inhibit topoisomerase I or topoisomerase II. In summary, compound 3 is a promising lead compound for a further structural variation in the design of new antitumour drugs.
Prolidase as a prodrug converting enzyme. II. Synthesis of proline analogue of Anthraquinone-2-carboxylic acid and its susceptibility to the action of prolidase
Rocz Akad Med Bialymst 1998;43:201-9.PMID:9972056doi
The feasibility to targeting prolidase as an antineoplastic prodrug--converting enzyme has been examined. The synthesis of proline analogue of Anthraquinone-2-carboxylic acid (potential antineoplastic agent) conjugated through imido-bond (potential target for prolidase action) has been performed. The product was found to be insoluble in aqueous solution while in the presence of 1% DMSO complete solubility of the compound was achieved. Evidence was provided that 1% DMSO does not affect prolidase activity, thus allowing for substrate susceptibility measurement in a such conditions. It has been presented that product of synthesis, N-(anthraquinone-2-carbonyl)-L-proline evokes susceptibility to the action of purified prolidase, comparable to the susceptibility of glycyl-L-proline (standard substrate for prolidase). Although insolubility of the proline analogue of Anthraquinone-2-carboxylic acid in aqueous solutions limit its potential therapeutic value, the presented data suggest that prolidase may have a broader substrate specificity than thought previously. It suggests that targeting of prolidase as a prodrug-converting enzyme may serve as a potential strategy in therapy of neoplastic diseases.