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Triazenes (2):
Recent article
Triazenes
Abstract
An efficient and highly versatile method for the synthesis of diverse regiospecific 1-arylbenzotriazoles being important medicinal scaffolds, by the copper (1) catalysed intramolecular N-arylation of diazoaminobenzenes of 2-haloaryldiazonium salts in PEG-water has been developed. A very simple react...
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PMID: 20820653
PDF is available here.
PDF is available here.
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Abstract
We aimed to investigate the effects of new NO/cyclic guanosine monophosphate (cGMP) pathway-affecting agents at the sheep sphincter of Oddi (SO) in vitro.
Sheep SO rings were mounted in organ baths and tested for isometric tension and cGMP levels in response to 3,3-bis(aminoethyl)-1-hydroxy-2-oxo-1-...
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PMID: 20697210
PDF is available here.
PDF is available here.
Abstract
These results suggest that the reduction in MYPT1 protein contributes to the development of tolerance of pulmonary arteries to NO. This may result from increased degradation of MYPT1 after prolonged PKG activation....
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PMID: 20418385
PDF is available here.
PDF is available here.
Journal of Virology (84)13 2010
Abstract
Rotaviruses are a major cause of acute gastroenteritis in children worldwide. Early stages of rotavirus assembly in infected cells occur in viroplasms. Confocal microscopy demonstrated that viroplasms associate with lipids and proteins (perilipin A, ADRP) characteristic of lipid droplets (LDs). LD-a...
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PMID: 20335253
PDF is available here.
PDF is available here.
Abstract
We designed RB24 to inhibit epidermal growth factor receptor (EGFR) or Her2 phosphorylation and to further degrade upon hydrolysis to 4-(3'-bromophenylamino)-6-aminoquinazoline (RB10; another EGFR/Her2 inhibitor) plus a strong DNA-alkylating species. 6-(3-Acetoxymethyl-3-methyltriazenyl)-4-(3'-bromo...
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PMID: 20348204
PDF is available here.
PDF is available here.
Abstract
Several triazenoindazoles 3a-e and triazinopyrazolopyridines 6a-i were prepared through the reaction of the corresponding 3-amino-4-chloroindazole and 3-aminopyrazolopyridine diazonium salts 2 and 5 with a number of secondary amines. All compounds were evaluated for their in vitro cytotoxic activity...
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PMID: 20607485
PDF is available here.
PDF is available here.
Abstract
A novel protocol for the gold nanoparticles (AuNPs) modification on the electrode surface was proposed, which was based on the self-assembly of AuNPs on the mercapto-diazoaminobenzene monolayer modified electrode. The mercapto-diazoaminobenzene monolayer was obtained by covalent immobilization of 4-...
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PMID: 20207131
PDF is available here.
PDF is available here.
Abstract
We designed AL237, a fluorescent prototype, to degrade into a green fluorescent DNA damaging species and FD105, a blue fluorescent EGFR inhibitor. Here we showed that AL237 damaged DNA in the 12.5 to 50 mumol/L range. Despite its size, it blocked EGFR phosphorylation in an enzyme assay (IC(50) = 0.2...
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PMID: 20354119
PDF is available here.
PDF is available here.
Abstract
A range of triazene derivatives were synthesized and investigated as prodrug candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). The prodrugs contained a tyramine or dopamine promoiety required for tyrosinase activation and this was joined via a urea functional group t...
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PMID: 19386398
PDF is available here.
PDF is available here.
Abstract
Twelve aminoarylazocompounds (A-C) and 46 aryltriazene 7 derivatives (D-G) have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of 10 RNA and DNA viruses. Eight aminoazocompounds and 27 aryltriazene derivatives exhibited ant...
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PMID: 19482481
PDF is available here.
PDF is available here.
Abstract
An in vitro model of mycobacterial growth arrest was developed using Mycobacterium bovis BCG. When an exponentially growing culture was transferred to an evacuated tube, growth continued; treatment with a source of nitric oxide (diethylenetriamine-nitric oxide adduct [DETA-NO] at 50 microM) halted g...
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PMID: 18955516
PDF is available here.
PDF is available here.
Plant, Cell & Environment (31)12 2008
Abstract
Salt stress induced an increase in endogenous carbon monoxide (CO) production and the activity of the CO synthetic enzyme haem oxygenase (HO) in wheat seedling roots. In addition, a 50% CO aqueous solution, applied daily, not only resulted in the enhancement of CO release, but led to a significant r...
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PMID: 18811735
PDF is available here.
PDF is available here.
Abstract
Data from this study indicate that exogenous nitric oxide application did not change the occurence of tympanosclerosis in the rat model. Other cytokine interactions are needed to start the reaction sequence leading to tympanosclerosis....
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PMID: 18945497
PDF is available here.
PDF is available here.
Cancer Letters (271)2 2008
Abstract
We have recently found that a zinc-binding compound, 5-chloro-7-iodo-8-hydroxyquinoline (clioquinol), kills cancer cells by transporting zinc into the cells. We therefore compared the action of clioquinol with two other cytotoxic zinc-binding compounds, N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenedia...
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PMID: 18639975
PDF is available here.
PDF is available here.
Abstract
Our data explain clinical studies describing a short-term but not a long-term benefit of NO treatment for patients with cardiovascular risk factors. The results could be a rational approach to develop a generation of NO donors accomplishing a retarded release from NO donors that mimic the low contin...
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PMID: 18578689
PDF is available here.
PDF is available here.
Abstract
Aminoglycoside mimetics inhibit bacterial translation by interfering with the ribosomal decoding site. To elucidate the structural properties of these compounds important for antibacterial activity, comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (C...
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PMID: 18372201
PDF is available here.
PDF is available here.
Abstract
We have previously shown that NO has stimulatory and inhibitory effects on insulin secretion at low and high concentrations, respectively. The present study investigated effects of NO on K ATP channels of rat beta cells by patch clamp analysis to elucidate the mechanism for the dual effect. NOC7 at...
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PMID: 18239934
PDF is available here.
PDF is available here.
Abstract
We tested the hypothesis that dietary consumption of aldehydes modulates myocardial IR injury and preconditioning. Mice were gavage-fed the alpha, beta-unsaturated aldehyde acrolein (5mg/kg) or water (vehicle) 24h prior to a 30-min coronary artery occlusion and 24-hour reperfusion. Myocardial infarc...
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PMID: 18468618
PDF is available here.
PDF is available here.
Journal of Antibiotics (61)5 2008
Abstract
As previously reported, triacsin C, a selective inhibitor of acyl-CoA synthetase, inhibited the synthesis of cholesteryl ester and triacylglycerol in mouse peritoneal macrophages, leading to a reduction of lipid droplets. Therefore, the in vivo efficacy was studied. Low-density lipoprotein receptor-...
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PMID: 18653998
PDF is available here.
PDF is available here.
Abstract
We tested the hypothesis that upper intestinal lipids activate an intestine-brain-liver neural axis to regulate glucose homeostasis. Here we demonstrate that direct administration of lipids into the upper intestine increased upper intestinal long-chain fatty acyl-coenzyme A (LCFA-CoA) levels and sup...
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PMID: 18401341
PDF is available here.
PDF is available here.
Abstract
We have reexamined this question in mouse islets and determined the role of changes in lipid synthesis in the effects of glucose. Glucose-stimulated insulin secretion (GSIS) and gene expression were examined in islets from C57BL/6 mice or littermates deleted for sterol-regulatory element binding pro...
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PMID: 18178930
PDF is available here.
PDF is available here.
Abstract
We provide evidence that NO enhances calcium-dependent nuclear accumulation and transcriptional activity of NFAT and induces phosphorylation of glycogen synthase kinase-3beta (GSK-3beta) in C2C12 myotubes. The calcium ionophore A23187 (1 microM for 9 h) or thapsigargin (2 microM for 4 h) increased N...
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PMID: 18272817
PDF is available here.
PDF is available here.
Neuroscience Letters (432)3 2008
Abstract
We studied the effects of cytokines on calcium-dependent glutamate release. Cytokines enhanced glutamate release and induced the expression of inducible nitric oxide synthase (iNOS) and the production of nitric oxide (NO). The inhibition of iNOS eliminated the cytokine-induced enhancement of glutama...
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PMID: 18255223
PDF is available here.
PDF is available here.
Abstract
We synthesized three new peptide aldehyde inhibitors linked to the benzamide derivative structure to use their cytotoxic activity against malignant melanoma cells. Of these, 10 displayed the highest cytotoxicity (0.18 +/- 0.16 microM). A radiosynthesis of the iodine aldehyde was performed. Its drug...
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PMID: 18237109
PDF is available here.
PDF is available here.
Nitric oxide does not downregulate Rho-kinase (ROCK-2) expression in rat coronary endothelial cells.
Abstract
We investigated the possible influence of NO on Rho kinase (ROCK-2 isoform) expressions in cultured rat coronary microvascular endothelial cells. The cells were isolated from Wistar rats on a Langendorff system, and were incubated overnight (approximately 16 h) with an NO generator, A-23187 (10 to 1...
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PMID: 18287881
PDF is available here.
PDF is available here.
Muscle & Nerve (37)2 2008
Abstract
We hypothesized that corticosteroid exposure reduces satellite cell activity in skeletal myofibers. Male Swiss-Webster mice were injected daily for 8 weeks with prednisolone (GC) or vehicle (control). Single myofibers were isolated from the gastrocnemius, centrifuged to mechanically activate satelli...
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PMID: 18004769
PDF is available here.
PDF is available here.
Abstract
Our results support a VEGF-dependent induction of Ang-2 in low flow areas, and FOXO1-dependent downregulation of Ang-2 in high flow areas. These data suggest a new mechanism of flow-dependent regulation of vessel stability and differentiation.
(c) 2007 Wiley-Liss, Inc....
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PMID: 17960565
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (72)25 2007
Abstract
A new class of 1,3-disubstituted-triazenes were synthesized by coupling functionalized benzimidazol-2-ylidenes, as their free N-heterocyclic carbenes or generated in situ from their respective benzimidazolium precursors, to various aryl azides in modest to excellent isolated yields (36-99%). Electro...
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PMID: 17608438
PDF is available here.
PDF is available here.
Pharmacological Research (56)4 2007
Abstract
Triazene compounds of clinical interest (i.e. dacarbazine and temozolomide) are a group of alkylating agents with similar chemical, physical, antitumour and mutagenic properties. Their mechanism of action is mainly related to methylation of O(6)-guanine, mediated by methyldiazonium ion, a highly rea...
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PMID: 17897837
PDF is available here.
PDF is available here.
Abstract
We describe the preparation of five triazene-arylene oligomers (3, 4, 7, 8, and 11) and investigations of their folding properties in aqueous solution. These oligomers contain four 2-fold rotors and populate a conformational ensemble comprising at least 10 states. Extensive 1D and 2D NMR studies as...
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PMID: 17696539
PDF is available here.
PDF is available here.
Abstract
We have recently reported that expression of FACL4 is upregulated in about 40% of human hepatocellular carcinoma (HCC) and 50% of HCC cell lines, suggesting that FACL4 may be involved in liver carcinogenesis. In this study, we investigated whether HCC cell growth is regulated by FACL4. Immunoblot an...
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PMID: 17934335
PDF is available here.
PDF is available here.
Abstract
We investigated the role of the intracellular antioxidant glutathione (GSH) in regulating specific signaling events that are associated with NO-mediated cell cycle arrest. Manipulation of intracellular GSH content through pharmacological inhibition of glutamate-cysteine ligase (GCL) indicated that G...
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PMID: 17443686
PDF is available here.
PDF is available here.
Circulation (116)5 2007
Abstract
In contrast to previous reports, we found that basal eNOS activity does not modulate infarct size in the nonpreconditioned state. However, eNOS is obligatorily required for the development of the cardioprotective effects of late PC and acts as the trigger of this process by activating the PKC epsilo...
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PMID: 17606840
PDF is available here.
PDF is available here.
Abstract
We conclude that prolonged NO treatment induces decreased acute NO responsiveness in part by decreasing both sGC expression and sGC-specific activity....
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PMID: 17384083
PDF is available here.
PDF is available here.
Abstract
These studies test the hypothesis that l-glutamine at its physiological plasma concentration, approximately 0.5 mM, can increase tissue content and net synthesis of glutamate in rat aortic segments in vitro, thereby mediating relaxation of the underlying smooth muscle in the elastic reservoir region...
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PMID: 17329397
PDF is available here.
PDF is available here.
Abstract
The photoswitchable N-terminal diazo and triazene-dipeptide aldehydes 8a-d, 10a,b, and 17a,b present predominantly as the (E)-isomer, which purportedly binds deep in the S3 pocket of calpain. All compounds are potent inhibitors of m-calpain, with 8b being the most active (IC50 of 35 nM). The diazo-c...
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PMID: 17497840
PDF is available here.
PDF is available here.
Abstract
We present a detailed analysis of the structural, infrared spectra and visible spectra of the 4-substituted aminoazo-benzenesulfonyl azides. The preparation of 4-sulfonyl azide benzenediazonium chloride with cyclic amines of various ring sizes (pyrrolidine, piperidine, 4-methylpiperidine, N-methylpi...
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PMID: 16965932
PDF is available here.
PDF is available here.
Abstract
We designed 6a-d and 18 to release an inhibitor of EGFR TK and a bifunctional alkylator. The combi-molecules blocked EGFR TK with potency increasing with the basicity of the mustard moiety. They selectively killed cells transfected with EGFR and were potent against the DU145 prostate cancer cells. C...
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PMID: 17472358
PDF is available here.
PDF is available here.
Abstract
We identified long-chain acyl-coenzyme A synthetase 3 (ACSL3) as a major LD-associated protein in the human hepatocyte cell line HuH7. In this study, we investigated whether droplet-associated ACSL is involved in lipid metabolism in LDs. Addition of oleic acid (OA) to culture medium was shown to enh...
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PMID: 17379924
PDF is available here.
PDF is available here.
Nitric Oxide (16)3 2007
Abstract
We evaluated radical scavengers as a regulator for S-thiolation and S-nitrosylation by NO released from NO-generator, 1-hydroxy-2-oxo-3-(N-methyl-3-aminopropyl)-3-methyl-1-triazene (P-NONOate). When glutathione was incubated with P-NONOate in 4% (vol/vol) O(2)-saturated buffer solution (pH 7.4) in t...
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PMID: 17293136
PDF is available here.
PDF is available here.
Cancer Letters (248)1 2007
Abstract
The radiosensitizing effect of nitric oxide (NO) on mouse and human tumor cells with different degrees of malignancy was evaluated. Cells pre-treated with the NO donor diethylenetriamine-NO (DETA-NO), were irradiated with gamma rays. Survival curves were obtained by clonogenicity and fitted to the l...
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PMID: 16899337
PDF is available here.
PDF is available here.
Journal of Antibiotics (60)3 2007
Abstract
Antimalarial activities have been identified in four microbial metabolites through a screening programme of existing compounds in the Kitasato Institute chemical library. Hedamycin showed selective and potent activity against both drug-resistant and drug-sensitive strains of Plasmodium falciparum. S...
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PMID: 17446697
PDF is available here.
PDF is available here.
Abstract
We studied the photodynamic effect on isolated stretch receptor that consists of only two sensory neurons enwrapped by satellite glial cells. Photodynamic therapy (PDT), a potent inducer of oxidative stress, is a prospective method for destruction of brain tumors. PDT induced functional inactivation...
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PMID: 17265456
PDF is available here.
PDF is available here.
Inorganic Chemistry (46)4 2007
Abstract
We report density-functional theory studies of the differing roles of these dithiol-bridging ligands in the infrared spectra of synthetic models and of computational representations of the diiron cluster of the active site. Our analysis shows distinct spectral features associated with the dithiol-br...
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PMID: 17256840
PDF is available here.
PDF is available here.
Abstract
Hartwig-Buchwald amination reactions of bromo- and chloroarenes were performed on solid supports with triazene-linked arenes. Immobilized 2-haloarenes were treated with diverse primary amines and anilines at 100 degrees C under palladium catalysis to yield N-substituted 2-aminoarenes. The latter wer...
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PMID: 17960895
PDF is available here.
PDF is available here.
Abstract
We demonstrate preprotachykinin-A-substance P (PPTA-SP) and activity-dependent neuroprotective protein-vasoactive intestinal peptide (ADNP-VIP) expression pattern using DRG neurons-Schwann cells coculture and axotomy model. In the presence of NGF, DRG cultures showed high levels of PPTA and ADNP mRN...
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PMID: 17952636
PDF is available here.
PDF is available here.
Abstract
A rapid and quantitative method for solid-phase methyl esterification of carboxy groups of various sialylated oligosaccharides has been established. The method employed a triazene derivative, 3-methyl-1-p-tolyltriazene, for facile derivatization of oligosaccharides immobilized onto general solid sup...
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PMID: 17372994
PDF is available here.
PDF is available here.
Abstract
We investigated the effect of NO on histone H2B gene expression in human and murine cell lines. We have shown that treatment of cells with chemical NO donors leads to decreasing the histone H2B mRNA level. Using luciferase assay with reporter gene regulated by H2B gene promoter, we showed that NO re...
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PMID: 17936982
PDF is available here.
PDF is available here.
Abstract
We investigated the effects of fatty acids and glucose on LD formation in a cultured human hepatocyte, HuH7, by adding them to culture media. Fatty acids with carbohydrate chains C12-C18 efficiently induced LDs, but those of C8 and C10 were ineffective. Glucose did not induce LD formation even in th...
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PMID: 17077510
PDF is available here.
PDF is available here.
Carcinogenesis (27)10 2006
Abstract
It is well documented that arachidonic acid (AA) and its metabolites are intimately linked to cancer biology. However, the downstream mechanism(s) that link AA levels to cancer cell proliferation remain to be elucidated. Initial experiments in the current study showed that exogenous AA and inhibitor...
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PMID: 16704987
PDF is available here.
PDF is available here.
Abstract
These data indicate that a low, clinically relevant dose of ketamine offer significant neuroprotection during prolonged exposure to NMDA but not to NOC. Combinations of reduced doses of ketamine and TPS exhibited enhanced neuroprotection against NMDA-induced neurotoxicity. Hence, combinations of the...
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PMID: 16928698
PDF is available here.
PDF is available here.
Immunology Letters (106)2 2006
Abstract
We studied the effect of low concentrations of NO in the IDO activity in the U-937 and THP-1 monocytic cell lines. Results demonstrated that NO caused a bimodal effect in IDO function in IFN-gamma-stimulated monocytic cells: while high micromolar concentrations of the NO donors SIN-1 and DETA-NO dec...
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PMID: 16797727
PDF is available here.
PDF is available here.
Abstract
Hypoxia/reoxygenation (H/R) in vitro induced cerebral endothelial dysfunction is mediated by superoxide production. However, the intracellular pathways involved remain unclear. The present study was designed to investigate the involvement of Rho-kinase and its interaction with nitric oxide (NO) in c...
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PMID: 16891909
PDF is available here.
PDF is available here.
Abstract
We have demonstrated that vascular endothelial growth factor (VEGF) is expressed in capillary pericytes of the developing corpus luteum (CL) and others have shown that basic fibroblast growth factor (FGF2) and angiopoietins (ANGPT) are present in the CL. VEGF and FGF2 target endothelial cells to ini...
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PMID: 16943586
PDF is available here.
PDF is available here.
Abstract
The synthesis, physicochemical characterization and preliminary pharmacological evaluation of the cytotoxic effects of two novel substances, 1-(4-benzoylphenyl)-3,3-dimethyltriazene and 1-(2-benzoylphenyl)-3,3-dimethyltriazene is presented. The cytotoxicity of the novel benzophenone-linked triazenes...
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PMID: 16826969
PDF is available here.
PDF is available here.
Abstract
We investigated the signal mediators and the cellular events involved in the nitric oxide (NO)-induced hepatocyte resistance to oxygen deprivation in isolated hepatocytes treated with the NO donor (Z)-1-(N-methyl-N-[6-(N-methylammoniohexyl)amino])diazen-1-ium-1,2-diolate (NOC-9). NOC-9 greatly induc...
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PMID: 16678013
PDF is available here.
PDF is available here.
Nitric Oxide (14)3 2006
Abstract
We investigated the mechanisms by which nitric oxide (NO) from an NO donor (DETA/NO) regulates proliferation of pheochromocytoma PC12 cells. The NO donor stimulated proliferation at low concentrations, but reversibly and completely inhibited proliferation at higher concentrations. The stimulation (b...
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PMID: 16300973
PDF is available here.
PDF is available here.
Abstract
We aimed to assess intrinsic smooth muscle mechanisms contributing to greater nitric oxide (NO) responsiveness in pulmonary vascular vs. airway smooth muscle. Porcine pulmonary artery smooth muscle (PASM) and tracheal smooth muscle (TSM) strips were used in concentration-response studies to the NO d...
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PMID: 16326756
PDF is available here.
PDF is available here.
Abstract
We conclude that AP severity was significantly diminished by glucocorticoids associated with DETA-NO, with the optimal dose and time point of administration being crucial to provide adequate protection against AP....
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PMID: 16683059
PDF is available here.
PDF is available here.
Neurosurgery (58)5 2006
Abstract
The animal receiving the highest dose of DETA/NO (3.2 mg/kg) died 46 hours after surgery. The remaining animals survived for the planned duration of the study. One animal in the group receiving the 1.9 mg/kg dose experienced a seizure 25 hours after surgery and remained lethargic for 2 days before m...
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PMID: 16639332
PDF is available here.
PDF is available here.