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Adamantane

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101. Pharmacological Characterization of the Spectrum of Antiviral Activity and Genetic Barrier to Drug Resistance of M2-S31N Channel Blockers (Full text)

Pharmacological Characterization of the Spectrum of Antiviral Activity and Genetic Barrier to Drug Resistance of M2-S31N Channel Blockers Adamantanes (amantadine and rimantadine) are one of the two classes of Food and Drug Administration-approved antiviral drugs used for the prevention and treatment of influenza A virus infections. They inhibit viral replication by blocking the wild-type (WT) M2 proton channel, thus preventing viral uncoating. However, their use was discontinued due (...) to widespread drug resistance. Among a handful of drug-resistant mutants, M2-S31N is the predominant mutation and persists in more than 95% of currently circulating influenza A strains. We recently designed two classes of M2-S31N inhibitors, S31N-specific inhibitors and S31N/WT dual inhibitors, which are represented by N-[(5-cyclopropyl-1,2-oxazol-3-yl)methyl]adamantan-1-amine (WJ379) and N-[(5-bromothiophen-2-yl)methyl]adamantan-1-amine (BC035), respectively. However, their antiviral activities against

2016 Molecular pharmacology PubMed abstract

102. Probing Lipophilic Adamantyl Group as the P1-Ligand for HIV-1 Protease Inhibitors: Design, Synthesis, Protein X-ray Structural Studies, and Biological Evaluation (Full text)

Probing Lipophilic Adamantyl Group as the P1-Ligand for HIV-1 Protease Inhibitors: Design, Synthesis, Protein X-ray Structural Studies, and Biological Evaluation A series of potent HIV-1 protease inhibitors with a lipophilic adamantyl P1 ligand have been designed, synthesized, and evaluated. We have developed an enantioselective synthesis of adamantane-derived hydroxyethylamine isosteres utilizing Sharpless asymmetric epoxidation as the key step. Various inhibitors incorporating P1

2016 Journal of medicinal chemistry PubMed abstract

103. Polysaccharide Nanoparticles for Efficient siRNA Targeting in Cancer Cells by Supramolecular pKa Shift (Full text)

assembly constructed by the dual host‒guest interactions of an adamantane-bis(diamine) conjugate (ADA) with cucurbit[6]uril (CB[6]) and a polysaccharide. The potential application of such biocompatible nanostructure was further implemented by the selective transportation of small interfering RNA (siRNA) in a controlled manner. It is demonstrated that the strong encapsulation of the ADA's diammonium tail by CB[6] not only reduced the cytotoxicity of the nano-scaled vehicle but also dramatically enhanced

2016 Scientific reports PubMed abstract

104. Acute myocardial infarction, associated with the use of a synthetic adamantyl-cannabinoid: a case report (Full text)

Acute myocardial infarction, associated with the use of a synthetic adamantyl-cannabinoid: a case report "Legal highs" are novel psychoactive substances that have evaded statutory control. Synthetic cannabinoid compounds with adamantane moieties have recently been identified, which have high potency at target receptors and are undetectable on conventional toxicology testing. However, little is known about any harmful effects, and their potential to cause serious ill health. We describe a case

2016 BMC pharmacology & toxicology PubMed abstract

105. Clinical, epidemiological and virological characteristics of the first detected human case of avian influenza A(H5N6) virus (Full text)

(H5N1) and A/chicken/Jiangxi/12782/2014(H10N6) viruses, respectively. The six internal genes were homologous to avian influenza A (H5N2) viruses isolated in duck from Jiangxi in China. This H5N6 virus has not gained genetic mutations necessary for human infection and was suggested to be sensitive to neuraminidase inhibitors, but resistant to adamantanes. Epidemiological investigation of the exposure history of the patient found that a live poultry market could be the source place of infection

2016 Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases PubMed abstract

106. A targeted nanoglobular contrast agent from host-guest self-assembly for MR cancer molecular imaging (Full text)

and effective cancer molecular MRI. Multiple β-cyclodextrins attached POSS (polyhedral oligomeric silsesquioxane) nanoglobule was used as host molecule. Adamantane-modified macrocyclic Gd(III) contrast agent, cRGD (cyclic RGDfK peptide) targeting ligand and fluorescent probe was used as guest molecules. The targeted host-guest nanoglobular contrast agent cRGD-POSS-βCD-(DOTA-Gd) specifically bond to αvβ3 integrin in malignant 4T1 breast tumor and provided greater contrast enhancement than the corresponding

2016 Biomaterials PubMed abstract

107. Supramolecular Probes for Assessing Glutamine Uptake Enable Semi-Quantitative Metabolic Models in Single Cells (Full text)

Supramolecular Probes for Assessing Glutamine Uptake Enable Semi-Quantitative Metabolic Models in Single Cells We describe a supramolecular surface competition assay for quantifying glutamine uptake from single cells. Cy3-labeled cyclodextrins were immobilized on a glass surface as a supramolecular host/FRET donor, and adamantane-BHQ2 conjugates were employed as the guest/quencher. An adamantane-labeled glutamine analog was selected through screening a library of compounds and validated by cell

2016 Journal of the American Chemical Society PubMed abstract

108. Proteasomal degradation of sphingosine kinase 1 and inhibition of dihydroceramide desaturase by the sphingosine kinase inhibitors, SKi or ABC294640, induces growth arrest in androgen-independent LNCaP-AI prostate cancer cells (Full text)

Proteasomal degradation of sphingosine kinase 1 and inhibition of dihydroceramide desaturase by the sphingosine kinase inhibitors, SKi or ABC294640, induces growth arrest in androgen-independent LNCaP-AI prostate cancer cells Sphingosine kinases (two isoforms termed SK1 and SK2) catalyse the formation of the bioactive lipid sphingosine 1-phosphate. We demonstrate here that the SK2 inhibitor, ABC294640 (3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide) or the SK1/SK2

2016 Oncotarget PubMed abstract

109. Evolution of hierarchical porous structures in supramolecular guest-host hydrogels (Full text)

pair adamantane (Ad-HA, guest) and β-cyclodextrin (CD-HA, host), as well as with methacrylate groups to both tether fluorescent agents and to covalently stabilize the material structure. We observed microporous materials in the hydrated state, which temporally arose from initially homogenous hydrogels composed of the two polymers. Independent fluorescent labeling of Ad-HA and CD-HA demonstrated spatiotemporal co-localization, indicative of guest-host polymer condensation on the microscale

2016 Soft matter PubMed abstract

110. KCNE1 induces fenestration in the Kv7.1/KCNE1 channel complex that allows for highly specific pharmacological targeting (Full text)

for the binding site for adamantane derivatives and their putative access pathway in Kv7.1/KCNE1 channels. The adamantane compounds, exemplified by JNJ303, are highly potent gating modifiers that bind to fenestrations that become available when KCNE1 accessory subunits are bound to Kv7.1 channels. This mode of regulation by auxiliary subunits may facilitate the future development of potent and highly subtype-specific Kv channel inhibitors.

2016 Nature communications PubMed abstract

111. Epoxygenated Fatty Acids Inhibit Retinal Vascular Inflammation (Full text)

(EDPs), were significantly decreased. Exogenous addition of 11,12-EET or 19,20-EDP when combined with 12-(3-adamantane-1-yl-ureido)-dodecanoic acid (AUDA), an inhibitor of epoxide hydrolysis, inhibited VCAM-1 and ICAM-1 expression and protein levels; conversely the diol product of 19,20-EDP hydrolysis, 19,20-DHDP, induced VCAM1 and ICAM1 expression. 11,12-EET and 19,20-EDP also inhibited leukocyte adherence to human retinal microvascular endothelial cell monolayers and leukostasis in an acute mouse

2016 Scientific reports PubMed abstract

112. A self-assembled cyclodextrin nanocarrier for photoreactive squaraine (Full text)

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine Photoreactive squaraines produce cytotoxic oxygen species under irradiation and have significant potential for photodynamic therapy. Herein we report that squaraines can be immobilized on a self-assembled nanocarrier composed of amphiphilic cyclodextrins to enhance their photochemical activity. To this end, a squaraine was equipped with two adamantane moieties that act as anchors for the cyclodextrin vesicle surface

2016 Beilstein journal of organic chemistry PubMed abstract

113. Novel Adamantanyl-Based Thiadiazolyl Pyrazoles Targeting EGFR in Triple-Negative Breast Cancer (Full text)

Novel Adamantanyl-Based Thiadiazolyl Pyrazoles Targeting EGFR in Triple-Negative Breast Cancer The epidermal growth factor receptor (EGFR) is a validated therapeutic target for triple-negative breast cancer (TNBC). In the present study, we synthesize novel adamantanyl-based thiadiazolyl pyrazoles by introducing the adamantane ring to thiazolopyrazoline. On the basis of loss of cell viability in TNBC cells, 4-(adamantan-1-yl)-2-(3-(2,4-dichlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl

2016 ACS Omega PubMed abstract

114. Case series: Antidepressant effects of low-affinity and low-trapping NMDA receptor antagonists did not predict response to ketamine in seven subjects (Full text)

, Non-U.S. Gov't 2016 11 22 England J Psychiatr Res 0376331 0022-3956 0 AZD6925 0 Antidepressive Agents 0 Excitatory Amino Acid Antagonists 0 Receptors, N-Methyl-D-Aspartate 25X51I8RD4 Niacinamide 690G0D6V8H Ketamine PJY633525U Adamantane W8O17SJF3T Memantine IM Adamantane analogs & derivatives therapeutic use Adult Antidepressive Agents therapeutic use Depression drug therapy Excitatory Amino Acid Antagonists therapeutic use Female Humans Ketamine therapeutic use Male Memantine therapeutic use

2016 Journal of psychiatric research PubMed abstract

115. Peramivir injection in the treatment of acute influenza: a review of the literature (Full text)

be considered for treatment and prophylaxis against influenza. Currently available antiviral drugs include neuraminidase inhibitors (NAIs), adamantanes, and a novel polymerase inhibitor (favipiravir). Peramivir is a recently US Food and Drug Administration-approved NAI for the treatment of acute uncomplicated influenza in adults. The chemical structure of peramivir allows it to bind to the influenza neuraminidase with much higher affinity than oseltamivir. Peramivir is effective against a variety

2016 Infection and drug resistance PubMed abstract

116. Inhibition of Soluble Epoxide Hydrolase Limits Mitochondrial Damage and Preserves Function Following Ischemic Injury (Full text)

injury caused by myocardial infarction.sEH null and WT littermate mice were subjected to surgical occlusion of the left anterior descending (LAD) artery or sham operation. A parallel group of WT mice received an sEH inhibitor, trans-4-[4-(3-adamantan-1-y1-ureido)-cyclohexyloxy]-benzoic acid (tAUCB; 10 mg/L) or vehicle in the drinking water 4 days prior and 7 days post-MI. Cardiac function was assessed by echocardiography prior- and 7-days post-surgery. Heart tissues were dissected into infarct, peri

2016 Frontiers in pharmacology PubMed abstract

117. Inhibition of Spinal Ca2+-Permeable AMPA Receptors with Dicationic Compounds Alleviates Persistent Inflammatory Pain without Adverse Effects (Full text)

effects because of the crucial role of CP-AMPARs in synaptic plasticity. Here we have tested whether the inhibition of spinal CP-AMPARs with dicationic compounds, the open-channel antagonists acting in an activity-dependent manner, can relieve inflammatory pain without adverse effects being developed. Dicationic compounds, N1-(1-phenylcyclohexyl)pentane-1,5-diaminium bromide (IEM-1925) and 1-trimethylammonio-5-1-adamantane-methyl-ammoniopentane dibromide (IEM-1460) were applied intrathecally (i.t

2016 Frontiers in cellular neuroscience PubMed abstract

118. Simultaneous expression and transportation of insulin by supramolecular polysaccharide nanocluster (Full text)

Simultaneous expression and transportation of insulin by supramolecular polysaccharide nanocluster Drug/gene transportation systems with stimuli-responsive release behaviors are becoming research hotspots in biochemical and biomedical fields. In this work, a glucose-responsive supramolecular nanocluster was successfully constructed by the intermolecular complexation of phenylboronic acid modified β-cyclodextrin with adamantane modified polyethylenimine, which could be used as a biocompatible

2016 Scientific reports PubMed abstract

119. [New attempt in a benefit evaluation]. (Full text)

0 Glucosides 0 Glycated Hemoglobin A 0 Sulfonylurea Compounds 0 hemoglobin A1c protein, human 6KY687524K glimepiride 9100L32L2N Metformin 9GB927LAJW saxagliptin PJY633525U Adamantane IM Adamantane analogs & derivatives therapeutic use Benzhydryl Compounds therapeutic use Diabetes Mellitus, Type 2 blood drug therapy Dipeptides therapeutic use Drug Therapy, Combination Glucosides therapeutic use Glycated Hemoglobin A analysis Humans Metformin therapeutic use Sulfonylurea Compounds therapeutic use

2016 MMW Fortschritte der Medizin Controlled trial quality: uncertain PubMed abstract

120. The effects and safety of vildagliptin on cardiac function after acute myocardial infarction. (Abstract)

I6B4B2U96P Vildagliptin PJY633525U Adamantane IM Adamantane administration & dosage analogs & derivatives Aged Diabetes Mellitus, Type 2 complications diagnosis drug therapy Echocardiography, Doppler Electrocardiography methods Female Follow-Up Studies Glomerular Filtration Rate drug effects Glycated Hemoglobin A metabolism Heart Function Tests drug effects Humans Incretins administration & dosage Male Middle Aged Myocardial Infarction complications diagnosis drug therapy Natriuretic Peptide, Brain blood

2016 International journal of cardiology Controlled trial quality: uncertain

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