Quinizarin
(Synonyms: 1,4-二羟基蒽醌; 1,4-Dihydroxyanthraquinone) 目录号 : GC61666
Quinizarin(1,4-Dihydroxyanthraquinone)是Doxorubicin、Daunorubicin、Adriamycin等抗癌药物的一部分，通过插入方式与DNA相互作用(Kd=86.1μM)。Quinizarin是一种杀菌剂和杀虫剂，并已显示出抑制肿瘤细胞生长的能力。
Cas No.:81-64-1
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
Quinizarin (1,4-Dihydroxyanthraquinone), a part of the anticancer agents such as Doxorubicin, Daunorubicin, and Adriamycin, interacts with DNA by intercalating mode (Kd=86.1 μM). Quinizarin is used as a fungicide and pesticide chemical and has shown the ability to inhibit tumor cell growth[1][2].
1,4-Dihydroxyanthraquinone (1,4-DHAQ, a fluorophore) doped cellulose (CL) (denoted as 1,4-DHAQ@CL) microporous nanofiber film has been achieved via simple electrospinning and subsequent deacetylating, and used for highly sensitive and selective fluorescence detection of Cu(2+) in aqueous solution[1].
[1]. VerebovÁ V, et al. Anthraquinones quinizarin and danthron unwind negatively supercoiled DNA and lengthen linear DNA. Biochem Biophys Res Commun. 2014;444(1):50-55. [2]. Dominic Cheuk, et al. Investigation into solid and solution properties of quinizarin. [3]. Wang M, et al. Electrospun 1,4-DHAQ-doped cellulose nanofiber films for reusable fluorescence detection of trace Cu2+ and further for Cr3+. Environ Sci Technol. 2012;46(1):367-373.
| Cas No. | 81-64-1 | SDF | |
| 别名 | 1,4-二羟基蒽醌; 1,4-Dihydroxyanthraquinone | ||
| Canonical SMILES | O=C1C2=C(C=CC=C2)C(C3=C(O)C=CC(O)=C13)=O | ||
| 分子式 | C14H8O4 | 分子量 | 240.21 |
| 溶解度 | 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 | 4.163 mL | 20.8151 mL | 41.6302 mL |
| 5 mM | 0.8326 mL | 4.163 mL | 8.326 mL |
| 10 mM | 0.4163 mL | 2.0815 mL | 4.163 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。
Quinizarin: a large aromatic molecule well suited for atomic layer deposition
Dalton Trans 2021 Jun 22;50(24):8307-8313.PMID:33977998DOI:10.1039/d1dt00683e.
Atomic layer deposition (ALD) is a remarkable synthesis tool due to the vast array of materials that can be deposited and the complexity of structures that can be designed. The low-temperature layer-by-layer approach even allows organic and inorganic components to be combined as hybrid or composite materials. The technique is then called molecular layer deposition (MLD). This opens the door for deposition of advanced optical materials using highly absorbing aromatic molecules. Unfortunately, most large aromatic molecules are difficult to sublime or have insufficient reactivity. This is a major barrier for ALD when designing with the use of organic components for dye-sensitized solar cells, luminescence, visible light photochemistry, chemical sensors and organic electronics. In this work, we introduce a well-known orange dye molecule, Quinizarin. This molecule has a large conjugated aromatic system with strong absorption of visible light and shows strong luminescence both in solutions and as a complex together with aluminium ions. Interestingly, Quinizarin also shows surprisingly good properties for film deposition due to reactive -OH groups and low sublimation temperature (130 °C). Strongly coloured pink hybrid films were deposited with trimethylaluminium and Quinizarin at 175 °C with a growth rate of 0.28 nm per cycle. These films were not luminescent although their optical absorption spectra are similar to those of the corresponding solution. An attempt was made to dilute Quinizarin through partial replacement with pentaerythritol as a multilayer structure or simultaneous co-pulsing, although this also did not produce luminescent films. The low sublimation temperature, good reactivity and large conjugated system of Quinizarin open the way for exploration of solid-state hybrid and organic films based on this molecule along many different technological pathways.
Quinizarin suppresses the differentiation of adipocytes and lipogenesis in vitro and in vivo via downregulation of C/EBP-beta/SREBP pathway
Life Sci 2021 Dec 15;287:120131.PMID:34767806DOI:10.1016/j.lfs.2021.120131.
Aims: Potential anti-obesity effects of Quinizarin, a plant anthraquinone, were investigated using 3 T3-L1 preadipocyte cells and high-fat diet (HD)-induced obese mice. Main method: Cell viability was determined using the MTT assay. Triglyceride (TG) and lipid accumulation were determined using a TG assay kit and Oil Red O staining, respectively. Adipogenic, lipogenic, and lipolytic gene and protein expression was measured by RT-PCR or Western blot. Serum biochemical indices, including cholesterol and blood glucose, in HD-fed obese mice were determined using corresponding assay kits. Histological analysis was performed with haematoxylin and eosin (H&E) staining. Results: Quinizarin (0-10 μM) significantly reduced intracellular TG and lipid droplets during the differentiation of preadipocytes. Quinizarin significantly suppressed the expression of adipocyte differentiation marker proteins, such as CCAAT/enhancer-binding protein β (C/EBP-β), C/EBP-α, PPAR-γ, and aP2, and lipogenic marker proteins, including SREBP1c, SREBP2, fatty acid synthase (FAS), and acetyl-CoA carboxylase 1 (ACC1), reduced ACC2 expression and increased carnitine palmitoyltransferase 1 (CPT1) expression. Oral administration of Quinizarin (15-30 mg/kg/day) to HD-fed mice for 6 weeks reduced the body weight gain and size of liver adipocytes and epididymal fat tissues, with significant reductions in liver TG and serum total cholesterol, blood glucose, LDL, and HDL levels. Significance: The results of this study indicated that Quinizarin exerts anti-obesity effects by inhibiting both adipogenesis and lipogenesis and stimulating lipolysis in vitro and in vivo mainly by downregulating the SREBP signalling pathway; thus, it might be a potent candidate as a health-beneficial food or therapeutic agent to prevent or treat obesity.
Monitoring the Activity of Immobilized Lipase with Quinizarin Diester Fluoro-Chromogenic Probe
Molecules 2017 Dec 4;22(12):2136.PMID:29207517DOI:10.3390/molecules22122136.
Quinizarin diester is used as a fluoro-chromogenic substrate of the activity of lipase supported in poly(methylmetacrylate) beads (CALB, Novozym® 435) dispersed in organic solvents. The monoester and diester of Quinizarin are both non-fluorescent species contrasting with the enzymatic product Quinizarin that shows optical absorption in the visible region and strong fluorescence signal. The enzymatic conversion is accomplished by spectroscopic measurements and it follows a sigmoid curve from which the mean reaction time of the enzymatic process can be determined. This parameter indicates the enzyme activity of the immobilized lipase. Its dependency with the amount of lipase allowed the determination of the ratio of the catalytic rate and the Michaelis constant (kc/Km) and the experimental value found was (1.0 ± 0.1) × 10-2 mg-1/min in the case of Quinizarin diacetate.
Building Molecular Complexity from Quinizarin: Conjoined Coumarins and Coronene Analogs
Chem Asian J 2019 May 15;14(10):1763-1770.PMID:30022613DOI:10.1002/asia.201800757.
The double Knoevenagel condensation of 1,4-dibenzoyloxyanthraquinone with methyl esters of arylacetic acids affords a series of compounds based upon a previously unknown 1,8-dioxa-benzo[e]pyrene-2,7-dione heterocyclic core. The aryl groups incorporated in the 3- and 6-positions can be oxidatively coupled to the π-expanded backbone to produce a further new heterocyclic core: 1,10-dioxa-dibenzo[dj]coronene-2,9-dione. The intriguing optical properties of these π-expanded coumarin derivatives are discussed and rationalized through quantum chemical calculations. The broad absorption bands of 1,8-dioxa-benzo[e]pyrene-2,7-dione-based dyes are attributed to both HOMO-1→LUMO and HOMO→LUMO transitions, which have a similar energy. Weakly coupled electron-donating aryl substituents result in a moderate bathochromic shift of both the absorption and emission by 30-60 nm in toluene. The emissive properties of these compounds are in part determined by the oscillator strength of the main transition, lifetimes of the excited state, and by the energy match of the excited state with a triplet state of a similar energy. The 1,10-dioxa-dibenzo[dj]coronene-2,9-dione displays a much smaller Stokes shift, yet a markedly increased fluorescence quantum yield of 90 % owing to the increased rigidity compared with the 1,8-dioxa-benzo[e]pyrene-2,7-dione core.
Study of Quinizarin Interaction with SDS Micelles as a Model System for Biological Membranes
Acta Chim Slov 2020 Jun;67(2):629-637.PMID:33855576doi
Investigation of the interaction of Quinizarin (Q), an analogue of the core unit of different anticancer drugs, with anionic SDS micelles has been performed by absorption and conductance measurements in 0.1 M phosphate buffer, pH 7.4 and over the temperature range of 298.15-323.15 K. The values of binding constant (Kb), partition coefficient (Kx) and the corresponding thermodynamic parameters (Gibbs free energy, enthalpy, entropy) for the binding and distribution of Quinizarin between the bulk aqueous solution and surfactant micelles have been determined and discussed in terms of possible intermolecular interactions. Values of critical micelle concentration (CMC) and degree of ionization (?) for SDS in the absence and the presence of Quinizarin have been evaluated from conductometric study. Comparing the absorption spectra of Quinizarin in SDS micelles with the spectra in different solvents revealed that Quinizarin molecules are located in the hydrophilic region of SDS micelles. The trend of changes in Gibbs free energy, enthalpy and entropy with temperature shows that both binding and partition processes are spontaneous and entropy driven. In addition, the hydrophobic interactions are the main forces involved in binding and partition processes.