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guanidino compounds

Wenqin Xiao, Bo Li, Xi Sun, Dandan Yu, Yongsheng Xie, Huiqun Wu, Shuaikang Chang, Yunfei Zhou, Houcai Wang, Xiucai Lan, Zhijian Xu, Jumei Shi, Weiliang Zhu
DCZ3301, a novel aryl-guanidino compound, was previously found to have potent anti-tumor activity in myeloma and B-cell lymphoma. In the present study, we investigated the effects of DCZ3301 on T-cell leukemia/lymphoma cells both in vitro and in vivo via cell proliferation, cell cycle analysis, apoptosis assay, mitochondrial membrane potential (MMP) assay, western blot analysis and tumor xenograft models. We found that DCZ3301 inhibited the viability of T-cell leukemia/lymphoma cells in a dose- and time-dependent manner...
April 23, 2018: Acta Biochimica et Biophysica Sinica
Azusa Kondoh, Shiori Akahira, Masafumi Oishi, Masahiro Terada
The formal [3+2] cycloaddition of epoxides with unsaturated compounds is a powerful methodology for the synthesis of densely functionalized five-membered heterocyclic compounds containing oxygen. We have developed a novel enantioselective formal [3+2] cycloaddition of epoxides under Brønsted base catalysis. The bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction of β,γ-epoxysulfones with imines, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines having two stereogenic centers including a quaternary one in a highly diastereo- and enantioselective manner...
April 12, 2018: Angewandte Chemie
Omar Alijevic, Hassan Hammoud, Anand Vaithia, Viktor Trendafilov, Maud Bollenbach, Martine Schmitt, Frederic Bihel, Stephan Kellenberger
Acid-sensing ion channels (ASICs) are neuronal Na+ -selective ion channels that open in response to a rapid extracellular acidification. They are involved in pain, fear, learning and neurodegeneration after ischemic stroke. 2-Guanidine-4-methylquinazoline (GMQ) was recently discovered as the first nonproton activator of ASIC3. GMQ is of interest as a gating modifier and pore blocker of ASICs. It has however a low potency, and exerts opposite effects on ASIC1a and ASIC3. To further explore the molecular mechanisms of GMQ action, we have used the guanidinium moiety of GMQ as a scaffold and tested the effects of different GMQ derivatives on the ASIC pH dependence and maximal current...
March 22, 2018: ACS Chemical Neuroscience
Nozomi Ueyama, Keita Sugimoto, Yuta Kudo, Ken-Ichi Onodera, Yuko Cho, Keiichi Konoki, Toshio Nishikawa, Mari Yotsu-Yamashita
Tetrodotoxin (TTX, 1) is a potent neurotoxin that is widely found in both of terrestrial and marine animals. However, the biosynthetic pathway and genes for TTX have not yet been elucidated. Previously, we proposed that TTX originates from a monoterpene, based on the structures of cyclic guanidino compounds commonly found in toxic newts. However, these compounds have not been detected in marine organisms. Instead, a series of deoxy analogues of TTX were found in toxic marine animals. In this study, we further screened for TTX-related compounds in marine animals...
March 5, 2018: Chemistry: a European Journal
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
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 22, 2017: Journal of Natural Products
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
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
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
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
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
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
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
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
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
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
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
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(CH3 CN)4 ]BF4 yield the Cu4 chain compounds [Cu4 (1)2 ](BF4 )4 (that crystallizes as [Cu4 (1)2 (CH3 CN)2 ](BF4 )4 ·2CH2 Cl2 ) 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...
November 14, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
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
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
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