Azobenzene
(Synonyms: 偶氮苯) 目录号 : GC30634
Azobenzene可以用作光触发器，用于设计和合成各种光响应系统。
Cas No.:103-33-3
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
Azobenzene can be used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems.
Photochromic compounds that undergo large conformational changes when exposed to light of appropriate wavelength are particularly attractive as molecular switch elements. Azobenzene is a popular choice among the chromophores. The thermodynamically favored trans isomer is rapidly converted to the cis isomer by irradiation at the wavelength of the π-π* transition, whereas the reverse process is achieved either (slowly) by thermal relaxation in the dark or (quickly) by irradiation at the wavelength of the n-π* transition. The azobenzene amino acid (aa) can be used as a photo-inducible conformational switch in polypeptides. A reversible conformational change of the peptide backbone is induced by switching between the cis and trans configurations of the azobenzene moiety by irradiation with light of suitable wavelength[1]. Azobenzene has been the most widely used optical trigger for the synthesis of photoresponsive systems ranging from poly-a-amino acids to innovative materials with light-controlled mechanical and optical properties. Its use in form of appropriate derivatives allow to generate cyclic peptide structures of constraint conformational space and thus to exploit its reversible photoisomerization to induce well defined transitions between different conformational states[2]. Azobenzene photoswitches can be used to drive functional changes in peptides, proteins, nucleic acids, lipids, and carbohydrates[3].
[1]. Aemissegger A, et al. Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides. Nat Protoc. 2007;2(1):161-7. [2]. Renner C, et al. Azobenzene as photoresponsive conformational switch in cyclic peptides. J Pept Res. 2005 Jan;65(1):4-14. [3]. Beharry AA, et al. Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011 Aug;40(8):4422-37.
| Cas No. | 103-33-3 | SDF | |
| 别名 | 偶氮苯 | ||
| Canonical SMILES | C1(/N=N/C2=CC=CC=C2)=CC=CC=C1 | ||
| 分子式 | C12H10N2 | 分子量 | 182.22 |
| 溶解度 | DMSO : ≥ 150 mg/mL (823.18 mM) | 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 | 5.4879 mL | 27.4394 mL | 54.8787 mL |
| 5 mM | 1.0976 mL | 5.4879 mL | 10.9757 mL |
| 10 mM | 0.5488 mL | 2.7439 mL | 5.4879 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。
Azobenzene as Antimicrobial Molecules
Azo molecules, characterized by the presence of a -N=N- double bond, are widely used in various fields due to their sensitivity to external stimuli, ch as light. The emergence of bacterial resistance has pushed research towards designing new antimicrobial molecules that are more efficient than those currently in use. Many authors have attempted to exploit the antimicrobial activity of azobenzene and to utilize their photoisomerization for selective control of the bioactivities of antimicrobial molecules, which is necessary for antibacterial therapy. This review will provide a systematic and consequential approach to coupling azobenzene moiety with active antimicrobial molecules and drugs, including small and large organic molecules, such as peptides. A selection of significant cutting-edge articles collected in recent years has been discussed, based on the structural pattern and antimicrobial performance, focusing especially on the photoactivity of azobenzene and the design of smart materials as the most targeted and desirable application.
Triggered azobenzene-based prodrugs and drug delivery systems
Azobenzene-based molecules show unique trans-cis isomerization upon ultraviolet light irradiation, which induce the change of polarity, crystallinity, stability, and binding affinity with pharmacological target. Moreover, azobenzene is the substrate of azoreductase that is often overexpressed in many pathological sites, e.g. hypoxic solid tumor. Therefore, azobenzene can be a multifunctional molecule in material science, pharmaceutical science and biomedicine because of its sensitivity to light, hypoxia and certain enzymes, hence showing potential application in site-specific smart therapy. Herein we focus on the employment of azobenzene and its derivatives for engineering triggered prodrugs and drug delivery systems, and provide an overview of photoswitchable azo-based prodrugs, the associated problems regarding the reversible isomerization and tissue penetration of ultraviolet (UV) light, as well as the potential solutions. We also present the advance of azo-bearing delivery vehicles wherein azobenzene acts as the linker, capping agent, and building block, and discuss the corresponding mechanisms for controlled cargo release, endocytosis enhancement and sensitization of free radical cancer therapy.
Designing azobenzene-based tools for controlling neurotransmission
Chemical and electrical signaling at the synapse is a dynamic process that is crucial to neurotransmission and pathology. Traditional pharmacotherapy has found countless applications in both academic labs and the clinic; however, diffusible drugs lack spatial and temporal precision when employed in heterogeneous tissues such as the brain. In the field of photopharmacology, chemical attachment of a synthetic photoswitch to a bioactive ligand allows cellular signaling to be controlled with light. Azobenzenes have remained the go-to photoswitch for biological applications due to their tunable photophysical properties, and can be leveraged to achieve reversible optical control of numerous receptors and ion channels. Here, we discuss the most recent advances in photopharmacology which will improve the use of azobenzene-based probes for neuroscience applications.
Azobenzene Photoswitch for Isomerization-Dependent Cancer Therapy via Azo-Combretastatin A4 and Phototrexate
The adverse effects of chemotherapeutic drugs to healthy organs/cells greatly limit their clinical efficacy and patient compliance. The unique behavior of azobenzene photoswitch offers a remarkable tool to address the side effects of chemotherapeutic drugs. The azobenzene moiety has been integrated within some chemotherapeutic drugs to realize photo-triggered activation of drug cytotoxicity. However, the clinical translation of these agents has been facing a few barriers. In this short review, we present our viewpoints on potential solutions to address the following challenges associated with azobenzene-based photoswitchable chemotherapeutic drugs, including poor tissue penetration of light, hypoxia-induced drug degradation in solid tumor and the autonomous cis-trans relaxation.
Dihydroazulene-Azobenzene-Dihydroazulene Triad Photoswitches
Photoswitch triads comprising two dihydroazulene (DHA) units in conjugation with a central trans-azobenzene (AZB) unit were prepared in stepwise protocols starting from meta- and para-disubstituted azobenzenes. The para-connected triad had significantly altered optical properties and lacked the photoactivity of the separate photochromes. In contrast, for the meta-connected triad, all three photochromes could be photoisomerized to generate an isomer with two vinylheptafulvene (VHF) units and a cis-azobenzene unit. Ultrafast spectroscopy of the photoisomerizations revealed a fast DHA-to-VHF photoisomerization and a slower trans-to-cis AZB photoisomerization. This meta triad underwent thermal VHF-to-DHA back-conversion with a similar rate of all VHFs, independent of the identity of the neighboring units, and in parallel thermal cis-to-trans AZB conversion. The experimental observations were supported by computation (excitation spectra and orbital analysis of the transitions).