Azulene
(Synonyms: 甘菊蓝; Cyclopentacycloheptene) 目录号 : GC39526
Azulene (Cyclopentacycloheptene) 是萘的异构体，具有高抗 HIV 活性。Azulene 是从洋甘菊精油中分离出来的，在药物化学中是一种支架。
Cas No.:275-51-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Azulene (Cyclopentacycloheptene) is as an isomer of naphthalene with high anti-HIV activity. Azulene, isolated from the distillation of chamomile oil, is a scaffold in medicinal chemistry[1][2][3].
[1]. Teppo O Leino, et al. Azulene-based Compounds for Targeting Orexin Receptors. Eur J Med Chem. 2018 Sep 5;157:88-100. [2]. Julia Peet, et al. Antiretroviral (HIV-1) Activity of Azulene Derivatives. Bioorg Med Chem. 2016 Apr 15;24(8):1653-7. [3]. David A. Becker, et al. A new synthesis of substituted azulenes. Journal of the American Chemical Society, 111(1), 389-391.
| Cas No. | 275-51-4 | SDF | |
| 别名 | 甘菊蓝; Cyclopentacycloheptene | ||
| Canonical SMILES | C12=CC=CC=CC1=CC=C2 | ||
| 分子式 | C10H8 | 分子量 | 128.17 |
| 溶解度 | DMSO : 100 mg/mL (780.21 mM; Need ultrasonic) | 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 | 7.8021 mL | 39.0107 mL | 78.0214 mL |
| 5 mM | 1.5604 mL | 7.8021 mL | 15.6043 mL |
| 10 mM | 0.7802 mL | 3.9011 mL | 7.8021 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。
Azulene-A Bright Core for Sensing and Imaging
Molecules 2021 Jan 12;26(2):353.PMID:33445502DOI:10.3390/molecules26020353.
Azulene is a hydrocarbon isomer of naphthalene known for its unusual colour and fluorescence properties. Through the harnessing of these properties, the literature has been enriched with a series of chemical sensors and dosimeters with distinct colorimetric and fluorescence responses. This review focuses specifically on the latter of these phenomena. The review is subdivided into two sections. Section one discusses turn-on fluorescent sensors employing Azulene, for which the literature is dominated by examples of the unusual phenomenon of Azulene protonation-dependent fluorescence. Section two focuses on fluorescent azulenes that have been used in the context of biological sensing and imaging. To aid the reader, the Azulene skeleton is highlighted in blue in each compound.
Synthesis of Azulene Derivatives from 2 H-Cyclohepta[ b]furan-2-ones as Starting Materials: Their Reactivity and Properties
Int J Mol Sci 2021 Oct 1;22(19):10686.PMID:34639027DOI:10.3390/ijms221910686.
A variety of synthetic methods have been developed for Azulene derivatives due to their potential applications in pharmaceuticals and organic materials. Particularly, 2H-cyclohepta[b]furan-2-one and its derivatives have been frequently used as promising precursors for the synthesis of azulenes. In this review, we describe the development of the synthesis of azulenes by the reaction of 2H-cyclohepta[b]furan-2-ones with olefins, active methylenes, enamines, and silyl enol ethers as well as their reactivity and properties.
Azulene-based fluorescent chemosensor for adenosine diphosphate
Chem Commun (Camb) 2021 Oct 12;57(81):10608-10611.PMID:34570136DOI:10.1039/d1cc04122c.
AzuFluor® 435-DPA-Zn, an Azulene fluorophore bearing two zinc(II)-dipicolylamine receptor motifs, exhibits fluorescence enhancement in the presence of adenosine diphosphate. Selectivity for ADP over ATP, AMP and PPi results from appropriate positioning of the receptor motifs, since an isomeric sensor cannot discriminate between ADP and ATP.
Azulene-Containing Squaraines for Photoacoustic Imaging and Photothermal Therapy
ACS Appl Mater Interfaces 2022 May 4;14(17):19192-19203.PMID:35438482DOI:10.1021/acsami.2c02308.
Photoacoustic imaging (PAI) guided photothermal therapy (PTT) can realize real-time diagnosis and in situ treatment of cancer at the same time. Absorption in the near-infrared (NIR) region with large molar extinction coefficient (ε) and high value of photothermal conversion efficiency (PCE) are key prerequisites for photothermal agents (PTAs) to realize dual PAI and PTT treatments. Squaraines have stable quinoid structures with strong planarity and rigidity, in favor of the NIR absorption and high ε values. On the other hand, Azulene derivatives mostly have very faint fluorescence emission, which is beneficial for photothermal transformation. Herein, two azulene-containing squaraines Az-SQ-1 and Az-SQ-2 are synthesized as high-performance PTAs. In comparison with Az-SQ-1, Az-SQ-2 possesses larger εmax of 3 × 105 M-1 cm-1 at 780 nm in organic solution and higher PCE of 53.2% in the form of nanoparticles under 808 nm laser irradiation. Accordingly, Az-SQ-2 NPs present stronger photoacoustic signals (about 15.1-times the background signal) and more efficient suppression of tumor growth. Our research indicates that the introduction of Azulene unit to traditional NIR dyes is a simple but effective approach to obtain outstanding PTAs in the aspect of phototheranostics.
Azulene hydrazide-hydrazones for selective targeting of pancreatic cancer cells
Biomed Pharmacother 2022 Nov;155:113736.PMID:36156366DOI:10.1016/j.biopha.2022.113736.
Dysregulation of iron homeostasis is one of the important processes in the development of many oncological diseases, such as pancreatic cancer. Targeting it with specific agents, such as an iron chelator, are promising therapeutic methods. In this study, we tested the cytotoxicity of novel Azulene hydrazide-hydrazone-based chelators against pancreatic cancer cell lines (MIA PaCa-2, PANC-1, AsPC-1). All prepared chelators (compounds 4-6) showed strong cytotoxicity against pancreatic cancer cell lines and high selectivity for cancer cell lines compared to the healthy line. Their cytotoxicity is lower than thiosemicarbazone-based chelators Dp44mT and DpC, but significantly higher than hydroxamic acid-based chelator DFO. The chelator tested showed mitochondrial and lysosomal co-localization and its mechanism of action was based on the induction of hypoxia-inducible factor-1-alpha (HIF-1α), N-myc downstream-regulated gene-1 (NDRG1) and transferrin receptor 1 (TfR1). This strongly implies that the cytotoxic effect of tested chelators could be associated with mitophagy induction. Lipinski's rule of five analyses was performed to determine whether the prepared compounds had properties ensuring their bioavailability. In addition, the drug-likeness and drug-score were calculated and discussed.