Guanidine (BioDeep_00000011652)

 

Secondary id: BioDeep_00000405464, BioDeep_00000864854

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Toxin


代谢物信息卡片


Monohydrochloride, guanidine

化学式: CH5N3 (59.048345)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 66.67%

分子结构信息

SMILES: C(=N)(N)N
InChI: InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)

描述信息

Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.; Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano. Despite the provocative simplicity of the molecule, the crystal structure was first described 148 years later.; Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH. With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed). Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. -- Wikipedia; Guanidines are a group of organic compounds sharing a common functional group with the general structure (R1R2N)(R3R4N)C=N-R5. The central bond within this group is that of an imine; the other recognizable motif within this group is an aminal. Examples of guanidines are arginine, triazabicyclodecene and saxitoxin. other derivatives could include guanidine hydroxide, the active ingredient in some non-lye relaxers. Guanidinium salts are well known for their denaturing action on proteins. Guanidinium chloride is one of the most effective denaturants. In 6 M GndHCl all proteins with an ordered structure lose their structure, and most of them become randomly coiled, that is, they do not contain any residual structure.
Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH. With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions. It is found in the urine as a normal product of protein metabolism. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Guanidine is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed). Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. -- Wikipedia.

同义名列表

35 个代谢物同义名

Monohydrochloride, guanidine; Monohydrobromide, guanidine; Guanidine monohydrochloride; guanidine monohydrobromide; Monohydroiodine, guanidine; Guanidine monohydroiodine; Hydrochloride, guanidine; (4-Aminobutyl) guanidine; Guanidine sulfate (1:1); Guanidine sulfate (2:1); Guanidine hydrochloride; Guanidine sulfite (1:1); Monohydrate, guanidine; Guanidine monohydrate; Chloride, guanidinium; Guanidinium chloride; Phosphate, guanidine; Guanidine phosphate; Chloride, guanidium; Sulfate, guanidine; Guanidium chloride; Nitrate, guanidine; Aminomethanamidine; Guanidine Sulfate; Guanidine nitrate; Aminoformamidine; H2N-C(=nh)-NH2; Carbamamidine; Guanidinium; Carbamidine; Imidourea; guanidine; Iminourea; Guanidin; Gu



数据库引用编号

16 个数据库交叉引用编号

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)

27 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

  • Dietmar Funck, Malte Sinn, Giuseppe Forlani, Jörg S Hartig. Guanidine production by plant homoarginine-6-hydroxylases. eLife. 2024 Apr; 12(?):. doi: 10.7554/elife.91458. [PMID: 38619227]
  • Lei Dong, Shuai Li, Jie Huang, Wen-Jun Li, Mukhtiar Ali. Co-occurrence, toxicity, and biotransformation pathways of metformin and its intermediate product guanylurea: Current state and future prospects for enhanced biodegradation strategy. The Science of the total environment. 2024 Apr; 921(?):171108. doi: 10.1016/j.scitotenv.2024.171108. [PMID: 38395159]
  • He Sun, Zhijiao Yan, Jiaxing Sun, Jianzhong Zhang, Hongmei Wang, Xinmin Jiang, Mingyue Wang, Xinglin Zhang, Yuting Xiao, Xiaoya Ji, Jinglong Tang, Dunqiang Ren. Polyhexamethylene guanidine accelerates the macrophage foamy formation mediated pulmonary fibrosis. Ecotoxicology and environmental safety. 2024 Mar; 272(?):116084. doi: 10.1016/j.ecoenv.2024.116084. [PMID: 38350217]
  • Jinwoo Park, Jina Ko, Siyoung Q Choi, KyuHan Kim, Dong Woog Lee. Adsorption of CMIT/MIT on the Model Pulmonary Surfactant Monolayers. Journal of oleo science. 2024; 73(4):437-444. doi: 10.5650/jos.ess23165. [PMID: 38556278]
  • Akalesh G Yadav, Prasanta K Mohapatra, Thichur P Valsala, Darshan B Sathe, Raj B Bhatt. Highly efficient separation of Am(III) and Pu(IV) from lean feeds and soil using an extraction chromatographic resin containing a diglycolamide in an ionic liquid. Journal of chromatography. A. 2023 Sep; 1707(?):464299. doi: 10.1016/j.chroma.2023.464299. [PMID: 37597478]
  • Aline Coqueiro, Daniara Cristina Fernandes, Amanda Danuello, Luis Octávio Regasini, Elaine Monteiro Cardoso-Lopes, Maria Cláudia Marx Young, Luce Maria Brandão Torres, Vicente Paulo Campos, Dulce Helena Siqueira Silva, Vanderlan da Silva Bolzani, Denilson Ferreira de Oliveira. Nematostatic activity of isoprenylated guanidine alkaloids from Pterogyne nitens and their interaction with acetylcholinesterase. Experimental parasitology. 2023 May; 250(?):108542. doi: 10.1016/j.exppara.2023.108542. [PMID: 37178971]
  • Lea Pašalić, Barbara Pem, Darija Domazet Jurašin, Mario Vazdar, Danijela Bakarić. Interaction of guanidinium and ammonium cations with phosphatidylcholine and phosphatidylserine lipid bilayers - Calorimetric, spectroscopic and molecular dynamics simulations study. Biochimica et biophysica acta. Biomembranes. 2023 04; 1865(4):184122. doi: 10.1016/j.bbamem.2023.184122. [PMID: 36739930]
  • Thi-Phuong Doan, Eun-Jin Park, Byeol Ryu, Hyo-Moon Cho, Sang-Jun Yoon, Gwan-Young Jung, Phuong-Thien Thuong, Won-Keun Oh. Unique guanidine-conjugated catechins from the leaves of Alchornea rugosa and their autophagy modulating activity. Phytochemistry. 2023 Feb; 206(?):113521. doi: 10.1016/j.phytochem.2022.113521. [PMID: 36435211]
  • Yijie Cheng, Yufei Zhang, Zhe Zhao, Gang Li, Jie Li, Anran Li, Yun Xue, Baolin Zhu, Zhongming Wu, Xinge Zhang. Guanidinium-Decorated Nanostructure for Precision Sonodynamic-Catalytic Therapy of MRSA-Infected Osteomyelitis. Advanced materials (Deerfield Beach, Fla.). 2022 Dec; 34(50):e2206646. doi: 10.1002/adma.202206646. [PMID: 36245331]
  • Jinchao Lou, Megan L Qualls, Macy M Hudson, Dillon P McBee, Joshua A Baccile, Michael D Best. Reactive Oxygen Species (ROS) Activated Liposomal Cell Delivery using a Boronate-Caged Guanidine Lipid. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Aug; 28(46):e202201057. doi: 10.1002/chem.202201057. [PMID: 35639353]
  • Feng Li, Liming Lin, Jiaying Chi, Hui Wang, Minqun Du, Disang Feng, Liqing Wang, Rui Luo, Hangping Chen, Guilan Quan, Jianfeng Cai, Xin Pan, Chuanbin Wu, Chao Lu. Guanidinium-rich lipopeptide functionalized bacteria-absorbing sponge as an effective trap-and-kill system for the elimination of focal bacterial infection. Acta biomaterialia. 2022 08; 148(?):106-118. doi: 10.1016/j.actbio.2022.05.052. [PMID: 35671875]
  • Qingqing Zhu, Shumin Yang, Chengguo Wei, Geming Lu, Kyung Lee, John Cijiang He, Ruijie Liu, Yifei Zhong. Puerarin attenuates diabetic kidney injury through interaction with Guanidine nucleotide-binding protein Gi subunit alpha-1 (Gnai1) subunit. Journal of cellular and molecular medicine. 2022 07; 26(14):3816-3827. doi: 10.1111/jcmm.17414. [PMID: 35678269]
  • Takashi Sasaki, Yoko Hirakawa, Fumiko Yamairi, Takashi Kurita, Karin Murahashi, Hirokazu Nishimura, Norihiko Iwazaki, Hidenori Yasuhara, Takashi Tateoka, Tetsuya Ohta, Satoshi Obika, Jun Kotera. Altered Biodistribution and Hepatic Safety Profile of a Gapmer Antisense Oligonucleotide Bearing Guanidine-Bridged Nucleic Acids. Nucleic acid therapeutics. 2022 06; 32(3):177-184. doi: 10.1089/nat.2021.0034. [PMID: 35073217]
  • Abhishek Gupta, Shalini Gupta, Ujjal Das, Surajit Sinha. Guanidinium-Functionalized Flexible Azaproline Transporter for Efficient Intracellular Delivery of Proapoptotic Peptide and PDL1 Antisense Morpholino Oligo in Human Carcinoma Cells In Vitro. Bioconjugate chemistry. 2022 05; 33(5):907-917. doi: 10.1021/acs.bioconjchem.2c00129. [PMID: 35486710]
  • Morten E Pedersen, Jesper Østergaard, Henrik Jensen. Quantification of Structural Integrity and Stability Using Nanograms of Protein by Flow-Induced Dispersion Analysis. Molecules (Basel, Switzerland). 2022 Apr; 27(8):. doi: 10.3390/molecules27082506. [PMID: 35458703]
  • Alfonso Barrios, Marilen Estrada, Joong Ho Moon. Carbamoylated Guanidine-Containing Polymers for Non-Covalent Functional Protein Delivery in Serum-Containing Media. Angewandte Chemie (International ed. in English). 2022 03; 61(12):e202116722. doi: 10.1002/anie.202116722. [PMID: 34995405]
  • Moumita Mukherjee, Pinki Saha Sardar, Maitrayee Basu Roy, Priyanka Mukherjee, Rina Ghosh, Sanjib Ghosh. Tracking Zone-wise perturbation during unfolding of some globular proteins using Eu(III) complex of Tetracycline as a probe exhibiting Stark splitting. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2022 Jan; 264(?):120231. doi: 10.1016/j.saa.2021.120231. [PMID: 34365134]
  • Gustavo Axel Elizalde-Velázquez, Leobardo Manuel Gómez-Oliván, Hariz Islas-Flores, María Dolores Hernández-Navarro, Sandra García-Medina, Marcela Galar-Martínez. Oxidative stress as a potential mechanism by which guanylurea disrupts the embryogenesis of Danio rerio. The Science of the total environment. 2021 Dec; 799(?):149432. doi: 10.1016/j.scitotenv.2021.149432. [PMID: 34365262]
  • Katherine Davies, Ulrike Arnold, Hubert Buczkowski, Christopher Burton, Stephen R Welch, Nicole Green, Rhea Strachan, Tracy Beetar-King, Peter Spencer, Nipunadi Hettiarachchi, Matthew J Hannah, Matthew Jones, Patricia A Cane, Christine B Bruce, Neil Woodford, Allen D G Roberts, Marian J Killip. Virucidal efficacy of guanidine-free inactivants and rapid test buffers against SARS-CoV-2. Scientific reports. 2021 12; 11(1):23379. doi: 10.1038/s41598-021-02942-4. [PMID: 34862448]
  • Eman M Saleh, Abdullah E Gouda, Amina M Medhat, Hend O Ahmed, Mohamed A Shemis. Expression of HCV genotype-4 core antigen in prokaryotic E. coli system for diagnosis of HCV infection in Egypt. Protein expression and purification. 2021 12; 188(?):105965. doi: 10.1016/j.pep.2021.105965. [PMID: 34461217]
  • Marko Jukič, Dušanka Janežič, Urban Bren. Potential Novel Thioether-Amide or Guanidine-Linker Class of SARS-CoV-2 Virus RNA-Dependent RNA Polymerase Inhibitors Identified by High-Throughput Virtual Screening Coupled to Free-Energy Calculations. International journal of molecular sciences. 2021 Oct; 22(20):. doi: 10.3390/ijms222011143. [PMID: 34681802]
  • Bo Wang, Yao Xu, Xin Wang, Joshua S Yuan, Carl H Johnson, Jamey D Young, Jianping Yu. A guanidine-degrading enzyme controls genomic stability of ethylene-producing cyanobacteria. Nature communications. 2021 08; 12(1):5150. doi: 10.1038/s41467-021-25369-x. [PMID: 34446715]
  • Pathomwat Wongrattanakamon, Jutamas Jiaranaikulwanitch, Opa Vajragupta, Supat Jiranusornkul, Chalermpong Saenjum, Wipawadee Yooin. Potential Anti-Alzheimer Agents from Guanidinyl Tryptophan Derivatives with Activities of Membrane Adhesion and Conformational Transition Inhibitions. Molecules (Basel, Switzerland). 2021 Aug; 26(16):. doi: 10.3390/molecules26164863. [PMID: 34443456]
  • Issei Kato, Yuuta Ukai, Noriyasu Kondo, Kohei Nozu, Chiaki Kimura, Kumi Hashimoto, Eri Mizusawa, Hideki Maki, Akira Naito, Makoto Kawai. Identification of Thiazoyl Guanidine Derivatives as Novel Antifungal Agents Inhibiting Ergosterol Biosynthesis for Treatment of Invasive Fungal Infections. Journal of medicinal chemistry. 2021 07; 64(14):10482-10496. doi: 10.1021/acs.jmedchem.1c00883. [PMID: 34189911]
  • Saradamoni Mondal, Kishore Babu Bobbili, Sumanta Paul, Musti J Swamy. DSC and FCS Studies Reveal the Mechanism of Thermal and Chemical Unfolding of CIA17, a Polydisperse Oligomeric Protein from Coccinia Indica. The journal of physical chemistry. B. 2021 07; 125(26):7117-7127. doi: 10.1021/acs.jpcb.1c02120. [PMID: 34167304]
  • Lambros J Tassoulas, Ashley Robinson, Betsy Martinez-Vaz, Kelly G Aukema, Lawrence P Wackett. Filling in the Gaps in Metformin Biodegradation: a New Enzyme and a Metabolic Pathway for Guanylurea. Applied and environmental microbiology. 2021 05; 87(11):. doi: 10.1128/aem.03003-20. [PMID: 33741630]
  • Luning Yu, Xinqi Kang, Mohammad Amin Alibakhshi, Mikhail Pavlenok, Michael Niederweis, Meni Wanunu. Stable polymer bilayers for protein channel recordings at high guanidinium chloride concentrations. Biophysical journal. 2021 05; 120(9):1537-1541. doi: 10.1016/j.bpj.2021.02.019. [PMID: 33617833]
  • Peiran Chen, Igor Vorobyov, Benoît Roux, Toby W Allen. Molecular Dynamics Simulations Based on Polarizable Models Show that Ion Permeation Interconverts between Different Mechanisms as a Function of Membrane Thickness. The journal of physical chemistry. B. 2021 02; 125(4):1020-1035. doi: 10.1021/acs.jpcb.0c08613. [PMID: 33493394]
  • Peibo Liang, Shengqiang Shen, Qingbo Xu, Simin Wang, Shuhui Jin, Huizhe Lu, Yanhong Dong, Jianjun Zhang. Design, synthesis biological activity, and docking of novel fluopyram derivatives containing guanidine group. Bioorganic & medicinal chemistry. 2021 01; 29(?):115846. doi: 10.1016/j.bmc.2020.115846. [PMID: 33191087]
  • Sukalyani Banik, Kaheerman Saibire, Shraddha Suryavanshi, Glenn Johns, Soumitesh Chakravorty, Robert Kwiatkowski, David Alland, Padmapriya P Banada. Inactivation of SARS-CoV-2 virus in saliva using a guanidium based transport medium suitable for RT-PCR diagnostic assays. PloS one. 2021; 16(6):e0252687. doi: 10.1371/journal.pone.0252687. [PMID: 34115762]
  • Jiayu Leong, Chuan Yang, Jason Tan, Bing Qian Tan, Sherwin Hor, James L Hedrick, Yi Yan Yang. Combination of guanidinium and quaternary ammonium polymers with distinctive antimicrobial mechanisms achieving a synergistic antimicrobial effect. Biomaterials science. 2020 Dec; 8(24):6920-6929. doi: 10.1039/d0bm00752h. [PMID: 32959808]
  • A B Sioofy-Khojine, A Honkimaa, H Hyöty. A preclinical assessment to repurpose drugs to target type 1 diabetes-associated type B coxsackieviruses. Diabetic medicine : a journal of the British Diabetic Association. 2020 11; 37(11):1849-1853. doi: 10.1111/dme.14175. [PMID: 31705692]
  • Nikki Kuhar, Siva Umapathy. Probing the Stepwise Unfolding of Bovine Serum Albumin Using 2D Correlation Raman Spectroscopic Analysis. Analytical chemistry. 2020 10; 92(19):13509-13517. doi: 10.1021/acs.analchem.0c02968. [PMID: 32865392]
  • Louise Hamborg, Emma Wenzel Horsted, Kristoffer Enøe Johansson, Martin Willemoës, Kresten Lindorff-Larsen, Kaare Teilum. Global analysis of protein stability by temperature and chemical denaturation. Analytical biochemistry. 2020 09; 605(?):113863. doi: 10.1016/j.ab.2020.113863. [PMID: 32738214]
  • Yinhua Zhang, Guoping Ren, Jackson Buss, Andrew J Barry, Gregory C Patton, Nathan A Tanner. Enhancing colorimetric loop-mediated isothermal amplification speed and sensitivity with guanidine chloride. BioTechniques. 2020 09; 69(3):178-185. doi: 10.2144/btn-2020-0078. [PMID: 32635743]
  • Brandon J Eudy, Caitlin E McDermott, Gabriel Fernandez, Clayton E Mathews, Jinping Lai, Robin P da Silva. Disruption of hepatic one-carbon metabolism impairs mitochondrial function and enhances macrophage activity in methionine-choline-deficient mice. The Journal of nutritional biochemistry. 2020 07; 81(?):108381. doi: 10.1016/j.jnutbio.2020.108381. [PMID: 32422424]
  • Yang Pan, Luyao Long, Daitao Zhang, Tingting Yuan, Shujuan Cui, Peng Yang, Quanyi Wang, Simei Ren. Potential False-Negative Nucleic Acid Testing Results for Severe Acute Respiratory Syndrome Coronavirus 2 from Thermal Inactivation of Samples with Low Viral Loads. Clinical chemistry. 2020 06; 66(6):794-801. doi: 10.1093/clinchem/hvaa091. [PMID: 32246822]
  • Chen Fan, Lijiao Wen, Xueli Cao. A biphasic system based on guanidinium ionic liquid: Preparative separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by countercurrent chromatography. Journal of chromatography. A. 2020 May; 1618(?):460872. doi: 10.1016/j.chroma.2020.460872. [PMID: 31959458]
  • Nina B Hentzen, Rina Mogaki, Saya Otake, Kou Okuro, Takuzo Aida. Intracellular Photoactivation of Caspase-3 by Molecular Glues for Spatiotemporal Apoptosis Induction. Journal of the American Chemical Society. 2020 05; 142(18):8080-8084. doi: 10.1021/jacs.0c01823. [PMID: 32275408]
  • Jing Wang, Chao Lu, Yin Shi, Xiaoqian Feng, Biyuan Wu, Guilin Zhou, Guilan Quan, Xin Pan, Jianfeng Cai, Chuanbin Wu. Structural Superiority of Guanidinium-Rich, Four-Armed Copolypeptides: Role of Multiple Peptide-Membrane Interactions in Enhancing Bacterial Membrane Perturbation and Permeability. ACS applied materials & interfaces. 2020 Apr; 12(16):18363-18374. doi: 10.1021/acsami.0c02752. [PMID: 32242658]
  • Alexander Bollenbach, Stepan Gambaryan, Igor Mindukshev, Andreas Pich, Dimitrios Tsikas. GC-MS and LC-MS/MS pilot studies on the guanidine (NG)-dimethylation in native, asymmetrically and symmetrically NG-dimethylated arginine-vasopressin peptides and proteins in human red blood cells. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Mar; 1141(?):122024. doi: 10.1016/j.jchromb.2020.122024. [PMID: 32062367]
  • Preeti Gupta, Faez Iqbal Khan, Dilkash Ambreen, Dakun Lai, Mohamed F Alajmi, Afzal Hussain, Asimul Islam, Faizan Ahmad, Md Imtaiyaz Hassan. Investigation of guanidinium chloride-induced unfolding pathway of sphingosine kinase 1. International journal of biological macromolecules. 2020 Mar; 147(?):177-186. doi: 10.1016/j.ijbiomac.2020.01.023. [PMID: 31917989]
  • Xue-Jie Qi, Xiang-Yun Liu, Lei-Meng-Yuan Tang, Pan-Feng Li, Feng Qiu, Ai-Hong Yang. Anti-depressant effect of curcumin-loaded guanidine-chitosan thermo-sensitive hydrogel by nasal delivery. Pharmaceutical development and technology. 2020 Mar; 25(3):316-325. doi: 10.1080/10837450.2019.1686524. [PMID: 31661648]
  • Mohd Ishtikhar, Zeba Siddiqui, Fohad Mabood Husain, Rais Ahmad Khan, Iftekhar Hassan. Comparative refolding of guanidinium hydrochloride denatured bovine serum albumin assisted by cationic and anionic surfactants via artificial chaperone protocol: Biophysical insight. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Jan; 225(?):117510. doi: 10.1016/j.saa.2019.117510. [PMID: 31520999]
  • Juanjuan Dang, Huan Ye, Yongjuan Li, Qiujun Liang, Xudong Li, Lichen Yin. Multivalency-assisted membrane-penetrating siRNA delivery sensitizes photothermal ablation via inhibition of tumor glycolysis metabolism. Biomaterials. 2019 12; 223(?):119463. doi: 10.1016/j.biomaterials.2019.119463. [PMID: 31521887]
  • Daniel M Evans, Jack Hughes, Leigh F Jones, Patrick J Murphy, Halina Falfushynska, Oksana Horyn, Inna M Sokolova, Jeppe Christensen, Simon J Coles, Piotr Rzymski. Elucidating cylindrospermopsin toxicity via synthetic analogues: An in vitro approach. Chemosphere. 2019 Nov; 234(?):139-147. doi: 10.1016/j.chemosphere.2019.06.021. [PMID: 31207420]
  • Elisabeth Gadermaier, Manfred Tesarz, Jacqueline Wallwitz, Gabriela Berg, Gottfried Himmler. Characterization of a sandwich ELISA for quantification of total human soluble neuropilin-1. Journal of clinical laboratory analysis. 2019 Sep; 33(7):e22944. doi: 10.1002/jcla.22944. [PMID: 31219204]
  • Hironori Izawa, Mizuki Kinai, Shinsuke Ifuku, Minoru Morimoto, Hiroyuki Saimoto. Guanidinylation of Chitooligosaccharides Involving Internal Cyclization of the Guanidino Group on the Reducing End and Effect of Guanidinylation on Protein Binding Ability. Biomolecules. 2019 07; 9(7):. doi: 10.3390/biom9070259. [PMID: 31284517]
  • Sumbul Afreen, Danish Idrees, Radhika Khera, Mohd Amir, Md Imtaiyaz Hassan, Saroj Mishra. Investigation of the role of central metal ion of Cyathus bulleri laccase 1 using guanidinium chloride-induced denaturation. International journal of biological macromolecules. 2019 Jul; 132(?):994-1000. doi: 10.1016/j.ijbiomac.2019.04.014. [PMID: 30953724]
  • Douglas A Higgins, John M Gladden, Jeff A Kimbrel, Blake A Simmons, Steven W Singer, Michael P Thelen. Guanidine Riboswitch-Regulated Efflux Transporters Protect Bacteria against Ionic Liquid Toxicity. Journal of bacteriology. 2019 07; 201(13):. doi: 10.1128/jb.00069-19. [PMID: 30988034]
  • Riya Modi, Laxmikanta Khamari, Atanu Nandy, Saptarshi Mukherjee. Spectroscopic probing of the refolding of an unfolded protein through the formation of mixed-micelles. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Jun; 216(?):52-60. doi: 10.1016/j.saa.2019.03.010. [PMID: 30878845]
  • Alessio Malfanti, Francesca Mastrotto, Yanxiao Han, Petr Král, Anna Balasso, Anna Scomparin, Sabina Pozzi, Ronit Satchi-Fainaro, Stefano Salmaso, Paolo Caliceti. Novel Oligo-Guanidyl-PEG Carrier Forming Rod-Shaped Polyplexes. Molecular pharmaceutics. 2019 04; 16(4):1678-1693. doi: 10.1021/acs.molpharmaceut.9b00014. [PMID: 30860853]
  • Ronivaldo Rodrigues da Silva, Nathalia Gonsales da Rosa, Lilian Caroline Gonçalves de Oliveira, Maria Aparecida Juliano, Luiz Juliano, Jose C Rosa, Hamilton Cabral. Biochemical Properties and Catalytic Specificity of a Novel Neutral Serine Peptidase Secreted by Fungus Pyrenochaetopsis sp. Applied biochemistry and biotechnology. 2019 Apr; 187(4):1158-1172. doi: 10.1007/s12010-018-2875-3. [PMID: 30178205]
  • Hanbi Kim, Jong Uk Lee, Soohyun Kim, Sojin Song, Sang Jun Sim. A Nanoplasmonic Biosensor for Ultrasensitive Detection of Alzheimer's Disease Biomarker Using a Chaotropic Agent. ACS sensors. 2019 03; 4(3):595-602. doi: 10.1021/acssensors.8b01242. [PMID: 30747516]
  • Hironori Izawa, Mizuki Kinai, Shinsuke Ifuku, Minoru Morimoto, Hiroyuki Saimoto. Guanidinylated chitosan inspired by arginine-rich cell-penetrating peptides. International journal of biological macromolecules. 2019 Mar; 125(?):901-905. doi: 10.1016/j.ijbiomac.2018.12.138. [PMID: 30572038]
  • Delphine Vincent, Simone Rochfort, German Spangenberg. Optimisation of Protein Extraction from Medicinal Cannabis Mature Buds for Bottom-Up Proteomics. Molecules (Basel, Switzerland). 2019 Feb; 24(4):. doi: 10.3390/molecules24040659. [PMID: 30781766]
  • Tai L Ng, Roman Rohac, Andrew J Mitchell, Amie K Boal, Emily P Balskus. An N-nitrosating metalloenzyme constructs the pharmacophore of streptozotocin. Nature. 2019 02; 566(7742):94-99. doi: 10.1038/s41586-019-0894-z. [PMID: 30728519]
  • Elaine Ballinger, John Mosior, Travis Hartman, Kristin Burns-Huang, Ben Gold, Roxanne Morris, Laurent Goullieux, Isabelle Blanc, Julien Vaubourgeix, Sophie Lagrange, Laurent Fraisse, Stéphanie Sans, Cedric Couturier, Eric Bacqué, Kyu Rhee, Sarah M Scarry, Jeffrey Aubé, Guangbin Yang, Ouathek Ouerfelli, Dirk Schnappinger, Thomas R Ioerger, Curtis A Engelhart, Jennifer A McConnell, Kathrine McAulay, Allison Fay, Christine Roubert, James Sacchettini, Carl Nathan. Opposing reactions in coenzyme A metabolism sensitize Mycobacterium tuberculosis to enzyme inhibition. Science (New York, N.Y.). 2019 02; 363(6426):. doi: 10.1126/science.aau8959. [PMID: 30705156]
  • Huijuan Yu, Wen-Chao Geng, Zhe Zheng, Jie Gao, Dong-Sheng Guo, Yuefei Wang. Facile Fluorescence Monitoring of Gut Microbial Metabolite Trimethylamine N-oxide via Molecular Recognition of Guanidinium-Modified Calixarene. Theranostics. 2019; 9(16):4624-4632. doi: 10.7150/thno.33459. [PMID: 31367245]
  • Walid M Abdelmagid, Taniya Adak, Jon O Freeman, Martin E Tanner. Studies with Guanidinium- and Amidinium-Based Inhibitors Suggest Minimal Stabilization of Allylic Carbocation Intermediates by Dehydrosqualene and Squalene Synthases. Biochemistry. 2018 09; 57(38):5591-5601. doi: 10.1021/acs.biochem.8b00731. [PMID: 30179505]
  • Rajesh Kumar, Deepak Sharma, Vinay Kumar, Rajesh Kumar. Factors defining the effects of macromolecular crowding on dynamics and thermodynamic stability of heme proteins in-vitro. Archives of biochemistry and biophysics. 2018 09; 654(?):146-162. doi: 10.1016/j.abb.2018.07.018. [PMID: 30048628]
  • D Eckhardt, X Li-Blatter, H-J Schönfeld, H Heerklotz, J Seelig. Cooperative unfolding of apolipoprotein A-1 induced by chemical denaturation. Biophysical chemistry. 2018 09; 240(?):42-49. doi: 10.1016/j.bpc.2018.05.005. [PMID: 29885564]
  • Hojat Veisi, Sepideh Najafi, Saba Hemmati. Pd(II)/Pd(0) anchored to magnetic nanoparticles (Fe3O4) modified with biguanidine-chitosan polymer as a novel nanocatalyst for Suzuki-Miyaura coupling reactions. International journal of biological macromolecules. 2018 Jul; 113(?):186-194. doi: 10.1016/j.ijbiomac.2018.02.120. [PMID: 29476850]
  • Idaira Pacheco-Fernández, Verónica Pino, Jacob Lorenzo-Morales, Juan H Ayala, Ana M Afonso. Salt-induced ionic liquid-based microextraction using a low cytotoxic guanidinium ionic liquid and liquid chromatography with fluorescence detection to determine monohydroxylated polycyclic aromatic hydrocarbons in urine. Analytical and bioanalytical chemistry. 2018 Jul; 410(19):4701-4713. doi: 10.1007/s00216-018-0946-5. [PMID: 29468293]
  • Lili Wen, Man Lyu, Huashuai Xiao, Hairong Lan, Zhili Zuo, Zongning Yin. Protein Aggregation and Performance Optimization Based on Microconformational Changes of Aromatic Hydrophobic Regions. Molecular pharmaceutics. 2018 06; 15(6):2257-2267. doi: 10.1021/acs.molpharmaceut.8b00115. [PMID: 29694051]
  • Felix Ameseder, Aurel Radulescu, Olaf Holderer, Peter Falus, Dieter Richter, Andreas M Stadler. Relevance of Internal Friction and Structural Constraints for the Dynamics of Denatured Bovine Serum Albumin. The journal of physical chemistry letters. 2018 May; 9(10):2469-2473. doi: 10.1021/acs.jpclett.8b00825. [PMID: 29688725]
  • Robert Hnasko, Alice Lin, Jeffery McGarvey, Larry Stanker. Enhanced detection of infectious prions by direct ELISA from the brains of asymptomatic animals using DRM2-118 monoclonal antibody and Gdn-HCl. Journal of immunological methods. 2018 05; 456(?):38-43. doi: 10.1016/j.jim.2018.02.010. [PMID: 29462604]
  • Kyo Bin Kang, Dong Young Lee, Mi Song Kim, Tae Bum Kim, Tae-Jin Yang, Sang Hyun Sung. Argininosecologanin, a secoiridoid-derived guanidine alkaloid from the roots of Lonicera insularis. Natural product research. 2018 Apr; 32(7):788-794. doi: 10.1080/14786419.2017.1361953. [PMID: 28774185]
  • Hiranmay Maity, Govardhan Reddy. Thermodynamics and Kinetics of Single-Chain Monellin Folding with Structural Insights into Specific Collapse in the Denatured State Ensemble. Journal of molecular biology. 2018 02; 430(4):465-478. doi: 10.1016/j.jmb.2017.09.009. [PMID: 28923469]
  • Mohammad Aasif Dar, Wahiduzzaman, Asimul Islam, Md Imtaiyaz Hassan, Faizan Ahmad. Counteraction of the deleterious effects of urea on structure and stability of mammalian kidney proteins by osmolytes. International journal of biological macromolecules. 2018 Feb; 107(Pt B):1659-1667. doi: 10.1016/j.ijbiomac.2017.10.021. [PMID: 29030186]
  • Sandhya Bhatia, G Krishnamoorthy, Jayant B Udgaonkar. Site-specific time-resolved FRET reveals local variations in the unfolding mechanism in an apparently two-state protein unfolding transition. Physical chemistry chemical physics : PCCP. 2018 Jan; 20(5):3216-3232. doi: 10.1039/c7cp06214a. [PMID: 29085950]
  • Xiaohua He, Gianluigi Ardissino, Stephanie Patfield, Luisa W Cheng, Christopher J Silva, Maurizio Brigotti. An Improved Method for the Sensitive Detection of Shiga Toxin 2 in Human Serum. Toxins. 2018 01; 10(2):. doi: 10.3390/toxins10020059. [PMID: 29385045]
  • Hui-Chuan Chang, Camy C-H Kung, Tzu-Ting Chang, Shu-Chuan Jao, Yu-Ting Hsu, Wen-Shan Li. Investigation of the proton relay system operative in human cystosolic aminopeptidase P. PloS one. 2018; 13(1):e0190816. doi: 10.1371/journal.pone.0190816. [PMID: 29351301]
  • Pavan Kumar Nareddy, Musti J Swamy. Differential scanning calorimetric and spectroscopic studies on the thermal and chemical unfolding of cucumber (Cucumis sativus) phloem exudate lectin. International journal of biological macromolecules. 2018 Jan; 106(?):95-100. doi: 10.1016/j.ijbiomac.2017.07.173. [PMID: 28778525]
  • Kizukala Jamir, Kottapalli Seshagirirao. Fluorescence quenching, structural and unfolding studies of a purified cysteine protease, ZCPG from Zingiber montanum rhizome. International journal of biological macromolecules. 2018 Jan; 106(?):277-283. doi: 10.1016/j.ijbiomac.2017.08.019. [PMID: 28802845]
  • Zhe Tan, Yogesh K Dhande, Theresa M Reineke. Cell Penetrating Polymers Containing Guanidinium Trigger Apoptosis in Human Hepatocellular Carcinoma Cells unless Conjugated to a Targeting N-Acetyl-Galactosamine Block. Bioconjugate chemistry. 2017 Dec; 28(12):2985-2997. doi: 10.1021/acs.bioconjchem.7b00598. [PMID: 29193962]
  • J E Burton, L Easterbrook, J Pitman, D Anderson, S Roddy, D Bailey, R Vipond, C B Bruce, A D Roberts. The effect of a non-denaturing detergent and a guanidinium-based inactivation agent on the viability of Ebola virus in mock clinical serum samples. Journal of virological methods. 2017 12; 250(?):34-40. doi: 10.1016/j.jviromet.2017.09.020. [PMID: 28941617]
  • Nozomi Watanabe, Keishi Suga, Hiroshi Umakoshi. Comparison of Physicochemical Membrane Properties of Vesicles Modified with Guanidinium Derivatives. The journal of physical chemistry. B. 2017 10; 121(39):9213-9222. doi: 10.1021/acs.jpcb.7b04007. [PMID: 28820256]
  • Christopher Cartmell, Daniel M Evans, Jessica M L Elwood, Hisham S Fituri, Patrick J Murphy, Thomas Caspari, Barbara Poniedziałek, Piotr Rzymski. Synthetic analogues of cyanobacterial alkaloid cylindrospermopsin and their toxicological activity. Toxicology in vitro : an international journal published in association with BIBRA. 2017 Oct; 44(?):172-181. doi: 10.1016/j.tiv.2017.07.007. [PMID: 28705760]
  • Pooja Malhotra, Prashant N Jethva, Jayant B Udgaonkar. Chemical Denaturants Smoothen Ruggedness on the Free Energy Landscape of Protein Folding. Biochemistry. 2017 08; 56(31):4053-4063. doi: 10.1021/acs.biochem.7b00367. [PMID: 28714672]
  • Jungkyun Im, Sanket Das, Dongjun Jeong, Chang-Jin Kim, Hyun-Suk Lim, Ki Hean Kim, Sung-Kee Chung. Intracellular and transdermal protein delivery mediated by non-covalent interactions with a synthetic guanidine-rich molecular carrier. International journal of pharmaceutics. 2017 Aug; 528(1-2):646-654. doi: 10.1016/j.ijpharm.2017.06.030. [PMID: 28634138]
  • Cuicui Liu, Qiliang Deng, Guozhen Fang, Meng Dang, Shuo Wang. Capillary electrochromatography immunoassay for alpha-fetoprotein based on poly(guanidinium ionic liquid) monolithic material. Analytical biochemistry. 2017 08; 530(?):50-56. doi: 10.1016/j.ab.2017.04.014. [PMID: 28454733]
  • Allison M Brady, Elizabeth R Unger, Gitika Panicker. Description of a novel multiplex avidity assay for evaluating HPV antibodies. Journal of immunological methods. 2017 08; 447(?):31-36. doi: 10.1016/j.jim.2017.04.004. [PMID: 28433580]
  • Stefania E Sestito, Fabio A Facchini, Ilaria Morbioli, Jean-Marc Billod, Sonsoles Martin-Santamaria, Alessandro Casnati, Francesco Sansone, Francesco Peri. Amphiphilic Guanidinocalixarenes Inhibit Lipopolysaccharide (LPS)- and Lectin-Stimulated Toll-like Receptor 4 (TLR4) Signaling. Journal of medicinal chemistry. 2017 06; 60(12):4882-4892. doi: 10.1021/acs.jmedchem.7b00095. [PMID: 28471658]
  • Bo Xu, Michael I Jacobs, Oleg Kostko, Musahid Ahmed. Guanidinium Group Remains Protonated in a Strongly Basic Arginine Solution. Chemphyschem : a European journal of chemical physics and physical chemistry. 2017 Jun; 18(12):1503-1506. doi: 10.1002/cphc.201700197. [PMID: 28231411]
  • Debparna Datta, Musti J Swamy. Fluorescence and circular dichroism studies on the accessibility of tryptophan residues and unfolding of a jacalin-related α-d-galactose-specific lectin from mulberry (Morus indica). Journal of photochemistry and photobiology. B, Biology. 2017 May; 170(?):108-117. doi: 10.1016/j.jphotobiol.2017.03.026. [PMID: 28414980]
  • Antti H Rantamäki, Suvi-Katriina Ruokonen, Evangelos Sklavounos, Lasse Kyllönen, Alistair W T King, Susanne K Wiedmer. Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes. Scientific reports. 2017 04; 7(?):46673. doi: 10.1038/srep46673. [PMID: 28429753]
  • Mohammad Aasif Dar, Asimul Islam, Md Imtaiyaz Hassan, Faizan Ahmad. Effect of mammalian kidney osmolytes on the folding pathway of sheep serum albumin. International journal of biological macromolecules. 2017 Apr; 97(?):625-634. doi: 10.1016/j.ijbiomac.2017.01.090. [PMID: 28119187]
  • Shashidhar Nizalapur, Onder Kimyon, Eugene Yee, Kitty Ho, Thomas Berry, Mike Manefield, Charles G Cranfield, Mark Willcox, David StC Black, Naresh Kumar. Amphipathic guanidine-embedded glyoxamide-based peptidomimetics as novel antibacterial agents and biofilm disruptors. Organic & biomolecular chemistry. 2017 Mar; 15(9):2033-2051. doi: 10.1039/c7ob00053g. [PMID: 28203673]
  • Bhaswati Sengupta, Nilimesh Das, Pratik Sen. Elucidation of μs dynamics of domain-III of human serum albumin during the chemical and thermal unfolding: A fluorescence correlation spectroscopic investigation. Biophysical chemistry. 2017 Feb; 221(?):17-25. doi: 10.1016/j.bpc.2016.11.006. [PMID: 27912144]
  • Athanasios Nikolaidis, Thomas Moschakis. Studying the denaturation of bovine serum albumin by a novel approach of difference-UV analysis. Food chemistry. 2017 Jan; 215(?):235-44. doi: 10.1016/j.foodchem.2016.07.133. [PMID: 27542472]
  • Wahiduzzaman, Mohammad Aasif Dar, Mohd Amir, Asimul Islam, Md Imtaiyaz Hassan, Faizan Ahmad. Purification, preliminary X-ray crystallography and biophysical studies of triose phosphate isomerase-β-globin subunit complex. International journal of biological macromolecules. 2017 Jan; 94(Pt B):746-753. doi: 10.1016/j.ijbiomac.2016.10.070. [PMID: 27780759]
  • Kun Wang, Susan D Arntfield. Probing the molecular forces involved in binding of selected volatile flavour compounds to salt-extracted pea proteins. Food chemistry. 2016 Nov; 211(?):235-42. doi: 10.1016/j.foodchem.2016.05.062. [PMID: 27283627]
  • Ning Zhang, Ziqiang Yan, Xue Zhao, Qing Chen, Mingming Ma. Efficient Mini-Transporter for Cytosolic Protein Delivery. ACS applied materials & interfaces. 2016 Oct; 8(39):25725-25732. doi: 10.1021/acsami.6b08202. [PMID: 27632582]
  • Tao Hu, Li Wang, Xiaolei Pan, Hualin Qi. Novel compound, organic cation transporter 3 detection agent and organic cation transporter 3 activity inhibitor, WO2015002150 A1: a patent evaluation. Expert opinion on therapeutic patents. 2016 Aug; 26(8):857-60. doi: 10.1080/13543776.2016.1180364. [PMID: 27097290]
  • Mohd Ishtikhar, Anam Khan, Chih-Kai Chang, Lilian Tsai-Wei Lin, Steven S-S Wang, Rizwan Hasan Khan. Effect of guanidine hydrochloride and urea on the interaction of 6-thioguanine with human serum albumin: a spectroscopic and molecular dynamics based study. Journal of biomolecular structure & dynamics. 2016 Jul; 34(7):1409-20. doi: 10.1080/07391102.2015.1054433. [PMID: 26208966]
  • Keishi Suga, Nozomi Watanabe, Hiroshi Umakoshi. Effect of Stearylguanidinium-Modified POPC Vesicles on the Melting Behavior of tRNA Molecules. The journal of physical chemistry. B. 2016 06; 120(25):5662-9. doi: 10.1021/acs.jpcb.6b04198. [PMID: 27220696]
  • Hongbo Yuan, Yibing Fan, Chengfen Xing, Ruimin Niu, Ran Chai, Yong Zhan, Junjie Qi, Hailong An, Jialiang Xu. Conjugated Polymer-Based Hybrid Materials for Turn-On Detection of CO2 in Plant Photosynthesis. Analytical chemistry. 2016 06; 88(12):6593-7. doi: 10.1021/acs.analchem.6b01489. [PMID: 27252118]
  • Vladimir F Lazarev, Alina D Nikotina, Pavel I Semenyuk, Diana B Evstafyeva, Elena R Mikhaylova, Vladimir I Muronetz, Maxim A Shevtsov, Anastasia V Tolkacheva, Anatoly V Dobrodumov, Alexey L Shavarda, Irina V Guzhova, Boris A Margulis. Small molecules preventing GAPDH aggregation are therapeutically applicable in cell and rat models of oxidative stress. Free radical biology & medicine. 2016 Mar; 92(?):29-38. doi: 10.1016/j.freeradbiomed.2015.12.025. [PMID: 26748070]