2835-59-8Relevant academic research and scientific papers
Are two azo groups better than one? Investigating the photoresponse of polymer-bisazobenzene complexes
Vapaavuori, Jaana,Goulet-Hanssens, Alexis,Heikkinen, Ismo T.S.,Barrett, Christopher J.,Priimagi, Arri
, p. 5089 - 5096 (2014)
Azobenzene chromophores are an ideal choice for material applications where functionality needs to be activated in a precise remote-controlled fashion. The azobenzene stimuli-response falls into two categories, either based on efficient trans-to-cis photoisomerization and a high cis yield enabling on-off type functions, or relying on a fast trans-cis-trans cycling creating motion in the material system. Herein, we show that using bisazochromophores instead of the more common monoazobenzene derivatives makes a difference in the performance of light-responsive azopolymers, more specifically in photo-orientation and all-optical surface patterning. Our findings point out that polymer-bisazobenzene complexes are an attractive alternative as high-performance photoreponsive materials and that although their properties are highly sensitive to the extent of conjugation in the system, they can be designed into relatively transparent films with high performance for all-optical patterning.
Rational Remodeling of Atypical Scaffolds for the Design of Photoswitchable Cannabinoid Receptor Tools
Hu, Tao,Hua, Tian,Li, Fei,Liu, Zhi-Jie,Makriyannis, Alexandros,Stevens, Raymond C.,Tao, Houchao,Tian, Cuiping,Xie, Linshan,Xu, Yueming,Xue, Dongxiang,Zhao, Fei,Zhao, Simeng,Zhao, Suwen,Zheng, Guoxun,Zhong, Guisheng,Zhou, Fang
, p. 13752 - 13765 (2021/09/20)
Azobenzene-embedded photoswitchable ligands are the widely used chemical tools in photopharmacological studies. Current approaches to azobenzene introduction rely mainly on the isosteric replacement of typical azologable groups. However, atypical scaffolds may offer more opportunities for photoswitch remodeling, which are chemically in an overwhelming majority. Herein, we investigate the rational remodeling of atypical scaffolds for azobenzene introduction, as exemplified in the development of photoswitchable ligands for the cannabinoid receptor 2 (CB2). Based on the analysis of residue-type clusters surrounding the binding pocket, we conclude that among the three representative atypical arms of the CB2 antagonist, AM10257, the adamantyl arm is the most appropriate for azobenzene remodeling. The optimizing spacer length and attachment position revealed AzoLig 9 with excellent thermal bistability, decent photopharmacological switchability between its two configurations, and high subtype selectivity. This structure-guided approach gave new impetus in the extension of new chemical spaces for tool customization for increasingly diversified photo-pharmacological studies and beyond.
Tuning of Bistability, Thermal Stability of the Metastable States, and Application Prospects in the C3-Symmetric Designs of Multiple Azo(hetero)arenes Systems
Gupta, Debapriya,Gaur, Ankit Kumar,Kumar, Pravesh,Kumar, Himanshu,Mahadevan, Anjali,Devi, Sudha,Roy, Saonli,Venkataramani, Sugumar
supporting information, p. 3463 - 3472 (2021/01/21)
Light-responsive molecular systems with multiple photoswitches in C3-symmetric designs have enormous application potential. The design part of such molecular systems is critical due to its influence in several properties associated with the photoswitches. In order to tune, and in the evaluation of the design–property relationship, we synthesized 18 tripodal systems with variations in the core, linkers, connectivity, and azo(hetero)arene photoswitches. Through extensive spectroscopic and computational studies, we envisaged the factors controlling near-quantitative photoisomerization in both the directions (bistability) and the thermal stability of the metastable states. Furthermore, we also evaluated the impact of designs in obtaining reversible photo-responsive sol-gel phase transitions, solvatochromism, photo- and thermochromism.
Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization
Luo, Jiajie,Qi, Hang,Qiao, Zhen,Tang, Xiaowen,Tang, Yi-Quan,Wang, KeWei,Wei, Ningning,Yin, Zhengji,Zhang, Yanru,Zhou, Qiqi,Zhu, Wei
supporting information, p. 16282 - 16292 (2021/11/12)
Transient receptor potential ankyrin 1 (TRPA1) channel, as a nonselective ligand-gated cation channel robustly in dorsal root ganglion sensory neurons, is implicated in sensing noxious stimuli and nociceptive signaling. However, small-molecule tools targeting TRPA1 lack temporal and spatial resolution, limiting their use for validation of TRPA1 as a therapeutic target for pain. In our previous work, we found that 4,4′-(diazene-1,2-diyl)dianiline (AB1) is a photoswitchable TRPA1 agonist, but the poor water solubility and activity hinder its further development. Here, we report a series of specific and potent azobenzene-derived photoswitchable TRPA1 agonists (series 1 and 2) that enable optical control of the TRPA1 channel. Two representative compounds 1g and 2c can alleviate capsaicin-induced pain in the cheek model of mice through channel desensitization but not in TRPA1 knockout mice. Taken together, our findings demonstrate that photoswitchable TRPA1 agonists can be used as pharmacological tools for study of pain signaling.
Cannabinoid receptor light-operated ligand and preparation method and application thereof
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Paragraph 0066; 0073; 0106-0112, (2021/01/24)
The invention relates to the technical field of biology, in particular to a novel cannabinoid receptor light-operated ligand and a preparation method and application thereof. Disclosed is the cannabinoid receptor light-operated ligand or the isomer prodrug, the solvate and the pharmaceutically acceptable salt of the cannabinoid receptor light-operated ligand, wherein the structural formula of thecannabinoid receptor light-operated ligand is A-linker-B; A is a transmembrane domain ligand structure, and B is a light-operated element; Linker is a subunit which is linear and has no activity on acannabinoid receptor light-operated ligand. According to the invention, the cannabinoid receptor ligand is integrated with azobenzene through a proper connector, so that the ligand configuration is changed under an illumination condition, and the activation or inhibition state of the cannabinoid receptor is regulated and controlled.
Azo aryl urea derivative, and preparation method and application thereof
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, (2020/06/17)
The invention relates to an azo aryl urea derivative, and a preparation and an application thereof, and concretely discloses a compound represented by formula (I), or an optical isomer, a cis-trans-isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. Definitions of substituent groups in the general formula are described in the specification and claims. The invention further discloses a composition containing the above compound, and an application thereof. The compound has excellent anticancer activity on HepG2 liver cancer cells, MGC803 gastric cancer cells,HCT116 colon cancer and the like.
Azobenzene-benzoylphenylureas as photoswitchable chitin synthesis inhibitors
Tian, Xue,Zhang, Chao,Xu, Qi,Li, Zhong,Shao, Xusheng
, p. 3320 - 3323 (2017/04/21)
Benzoylphenylureas (BPUs) are used as synthetic insect growth regulators for inhibiting chitin synthesis. Merging insecticidal BPUs with photoswitchable azobenzene generated photoresponsive chitin synthesis inhibitors. A prepared azobenzene-benzoylphenylurea can be activated upon irradiation with UV light, and shows 6-fold and 2-fold activity difference to armyworm (Mythimna separata) and German cockroach (Blattella germanica) sulfonylurea receptors, respectively. This is the first example of a photoswitchable BPU insecticide. The generation of such a photoresponsive BPU insecticide allows for modulation of the insecticidal activity by light, and may facilitate the spatiotemporal control over the sulfonylurea receptor and the mechanistic study of this kind of insecticide.
Connectivity matters-ultrafast isomerization dynamics of bisazobenzene photoswitches
Slavov, Chavdar,Yang, Chong,Schweighauser, Luca,Boumrifak, Chokri,Dreuw, Andreas,Wegner, Hermann A.,Wachtveitl, Josef
, p. 14795 - 14804 (2016/07/06)
We have investigated the ultrafast dynamics of o-, m- and p-bisazobenzenes, which represent elementary building blocks for photoswitchable multiazobenzene nanostructures. The connectivity pattern within bisazobenzenes and the ensuing complex interactions between the individual azobenzene units determines the ultrafast dynamics of these compounds and their photochemical properties. While retaining a relatively high E → Z isomerization quantum yield, o-bisazobenzene exhibits a very high thermal relaxation rate (half-life of 1.6 ms). Our theoretical calculations reveal that the geometry allows intramolecular excitonic interaction between the azobenzene units, which is reflected in the femtosecond transient absorption data via the simultaneous bleaching of the two excitonic bands. In contrast, the properties of m-bisazobenzene are very similar to the monomeric azobenzene, with the two units acting nearly independently from each other. The highest degree of π conjugation extending over the two azobenzene units was observed for p-bisazobenzene, which results in strong planarity of the molecule, reduced excited state lifetime and relatively low isomerization quantum yield. Multiphotochromic systems bridge the gap between molecular photoswitches and macroscopic function and thus, understanding the properties of bisazobenzenes opens the way to the design and development of new structures with extensive and versatile applications.
Light-Controlled Histone Deacetylase (HDAC) Inhibitors: Towards Photopharmacological Chemotherapy
Szymanski, Wiktor,Ourailidou, Maria E.,Velema, Willem A.,Dekker, Frank J.,Feringa, Ben L.
, p. 16517 - 16524 (2015/11/09)
Cancer treatment suffers from limitations that have a major impact on the patient's quality of life and survival. In the case of chemotherapy, the systemic distribution of cytotoxic drugs reduces their efficacy and causes severe side effects due to nonselective toxicity. Photopharmacology allows a novel approach to address these problems because it employs external, local activation of chemotherapeutic agents by using light. The development of photoswitchable histone deacetylase (HDAC) inhibitors as potential antitumor agents is reported herein. Analogues of the clinically used chemotherapeutic agents vorinostat, panobinostat, and belinostat were designed with a photoswitchable azobenzene moiety incorporated into their structure. The most promising compound exhibits high inhibitory potency in the thermodynamically less stable cis form and a significantly lower activity for the trans form, both in terms of HDAC activity and proliferation of HeLa cells. This approach offers a clear prospect towards local photoactivation of HDAC inhibition to avoid severe side effects in chemotherapy.
meta-Aminoazobenzene as a thermo-insensitive photo-regulator of DNA- duplex formation
Asanuma, Hiroyuki,Liang, Xingguo,Komiyama, Makoto
, p. 1055 - 1058 (2007/10/03)
meta-Aminoazobenzene has been introduced in the side chain of oligonucleotides as a photo-responsive molecule. Compared with the para- aminoazobenzene which was previously used, the thermal cis→trans isomerization was much slower: the half-lives of the ci
