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https://www.readbyqxmd.com/read/29231845/maillard-proteomics-opening-new-pages
#1
REVIEW
Alena Soboleva, Rico Schmidt, Maria Vikhnina, Tatiana Grishina, Andrej Frolov
Protein glycation is a ubiquitous non-enzymatic post-translational modification, formed by reaction of protein amino and guanidino groups with carbonyl compounds, presumably reducing sugars and α-dicarbonyls. Resulting advanced glycation end products (AGEs) represent a highly heterogeneous group of compounds, deleterious in mammals due to their pro-inflammatory effect, and impact in pathogenesis of diabetes mellitus, Alzheimer's disease and ageing. The body of information on the mechanisms and pathways of AGE formation, acquired during the last decades, clearly indicates a certain site-specificity of glycation...
December 12, 2017: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/29112820/daedophamide-a-cytotoxic-cyclodepsipeptide-from-a-daedalopelta-sp-sponge-collected-in-indonesia
#2
Carlos Urda, Rogelio Fernández, Jaime Rodríguez, Marta Pérez, Carlos Jiménez, Carmen Cuevas
A new cyclodepsipeptide, daedophamide (1), has been isolated from a Daedalopelta sp. marine sponge collected from Alor Island (Indonesia). The planar structure of 1 was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. Daedophamide (1) contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6,8-tetramethylnonanoic acid (Htemna). The amino acid constituents were identified as l-Leu, N-Me-l-Gln, d-Arg, d-Asp, d-allo-Thr, l-Pip, d-Ala, d-Ser, 3,4-dimethyl-Gln, O-MeThr, and 4-amino-7-guanidino-2,3-dihydroxyheptanoic acid (Agdha)...
November 7, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/29109769/preclinical-activity-of-dcz3301-a-novel-aryl-guanidino-compound-in-the-therapy-of-multiple-myeloma
#3
Minjie Gao, Bo Li, Xi Sun, Yunfei Zhou, Yingcong Wang, Van S Tompkins, Zhijian Xu, Nekitsing Indima, Houcai Wang, Wenqin Xiao, Lu Gao, Gege Chen, Huiqun Wu, Xiaosong Wu, Yuanyuan Kong, Bingqian Xie, Yiwen Zhang, Gaomei Chang, Liangning Hu, Guang Yang, Bojie Dai, Yi Tao, Weiliang Zhu, Jumei Shi
We synthesized a novel aryl-guanidino compound, DCZ3301, and found that it has potent cytotoxicity against multiple human cancer cell lines. The anticancer activity was most potent against multiple myeloma (MM). DCZ3301 induced cytotoxicity in MM cell lines, as well as patient myeloma cells, in part by decreasing mitochondrial membrane potential to induce apoptosis. In contrast, DCZ3301 had no cytotoxic effect on normal cells. DCZ3301 also inhibited cell cycling and caused a G2/M accumulation that corresponded with downregulation of Cdc25C, CDK1, and Cyclin B1...
2017: Theranostics
https://www.readbyqxmd.com/read/28993161/new-class-of-early-stage-enterovirus-inhibitors-with-a-novel-mechanism-of-action
#4
Yipeng Ma, Rana Abdelnabi, Leen Delang, Mathy Froeyen, Walter Luyten, Johan Neyts, Carmen Mirabelli
4-dimethylamino benzoic acid (compound 12, synonym: 4EDMAB) was identified as an in vitro inhibitor of Coxsackie virus B3 (CVB3) replication in CPE-based assays (EC50 of 9.1 ± 1.5 μM). Next, the activity of twenty-three analogues was assessed, their structure-activity relationship was deduced and a more potent analogue was identified (EC50 of 2.6 ± 0.5 μM). The antiviral activity of 4EDMAB was further confirmed by quantifying viral RNA yield. Time-of-drug-addition assay revealed that 4EDMAB exerts its antiviral activity at the early stages of virus replication...
October 7, 2017: Antiviral Research
https://www.readbyqxmd.com/read/28827534/positively-charged-cyclodextrins-as-effective-molecular-transporters-of-active-phosphorylated-forms-of-gemcitabine-into-cancer-cells
#5
Violeta Rodriguez-Ruiz, Andrey Maksimenko, Giuseppina Salzano, Maria Lampropoulou, Yannis G Lazarou, Valentina Agostoni, Patrick Couvreur, Ruxandra Gref, Konstantina Yannakopoulou
Positively charged cyclodextrins (PCCDs) are molecular carriers of particular interest for their ability to readily enter into cancer cells. Of main interest, guanidino- and aminoalkyl- PCCDs can be conveniently synthesized and form stable and strong inclusion complexes with various active molecules bearing phosphate groups. We have addressed here the challenge to deliver into cancer cells phosphorylated gemcitabine drugs well known for their instability and inability to permeate cell membranes. NMR data corroborated by semiempirical theoretical calculations have shown that aminoalkyl-CDs form sufficiently stable complexes with both mono- and tri-phosphate forms of gemcitabine by simple mixing of the compounds in aqueous solution at physiological pH...
August 21, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28611063/global-proteomic-analysis-of-advanced-glycation-end-products-in-the-arabidopsis-proteome-provides-evidence-for-age-related-glycation-hot-spots
#6
Tatiana Bilova, Gagan Paudel, Nikita Shilyaev, Rico Schmidt, Dominic Brauch, Elena Tarakhovskaya, Svetlana Milrud, Galina Smolikova, Alain Tissier, Thomas Vogt, Andrea Sinz, Wolfgang Brandt, Claudia Birkemeyer, Ludger A Wessjohann, Andrej Frolov
Glycation is a post-translational modification resulting from the interaction of protein amino and guanidino groups with carbonyl compounds. Initially, amino groups react with reducing carbohydrates, yielding Amadori and Heyns compounds. Their further degradation results in formation of advanced glycation end products (AGEs), also originating from α-dicarbonyl products of monosaccharide autoxidation and primary metabolism. In mammals, AGEs are continuously formed during the life of the organism, accumulate in tissues, are well-known markers of aging, and impact age-related tissue stiffening and atherosclerotic changes...
September 22, 2017: Journal of Biological Chemistry
https://www.readbyqxmd.com/read/28385094/effects-of-ns2b-ns3-protease-and-furin-inhibition-on-west-nile-and-dengue-virus-replication
#7
Jenny Kouretova, M Zouhir Hammamy, Anton Epp, Kornelia Hardes, Stephanie Kallis, Linlin Zhang, Rolf Hilgenfeld, Ralf Bartenschlager, Torsten Steinmetzer
West Nile virus (WNV) and Dengue virus (DENV) replication depends on the viral NS2B-NS3 protease and the host enzyme furin, which emerged as potential drug targets. Modification of our previously described WNV protease inhibitors by basic phenylalanine analogs provided compounds with reduced potency against the WNV and DENV protease. In a second series, their decarboxylated P1-trans-(4-guanidino)cyclohexylamide was replaced by an arginyl-amide moiety. Compound 4-(guanidinomethyl)-phenylacetyl-Lys-Lys-Arg-NH2 inhibits the NS2B-NS3 protease of WNV with an inhibition constant of 0...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
https://www.readbyqxmd.com/read/28334511/elongated-and-shortened-peptidomimetic-inhibitors-of-the-proprotein-convertase-furin
#8
Kornelia Hardes, Teodora Ivanova, Bastian Thaa, Gerald M McInerney, Tove Irene Klokk, Kirsten Sandvig, Sebastian Künzel, Iris Lindberg, Torsten Steinmetzer
Novel elongated and shortened derivatives of the peptidomimetic furin inhibitor phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide were synthesized. The most potent compounds, such as N(α) (carbamidoyl)Arg-Arg-Val-Arg-4-amidinobenzylamide (Ki =6.2 pm), contain additional basic residues at the N terminus and inhibit furin in the low-picomolar range. Furthermore, to decrease the molecular weight of this inhibitor type, compounds that lack the P5 moiety were prepared. The best inhibitors of this series, 5-(guanidino)valeroyl-Val-Arg-4-amidinobenzylamide and its P3 tert-leucine analogue displayed Ki values of 2...
April 20, 2017: ChemMedChem
https://www.readbyqxmd.com/read/28224912/high-throughput-screening-and-quantitation-of-guanidino-and-ureido-compounds-using-liquid-chromatography-drift-tube-ion-mobility-spectrometry-mass-spectrometry
#9
Ruo-Jing Fan, Fang Zhang, Xiu-Ping Chen, Wan-Shu Qi, Qing Guan, Tuan-Qi Sun, Yin-Long Guo
The present work focused on the high-throughput screening and quantitation of guanidino compounds (GCs) and ureido compounds (UCs) in human thyroid tissues. The strategy employed benzylic rearrangement stable isotope labeling (BRSIL) for the sample preparation and then detection using liquid chromatography-drift tube ion mobility spectrometry-quadrupole time of flight mass spectrometry (LC-DTIMS-QTOF MS). A short reversed-phase LC realized an on-line desalting and a measurement cycle of 5.0 min. DTIMS separation enhanced the better specificity and selectivity for the benzil labeled GCs and UCs...
April 8, 2017: Analytica Chimica Acta
https://www.readbyqxmd.com/read/28211142/a-stable-hexakis-guanidino-benzene-realization-of-the-strongest-neutral-organic-four-electron-donor
#10
Benjamin Eberle, Elisabeth Kaifer, Hans-Jörg Himmel
The growing demand for efficient batteries has stimulated the search for redox-active organic compounds with multistage redox behavior, as materials with large charge capacity. Herein we report the synthesis and properties of the first hexakis(guanidino)benzene derivative: a strong neutral organic electron donor with reversible multistage redox behavior and a record low redox potential for donation of four electrons. Detailed structural and spectroscopic characterization of three redox states (0, +2, and +4) reveal its unique electronic features...
March 13, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28011211/2-guanidino-quinazolines-as-a-novel-class-of-translation-inhibitors
#11
E S Komarova Andreyanova, I A Osterman, P I Pletnev, Y A Ivanenkov, A G Majouga, A A Bogdanov, P V Sergiev
A variety of structurally unrelated organic compounds has been reported to have antibacterial activity. Among these, certain small-molecule translation inhibitors have attracted a great deal of attention, due to their relatively high selectivity against prokaryotes, and an appropriate therapeutic index with minor "off target" effects. However, ribosomes are being considered as poorly druggable biological targets, thereby making some routine computational-based approaches to rational drug design and its development rather ineffective...
February 2017: Biochimie
https://www.readbyqxmd.com/read/27794395/arginine-kinase-in-toxocara-canis-exon-intron-organization-functional-analysis-of-site-directed-mutants-and-evaluation-of-putative-enzyme-inhibitors
#12
Susiji Wickramasinghe, Lalani Yatawara, Mitsuru Nagataki, Takeshi Agatsuma
OBJECTIVES: To determine exon/intron organization of the Toxocara canis (T. canis) AK (TCAK) and to test green and black tea and several other chemicals against the activity of recombinant TCAK in the guanidino-specific region by site-directed mutants. METHODS: Amplification of genomic DNA fragments containing introns was carried out by PCRs. The open-reading frame (1200 bp) of TCAK (wild type) was cloned into the BamH1/SalI site of pMAL-c2X. The maltose-binding protein-TCAK fusion protein was expressed in Escherichia coli TB1 cells...
October 2016: Asian Pacific Journal of Tropical Medicine
https://www.readbyqxmd.com/read/27714901/fusaricidins-from-paenibacillus-polymyxa-m-1-a-family-of-lipohexapeptides-of-unusual-complexity-a-mass-spectrometric-study
#13
Joachim Vater, Stefanie Herfort, Joerg Doellinger, Max Weydmann, Kristin Dietel, Sebastian Faetke, Peter Lasch
Paenibacillus polymyxa are rhizobacteria with a high potential to produce natural compounds of biotechnological and medical interest. Main products of P. polymyxa are fusaricidins, a large family of antifungal lipopeptides with a 15-guanidino-3-hydroxypentadecanoic acid (GHPD) as fatty acid side chain. We use the P. polymyxa strain M-1 as a model organism for the exploration of the biosynthetic potential of these rhizobacteria. Using matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) about 40 new fusaricidins were detected which were fractionated by reversed-phase (rp) HPLC...
January 2017: Journal of Mass Spectrometry: JMS
https://www.readbyqxmd.com/read/27711819/construction-of-copper-chains-with-new-fluorescent-guanidino-functionalized-naphthyridine-ligands
#14
Christoph Krämer, Simone Leingang, Olaf Hübner, Elisabeth Kaifer, Hubert Wadepohl, Hans-Jörg Himmel
The three new blue-fluorescent ligands 2,7-bis(tetramethylguanidino)-1,8-naphthyridine (1), 2,7-bis(N,N'-dimethylethylene-guanidino)-1,8-naphthyridine (2) and 2,7-bis(N,N'-diisopropylguanidino)-1,8-naphthyridine (3) are synthesized, and their optical properties (electronic absorption and emission spectroscopy) studied. Reactions of 1 or 2 with [Cu(CH3CN)4]BF4 yield the Cu4 chain compounds [Cu4(1)2](BF4)4 (that crystallizes as [Cu4(1)2(CH3CN)2](BF4)4·2CH2Cl2) and [Cu4(2)2](BF4)4. The variations of the optical properties upon coordination are evaluated, and the electronic transitions identified by time-dependent DFT (TD-DFT) calculations...
October 3, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/27692327/papaya-latex-supernatant-has-a-potent-effect-on-the-free-living-stages-of-equid-cyathostomins-in-vitro
#15
L E Peachey, G L Pinchbeck, J B Matthews, F A Burden, J M Behnke, J E Hodgkinson
The control of equid gastrointestinal nematodes in developed countries, in particular the cyathostomins, is threatened by high levels of anthelmintic resistance. In recent years, there has been increasing interest in the evaluation of traditional 'ethnoveterinary' medicines as alternatives to chemical anthelmintics. The cysteine proteinases (CPs), a group of enzymes derived from fruits such as papaya (Carica papaya), pineapple (Ananas comosus) and figs (Ficus spp.), have shown good efficacy against adult stages of a range of parasitic nematodes, in vitro and in vivo...
September 15, 2016: Veterinary Parasitology
https://www.readbyqxmd.com/read/27659246/platform-for-determining-the-inhibition-profile-of-neuraminidase-inhibitors-in-an-influenza-virus-n1-background
#16
Anja Hoffmann, Dennis Schade, Johannes Kirchmair, Bernd Clement, Andreas Sauerbrei, Michaela Schmidtke
Efforts to develop novel neuraminidase inhibitors (NAIs) for the treatment of influenza are ongoing. Novel NAIs should in particular be also effective against seasonal and/or pandemic N1 that carry a H274Y or N294S substitution (N2 numbering), which are most commonly linked to oseltamivir resistance. Here we report a platform for profiling the efficacy of novel NAIs in the N1 genetic background of influenza A virus. Employing reverse genetics, a set of influenza virus variants containing an amino acid substitution associated with oseltamivir resistance in N1 isolates (H274Y, N294S, Y155H or Q136L) was generated...
November 2016: Journal of Virological Methods
https://www.readbyqxmd.com/read/27430589/dehydrogenative-coupling-reactions-with-oxidized-guanidino-functionalized-aromatic-compounds-novel-options-for-%C3%AF-bond-activation
#17
Ute Wild, Stefanie Federle, Arne Wagner, Elisabeth Kaifer, Hans-Jörg Himmel
We present a new option for metal-free σ-bond activation, making use of oxidized, guanidino-functionalized aromatic compounds (GFAs). We demonstrate this new option by the homocoupling reactions of thiols and phosphines. The kinetics and the reaction pathway were studied by a number of experiments (including heterocoupling of thiols and phosphines), supported by quantum-chemical computations. Reaction of the oxidized GFA with p-dihydrobenzoquinone to give p-benzoquinone shows that typical proton-coupled electron-transfer reactions are also possible...
August 16, 2016: Chemistry: a European Journal
https://www.readbyqxmd.com/read/27401086/creatine-transporter-deficiency-leads-to-increased-whole-body-and-cellular-metabolism
#18
Marla K Perna, Amanda N Kokenge, Keila N Miles, Kenea C Udobi, Joseph F Clark, Gail J Pyne-Geithman, Zaza Khuchua, Matthew R Skelton
Creatine (Cr) is a guanidino compound required for rapid replenishment of ATP in cells with a high-energy demand. In humans, mutations in the Cr transporter (CRT;SLC6A8) prevent Cr entry into tissue and result in a significant intellectual impairment, epilepsy, and aphasia. The lack of Cr on both the whole body and cellular metabolism was evaluated in Crt knockout (Crt (-/y) ) mice, a high-fidelity model of human CRT deficiency. Crt (-/y) mice have reduced body mass and, however, show a twofold increase in body fat...
August 2016: Amino Acids
https://www.readbyqxmd.com/read/27093092/experimental-basicities-of-phosphazene-guanidinophosphazene-and-proton-sponge-superbases-in-the-gas-phase-and-solution
#19
Ivari Kaljurand, Jaan Saame, Toomas Rodima, Ivar Koppel, Ilmar A Koppel, Julius F Kögel, Jörg Sundermeyer, Uwe Köhn, Martyn P Coles, Ivo Leito
Experimental gas-phase superbasicity scale spanning 20 orders of magnitude and ranging from bicyclic guanidine 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene to triguanidinophosphazenes and P3 phosphazenes is presented together with solution basicity data in acetonitrile and tetrahydrofuran. The most basic compound in the scale-triguanidinophosphazene Et-N═P[N═C(NMe2)2]3-has the highest experimental gas-phase basicity of an organic base ever reported: 273.9 kcal mol(-1). The scale includes besides the higher homologues of classical superbasic phosphazenes and several guanidino-substituted phosphazenes also a number of recently introduced bisphosphazene and bis-guanidino proton sponges...
April 28, 2016: Journal of Physical Chemistry. A
https://www.readbyqxmd.com/read/26891461/small-molecule-cd4-mimics-containing-mono-cyclohexyl-moieties-as-hiv-entry-inhibitors
#20
Nami Ohashi, Shigeyoshi Harada, Takaaki Mizuguchi, Yu Irahara, Yuko Yamada, Misato Kotani, Wataru Nomura, Shuzo Matsushita, Kazuhisa Yoshimura, Hirokazu Tamamura
CD4 mimics are small molecules that inhibit the protein-protein interaction between gp120 and CD4, which is a key interaction for the entry of human immunodeficiency virus (HIV) into host immune cells. In the present study, mono-cyclohexyl-type CD4 mimics were designed to form hydrophobic and electrostatic interactions with Val430 and Asp368 located in the entrance of the Phe43 cavity of gp120, the interaction site of CD4. YIR-329, a novel 1-azaspiro[5.5]undecane derivative with a cyclohexyl ring attached to the piperidine ring, exhibited only slightly weaker anti-HIV activity than a previously described lead HAR-171, and modeling results indicated the formation of advantageous interactions by the para-chlorophenyl moiety of YIR-329...
April 19, 2016: ChemMedChem
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