azobenzene (BioDeep_00000002414)
代谢物信息卡片
azobenzene
化学式: C12H10N2 (182.0844)
中文名称: 偶氮苯
谱图信息:
最多检出来源 Homo sapiens(plant) 12.22%
分子结构信息
SMILES: C1=CC=C(C=C1)N=NC2=CC=CC=C2
InChI: InChI=1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:190358
- ChEBI: CHEBI:58996
- ChEBI: CHEBI:58997
- KEGG: C19334
- PubChem: 2272
- Metlin: METLIN43490
- ChEMBL: CHEMBL3039456
- ChEMBL: CHEMBL3184266
- ChEMBL: CHEMBL58835
- CAS: 17082-12-1
- CAS: 1080-16-6
- CAS: 103-33-3
- MoNA: AU244004
- MoNA: AU244001
- MoNA: AU244005
- MoNA: AU244006
- MoNA: AU244002
- MoNA: AU244003
- PMhub: MS000002549
- PubChem: 124490006
- KNApSAcK: 58996
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Johannes Morstein, Alexander Amatuni, Anton Shuster, Wolfgang Kuttenlochner, Tongil Ko, Daniel Abegg, Michael Groll, Alexander Adibekian, Hans Renata, Dirk H Trauner. Optical Control of Proteasomal Protein Degradation with a Photoswitchable Lipopeptide.
Angewandte Chemie (International ed. in English).
2023 Dec; ?(?):e202314791. doi:
10.1002/anie.202314791. [PMID: 38109686] - Mina Aleksanyan, Andrea Grafmüller, Fucsia Crea, Vasil N Georgiev, Naresh Yandrapalli, Stephan Block, Joachim Heberle, Rumiana Dimova. Photomanipulation of Minimal Synthetic Cells: Area Increase, Softening, and Interleaflet Coupling of Membrane Models Doped with Azobenzene-Lipid Photoswitches.
Advanced science (Weinheim, Baden-Wurttemberg, Germany).
2023 11; 10(31):e2304336. doi:
10.1002/advs.202304336. [PMID: 37653602] - Larissa Socrier, Claudia Steinem. Photo-Lipids: Light-Sensitive Nano-Switches to Control Membrane Properties.
ChemPlusChem.
2023 11; 88(11):e202300203. doi:
10.1002/cplu.202300203. [PMID: 37395458] - Xiao-Kang Fu, Si-Qi Han, Wei Ha, Yan-Ping Shi. Click Chemoselective Probe with a Photoswitchable Handle for Highly Sensitive Determination of Steroid Hormones in Food Samples.
Journal of agricultural and food chemistry.
2023 Oct; 71(40):14814-14824. doi:
10.1021/acs.jafc.3c05262. [PMID: 37782472] - Jonas E Warias, Franziska Reise, Svenja C Hövelmann, Rajendra P Giri, Michael Röhrl, Jule Kuhn, Malte Jacobsen, Kuntal Chatterjee, Thomas Arnold, Chen Shen, Sven Festersen, Andrea Sartori, Philipp Jordt, Olaf M Magnussen, Thisbe K Lindhorst, Bridget M Murphy. Photoinduced bidirectional switching in lipid membranes containing azobenzene glycolipids.
Scientific reports.
2023 Jul; 13(1):11480. doi:
10.1038/s41598-023-38336-x. [PMID: 37455299] - Ting Zhao, Bokai Gong, Shiqin Luo, Rongping Zhang, Ling Zhang, Yuan Huang, Huile Gao, Tao Gong. A fibroblastic foci-targeting and hypoxia-cleavable delivery system of pirfenidone for the treatment of idiopathic pulmonary fibrosis.
Acta biomaterialia.
2023 Jun; ?(?):. doi:
10.1016/j.actbio.2023.06.024. [PMID: 37356783] - Joana N Martins, Beatriz Raimundo, Alicia Rioboo, Yeray Folgar-Cameán, Javier Montenegro, Nuno Basílio. Photoswitchable Calixarene Activators for Controlled Peptide Transport across Lipid Membranes.
Journal of the American Chemical Society.
2023 06; 145(24):13126-13133. doi:
10.1021/jacs.3c01829. [PMID: 37289668] - Silvio Osella, Giovanni Granucci, Maurizio Persico, Stefan Knippenberg. Dual photoisomerization mechanism of azobenzene embedded in a lipid membrane.
Journal of materials chemistry. B.
2023 03; 11(11):2518-2529. doi:
10.1039/d2tb02767d. [PMID: 36852914] - Larissa Socrier, Somayeh Ahadi, Mathias Bosse, Cindy Montag, Daniel B Werz, Claudia Steinem. Optical Manipulation of Gb3 Enriched Lipid Domains: Impact of Isomerization on Gb3 -Shiga Toxin B Interaction.
Chemistry (Weinheim an der Bergstrasse, Germany).
2023 Jan; 29(4):e202202766. doi:
10.1002/chem.202202766. [PMID: 36279320] - Chaonan Li, Ya Wang, Zihao Wang, Xiaogang Li. β-Cyclodextrin/Azobenzene Microspheres Loaded with Paraquat Are Safe and Effective.
Langmuir : the ACS journal of surfaces and colloids.
2023 01; 39(1):638-646. doi:
10.1021/acs.langmuir.2c03004. [PMID: 36542801] - Xue Liu, Zhenfeng Wu, Chunjing Guo, Huimin Guo, Yanguo Su, Qiang Chen, Changgang Sun, Qingming Liu, Daquan Chen, Hongjie Mu. Hypoxia responsive nano-drug delivery system based on angelica polysaccharide for liver cancer therapy.
Drug delivery.
2022 Dec; 29(1):138-148. doi:
10.1080/10717544.2021.2021324. [PMID: 34967268] - Jana Volarić, Jeffrey Buter, Albert M Schulte, Keimpe-Oeds van den Berg, Eduardo Santamaría-Aranda, Wiktor Szymanski, Ben L Feringa. Design and Synthesis of Visible-Light-Responsive Azobenzene Building Blocks for Chemical Biology.
The Journal of organic chemistry.
2022 11; 87(21):14319-14333. doi:
10.1021/acs.joc.2c01777. [PMID: 36285612] - Hyunsu Kim, Jing Li, Yves S Y Hsieh, Maenghyo Cho, Sung-Hoon Ahn, Chenzhe Li. Photo-Programmed Deformations in Rigid Liquid Crystalline Polymers Triggered by Body Temperature.
Small (Weinheim an der Bergstrasse, Germany).
2022 11; 18(44):e2203772. doi:
10.1002/smll.202203772. [PMID: 36169084] - Wanbing Li, Haibo Zhang, Zhaolan Zhai, Xujuan Huang, Shibin Shang, Zhanqian Song. Fast and Reversible Photoresponsive Self-Assembly Behavior of Rosin-Based Amphiphilic Polymers.
Journal of agricultural and food chemistry.
2022 Oct; 70(40):12885-12896. doi:
10.1021/acs.jafc.2c04389. [PMID: 36175382] - Boying Xu, Jinquan Ding, Adriano Caliari, Nan Lu, Fuhai Han, Yang Xia, Jian Xu, Tetsuya Yomo. Photoinducible Azobenzene trimethylammonium bromide (AzoTAB)-mediated giant vesicle fusion compatible with synthetic protein translation reactions.
Biochemical and biophysical research communications.
2022 08; 618(?):113-118. doi:
10.1016/j.bbrc.2022.06.035. [PMID: 35717905] - Zhi Qiao, Wen Fu, Qiutang Huang, Zhong Li, Chunqing Zhao, Xusheng Shao. Optical Regulation of GABA Receptor by Visible Light via Azobenzene-Phenylpyrazole.
Journal of agricultural and food chemistry.
2022 May; 70(18):5541-5550. doi:
10.1021/acs.jafc.2c01463. [PMID: 35475355] - Jundong Zhu, Tao Guo, Zheng Wang, Yanjun Zhao. Triggered azobenzene-based prodrugs and drug delivery systems.
Journal of controlled release : official journal of the Controlled Release Society.
2022 05; 345(?):475-493. doi:
10.1016/j.jconrel.2022.03.041. [PMID: 35339578] - Arianna Magni, Gaia Bondelli, Giuseppe M Paternò, Samim Sardar, Valentina Sesti, Cosimo D'Andrea, Chiara Bertarelli, Guglielmo Lanzani. Azobenzene photoisomerization probes cell membrane viscosity.
Physical chemistry chemical physics : PCCP.
2022 Apr; 24(15):8716-8723. doi:
10.1039/d1cp05881a. [PMID: 35373231] - Aidan Kerckhoffs, Zonghua Bo, Samuel E Penty, Fernanda Duarte, Matthew J Langton. Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport.
Organic & biomolecular chemistry.
2021 10; 19(41):9058-9067. doi:
10.1039/d1ob01457a. [PMID: 34617944] - Chunying Li, Hui Chen, Xiaohai Yang, Kemin Wang, Jianbo Liu. An ion transport switch based on light-responsive conformation-dependent G-quadruplex transmembrane channels.
Chemical communications (Cambridge, England).
2021 Aug; 57(66):8214-8217. doi:
10.1039/d1cc03273a. [PMID: 34308935] - Estelle Léonard, Antoine Fayeulle. Azo-Dyes-Grafted Oligosaccharides-From Synthesis to Applications.
Molecules (Basel, Switzerland).
2021 May; 26(11):. doi:
10.3390/molecules26113063. [PMID: 34063753] - Dirk Leifert, Alex S Moreland, Jakkarin Limwongyut, Alexander A Mikhailovsky, Guillermo C Bazan. Photoswitchable Conjugated Oligoelectrolytes for a Light-Induced Change of Membrane Morphology.
Angewandte Chemie (International ed. in English).
2020 11; 59(46):20333-20337. doi:
10.1002/anie.202004448. [PMID: 32596843] - Dinaer Mulatihan, Tao Guo, Yanjun Zhao. Azobenzene Photoswitch for Isomerization-Dependent Cancer Therapy via Azo-Combretastatin A4 and Phototrexate.
Photochemistry and photobiology.
2020 11; 96(6):1163-1168. doi:
10.1111/php.13292. [PMID: 32521572] - Oskar Klaja, James A Frank, Dirk Trauner, Ana-Nicoleta Bondar. Potential energy function for a photo-switchable lipid molecule.
Journal of computational chemistry.
2020 10; 41(27):2336-2351. doi:
10.1002/jcc.26387. [PMID: 32749723] - Chiara Fedele, Elina Mäntylä, Brian Belardi, Tiama Hamkins-Indik, Silvia Cavalli, Paolo A Netti, Daniel A Fletcher, Soile Nymark, Arri Priimagi, Teemu O Ihalainen. Azobenzene-based sinusoidal surface topography drives focal adhesion confinement and guides collective migration of epithelial cells.
Scientific reports.
2020 09; 10(1):15329. doi:
10.1038/s41598-020-71567-w. [PMID: 32948792] - Yuan Qi Yeoh, John R Horsley, Jingxian Yu, Steven W Polyak, Blagojce Jovcevski, Andrew D Abell. Short Photoswitchable Antibacterial Peptides.
ChemMedChem.
2020 08; 15(16):1505-1508. doi:
10.1002/cmdc.202000280. [PMID: 32558320] - Xiao-Bo Zhao, Wei Ha, Kun Gao, Yan-Ping Shi. Precisely Traceable Drug Delivery of Azoreductase-Responsive Prodrug for Colon Targeting via Multimodal Imaging.
Analytical chemistry.
2020 07; 92(13):9039-9047. doi:
10.1021/acs.analchem.0c01220. [PMID: 32501673] - Liangliang Zhang, Xiaoyu Zhang, Pengju Feng, Qi Han, Wei Liu, Ying Lu, Chunxia Song, Fengyu Li. Photodriven Regeneration of G-Quadruplex Aptasensor for Sensitively Detecting Thrombin.
Analytical chemistry.
2020 06; 92(11):7419-7424. doi:
10.1021/acs.analchem.0c00380. [PMID: 32268723] - Mattia Lorenzo DiFrancesco, Francesco Lodola, Elisabetta Colombo, Luca Maragliano, Mattia Bramini, Giuseppe Maria Paternò, Pietro Baldelli, Mauro Dalla Serra, Lorenzo Lunelli, Marta Marchioretto, Giorgio Grasselli, Simone Cimò, Letizia Colella, Daniele Fazzi, Fausto Ortica, Vito Vurro, Cyril Giles Eleftheriou, Dmytro Shmal, José Fernando Maya-Vetencourt, Chiara Bertarelli, Guglielmo Lanzani, Fabio Benfenati. Neuronal firing modulation by a membrane-targeted photoswitch.
Nature nanotechnology.
2020 04; 15(4):296-306. doi:
10.1038/s41565-019-0632-6. [PMID: 32015505] - A Franche, A Fayeulle, L Lins, M Billamboz, I Pezron, M Deleu, E Léonard. Amphiphilic azobenzenes: Antibacterial activities and biophysical investigation of their interaction with bacterial membrane lipids.
Bioorganic chemistry.
2020 01; 94(?):103399. doi:
10.1016/j.bioorg.2019.103399. [PMID: 31706683] - Hongzhang Deng, Lisen Lin, Sheng Wang, Guocan Yu, Zijian Zhou, Yijing Liu, Gang Niu, Jibin Song, Xiaoyuan Chen. X-ray-Controlled Bilayer Permeability of Bionic Nanocapsules Stabilized by Nucleobase Pairing Interactions for Pulsatile Drug Delivery.
Advanced materials (Deerfield Beach, Fla.).
2019 Sep; 31(37):e1903443. doi:
10.1002/adma.201903443. [PMID: 31379091] - Prashant C Donthamsetti, Johannes Broichhagen, Vojtech Vyklicky, Cherise Stanley, Zhu Fu, Meike Visel, Joshua L Levitz, Jonathan A Javitch, Dirk Trauner, Ehud Y Isacoff. Genetically Targeted Optical Control of an Endogenous G Protein-Coupled Receptor.
Journal of the American Chemical Society.
2019 07; 141(29):11522-11530. doi:
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Chemistry and physics of lipids.
2019 05; 220(?):1-5. doi:
10.1016/j.chemphyslip.2019.02.002. [PMID: 30779906] - Xueru Zhang, Bin Lei, Yizhou Wang, Shouhong Xu, Honglai Liu. Dual-Sensitive On-Off Switch in Liposome Bilayer for Controllable Drug Release.
Langmuir : the ACS journal of surfaces and colloids.
2019 04; 35(15):5213-5220. doi:
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Amino acids.
2019 Mar; 51(3):549-563. doi:
10.1007/s00726-018-02691-1. [PMID: 30604096] - Mengwu Mo, Dejia Kong, Heming Ji, Dao Lin, Xinjing Tang, Zhenjun Yang, Yujian He, Li Wu. Reversible Photocontrol of Thrombin Activity by Replacing Loops of Thrombin Binding Aptamer using Azobenzene Derivatives.
Bioconjugate chemistry.
2019 01; 30(1):231-241. doi:
10.1021/acs.bioconjchem.8b00848. [PMID: 30582682] - Igor V Komarov, Sergii Afonin, Oleg Babii, Tim Schober, Anne S Ulrich. Efficiently Photocontrollable or Not? Biological Activity of Photoisomerizable Diarylethenes.
Chemistry (Weinheim an der Bergstrasse, Germany).
2018 Aug; 24(44):11245-11254. doi:
10.1002/chem.201801205. [PMID: 29633378] - Cheng Gao, Qiaoxian Huang, Qingping Lan, Yu Feng, Fan Tang, Maggie P M Hoi, Jianxiang Zhang, Simon M Y Lee, Ruibing Wang. A user-friendly herbicide derived from photo-responsive supramolecular vesicles.
Nature communications.
2018 07; 9(1):2967. doi:
10.1038/s41467-018-05437-5. [PMID: 30054483] - Kyoung-Yong Chun, Young Jun Son, Sunghwan Jo, Chang-Soo Han. Stomata-Inspired Photomechanical Ion Nanochannels Modified by Azobenzene Composites.
Small (Weinheim an der Bergstrasse, Germany).
2018 04; 14(17):e1703618. doi:
10.1002/smll.201703618. [PMID: 29611261] - M Deiana, Z Pokladek, M Dudek, S G Mucha, L M Mazur, K Pawlik, P Mlynarz, M Samoc, K Matczyszyn. Remote-control of the enantiomeric supramolecular recognition mediated by chiral azobenzenes bound to human serum albumin.
Physical chemistry chemical physics : PCCP.
2017 Aug; 19(32):21272-21275. doi:
10.1039/c7cp03336b. [PMID: 28759068] - Silvio Osella, Stefan Knippenberg. Triggering On/Off States of Photoswitchable Probes in Biological Environments.
Journal of the American Chemical Society.
2017 03; 139(12):4418-4428. doi:
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Nature protocols.
2016 10; 11(10):1788-97. doi:
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Chemphyschem : a European journal of chemical physics and physical chemistry.
2016 Aug; 17(16):2503-8. doi:
10.1002/cphc.201600362. [PMID: 27146320] - Prajakta Kulkarni, Manas K Haldar, Preeya Katti, Courtney Dawes, Seungyong You, Yongki Choi, Sanku Mallik. Hypoxia Responsive, Tumor Penetrating Lipid Nanoparticles for Delivery of Chemotherapeutics to Pancreatic Cancer Cell Spheroids.
Bioconjugate chemistry.
2016 08; 27(8):1830-8. doi:
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The journal of physical chemistry. B.
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Journal of the American Chemical Society.
2016 Jan; 138(3):955-61. doi:
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Talanta.
2015 Nov; 144(?):312-7. doi:
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Organic & biomolecular chemistry.
2015 Aug; 13(29):8067-70. doi:
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Chemical communications (Cambridge, England).
2015 Jun; 51(56):11321-4. doi:
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Langmuir : the ACS journal of surfaces and colloids.
2015 Jun; 31(25):6981-7. doi:
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Chemical communications (Cambridge, England).
2014 Dec; 50(97):15305-8. doi:
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Langmuir : the ACS journal of surfaces and colloids.
2014 Aug; 30(31):9361-9. doi:
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Sub-cellular biochemistry.
2014; 77(?):151-61. doi:
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Chemistry (Weinheim an der Bergstrasse, Germany).
2013 Dec; 19(52):18004-10. doi:
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Chemical communications (Cambridge, England).
2013 Nov; 49(87):10311-3. doi:
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Chemical communications (Cambridge, England).
2013 Mar; 49(24):2454-6. doi:
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Journal of the American Chemical Society.
2012 Dec; 134(48):19909-14. doi:
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Photochemistry and photobiology.
2012 Jul; 88(4):876-83. doi:
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Journal of the American Chemical Society.
2012 Mar; 134(10):4898-904. doi:
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Angewandte Chemie (International ed. in English).
2012 Feb; 51(9):2132-6. doi:
10.1002/anie.201106777. [PMID: 22262500] - Rumman Ahmed, Arri Priimagi, Charl F J Faul, Ian Manners. Redox-active, organometallic surface-relief gratings from azobenzene-containing polyferrocenylsilane block copolymers.
Advanced materials (Deerfield Beach, Fla.).
2012 Feb; 24(7):926-31. doi:
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Analytical chemistry.
2011 Dec; 83(24):9651-9. doi:
10.1021/ac202517x. [PMID: 22043937] - Xiaolong Liang, Xiuli Yue, Zhifei Dai, Jun-ichi Kikuchi. Photoresponsive liposomal nanohybrid cerasomes.
Chemical communications (Cambridge, England).
2011 Apr; 47(16):4751-3. doi:
10.1039/c1cc00063b. [PMID: 21409244] - Pengfei Duan, Yuangang Li, Liangchun Li, Jingen Deng, Minghua Liu. Multiresponsive chiroptical switch of an azobenzene-containing lipid: solvent, temperature, and photoregulated supramolecular chirality.
The journal of physical chemistry. B.
2011 Apr; 115(13):3322-9. doi:
10.1021/jp110636b. [PMID: 21405142] - Ellen H G Backus, Johanna M Kuiper, Jan B F N Engberts, Bert Poolman, Mischa Bonn. Reversible optical control of monolayers on water through photoswitchable lipids.
The journal of physical chemistry. B.
2011 Mar; 115(10):2294-302. doi:
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