Imidazole (BioDeep_00000003028)
Secondary id: BioDeep_00000405449, BioDeep_00000712916
human metabolite PANOMIX_OTCML-2023
代谢物信息卡片
N,N-1,2-ethenediylmethanimidamide
化学式: C3H4N2 (68.0374464)
中文名称: 咪唑, 咪唑
谱图信息:
最多检出来源 Homo sapiens(blood) 35.62%
分子结构信息
SMILES: C1=CN=CN1
InChI: InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
描述信息
Imidazole is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms. Imidazole is a heterocyclic aromatic organic compound. It is classified as an alkaloid. The ring system of the molecule is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin.
Isolated from the seeds of Lens culinaris (lentil)and is also present in the seeds of other legumes: Macrotyloma uniflorum (horse gram), Psophocarpus tetragonolobus (winged bean), Vigna radiata (mung bean)
CONFIDENCE standard compound; INTERNAL_ID 8091
D004791 - Enzyme Inhibitors
KEIO_ID I046
同义名列表
26 个代谢物同义名
N,N-1,2-ethenediylmethanimidamide; 1,3-Diaza-2,4-cyclopentadiene; Imidazole conjugate monoacid; Imidazole monohydrochloride; Imidazole monophosphonate; N,N-vinyleneformamidine; Imidazolium chloride; {Pyrro[b]monazole}; Imidazole acetate; Imidazole citrate; Imidazole sodium; Pyrro(b)monazole; Pyrro[b]monazole; Al-imidazole; Cu-imidazole; 1H-Imidazole; 1,3-Diazole; Glyoxaline; imidazole; Glyoxalin; Iminazole; Imidazol; Miazole; Imutex; IMD; Him
数据库引用编号
26 个数据库交叉引用编号
- ChEBI: CHEBI:14434
- ChEBI: CHEBI:16069
- KEGG: C01589
- PubChem: 795
- HMDB: HMDB0001525
- Metlin: METLIN4190
- DrugBank: DB03366
- ChEMBL: CHEMBL540
- Wikipedia: Imidazole
- foodb: FDB012307
- chemspider: 773
- CAS: 227760-40-9
- CAS: 6745-43-3
- CAS: 288-32-4
- MoNA: SM809101
- MoNA: KO003222
- MoNA: KO003226
- MoNA: KO003224
- MoNA: KO003223
- MoNA: KO003225
- PMhub: MS000007766
- PubChem: 4744
- PDB-CCD: IMD
- 3DMET: B00326
- NIKKAJI: J2.566F
- RefMet: Imidazole
分类词条
相关代谢途径
Reactome(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)
5 个相关的物种来源信息
- 3864 Lens culinaris: 10.1016/S0031-9422(00)82479-6
- 9606 Homo sapiens: 10.1007/S11306-009-0155-5
- 3864 Lens culinaris: 10.1016/S0031-9422(00)82479-6
- 9606 Homo sapiens: 10.1007/S11306-009-0155-5
- 9606 Homo sapiens: -
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
- Isaac Duah Boateng, Xiao-Ming Yang, Hengbo Yin, Weimin Liu. Separation and purification of polyprenols from Ginkgo biloba leaves by silver ion anchored on imidazole-based ionic liquid functionalized mesoporous MCM-41 sorbent.
Food chemistry.
2024 Aug; 450(?):139284. doi:
10.1016/j.foodchem.2024.139284. [PMID: 38640543] - Yali Yang, Jia Chen, Xiaojing Liang, Bei Liu, Kaijun Quan, Xiuhui Liu, Hongdeng Qiu. Adjustable chromatographic performance of silica-based mixed-mode stationary phase through the control of co-grafting amounts of imidazole and C18 chain.
Journal of chromatography. A.
2024 May; 1722(?):464889. doi:
10.1016/j.chroma.2024.464889. [PMID: 38598894] - Ju Liu, Jing Ren, Simin Li, Hongyan He, Yanlei Wang. Protein Interface Regulating the Inserting Process of Imidazole Ionic Liquids into the Cell Membrane.
The journal of physical chemistry. B.
2024 May; 128(18):4456-4463. doi:
10.1021/acs.jpcb.3c08451. [PMID: 38691101] - Subhankar Mandal, Prashantha Kumar Br, Md Tanjim Alam, Prem Prakash Tripathi, Bhavya Channappa. Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays.
ACS chemical neuroscience.
2022 05; 13(9):1433-1445. doi:
10.1021/acschemneuro.2c00076. [PMID: 35417128] - Yan Song, Yuan Sun, Minglu Tang, Zhengya Yue, Jiatong Ni, Junge Zhao, Wenxin Wang, Tiedong Sun, Lianxu Shi, Lei Wang. Polyoxometalate Modified by Zeolite Imidazole Framework for the pH-Responsive Electrodynamic/Chemodynamic Therapy.
ACS applied materials & interfaces.
2022 Feb; 14(4):4914-4920. doi:
10.1021/acsami.1c19985. [PMID: 35050579] - Wen-Yi Low, Shuhua Thong, Shu-Sin Chng. ATP disrupts lipid-binding equilibrium to drive retrograde transport critical for bacterial outer membrane asymmetry.
Proceedings of the National Academy of Sciences of the United States of America.
2021 12; 118(50):. doi:
10.1073/pnas.2110055118. [PMID: 34873038] - Shengzhuang Tang, Jesse Chen, Jayme Cannon, Zhengyi Cao, James R Baker, Su He Wang. Dendrimer-based posaconazole nanoplatform for antifungal therapy.
Drug delivery.
2021 Dec; 28(1):2150-2159. doi:
10.1080/10717544.2021.1986605. [PMID: 34617850] - Xiaotong Xu, Yuyu Ma, Shujiang Ding, Yinhuan Li. Glucose oxidase@zinc-doped zeolitic imidazolate framework-67 as an effective cascade catalyst for one-step chemiluminescence sensing of glucose.
Mikrochimica acta.
2021 11; 188(12):427. doi:
10.1007/s00604-021-05096-2. [PMID: 34812945] - Katarzyna Gałczyńska, Karol Ciepluch, Krystyna Kurdziel, Ralf Biehl, Michał Arabski. Spectroscopic and Small-angle X-ray scattering analysis of binding between Copper(II) -1-allylimidazole complex, a potential anti-tumor agent, and bovine serum albumin.
Bioorganic chemistry.
2021 11; 116(?):105327. doi:
10.1016/j.bioorg.2021.105327. [PMID: 34507233] - Zunhua Yang, Yuanying Fang, Jae-Min Kim, Kyung-Tae Lee, Haeil Park. Synthesis of Halogenated 1,5-Diarylimidazoles and Their Inhibitory Effects on LPS-Induced PGE2 Production in RAW 264.7 Cells.
Molecules (Basel, Switzerland).
2021 Oct; 26(20):. doi:
10.3390/molecules26206093. [PMID: 34684673] - Jing Liu, Wan-Dong She, Fu-Sen Wang, Qing Zhou. Two New Coordination Polymers: Selective Detection of Cu(II) Ion and Treatment Activity on Inner Ear Damage.
Journal of fluorescence.
2021 Sep; 31(5):1343-1352. doi:
10.1007/s10895-021-02768-3. [PMID: 34129124] - Jakub Suchodolski, Joanna Feder-Kubis, Anna Krasowska. Antiadhesive Properties of Imidazolium Ionic Liquids Based on (-)-Menthol Against Candida spp.
International journal of molecular sciences.
2021 Jul; 22(14):. doi:
10.3390/ijms22147543. [PMID: 34299160] - Anna L L Matos, Fabian Keller, Tristan Wegner, Carla Elizabeth Cadena Del Castillo, David Grill, Sergej Kudruk, Anne Spang, Frank Glorius, Andreas Heuer, Volker Gerke. CHIMs are versatile cholesterol analogs mimicking and visualizing cholesterol behavior in lipid bilayers and cells.
Communications biology.
2021 06; 4(1):720. doi:
10.1038/s42003-021-02252-5. [PMID: 34117357] - Wensheng Yu, Jian Liu, Dane Clausen, Younong Yu, Joseph L Duffy, Ming Wang, Shouning Xu, Lin Deng, Takao Suzuki, Christine C Chung, Robert W Myers, Daniel J Klein, James I Fells, M Katharine Holloway, Jin Wu, Guoxin Wu, Bonnie J Howell, Richard J O Barnard, Joseph Kozlowski. Discovery of Ethyl Ketone-Based Highly Selective HDACs 1, 2, 3 Inhibitors for HIV Latency Reactivation with Minimum Cellular Potency Serum Shift and Reduced hERG Activity.
Journal of medicinal chemistry.
2021 04; 64(8):4709-4729. doi:
10.1021/acs.jmedchem.0c02150. [PMID: 33797924] - Wenbin Wang, Jing Lu, Lulu Hao, Huaixia Yang, Xuejie Song, Fuchun Si. Electrochemical detection of alkaline phosphatase activity through enzyme-catalyzed reaction using aminoferrocene as an electroactive probe.
Analytical and bioanalytical chemistry.
2021 Mar; 413(7):1827-1836. doi:
10.1007/s00216-020-03150-1. [PMID: 33481047] - Mingxuan Ma, Cheng Chen, Xinqi Zhu, Xiaoqi Li, Yingxiang Du, Liu Zhang, Jie Gan. A porous layer open-tubular capillary column supported with pepsin and zeolitic imidazolate framework for enantioseparation of four basic drugs in capillary electrochromatography.
Journal of chromatography. A.
2021 Jan; 1637(?):461866. doi:
10.1016/j.chroma.2020.461866. [PMID: 33422798] - Mahsa Mahmoodi, Vahid Javanbakht. Fabrication of Zn-based magnetic zeolitic imidazolate framework bionanocomposite using basil seed mucilage for removal of azo cationic and anionic dyes from aqueous solution.
International journal of biological macromolecules.
2021 Jan; 167(?):1076-1090. doi:
10.1016/j.ijbiomac.2020.11.062. [PMID: 33186651] - Mo Wang, Lu Zhang, Xiaohong Huo, Zhenfeng Zhang, Qianjia Yuan, Panpan Li, Jianzhong Chen, Yashi Zou, Zhengxing Wu, Wanbin Zhang. Catalytic Asymmetric Synthesis of the anti-COVID-19 Drug Remdesivir.
Angewandte Chemie (International ed. in English).
2020 11; 59(47):20814-20819. doi:
10.1002/anie.202011527. [PMID: 32870563] - Parvaneh Peyvand, Zahra Vaezi, Mosslim Sedghi, Nima Dalir, Leila Ma'mani, Hossein Naderi-Manesh. Imidazolium-based ionic liquid functionalized mesoporous silica nanoparticles as a promising nano-carrier: response surface strategy to investigate and optimize loading and release process for Lapatinib delivery.
Pharmaceutical development and technology.
2020 Nov; 25(9):1150-1161. doi:
10.1080/10837450.2020.1803909. [PMID: 32746669] - Xiaoxu Kang, Yushu Wang, Zhigang Chen, Yixin Wu, Hao Chen, Xi Yang, Changyuan Yu. Imidazole modified Pt(iv) prodrug-loaded multi-stage pH responsive nanoparticles to overcome cisplatin resistance.
Chemical communications (Cambridge, England).
2020 Sep; 56(76):11271-11274. doi:
10.1039/d0cc01846e. [PMID: 32830841] - Xi Zhou, Wen Zhao, Muxue Wang, Shuai Zhang, Yunhong Li, Wenxin Hu, Lei Ren, Shenglin Luo, Zhiwei Chen. Dual-Modal Therapeutic Role of the Lactate Oxidase-Embedded Hierarchical Porous Zeolitic Imidazolate Framework as a Nanocatalyst for Effective Tumor Suppression.
ACS applied materials & interfaces.
2020 Jul; 12(29):32278-32288. doi:
10.1021/acsami.0c05783. [PMID: 32580547] - Giulia Mastellone, Idaira Pacheco-Fernández, Patrizia Rubiolo, Verónica Pino, Cecilia Cagliero. Sustainable Micro-Scale Extraction of Bioactive Phenolic Compounds from Vitis vinifera Leaves with Ionic Liquid-Based Surfactants.
Molecules (Basel, Switzerland).
2020 Jul; 25(13):. doi:
10.3390/molecules25133072. [PMID: 32640534] - Bodee Nutho, Salila Pengthaisong, Anupong Tankrathok, Vannajan Sanghiran Lee, James R Ketudat Cairns, Thanyada Rungrotmongkol, Supot Hannongbua. Structural Basis of Specific Glucoimidazole and Mannoimidazole Binding by Os3BGlu7.
Biomolecules.
2020 06; 10(6):. doi:
10.3390/biom10060907. [PMID: 32549280] - Heba E Hashem, Abd El-Galil E Amr, Eman S Nossier, Elsayed A Elsayed, Eman M Azmy. Synthesis, Antimicrobial Activity and Molecular Docking of Novel Thiourea Derivatives Tagged with Thiadiazole, Imidazole and Triazine Moieties as Potential DNA Gyrase and Topoisomerase IV Inhibitors.
Molecules (Basel, Switzerland).
2020 Jun; 25(12):. doi:
10.3390/molecules25122766. [PMID: 32549386] - Chao Zhong, Zhixian Lei, Huan Huang, Mingyue Zhang, Zongwei Cai, Zian Lin. One-pot synthesis of trypsin-based magnetic metal-organic frameworks for highly efficient proteolysis.
Journal of materials chemistry. B.
2020 06; 8(21):4642-4647. doi:
10.1039/c9tb02315a. [PMID: 32373807] - Argyro G Fragkaki, Georgia Petropoulou, Ioanna Athanasiadou, Polyxeni Kiousi, Nassia Kioukia-Fougia, Helen Archontaki, Evangelos Bakeas, Yiannis S Angelis. Determination of anabolic androgenic steroids as imidazole carbamate derivatives in human urine using liquid chromatography-tandem mass spectrometry.
Journal of separation science.
2020 Jun; 43(11):2154-2161. doi:
10.1002/jssc.202000036. [PMID: 32166888] - Y F Neves, A C L Eloi, H M M de Freitas, E G O Soares, D Rivillo, V Demétrio da Silva, H S Schrekker, J L Badel. Imidazolium salts as alternative compounds to control diseases caused by plant pathogenic bacteria.
Journal of applied microbiology.
2020 May; 128(5):1236-1247. doi:
10.1111/jam.14575. [PMID: 31922640] - Madhu Tippannanavar, Ankita Verma, Rajesh Kumar, Robin Gogoi, Aditi Kundu, Neeraj Patanjali. Preparation of Nanofungicides Based on Imidazole Drugs and Their Antifungal Evaluation.
Journal of agricultural and food chemistry.
2020 Apr; 68(16):4566-4578. doi:
10.1021/acs.jafc.9b06387. [PMID: 32227935] - Iqubal Singh, Vijay Luxami, Kamaldeep Paul. Synthesis, cytotoxicity, pharmacokinetic profile, binding with DNA and BSA of new imidazo[1,2-a]pyrazine-benzo[d]imidazol-5-yl hybrids.
Scientific reports.
2020 04; 10(1):6534. doi:
10.1038/s41598-020-63605-4. [PMID: 32300169] - Lizhen He, Guanning Huang, Hongxing Liu, Chengcheng Sang, Xinxin Liu, Tianfeng Chen. Highly bioactive zeolitic imidazolate framework-8-capped nanotherapeutics for efficient reversal of reperfusion-induced injury in ischemic stroke.
Science advances.
2020 03; 6(12):eaay9751. doi:
10.1126/sciadv.aay9751. [PMID: 32206718] - Lise Dieltjens, Kenny Appermans, Maries Lissens, Bram Lories, Wook Kim, Erik V Van der Eycken, Kevin R Foster, Hans P Steenackers. Inhibiting bacterial cooperation is an evolutionarily robust anti-biofilm strategy.
Nature communications.
2020 01; 11(1):107. doi:
10.1038/s41467-019-13660-x. [PMID: 31919364] - Jin Zhou, Tharin Limsakun, Ophelia Yin, Vance Warren, Cynthia Zamora, George Atiee, Jarema Kochan, Joseph Pav, Fumiaki Kobayashi, Vijay Vashi, Victor Dishy. First-in-Human Study to Assess the Safety, Pharmacokinetics, and Pharmacodynamics of an Oral Formulation of DS-1040, an Inhibitor of the Activated Form of Thrombin-Activatable Fibrinolysis Inhibitor, in Healthy Subjects.
Journal of clinical pharmacology.
2019 12; 59(12):1669-1677. doi:
10.1002/jcph.1474. [PMID: 31243790] - Anne B Kim, William K Milsom. pH regulation in hibernation: Implications for ventilatory and metabolic control.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology.
2019 11; 237(?):110536. doi:
10.1016/j.cbpa.2019.110536. [PMID: 31401311] - Masari Otsuki, Noboru Fukuda, Takashi Inoue, Takayuki Mineshige, Tomoyasu Otsuki, Shu Horikoshi, Morito Endo, Masanori Abe. Preclinical Study of DNA-Recognized Peptide Compound Pyrrole-Imidazole Polyamide Targeting Human TGF-β1 Promoter for Progressive Renal Diseases in the Common Marmoset.
Molecules (Basel, Switzerland).
2019 Sep; 24(17):. doi:
10.3390/molecules24173178. [PMID: 31480595] - Kendall Cook, Katharine Tarnawsky, Alana J Swinton, Daniel D Yang, Alexandria S Senetra, Gregory A Caputo, Benjamin R Carone, Timothy D Vaden. Correlating Lipid Membrane Permeabilities of Imidazolium Ionic Liquids with their Cytotoxicities on Yeast, Bacterial, and Mammalian Cells.
Biomolecules.
2019 06; 9(6):. doi:
10.3390/biom9060251. [PMID: 31242711] - Ondrej Stepanek, Niyada Hin, Ajit G Thomas, Ranjeet P Dash, Jesse Alt, Rana Rais, Camilo Rojas, Barbara S Slusher, Takashi Tsukamoto. Neutral sphingomyelinase 2 inhibitors based on the 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol scaffold.
European journal of medicinal chemistry.
2019 May; 170(?):276-289. doi:
10.1016/j.ejmech.2019.03.015. [PMID: 30921693] - Jan Frömmel, Radka Končitíková, David Kopečný, Miroslav Soural, Marek Šebela. Oxidation of imidazole- and pyrazole-derived aldehydes by plant aldehyde dehydrogenases from the family 2 and 10.
Chemico-biological interactions.
2019 May; 304(?):194-201. doi:
10.1016/j.cbi.2019.02.008. [PMID: 30768969] - Burak Kuzu, Meltem Tan, Parham Taslimi, İlhami Gülçin, Mehmet Taşpınar, Nurettin Menges. Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases.
Bioorganic chemistry.
2019 05; 86(?):187-196. doi:
10.1016/j.bioorg.2019.01.044. [PMID: 30711701] - Ruchika Saroa, Deepender Kaushik, Upma Bagai, Sukhbir Kaur, Deepak B Salunke. Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host.
Bioorganic & medicinal chemistry letters.
2019 05; 29(9):1099-1105. doi:
10.1016/j.bmcl.2019.02.029. [PMID: 30850167] - Agnieszka Hryniewicka, Marta Malinowska, Tomasz Hauschild, Katarzyna Pieczul, Jacek W Morzycki. Synthesis and antimicrobial properties of steroid-based imidazolium salts.
The Journal of steroid biochemistry and molecular biology.
2019 05; 189(?):65-72. doi:
10.1016/j.jsbmb.2019.02.006. [PMID: 30797035] - Guogang Deng, Bei Zhou, Jing Wang, Zhuo Chen, Liang Gong, Yaxiao Gong, Dongmei Wu, Yan Li, Hongbin Zhang, Xiaodong Yang. Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
European journal of medicinal chemistry.
2019 Apr; 168(?):232-252. doi:
10.1016/j.ejmech.2019.02.025. [PMID: 30822712] - Yannick Hövelmann, Maria Hahn, Florian Hübner, Hans-Ulrich Humpf. Detection of Novel Cytotoxic Imidazole Alkaloids in Tomato Products by LC-MS/MS.
Journal of agricultural and food chemistry.
2019 Apr; 67(13):3670-3678. doi:
10.1021/acs.jafc.9b00461. [PMID: 30860836] - Pei-Yi Wang, Ming-Wei Wang, Dan Zeng, Meng Xiang, Jia-Rui Rao, Qing-Qing Liu, Li-Wei Liu, Zhi-Bing Wu, Zhong Li, Bao-An Song, Song Yang. Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases.
Journal of agricultural and food chemistry.
2019 Apr; 67(13):3535-3545. doi:
10.1021/acs.jafc.8b06242. [PMID: 30835115] - Lei Liu, Yang Hu, Jianfei Lu, Gaoxue Wang. An imidazole coumarin derivative enhances the antiviral response to spring viremia of carp virus infection in zebrafish.
Virus research.
2019 04; 263(?):112-118. doi:
10.1016/j.virusres.2019.01.009. [PMID: 30658072] - Agnieszka Zagórska, Anna Partyka, Adam Bucki, Marcin Kołaczkowski, Magdalena Jastrzębska-Więsek, Anna Czopek, Agata Siwek, Monika Głuch-Lutwin, Marek Bednarski, Marek Bajda, Jakub Jończyk, Kamil Piska, Paulina Koczurkiewicz, Anna Wesołowska, Maciej Pawłowski. Characteristics of metabolic stability and the cell permeability of 2-pyrimidinyl-piperazinyl-alkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione with antidepressant- and anxiolytic-like activities.
Chemical biology & drug design.
2019 04; 93(4):511-521. doi:
10.1111/cbdd.13442. [PMID: 30422400] - Sumanta Ghosh, Anindita Mahapatra, Krishnananda Chattopadhyay. Modulation of α-Synuclein Aggregation by Cytochrome c Binding and Hetero-dityrosine Adduct Formation.
ACS chemical neuroscience.
2019 03; 10(3):1300-1310. doi:
10.1021/acschemneuro.8b00393. [PMID: 30620180] - James E Keener, Dane Evan Zambrano, Guozhi Zhang, Ciara K Zak, Deseree J Reid, Bhushan S Deodhar, Jeanne E Pemberton, James S Prell, Michael T Marty. Chemical Additives Enable Native Mass Spectrometry Measurement of Membrane Protein Oligomeric State within Intact Nanodiscs.
Journal of the American Chemical Society.
2019 01; 141(2):1054-1061. doi:
10.1021/jacs.8b11529. [PMID: 30586296] - Junguo Ma, Xinxin Li, Mengke Cui, Weiguo Li, Xiaoyu Li. Negative impact of the imidazolium-based ionic liquid [C8mim]Br on silver carp (Hypophthalmichthys molitrix): Long-term and low-level exposure.
Chemosphere.
2018 Dec; 213(?):358-367. doi:
10.1016/j.chemosphere.2018.09.075. [PMID: 30241080] - Aleksandar Tot, Milan Vraneš, Ivana Maksimović, Marina Putnik-Delić, Milena Daničić, Slobodan Gadžurić. Evaluation of the impact of different alkyl length and type of substituent in imidazolium ionic liquids on cucumber germination, growth and oxidative stress.
Environmental science and pollution research international.
2018 Dec; 25(35):35594-35601. doi:
10.1007/s11356-018-3534-5. [PMID: 30353431] - Wei Liu, Ruya Wang, Fan Hu, Pinping Wu, Tao Huang, Meriem Fizir, Hua He. Novel mixed hemimicelles based on nonionic surfactant-imidazolium ionic liquid and magnetic halloysite nanotubes as efficient approach for analytical determination.
Analytical and bioanalytical chemistry.
2018 Nov; 410(28):7357-7371. doi:
10.1007/s00216-018-1348-4. [PMID: 30294762] - Yu-Feng Shen, Lei Liu, Chen-Zhang Feng, Yang Hu, Cheng Chen, Gao-Xue Wang, Bin Zhu. Synthesis and antiviral activity of a new coumarin derivative against spring viraemia of carp virus.
Fish & shellfish immunology.
2018 Oct; 81(?):57-66. doi:
10.1016/j.fsi.2018.07.005. [PMID: 29981474] - Mahmoud H El-Maghrabey, Taro Nakatani, Naoya Kishikawa, Naotaka Kuroda. Aromatic aldehydes as selective fluorogenic derivatizing agents for α-dicarbonyl compounds. Application to HPLC analysis of some advanced glycation end products and oxidative stress biomarkers in human serum.
Journal of pharmaceutical and biomedical analysis.
2018 Sep; 158(?):38-46. doi:
10.1016/j.jpba.2018.05.012. [PMID: 29860177] - Fumiya Tatsuno, Seon Hwa Lee, Tomoyuki Oe. Imidazole dipeptides can quench toxic 4-oxo-2(E)-nonenal: Molecular mechanism and mass spectrometric characterization of the reaction products.
Journal of peptide science : an official publication of the European Peptide Society.
2018 Aug; 24(8-9):e3097. doi:
10.1002/psc.3097. [PMID: 29971858] - Lizhen Qiao, Wangjie Lv, Mengmeng Chang, Xianzhe Shi, Guowang Xu. Surface-bonded amide-functionalized imidazolium ionic liquid as stationary phase for hydrophilic interaction liquid chromatography.
Journal of chromatography. A.
2018 Jul; 1559(?):141-148. doi:
10.1016/j.chroma.2017.07.037. [PMID: 28734605] - Aarti Sawant-Basak, R Scott Obach, Angela Doran, Peter Lockwood, Klaas Schildknegt, Hongying Gao, Jessica Mancuso, Susanna Tse, Thomas A Comery. Metabolism of a 5HT6 Antagonist, 2-Methyl-1-(Phenylsulfonyl)-4-(Piperazin-1-yl)-1H-Benzo[d]imidazole (SAM-760): Impact of Sulfonamide Metabolism on Diminution of a Ketoconazole-Mediated Clinical Drug-Drug Interaction.
Drug metabolism and disposition: the biological fate of chemicals.
2018 Jul; 46(7):934-942. doi:
10.1124/dmd.118.080457. [PMID: 29695615] - Stephane Jeanmart, Julien Gagnepain, Pulakesh Maity, Clemens Lamberth, Fredrik Cederbaum, Ramya Rajan, Olivier Jacob, Mathias Blum, Stephane Bieri. Synthesis and fungicidal activity of novel imidazole-based ketene dithioacetals.
Bioorganic & medicinal chemistry.
2018 05; 26(8):2009-2016. doi:
10.1016/j.bmc.2018.02.051. [PMID: 29530348] - Christopher Stoffels, Mhmd Oumari, Aris Perrou, Andreas Termath, Waldemar Schlundt, Hans-Günther Schmalz, Mathias Schäfer, Vera Wewer, Sabine Metzger, Edgar Schömig, Dirk Gründemann. Ergothioneine stands out from hercynine in the reaction with singlet oxygen: Resistance to glutathione and TRIS in the generation of specific products indicates high reactivity.
Free radical biology & medicine.
2017 12; 113(?):385-394. doi:
10.1016/j.freeradbiomed.2017.10.372. [PMID: 29074402] - Khalid Z Masoodi, Yadong Xu, Javid A Dar, Kurtis Eisermann, Laura E Pascal, Erica Parrinello, Junkui Ai, Paul A Johnston, Joel B Nelson, Peter Wipf, Zhou Wang. Inhibition of Androgen Receptor Nuclear Localization and Castration-Resistant Prostate Tumor Growth by Pyrroloimidazole-based Small Molecules.
Molecular cancer therapeutics.
2017 10; 16(10):2120-2129. doi:
10.1158/1535-7163.mct-17-0176. [PMID: 28655783] - Tao Lv, Pedro N Carvalho, Mònica Escolà Casas, Ulla E Bollmann, Carlos A Arias, Hans Brix, Kai Bester. Enantioselective uptake, translocation and degradation of the chiral pesticides tebuconazole and imazalil by Phragmites australis.
Environmental pollution (Barking, Essex : 1987).
2017 Oct; 229(?):362-370. doi:
10.1016/j.envpol.2017.06.017. [PMID: 28609737] - Hong-Bing Liu, Gianluigi Lauro, Robert D O'Connor, Katheryn Lohith, Michelle Kelly, Patrick Colin, Giuseppe Bifulco, Carole A Bewley. Tulongicin, an Antibacterial Tri-Indole Alkaloid from a Deep-Water Topsentia sp. Sponge.
Journal of natural products.
2017 09; 80(9):2556-2560. doi:
10.1021/acs.jnatprod.7b00452. [PMID: 28837335] - Lakkoji Satish, Sabera Millan, Harekrushna Sahoo. Spectroscopic insight into the interaction of bovine serum albumin with imidazolium-based ionic liquids in aqueous solution.
Luminescence : the journal of biological and chemical luminescence.
2017 Aug; 32(5):695-705. doi:
10.1002/bio.3239. [PMID: 27808452] - Jefferson A Rocha, Ivanilza M Andrade, Leiz M C Véras, Patrick V Quelemes, David F Lima, Maria J S Soares, Pedro L S Pinto, Simon J Mayo, Galya Ivanova, Maria Rangel, Manuela Correia, Ana Carolina Mafud, Yvonne P Mascarenhas, Cristina Delerue-Matos, Josué de Moraes, Peter Eaton, José R S A Leite. Anthelmintic, Antibacterial and Cytotoxicity Activity of Imidazole Alkaloids from Pilocarpus microphyllus Leaves.
Phytotherapy research : PTR.
2017 Apr; 31(4):624-630. doi:
10.1002/ptr.5771. [PMID: 28111828] - A Ribar, K Fink, Z Li, S Ptasińska, I Carmichael, L Feketeová, S Denifl. Stripping off hydrogens in imidazole triggered by the attachment of a single electron.
Physical chemistry chemical physics : PCCP.
2017 Mar; 19(9):6406-6415. doi:
10.1039/c6cp08773f. [PMID: 28198894] - Gen Liu, Yan Xu, Yide Han, Junbiao Wu, Junli Xu, Hao Meng, Xia Zhang. Immobilization of lysozyme proteins on a hierarchical zeolitic imidazolate framework (ZIF-8).
Dalton transactions (Cambridge, England : 2003).
2017 Feb; 46(7):2114-2121. doi:
10.1039/c6dt04582k. [PMID: 28119966] - Youngsu You, Hee Sun Kim, Il Hak Bae, Seung Gi Lee, Min Hyeok Jee, Gyochang Keum, Sung Key Jang, B Moon Kim. New potent biaryl sulfate-based hepatitis C virus inhibitors.
European journal of medicinal chemistry.
2017 Jan; 125(?):87-100. doi:
10.1016/j.ejmech.2016.09.031. [PMID: 27657807] - Takuya Kanno, Kaori Yasutake, Kazunori Tanaka, Shinji Hadano, Joh-E Ikeda. A novel function of N-linked glycoproteins, alpha-2-HS-glycoprotein and hemopexin: Implications for small molecule compound-mediated neuroprotection.
PloS one.
2017; 12(10):e0186227. doi:
10.1371/journal.pone.0186227. [PMID: 29016670] - Ilona Schelle, Janina Bruening, Mareike Buetepage, Harald Genth. Role of p38alpha/beta MAP Kinase in Cell Susceptibility to Clostridium sordellii Lethal Toxin and Clostridium difficile Toxin B.
Toxins.
2016 12; 9(1):. doi:
10.3390/toxins9010002. [PMID: 28025502] - Roberta J Melander, Hong-Bing Liu, Matthew D Stephens, Carole A Bewley, Christian Melander. Marine sponge alkaloids as a source of anti-bacterial adjuvants.
Bioorganic & medicinal chemistry letters.
2016 12; 26(24):5863-5866. doi:
10.1016/j.bmcl.2016.11.018. [PMID: 27876320] - Da Wang, Djurre H de Jong, Andreas Rühling, Volker Lesch, Karina Shimizu, Stephanie Wulff, Andreas Heuer, Frank Glorius, Hans-Joachim Galla. Imidazolium-Based Lipid Analogues and Their Interaction with Phosphatidylcholine Membranes.
Langmuir : the ACS journal of surfaces and colloids.
2016 12; 32(48):12579-12592. doi:
10.1021/acs.langmuir.6b02496. [PMID: 27934518] - A D Ribas, E M Del Ponte, A M Dalbem, D Dalla-Lana, C Bündchen, R K Donato, H S Schrekker, A M Fuentefria. Imidazolium salts with antifungal potential for the control of head blight of wheat caused by Fusarium graminearum.
Journal of applied microbiology.
2016 Aug; 121(2):445-52. doi:
10.1111/jam.13125. [PMID: 26972421] - Mahboube Eslami Moghadam, Adeleh Divsalar, Abdolghafar Abolhosseini Shahrnoy, Ali Akbar Saboury. Synthesis, cytotoxicity assessment, and interaction and docking of novel palladium(II) complexes of imidazole derivatives with human serum albumin.
Journal of biomolecular structure & dynamics.
2016 Aug; 34(8):1751-62. doi:
10.1080/07391102.2015.1090345. [PMID: 26338667] - Jochen P Müller, Achim Löf, Salomé Mielke, Tobias Obser, Linda K Bruetzel, Willem Vanderlinden, Jan Lipfert, Reinhard Schneppenheim, Martin Benoit. pH-Dependent Interactions in Dimers Govern the Mechanics and Structure of von Willebrand Factor.
Biophysical journal.
2016 Jul; 111(2):312-322. doi:
10.1016/j.bpj.2016.06.022. [PMID: 27463134] - Theocharis E Kydonaki, Evangelos Tsoukas, Filipa Mendes, Antonios G Hatzidimitriou, António Paulo, Lefkothea C Papadopoulou, Dionysia Papagiannopoulou, George Psomas. Synthesis, characterization and biological evaluation of (99m)Tc/Re-tricarbonyl quinolone complexes.
Journal of inorganic biochemistry.
2016 07; 160(?):94-105. doi:
10.1016/j.jinorgbio.2015.12.010. [PMID: 26795497] - Wenying Li, Weiping Zhao, Xiaohong Liu, Xiaohua Huang, Omar D Lopez, John E Leet, R Marcus Fancher, Van Nguyen, Jason Goodrich, John Easter, Yang Hong, Janet Caceres-Cortes, Shu Y Chang, Li Ma, Makonen Belema, Lawrence G Hamann, Min Gao, Mingshe Zhu, Yue-Zhong Shu, W Griffith Humphreys, Benjamin M Johnson. Biotransformation of Daclatasvir In Vitro and in Nonclinical Species: Formation of the Main Metabolite by Pyrrolidine δ-Oxidation and Rearrangement.
Drug metabolism and disposition: the biological fate of chemicals.
2016 06; 44(6):809-20. doi:
10.1124/dmd.115.068866. [PMID: 27029743] - Jianghong Dong, Shengwei Chen, Runfeng Li, Wei Cui, Haiming Jiang, Yixia Ling, Zifeng Yang, Wenhui Hu. Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus.
European journal of medicinal chemistry.
2016 Jan; 108(?):605-615. doi:
10.1016/j.ejmech.2015.12.013. [PMID: 26722757] - Yuanyuan Yue, Qiao Dong, Yajie Zhang, Xiaoge Li, Xuyang Yan, Yahui Sun, Jianming Liu. Synthesis of imidazole derivatives and the spectral characterization of the binding properties towards human serum albumin.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2016 Jan; 153(?):688-703. doi:
10.1016/j.saa.2015.09.023. [PMID: 26474241] - Lucyna Dymińska. Imidazopyridines as a source of biological activity and their pharmacological potentials-Infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials.
Bioorganic & medicinal chemistry.
2015 Sep; 23(18):6087-99. doi:
10.1016/j.bmc.2015.07.045. [PMID: 26314922] - Lan-Xiang Liu, Xue-Quan Wang, Bei Zhou, Li-Juan Yang, Yan Li, Hong-Bin Zhang, Xiao-Dong Yang. Synthesis and antitumor activity of novel N-substituted carbazole imidazolium salt derivatives.
Scientific reports.
2015 Aug; 5(?):13101. doi:
10.1038/srep13101. [PMID: 26287982] - Tahereh Khajvand, Olia Alijanpour, Mohammad Javad Chaichi, Majid Vafaeezadeh, Mohammad Mahmoodi Hashemi. Imidazolium-based ionic liquid derivative/Cu(II) complexes as efficient catalysts of the lucigenin chemiluminescence system and its application to H2O 2 and glucose detection.
Analytical and bioanalytical chemistry.
2015 Aug; 407(20):6127-36. doi:
10.1007/s00216-015-8795-y. [PMID: 26163131] - Marion Raters, Paul W Elsinghorst, Stephanie Goetze, Anna Dingel, Reinhard Matissek. Determination of 2-Methylimidazole, 4-Methylimidazole, and 2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole in Licorice Using High-Performance Liquid Chromatography-Tandem Mass Spectrometry Stable-Isotope Dilution Analysis.
Journal of agricultural and food chemistry.
2015 Jul; 63(25):5930-4. doi:
10.1021/acs.jafc.5b01493. [PMID: 26073294] - Franziska Bezold, Johannes Goll, Mirjana Minceva. Study of the applicability of non-conventional aqueous two-phase systems in counter-current and centrifugal partition chromatography.
Journal of chromatography. A.
2015 Apr; 1388(?):126-32. doi:
10.1016/j.chroma.2015.02.021. [PMID: 25736304] - Hwankyu Lee, Tae-Joon Jeon. The binding and insertion of imidazolium-based ionic surfactants into lipid bilayers: the effects of the surfactant size and salt concentration.
Physical chemistry chemical physics : PCCP.
2015 Feb; 17(8):5725-33. doi:
10.1039/c4cp05537c. [PMID: 25623225] - Abdolreza Yazdani, Nancy Janzen, Laura Banevicius, Shannon Czorny, John F Valliant. Imidazole-based [2 + 1] Re(I)/99mTc(I) complexes as isostructural nuclear and optical probes.
Inorganic chemistry.
2015 Feb; 54(4):1728-36. doi:
10.1021/ic502663p. [PMID: 25634699] - Kilani Ben Rejeb, Maâli Benzarti, Ahmed Debez, Christophe Bailly, Arnould Savouré, Chedly Abdelly. NADPH oxidase-dependent H2O2 production is required for salt-induced antioxidant defense in Arabidopsis thaliana.
Journal of plant physiology.
2015 Feb; 174(?):5-15. doi:
10.1016/j.jplph.2014.08.022. [PMID: 25462961] - Kamla Rawat, H B Bohidar. Heparin-like native protein aggregate dissociation by 1-alkyl-3-methyl imidazolium chloride ionic liquids.
International journal of biological macromolecules.
2015 Feb; 73(?):23-30. doi:
10.1016/j.ijbiomac.2014.10.057. [PMID: 25445684] - Mei Qiao, Jiawei Sun, Na Liu, Tianjie Sun, Gang Liu, Shengfang Han, Chunyan Hou, Dongmei Wang. Changes of Nitric Oxide and Its Relationship with H2O2 and Ca2+ in Defense Interactions between Wheat and Puccinia Triticina.
PloS one.
2015; 10(7):e0132265. doi:
10.1371/journal.pone.0132265. [PMID: 26185989] - Zuzanna Pietralik, Żaneta Kołodziejska, Marek Weiss, Maciej Kozak. Gemini Surfactants Based on Bis-Imidazolium Alkoxy Derivatives as Effective Agents for Delivery of Nucleic Acids: A Structural and Spectroscopic Study.
PloS one.
2015; 10(12):e0144373. doi:
10.1371/journal.pone.0144373. [PMID: 26641889] - Iu E Kolupaev, A A Vaĭner, T O Iastreb, A I Oboznyĭ, V A Khripach. [The role of reactive oxygen species and calcium ions in the implementation of the stress-protective effect of brassinosteroids on plant cells].
Prikladnaia biokhimiia i mikrobiologiia.
2014 Nov; 50(6):593-8. doi:
10.7868/s0555109914060075. [PMID: 25726668] - Jing Kang, Lu Han, Zhonglin Chen, Jimin Shen, Jun Nan, Yihua Zhang. Sensitized chemiluminescence of 2-phenyl-4,5-di(2-furyl)-1H-imidazole/K₃Fe(CN)₆/propyl gallate system combining with solid-phase extraction for the determination of propyl gallate in edible oil.
Food chemistry.
2014 Sep; 159(?):445-50. doi:
10.1016/j.foodchem.2014.03.042. [PMID: 24767080] - Nan Zhang, Zhaohui Zhang, Iris L K Wong, Shengbiao Wan, Larry M C Chow, Tao Jiang. 4,5-Di-substituted benzyl-imidazol-2-substituted amines as the structure template for the design and synthesis of reversal agents against P-gp-mediated multidrug resistance breast cancer cells.
European journal of medicinal chemistry.
2014 Aug; 83(?):74-83. doi:
10.1016/j.ejmech.2014.06.016. [PMID: 24952376] - Marc Vidal, Andreea Schmitzer. Molecular parameters and transmembrane transport mechanism of imidazolium-functionalized binols.
Chemistry (Weinheim an der Bergstrasse, Germany).
2014 Aug; 20(32):9998-10004. doi:
10.1002/chem.201402602. [PMID: 25043746] - Yongling Liu, Tao Chen, Chen Chen, Denglang Zou, Yulin Li. [Isolation and preparation of an imidazole alkaloid from radix radix of Aconitum pendulum Busch by semi-preparative high-speed counter-current chromatography].
Se pu = Chinese journal of chromatography.
2014 May; 32(5):543-6. doi:
10.3724/sp.j.1123.2013.12007. [PMID: 25185318] - Francesca Vinchi, Giada Ingoglia, Deborah Chiabrando, Sonia Mercurio, Emilia Turco, Lorenzo Silengo, Fiorella Altruda, Emanuela Tolosano. Heme exporter FLVCR1a regulates heme synthesis and degradation and controls activity of cytochromes P450.
Gastroenterology.
2014 May; 146(5):1325-38. doi:
10.1053/j.gastro.2014.01.053. [PMID: 24486949] - Juliana Tonini Mesquita, Thais Alves da Costa-Silva, Samanta Etel Treiger Borborema, André Gustavo Tempone. Activity of imidazole compounds on Leishmania (L.) infantum chagasi: reactive oxygen species induced by econazole.
Molecular and cellular biochemistry.
2014 Apr; 389(1-2):293-300. doi:
10.1007/s11010-013-1954-6. [PMID: 24374794] - Xiaoqiang Qiao, Rui Wang, Hongyuan Yan, Tao Wang, Qun Zhao, Lihua Zhang, Yukui Zhang. Development of a novel imidazolium-based aromatic quaternary ammonium tag: synthesis and application to the efficient analysis of cysteinyl-peptides by mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2014 Feb; 28(3):256-64. doi:
10.1002/rcm.6785. [PMID: 24375876] - Brian San Francisco, Robert G Kranz. Interaction of holoCcmE with CcmF in heme trafficking and cytochrome c biosynthesis.
Journal of molecular biology.
2014 Feb; 426(3):570-85. doi:
10.1016/j.jmb.2013.10.025. [PMID: 24513106] - Jijin Gu, Xinyi Chen, Hongliang Xin, Xiaoling Fang, Xianyi Sha. Serum-resistant complex nanoparticles functionalized with imidazole-rich polypeptide for gene delivery to pulmonary metastatic melanoma.
International journal of pharmaceutics.
2014 Jan; 461(1-2):559-69. doi:
10.1016/j.ijpharm.2013.12.029. [PMID: 24370843] - Mark A Babizhayev. Biochemical, Biomedical and Metabolic Aspects of Imidazole-Containing Dipeptides with the Inherent Complexity to Neurodegenerative Diseases and Various States of Mental Well-Being: A Challenging Correction and Neurotherapeutic Pharmaceutical Biotechnology for Treating Cognitive Deficits, Depression and Intellectual Disabilities.
Current pharmaceutical biotechnology.
2014; 15(8):738-78. doi:
10.2174/1389201015666140827104918. [PMID: 25158972] - Josiah P Zayner, Tobin R Sosnick. Factors that control the chemistry of the LOV domain photocycle.
PloS one.
2014; 9(1):e87074. doi:
10.1371/journal.pone.0087074. [PMID: 24475227]