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guanidino compounds

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...
October 6, 2016: 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(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
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
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
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
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
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
Rizwan Ali Zounr, Mumammad Yar Khuhawar, Taj Muhammad Jahangir, Malik Alamgir
An improved GC method in terms of sensitivity and decrease in the analysis time has been developed for the analysis of eight guanidino compounds: guanidine (G), methylguanidine (MG), creatinine (CTN), guanidinoacetic acid (GAA), guanidinobutyric acid (GBA), guanidinopropionic acid (GPA), argenine (Arg), and guanidinosuccinic acid (GSA), using isovaleroylacetone (IVA) and ethyl chloroformate (ECF) as derivatizing reagents. The separation was obtained from column HP-5 (30 m × 0.32 mm i.d.) with film thickness of 0...
2016: Analytical Sciences: the International Journal of the Japan Society for Analytical Chemistry
Ruo-Jing Fan, Qing Guan, Fang Zhang, Jia-Peng Leng, Tuan-Qi Sun, Yin-Long Guo
Benzylic rearrangement stable isotope labeling (BRSIL) was explored to quantify the guanidino and ureido compounds (GCs and UCs). This method employed a common reagent, benzil, to label the guanidino and ureido groups through nucleophilic attacking then benzylic migrating. The use of BRSIL was investigated in the analysis of five GCs (creatine, l-arginine, homoarginine, 4-guanidinobutyric acid, and methylguanidine) and two UCs (urea and citrulline). The labeling was found simple and specific. The introduction of bi-phenyl group and the generation of nitrogen heterocyclic ring in the benzil-d0/d5 labeled GCs and UCs improved the retention behaviors in liquid chromatography (LC) and increased the sensitivity of electrospray ionization mass spectrometry (ESI MS) detection...
February 18, 2016: Analytica Chimica Acta
Benjamin Eberle, Marko Damjanović, Markus Enders, Simone Leingang, Jessica Pfisterer, Christoph Krämer, Olaf Hübner, Elisabeth Kaifer, Hans-Jörg Himmel
In this work, the oxidation of several new dinuclear metal (M) acetate complexes of the redox-active guanidino-functionalized aromatic compound (GFA) 1,2,4,5-tetrakis(tetramethylguanidino)benzene (1) was studied. The complexes [1{M(OAc)2}2] (M = Ni or Pd) were oxidized to the radical monocationic complexes [1{M(OAc)2}2](+ •). From CV (cyclic voltammetry) measurements, the Gibbs free enthalpy for disproportionation of [1{M(OAc)2}2](+ •) into [1{M(OAc)2}2] and [1{M(OAc)2}2](2+) could be estimated to be roughly +20 kJ mol(-1) in CH2Cl2 solution...
February 15, 2016: Inorganic Chemistry
Romain Chevrot, Sandrine Didelot, Larissa Van den Bossche, Fatoumata Tambadou, Thibault Caradec, Pierre Marchand, Esther Izquierdo, Valérie Sopéna, Jocelyne Caillon, Cyrille Barthélémy, Ann Van Schepdael, Jos Hoogmartens, Eric Rosenfeld
The important viscosity of the respiratory tract mucus of Cystic fibrosis (CF) patients impairs the mucociliary transport system and allows the growth of numerous micro-organisms. Among them, Pseudomonas aeruginosa and Staphylococcus aureus are known to be responsible for pulmonary infections. We imagined that CF microflora could also harbour micro-organisms naturally equipped to compete with these pathogens. A method was developed to recover these antibiotic-producing strains within 20 CF sputum. Using this approach, we have isolated an unusual Gram-positive bacterium identified as Paenibacillus alvei by Api galleries and 16S rRNA gene sequence analysis...
March 2013: Probiotics and Antimicrobial Proteins
Ahmed Malki, Hayam M A Ashour, Rasha Y Elbayaa, Doaa A E Issa, Hassan A Aziz, Xiaozhuo Chen
Novel 1,5-diphenyl-6-substituted-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones were synthesized and characterized. All compounds were screened for their anti-proliferative activities in five different cancer cell lines. The results showed that compounds 7a and 7b comprising aminoguanidino or guanidino moiety at position 6 inhibited proliferation of RKO colon cancer cells with IC50 of 8 and 4 μM, respectively. Compounds 7a and 7b induced apoptosis in RKO cells, which was confirmed by TUNEL and annexin V-FITC assays...
December 2016: Journal of Enzyme Inhibition and Medicinal Chemistry
Hui Hong, Markiyan Samborskyy, Frederick Lindner, Peter F Leadlay
Desertomycin A is an aminopolyol polyketide containing a macrolactone ring. We have proposed that desertomycin A and similar compounds (marginolactones) are formed by polyketide synthases primed not with γ-aminobutanoyl-CoA but with 4-guanidinylbutanoyl-CoA, to avoid facile cyclization of the starter unit. This hypothesis requires that there be a final-stage de-amidination of the corresponding guanidino-substituted natural product, but no enzyme for such a process has been described. We have now identified candidate amidinohydrolase genes within the desertomycin and primycin clusters...
January 18, 2016: Angewandte Chemie
Jessica K Holien, Elena V Gazina, Robert W Elliott, Bevyn Jarrott, Craig E Cameron, Spencer J Williams, Michael W Parker, Steven Petrou
Coxsackievirus B3 (CVB3) is a picornavirus that is responsible for a significant proportion of human myocarditis. However, no antiviral treatment is currently available to treat this disease or indeed any picornaviral infections. Previously it was shown that amiloride and its derivative 5-(N-ethyl-N-isopropyl)amiloride inhibit the in vitro enzymatic activity of CVB3 RNA polymerase (3D(pol)). Here we measure and compare the inhibitory activity of ten amiloride analogues against CVB3 3D(pol). We show that replacement of the 3,5-diaminopyrazinyl moiety of amiloride causes loss of the inhibitory activity, whereas modifications at the 5-amino and guanidino groups increase or decrease potency...
2014: Journal of Proteomics & Bioinformatics
Alexandra Ziesak, Tobias Wesp, Olaf Hübner, Elisabeth Kaifer, Hubert Wadepohl, Hans-Jörg Himmel
The redox-active GFA (Guanidino-Functionalized Aromatic compound) 1,4,5,8-tetrakis(tetramethylguanidino)-naphthalene (6) is used to synthesize new dinuclear copper complexes of the formula [6(CuX2)2] with different electronic structures. With X = OAc, a dinuclear Cu(II) complex of the neutral GFA is obtained (electronic structure [Cu(II)-GFA-Cu(II)], two unpaired electrons), and with X = Br a diamagnetic dinuclear Cu(I) complex of the dicationic GFA (electronic structure [Cu(I)-GFA(2+)-Cu(I)], closed-shell singlet state)...
November 28, 2015: Dalton Transactions: An International Journal of Inorganic Chemistry
Marisa I S Mendes, Desirée E C Smith, João B Vicente, Isabel Tavares De Almeida, Tawfeg Ben-Omran, Gajja S Salomons, Isabel A Rivera, Paula Leandro, Henk J Blom
The key regulatory point of L-methionine (Met) and L-homocysteine (Hcy) degradation is catalyzed by cystathionine beta-synthase (CBS). CBS deficiency is caused by mutations in CBS gene, often resulting in protein misfolding. The prevalence of CBS deficiency in Qatar is 1/1800, ∼200-fold higher than the worldwide prevalence of 1/344 000. Almost all patients bear the CBS p.R336C variant. More than 20 years ago, it was shown in vitro that two unrelated protein variants with a substitution of an arginine (Arg) residue by cysteine (Cys) could be rescued by cysteamine (mercaptoethylamine), likely via formation of a disulfide between Cys and cysteamine, functionally mimicking the wild-type (WT) Arg side-chain...
December 20, 2015: Human Molecular Genetics
Jens Martens-Lobenhoffer, Stefanie M Bode-Böger, Bernd Clement
The L-arginine metabolites methylated at the guanidino moiety, such as N(G)-monomethyl-L-arginine (LNMMA), asymmetric N(G),N(G)-dimethyl-L-arginine (ADMA), and symmetric N(G),N(G')-dimethyl-L-arginine (SDMA), are long known to be present in human plasma. Far less is known about the structural isomer of LNMMA, N(δ)-monomethyl-L-arginine (δ-MMA). In prior work, it has been detected in yeast proteins, but it has not been investigated in mammalian plasma or cells. In this work, we present a method for the simultaneous and unambiguous quantification of LNMMA and δ-MMA in human plasma that is capable of detecting δ-MMA separately from LNMMA...
January 15, 2016: Analytical Biochemistry
Adrian Westhaus, Eva Maria Blumrich, Ralf Dringen
Metformin is the most frequently used drug for the treatment of type 2 diabetes in humans. However, only little is known about effects of metformin on brain metabolism. To investigate potential metabolic consequences of an exposure of brain cells to metformin, we incubated rat astrocyte-rich primary cultures with this compound. Metformin in concentrations of up to 30 mM did not acutely compromise the viability of astrocytes, but caused a time- and concentration-dependent increase in cellular glucose consumption and lactate production...
October 3, 2015: Neurochemical Research
Annabelle Biscans, Sonia Rouanet, Jean-Rémi Bertrand, Jean-Jacques Vasseur, Christelle Dupouy, Françoise Debart
We report on the synthesis and properties of oligonucleotides (ONs) with 2'-O-acetalester modifications containing cationic side chains in a prodrug-like approach. In the aim to improve cell penetration and nuclease resistance, various different amino- or guanidino-acetalester were grafted to 2'-OH of uridine and the corresponding phosphoramidites were incorporated into ONs. Introduction of 2'-O-(2-aminomethyl-2-ethyl)butyryloxymethyl (AMEBuOM) modification into 2'-OMe ONs leads to high resistance towards enzymatic degradation and to destabilization of duplexes with complementary RNA strand...
September 1, 2015: Bioorganic & Medicinal Chemistry
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