Azure B
(Synonyms: 天青B,Azure B chloride) 目录号 : GC39187
Azure B 是一种阳离子染料 (cationic dye)，是 Methylene blue 的主要代谢物，用于 Azure 曙红染色剂以进行血液涂片染色。Azure B 是一种高效、选择性和可逆的抑制单胺氧化酶 (MAO)-A 的抑制剂，对重组人的 MAO-A 和 MAO-B 的IC50 分别为 11 和 968 nM。Azure B 具有显著的抗抑郁作用。
Cas No.:531-55-5
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
Azure B is a cationic dye and the major metabolite of Methylene blue. Azure B is used in making Azure eosin stains for blood smear staining. Azure B is a high-potency, selective and reversible inhibitor of monoamine oxidases (MAO)-A, with IC50s of 11 and 968 nM for recombinant human MAO-A and MAO-B, respectively. Azure B possesses significant antidepressant-like effects[1][2].
[1]. LÖhr W,et al. The azure dyes: their purification and physicochemical properties. II. Purification of azure B. Stain Technol. 1975 May;50(3):149-56. [2]. Delport A, et al. Azure B and a synthetic structural analogue of methylene blue, ethylthioninium chloride, present with antidepressant-like properties. Life Sci. 2014 Nov 11;117(2):56-66.
| Cas No. | 531-55-5 | SDF | |
| 别名 | 天青B,Azure B chloride | ||
| Canonical SMILES | CNC1=CC2=[S+]C3=C(C=CC(N(C)C)=C3)N=C2C=C1.[Cl-] | ||
| 分子式 | C15H16ClN3S | 分子量 | 305.83 |
| 溶解度 | DMSO : 10 mg/mL (32.70 mM; ultrasonic and warming and heat to 60°C) | 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 | 3.2698 mL | 16.349 mL | 32.6979 mL |
| 5 mM | 0.654 mL | 3.2698 mL | 6.5396 mL |
| 10 mM | 0.327 mL | 1.6349 mL | 3.2698 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。
Azure B affects amyloid precursor protein metabolism in PS70 cells
Chem Biol Interact 2019 Feb 1;299:88-93.PMID:30500345DOI:10.1016/j.cbi.2018.11.023.
Alzheimer's disease (AD), the most common form of dementia, is characterized by abundant deposition of amyloid-β (Aβ) peptide that is the result of sequential cleavage of amyloid precursor protein (APP) by β-secretase and γ-secretase. Several studies have documented that inhibition of Aβ peptide synthesis or facilitating its degradation is one of the attractive therapeutic strategies in AD. Methylene blue (MethB), which has recently been investigated in Phase II clinical trials, is a prominent inhibitor in reducing Aβ oligomers. Herein, we wonder whether the mitigating effects of MethB on amyloid metabolism are related to the activity of its major metabolite, Azure B. The goal of this study was to investigate the effects of Azure B, which is also a cholinesterase inhibitor, on APP processing by using Chinese hamster ovary cells stably expressing human wild-type APP and presenilin 1 (PS70). Azure B significantly decreased the levels of secreted APPα (sAPPα) and Aβ40/42 in culture medium with a dose-dependent manner. A significant decrease was also observed in the levels of intracellular APP without affecting the cell viability. In parallel with the decrease of APP and APP metabolites, the activity of β-secretase 1 (BACE1) was significantly attenuated compared to control. Overall, our results show that Azure B has a large contribution for the pharmacological profile of MethB in APP metabolism.
Azure B as a novel cyanide antidote: Preclinical in-vivo studies
Toxicol Rep 2020 Oct 20;7:1459-1464.PMID:33194557DOI:10.1016/j.toxrep.2020.10.015.
We have determined the effects of Azure B (AzB), the main demethylated metabolite of methylene blue (MB), on a model of lethal cyanide intoxication. Our rationale was the following: AzB 1- possesses redox properties very similar to those of MB, which is a potent cyanide antidote, 2- may present a higher intracellular diffusibility than MB, 3- is already present in commercially available solutions of MB, and 4- appears very quickly in the blood after MB administration. AzB could therefore be a member of the phenothiazium chromophore family of interest to treat cyanide intoxication. We found, in spontaneously breathing urethane sedated rats, that AzB mimicked the effects of MB by increasing metabolism, ventilation and cardiac contractility up to 30-40 mg/kg. AzB had a lethal toxicity when the dose of 60 mg/kg was reached. Doses of AzB were therefore chosen in keeping with these data and the doses of MB previously used against cyanide intoxication (4-20 mg/kg) in the rat - doses corresponding to those used in humans to treat methemoglobinemia. KCN, infused at the rate of 0.375 mg/kg/min iv for 13 min, was fatal within 15 min in 100 % of our un-anesthetized rats. AzB at the dose of 4 mg/kg (n = 5) or 10 mg/kg (n = 5) administered 3 min into cyanide infusion allowed 100 % of the animals to survive with no clinical sequelae. The onset of coma was also significantly delayed and no apnea or gasping occurred. At the dose of 20 mg/kg, AzB was much less effective. At 4 mg/kg, the antidotal effects of AzB were significantly better than those produced by MB at the same dose and were not different from the effects produced by 20 mg/kg MB. We conclude that AzB is a potent cyanide antidote at relatively low doses.
Probing multifunctional Azure B conjugated gold nanoparticles with serum protein binding properties for trimodal photothermal, photodynamic, and chemo therapy: Biophysical and photophysical investigations
Biomater Adv 2022 Mar;134:112678.PMID:35606220DOI:10.1016/j.msec.2022.112678.
Multimodal or combination therapy has been considered as a powerful approach for treatment of complex diseases like cancer. The fascinating physicochemical and optoelectronic properties of gold nanoparticles make them potential candidate for cancer therapeutic and diagnostic applications. Herein, we design a multifunctional nanosystem by conjugating a photosensitizer, Azure B (AB) with citrate reduced gold nanoparticles (CI-Au NPs) through non-covalent interactions. The conjugation of AB with CI-Au NPs was confirmed through UV-Visible absorption spectroscopy and Fourier Transform Infra-red (FT-IR) spectroscopy. The morphology, size, and charge of the prepared nano-conjugates (AB@CI-Au NPs) were determined by transmission electron microscopy (TEM), Dynamic light scattering (DLS), and zeta potential measurements. The proficiency of AB@CI-Au NPs for cancer photo-therapies was demonstrated by evaluating their potential for photothermal heating and singlet oxygen generation in solution upon Visible laser (635 nm, 500 mW/cm2) irradiation. The AB@CI-Au NPs display superior heating efficiency than CI-Au NPs alone or free AB, and offer better photostability as well as singlet oxygen generation rate compared to free photosensitizer. The interaction of AB@CI-Au NPs with Calf thymus DNA (Ct-DNA) and transport protein Bovine Serum Albumin (BSA) were studied using various biophysical techniques including Circular dichroism, UV-Visible and fluorescence spectroscopic studies. AB@CI-Au NPs show intercalative binding with Ct-DNA by inducing local perturbations in double helical structure and hence can exert chemotherapeutic action by targeting DNA. AB@CI-Au NPs also display moderate binding with BSA without any adverse effect on BSA structure, which is desirable for significant biodistribution and pharmacokinetics of AB@CI-Au NPs. Also, in vitro cytotoxicity of the AB@CI-Au NPs with and without laser irradiation (635 nm, 500 mW/cm2) was demonstrated using the hepatocellular carcinoma (HepG2) cell lines. Our findings through photophysical and biophysical studies strongly recommend the exploitation of AB@CI-Au NPs nanoconjugates as a multifunctional probe for trimodal anticancer therapy.
Azure B, a metabolite of methylene blue, is a high-potency, reversible inhibitor of monoamine oxidase
Toxicol Appl Pharmacol 2012 Feb 1;258(3):403-9.PMID:22197611DOI:10.1016/j.taap.2011.12.005.
Methylene blue (MB) has been shown to act at multiple cellular and molecular targets and as a result possesses diverse medical applications. Among these is a high potency reversible inhibition of monoamine oxidase A (MAO-A) that may, at least in part, underlie its adverse effects but also its psycho- and neuromodulatory actions. MB is metabolized to yield N-demethylated products of which Azure B, the monodemethyl species, is the major metabolite. Similar to MB, Azure B also displays a variety of biological activities and may therefore contribute to the pharmacological profile of MB. Based on these observations, the present study examines the interactions of Azure B with recombinant human MAO-A and -B. The results show that Azure B is a potent MAO-A inhibitor (IC₅₀=11 nM), approximately 6-fold more potent than is MB (IC₅₀=70 nM) under identical conditions. Measurements of the time-dependency of inhibition suggest that the interaction of Azure B with MAO-A is reversible. Azure B also reversibly inhibits the MAO-B isozyme with an IC₅₀ value of 968 nM. These results suggest that Azure B may be a hitherto under recognized contributor to the pharmacology and toxicology of MB by blocking central and peripheral MAO-A activity and as such needs to be considered during its use in humans and animals.
Electrochemical Sensor Based on Poly(Azure B)-DNA Composite for Doxorubicin Determination
Sensors (Basel) 2019 May 5;19(9):2085.PMID:31060322DOI:10.3390/s19092085.
A new voltammetric DNA sensor has been developed for doxorubicin determination on the platform of a glassy carbon electrode (GCE) covered with electropolymerized Azure B film and physically adsorbed native DNA. The redox properties of polymeric Azure B were monitored at various pH and scan rates. DNA application decreased the peak currents related to polymeric and monomeric forms of the dye, whereas incubation in doxorubicin solution partially restored the peaks in accordance with the drug and DNA concentration. The relative shift of the cathodic peak current caused by doxorubicin depended on the nominal DNA concentration and its application mode. In optimal conditions, the DNA sensor makes it possible to determine between 0.1 μM to 0.1 nM doxorubicin (limit of detection 7×10-11 M). The DNA sensor was tested on commercial doxorubicin formulations and on artificial samples the mimicked electrolyte content of human serum.