107 results on '"Cook SP"'
Search Results
2. Effectiveness of adenoidectomy and laser tympanic membrane fenestration.
- Author
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Cook SP, Brodsky L, Reilly JS, Deutsch E, Waner M, Brookhouser P, Pizzuto M, Poje C, Nagy M, Shaha SH, Chait D, and Bower C
- Published
- 2001
3. Obstructive sleep apnea in Schwartz-Jampel syndrome.
- Author
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Cook SP and Borkowski WJ
- Published
- 1997
4. Bupivacaine injection to control tonsillectomy pain.
- Author
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Cook SP
- Published
- 2001
- Full Text
- View/download PDF
5. Metal-free, photoinduced remote C(sp 3 )-H borylation.
- Author
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He J and Cook SP
- Abstract
Here, we describe a protocol for the metal-free, photo-induced borylation of unactivated C(sp
3 )-H bonds distal to an O -oxalate hydroxamic ester functionality. The methodology requires only substrate and bis(catecholato)diboron under light irradiation to effect the desired transformation. A range of linear and cyclic tertiary and secondary borylation products are obtained in good yields and high site-selectivity enabling the late-stage C(sp3 )-H borylation of natural product derivatives and drug-like compounds., Competing Interests: The authors declare no conflicts of interest., (This journal is © The Royal Society of Chemistry.)- Published
- 2023
- Full Text
- View/download PDF
6. Fluorosulfonamide-Directed Heteroarylation of Aliphatic C(sp 3 )-H Bonds.
- Author
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Pinter EN, Sheldon ZS, Modak A, and Cook SP
- Abstract
Herein, we describe a formal dehydrogenative cross coupling of heterocycles with unactivated aliphatic amines. The resulting transformation enables the direct alkylation of common heterocycles by merging N-F-directed 1,5-HAT with Minisci chemistry, leading to predictable site selectivity. The reaction provides a direct route for the transformation of simple alkyl amines to value-added products under mild reaction conditions, making this an attractive option for C(sp
3 )-H heteroarylation.- Published
- 2023
- Full Text
- View/download PDF
7. Iron-Catalyzed, Directed Benzylic Borylation.
- Author
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Lee H, He T, and Cook SP
- Subjects
- Catalysis, Boron chemistry, Iron chemistry, Esters chemistry
- Abstract
Herein, we describe an iron-catalyzed benzylic C-H borylation reaction. The reaction targets primary and secondary C(sp
3 )-H bonds to deliver high-value boronic esters under mild conditions with short (7-8 min) reaction times. Functional groups are well tolerated, and complete site selectivity is observed in the presence of multiple benzylic C-H bonds.- Published
- 2023
- Full Text
- View/download PDF
8. Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds.
- Author
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Liu ZY and Cook SP
- Subjects
- Catalysis, Carbon chemistry, Nickel chemistry
- Abstract
Herein, we describe the nickel-catalyzed reductive arylation of remote C(sp
3 )-H bonds with aryl electrophiles. The reaction targets secondary and tertiary C(sp3 )-H bonds to deliver all-carbon quaternary centers. The success of this method relies on a novel amidyl radical precursor that tolerates reducing conditions, namely O -oxalate hydroxamic acid esters.- Published
- 2022
- Full Text
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9. Impact of Biochar on Douglas-Fir Tussock Moth ( Orgyia pseudotsugata Lepidoptera: Erebidae) Larvae Reared on Synthetic Diet.
- Author
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Rice-Marshall S, Cook SP, and Randall J
- Abstract
The use of biochar as a soil amendment in forest ecosystems can be beneficial in the restoration of degraded soils. Forest insects such as the Douglas-fir tussock moth, Orgyia pseudotsugata (McDonnough) (Lepidoptera: Erebidae), may be exposed to biochar when the material is applied. Two experiments were conducted using biochar either (1) applied to the surface of the diet at three rates (0, 5, and 10 mg) or (2) incorporated into synthetic diet at four rates (0, 10, 20, and 40% volume/volume). The objective of both experiments was to determine if biochar on the surface or incorporated into a synthetic diet affected development and survival of O. pseudotsugata larvae. In both experiments, there was a significant decrease in estimated time to larval mortality in all biochar treatments compared to untreated controls. In the surface-applied biochar experiment, there was a significant difference in larval weight gain at day 12 between the control and 10 mg biochar treatments. In the experiment with biochar incorporated into the diet, mean larval weight at day 12 was highest in the low (10%) biochar treatment compared to all other treatments, although weight gain was only significantly different between the low- and high-concentration (40%) biochar treatments. Our results suggest that larvae, feeding on a low amount of biochar in the synthetic diet, may respond by engaging in compensatory feeding behavior. Fewer surviving larvae in the biochar treatment groups may contribute to the lack of significance found in the comparison of weight gain at day 24 in each experiment.
- Published
- 2021
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10. Csp 3 -H Trifluoromethylation of Unactivated Aliphatic Systems.
- Author
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He J, Nguyen TN, Guo S, and Cook SP
- Abstract
A straightforward method for the undirected trifluoromethylation of unactivated methylene units was developed. The reaction proceeds in aqueous acetonitrile with Grushin's reagent, bpyCu(CF
3 )3 , under broad-spectrum white-light irradiation. The trifluoromethylation tolerates a wide range of functional groups including ketones, esters, nitriles, amides, alcohols, and carboxylic acids. The C-H cleavage step is performed via intermolecular H atom abstraction, and the selectivities across a range of methylene units are reported. Mechanistic studies offer a general reaction coordinate for the overall transformation.- Published
- 2021
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11. Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O -Alkyl Thiocarbonates.
- Author
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Liu ZY and Cook SP
- Subjects
- Alcohols chemistry, Catalysis, Methylation, Molecular Structure, Alkenes chemistry, Alkynes chemistry, Copper chemistry, Sulfhydryl Compounds chemistry
- Abstract
The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O -alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.
- Published
- 2021
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- View/download PDF
12. Identification of a Male-Produced Volatile Pheromone for Phymatodes dimidiatus (Coleoptera: Cerambycidae) and Seasonal Flight Phenology of Four Phymatodes Species Endemic to the North American Intermountain West.
- Author
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Lyons-Yerion CD, Barbour JD, Mongold-Diers JA, Williams CJ, and Cook SP
- Subjects
- Animals, Idaho, Male, Pheromones, Reproductive Isolation, Seasons, United States, Coleoptera, Sex Attractants
- Abstract
Research over the last 15 yr has shown widespread pheromone parsimony within the coleopteran family Cerambycidae, with a number of highly conserved pheromone motifs, often shared within and across subfamilies, tribes, and genera. Our goals were to increase our understanding of the evolution of volatile pheromones within the Cerambycidae, their role in reproductive isolation and to identify pheromones for use in the development of lures for monitoring cerambycids. Over 3 yr, we tested 12 compounds known to be cerambycid pheromones as possible attractants at sites across Idaho. This study focused on species within the cerambycine genus Phymatodes (Tribe: Callidiini). We also collected and analyzed headspace volatiles of captured Phymatodes dimidiatus (Kirby). Our results demonstrate that (R)-2-methylbutan-1-ol is a male-produced volatile pheromone for P. dimidiatus. These results are consistent with prior research suggesting that (R)-2-methylbutan-1-ol and (R)-3-hydroxyhexan-2-one, individually or in a blend of both compounds, commonly serve as pheromones for Phymatodes spp. We captured Phymatodes starting in mid-May, continuing through mid-August. Our data indicate that flight periods of Phymatodes spp. in Idaho overlap. These species may be utilizing various mechanisms to ensure reproductive isolation, such as the production of different volatile pheromones, minor components, and/or proportions of components, utilizing different host species and/or host volatiles, differing daily activity periods, and/or occupying different heights in the tree canopy. Our results contribute to the basic understanding of the chemical and behavioral ecology of the Cerambycidae and can be applied to the development of pheromone lures for monitoring of economically important or endangered species., (© The Author(s) 2020. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.)
- Published
- 2020
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13. Cu-Catalyzed C-N Coupling with Sterically Hindered Partners.
- Author
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Modak A, Nett AJ, Swift EC, Haibach MC, Chan VS, Franczyk TS, Shekhar S, and Cook SP
- Abstract
Copper, an earth-abundant metal, has reemerged as a viable alternative to the versatile Pd-catalyzed C-N coupling. Coupling sterically hindered reaction partners, however, remains challenging. Herein, we disclose the discovery and development of a pyrrole-ol ligand to facilitate the coupling of ortho -substituted aryl iodides with sterically hindered amines. The ligand was discovered through a library screening approach and highlights the value of mining heteroatom-rich pharmaceutical libraries for useful ligand motifs. Further evaluation revealed that this ligand is uniquely effective in these challenging transformations. The reaction enables the coupling of sterically hindered primary and secondary amines, anilines, and amides with broad functional group tolerance., Competing Interests: The authors declare the following competing financial interest(s): E.C.S., M.C.H., T.S.F., and S.S. are AbbVie employees and may own AbbVie stocks. A.J.N. and V.S.C. were employees of AbbVie and may own AbbVie stocks. A.J.N. is currently an employee of Dow Chemicals. V.S.C. is currently an employee of Seattle Genetics. A.M. is a postdoctoral associate, and S.P.C. is an Associate Professor at Indiana University and have no conflicts of interest to disclose. The authors wish to acknowledge Dr. Seble Wagaw and Dr. DavidM. Barnes for helpful discussions. S.W. and D.M.B. are AbbVie employees and may own AbbVie stocks.
- Published
- 2020
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14. Assessment of variables that influence agreement between reviewers for Foot & Ankle International.
- Author
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Kwon JY, Gonzalez T, Miller C, Cook SP, Briceno J, Velasco BT, and Thordarson D
- Subjects
- Humans, Orthopedics, Peer Review, Research standards, Periodicals as Topic
- Abstract
Introduction: A common criticism of the peer-review process is the often disparate nature of reviewer recommendations when a decision is rendered which belies the supposed uniformity of the process. The purpose of this investigation was to examine level of agreement between reviewers for Foot & Ankle International (FAI) and analyze variables which may have influenced agreement in order to better understand the peer-review process., Methods: Approval to conduct this investigation was obtained from the Executive Board and Editor in Chief of FAI. All manuscripts submitted to FAI during the calendar year 2016 which underwent formal peer-review were included in the analysis. For each reviewed manuscript, demographic data was collected regarding specific reviewer and manuscript characteristics in a de-identified manner., Results: 442 manuscripts underwent formal blinded peer-review by two independent reviewers during the study period. Only 199 manuscripts (45%) had a decision rendered in which both reviewers agreed on the same initial recommendation. There were no differences in demographic characteristics between the group of reviewers who agreed as compared to those who disagreed on the initial round of peer review. A similar number of indexed peer-reviewed publications between reviewers correlated with increased levels of agreement., Conclusions: During the study period, there was 45% initial agreement between reviewers for FAI when assessing the same manuscript. Aside from research productivity, no other reviewer-specific variables examined in this investigation were found to correlate with agreement. Specific recommendations and changes may be considered to increase the efficiency and effectiveness of the peer-review process., (Copyright © 2019 European Foot and Ankle Society. Published by Elsevier Ltd. All rights reserved.)
- Published
- 2020
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15. N-Directed fluorination of unactivated Csp 3 -H bonds.
- Author
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Pinter EN, Bingham JE, AbuSalim DI, and Cook SP
- Abstract
Site-selective fluorination of aliphatic C-H bonds remains synthetically challenging. While directed C-H fluorination represents the most promising approach, the limited work conducted to date has enabled just a few functional groups as the arbiters of direction. Leveraging insights gained from both computations and experimentation, we enabled the use of the ubiquitous amine functional group as a handle for the directed C-H fluorination of Csp
3 -H bonds. By converting primary amines to adamantoyl-based fluoroamides, site-selective C-H fluorination proceeds under the influence of a simple iron catalyst in 20 minutes. Computational studies revealed a unique reaction coordinate for the catalytic process and offer an explanation for the high site selectivity., Competing Interests: The authors declare no conflicts of interest., (This journal is © The Royal Society of Chemistry.)- Published
- 2019
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16. Copper-Catalyzed, N-Directed Csp 3 -H Trifluoromethylthiolation (-SCF 3 ) and Trifluoromethylselenation (-SeCF 3 ).
- Author
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Modak A, Pinter EN, and Cook SP
- Subjects
- Catalysis, Copper chemistry, Halogenation, Methylation, Organoselenium Compounds chemical synthesis, Sulfhydryl Compounds chemical synthesis, Fluorine chemistry, Organoselenium Compounds chemistry, Sulfhydryl Compounds chemistry
- Abstract
A direct and versatile copper-catalyzed trifluoromethylthiolation and trifluoromethylselenation of primary, secondary, and tertiary aliphatic C-H bonds was developed. The reaction provides direct access to molecules containing these emerging moieties in the presence of a wide range of common functional groups and in complex molecular environments.
- Published
- 2019
- Full Text
- View/download PDF
17. Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification.
- Author
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Groendyke BJ, Modak A, and Cook SP
- Subjects
- Ethers chemistry, Molecular Structure, Sulfides chemistry, Ethers chemical synthesis, Peroxides chemistry, Sulfides chemical synthesis
- Abstract
Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
- Published
- 2019
- Full Text
- View/download PDF
18. Synthesis of Tetrahydroisoquinolines Through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination.
- Author
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Marcyk PT and Cook SP
- Subjects
- Amination, Catalysis, Molecular Structure, Stereoisomerism, Tetrahydroisoquinolines chemistry, Alcohols chemistry, Iron chemistry, Tetrahydroisoquinolines chemical synthesis
- Abstract
Rapid assembly of saturated nitrogen heterocycles-the synthetically more challenging variants of their aromatic relatives-can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.
- Published
- 2019
- Full Text
- View/download PDF
19. 1,2-(Bis)trifluoromethylation of Alkynes: A One-Step Reaction to Install an Underutilized Functional Group.
- Author
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Guo S, AbuSalim DI, and Cook SP
- Subjects
- Catalysis, Methylation, Molecular Structure, Oxidation-Reduction, Alkenes chemistry, Alkynes chemistry, Copper chemistry, Hydrocarbons, Fluorinated chemistry
- Abstract
Modifying the electronic properties of olefins is the quintessential approach to tuning alkene reactivity. In this context, the exploration of trifluoromethyl groups as divergent electronic modifiers has not been considered. In this work, we describe a copper-mediated 1,2-(bis)trifluoromethylation of acetylenes to create E-hexafluorobutenes (E-HFBs) under blue light in a single step. The reaction proceeds with high yield and E/Z selectivity. Since the alkyne captures two trifluoromethyl groups from each molecule of bpyCu(CF
3 )3 , mechanistic studies were conducted to illuminate the role of the reactants. Interestingly, E-HFBs exhibit remarkable stability to standard olefin functionalization reactions in spite of the pendant trifluoromethyl groups. This finding has significant implications for medicine, agroscience, and materials., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)- Published
- 2019
- Full Text
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20. A microdroplet-accelerated Biginelli reaction: mechanisms and separation of isomers using IMS-MS.
- Author
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Sahota N, AbuSalim DI, Wang ML, Brown CJ, Zhang Z, El-Baba TJ, Cook SP, and Clemmer DE
- Abstract
Electrospray ionization (ESI) combined with ion mobility spectrometry (IMS) and mass spectrometry (MS) techniques is used to examine the Biginelli reaction in an ensemble of ions generated from droplets. We find evidence for rapid dihydropyrimidinone formation from condensation of ethyl acetoacetate, benzaldehyde, and urea on the very short timescales associated with the electrospray process (∼10 μs to ∼1.0 ms). Control bulk-solution reactions show no product formation even after several days. This implies that the in-droplet reaction rate is enhanced by an astonishing factor. Examination of the reaction conditions and characterization of the intermediates en route to product shows evidence for variations in the reaction mechanism. IMS separation shows that the Knoevenagel condensation intermediate from benzaldehyde and ethyl acetoacetate exists as both the cis - and trans -isomer, in a ∼5 to 1 ratio. We suggest that the dramatic acceleration arises because of increased reagent confinement as electrosprayed droplets shrink. The ability of IMS-MS to resolve intermediates (including isomers) provides a new means of understanding reaction pathways.
- Published
- 2019
- Full Text
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21. Iron-Catalyzed Hydroamination and Hydroetherification of Unactivated Alkenes.
- Author
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Marcyk PT and Cook SP
- Subjects
- Catalysis, Ligands, Molecular Structure, Alkenes chemistry, Iron chemistry
- Abstract
The hydrofunctionalization of alkenes, explored for over 100 years, offers the potential for a direct, atom-economical approach to value-added products. While thermodynamically favored, the kinetic barrier to such processes necessitates the use of catalysts to control selectivity and reactivity. Modern variants typically rely on noble metals that require different ligands for each class of hydrofunctionalization, thereby limiting generality. This Letter describes a general iron-based system that catalyzes the hydroamination and hydroetherification of simple unactivated olefins.
- Published
- 2019
- Full Text
- View/download PDF
22. Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.
- Author
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Marcyk PT, Jefferies LR, AbuSalim DI, Pink M, Baik MH, and Cook SP
- Subjects
- Molecular Structure, Stereoisomerism, Alcohols chemistry, Sulfonamides chemistry
- Abstract
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Published
- 2019
- Full Text
- View/download PDF
23. Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.
- Author
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Guo S, AbuSalim DI, and Cook SP
- Subjects
- Trifluoroacetic Acid chemistry, Benzene Derivatives chemical synthesis, Hydrocarbons, Fluorinated chemical synthesis, Toluene chemistry
- Abstract
The installation of trifluoromethyl groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. Consequently, the rapid introduction of this critical functional group in a predictable fashion would benefit current practitioners in those fields. This communication describes a mild trifluoromethylation of benzylic C-H bonds with high selectivity for the least hindered hydrogen atom. The reaction provides monotrifluoromethylation and proceeds in an environmentally friendly acetone/water solvent system. The method can be used to install benzylic trifluoromethyl groups on highly functionalized drug molecules.
- Published
- 2018
- Full Text
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24. Recognition Without Words: Using Taste to Explore Survival Processing.
- Author
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Hallock HL, Garman HD, Cook SP, and Gallagher SP
- Abstract
Many educational demonstrations of memory and recall employ word lists and number strings; items that lend themselves to semantic organization and "chunking." By applying taste recall to the adaptive memory paradigm, which evaluates memory from a survival-based evolutionary perspective, we have developed a simple, inexpensive exercise that defies mnemonic strategies. Most adaptive memory studies have evaluated recall of words encountered while imagining survival and non-survival scenarios. Here, we've left the lexical domain and hypothesized that taste memory, as measured by recognition, would be best when acquisition occurs under imagined threat of personal harm, namely poisoning. We tested participants individually while they evaluated eight teas in one of three conditions: in one, they evaluated the toxicity of the tea (survival condition), in a second, they considered the marketability of the tea and, in the third, they evaluated the bitterness of the tea. After a filler task, a surprise recognition task required the participants to taste and identify the eight original teas from a group of 16 that included eight novel teas. The survival condition led to better recognition than the bitterness condition but, surprisingly, it did not yield better recognition than the marketing condition. A second experiment employed a streamlined design more appropriate for classroom settings and failed to support the hypothesis that planning enhanced recognition in survival scenarios. This simple technique has, at least, revealed a robust levels-of-processing effect for taste recognition and invites students to consider the adaptive advantages of all forms of memory.
- Published
- 2017
25. LepNet: The Lepidoptera of North America Network.
- Author
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Seltmann KC, Cobb NS, Gall LF, Bartlett CR, Basham MA, Betancourt I, Bills C, Brandt B, Brown RL, Bundy C, Caterino MS, Chapman C, Cognato A, Colby J, Cook SP, Daly KM, Dyer LA, Franz NM, Gelhaus JK, Grinter CC, Harp CE, Hawkins RL, Heydon SL, Hill GM, Huber S, Johnson N, Kawahara AY, Kimsey LS, Kondratieff BC, Krell FT, Leblanc L, Lee S, Marshall CJ, McCabe LM, McHugh JV, Menard KL, Opler PA, Palffy-Muhoray N, Pardikes N, Peterson MA, Pierce NE, Poremski A, Sikes DS, Weintraub JD, Wikle D, Zaspel JM, and Zolnerowich G
- Subjects
- Animals, Biodiversity, Butterflies, Museums, North America, United States, Lepidoptera
- Abstract
The Lepidoptera of North America Network, or LepNet, is a digitization effort recently launched to mobilize biodiversity data from 3 million specimens of butterflies and moths in United States natural history collections (http://www.lep-net.org/). LepNet was initially conceived as a North American effort but the project seeks collaborations with museums and other organizations worldwide. The overall goal is to transform Lepidoptera specimen data into readily available digital formats to foster global research in taxonomy, ecology and evolutionary biology.
- Published
- 2017
- Full Text
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26. Repetition-lag memory training is feasible in patients with chronic stroke, including those with memory problems.
- Author
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Stamenova V, Jennings JM, Cook SP, Gao F, Walker LA, Smith AM, and Davidson PS
- Subjects
- Aged, Female, Humans, Male, Memory Disorders etiology, Memory Disorders psychology, Middle Aged, Stroke complications, Treatment Outcome, Learning physiology, Memory Disorders rehabilitation, Mental Recall physiology, Stroke psychology, Stroke Rehabilitation methods
- Abstract
Primary Objective: Repetition-lag memory training was developed to increase individuals' use of recollection as opposed to familiarity in recognition memory. The goals of this study were to examine the feasibility of repetition-lag training in patients with chronic stroke and to explore whether the training might show suggestions of transfer to non-trained tasks., Research Design: Quasi-experimental., Methods and Procedures: Patients (n = 17) took part in six repetition-lag training sessions and their gains on the training and non-trained tasks were compared to those of age-matched healthy controls (n = 30)., Main Outcomes and Results: All but two patients completed the training, indicating that the method is feasible with a wide range of patients with stroke. The amount patients gained on the training task was similar to that of healthy controls (that is, the Group × Time interactions were by-and-large not significant), suggesting that patients with stroke might benefit to the same degree as healthy adults from this training. Both groups showed some indication of transfer to the non-trained backward digit span task and visuospatial memory., Conclusions: These findings show that repetition-lag memory training is a possible approach with patients with stroke to enhance recollection. Further research on the method's efficacy and effectiveness is warranted.
- Published
- 2017
- Full Text
- View/download PDF
27. Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination.
- Author
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Groendyke BJ, AbuSalim DI, and Cook SP
- Abstract
This communication describes a mild, amide-directed fluorination of benzylic, allylic, and unactivated C-H bonds mediated by iron. Upon exposure to a catalytic amount of iron(II) triflate (Fe(OTf)
2 ), N-fluoro-2-methylbenzamides undergo chemoselective fluorine transfer to provide the corresponding fluorides in high yield. The reaction demonstrates broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic and computational experiments suggest that the reaction proceeds through short-lived radical intermediates with F-transfer mediated directly by iron.- Published
- 2016
- Full Text
- View/download PDF
28. Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides.
- Author
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Atack TC and Cook SP
- Abstract
The use of low-cost manganese(II) bromide (MnBr2) and tetramethylethylenediamine (TMEDA) catalyzes the cross coupling of (bis)pinacolatodiboron with a wide range of alkyl halides, demonstrating the first manganese-catalyzed coupling with alkyl electrophiles. This method allows access to primary, secondary, and tertiary boronic esters from the parent chlorides, which were previously inaccessible as coupling partners. The reaction proceeds in high yield with as little as 1000 ppm catalyst loading, while 5 mol % can provide high yields in as little as 30 min. Finally, radical-clock experiments revealed that at 0 °C direct borylation outcompetes alternative radical processes, thereby providing synthetically useful, temperature-controlled reaction outcomes.
- Published
- 2016
- Full Text
- View/download PDF
29. Corrigendum: Training Recollection in Healthy Older Adults: Clear Improvements on the Training Task, but Little Evidence of Transfer.
- Author
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Stamenova V, Jennings JM, Cook SP, Walker LA, Smith AM, and Davidson PS
- Abstract
[This corrects the article on p. 898 in vol. 8, PMID: 25477801.].
- Published
- 2015
- Full Text
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30. Training recollection in healthy older adults: clear improvements on the training task, but little evidence of transfer.
- Author
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Stamenova V, Jennings JM, Cook SP, Walker LA, Smith AM, and Davidson PS
- Abstract
Normal aging holds negative consequences for memory, in particular for the ability to recollect the precise details of an experience. With this in mind, Jennings and Jacoby (2003) developed a recollection training method using a single-probe recognition memory paradigm in which new items (i.e., foils) were repeated during the test phase at increasingly long intervals. In previous reports, this method has appeared to improve older adults' performance on several non-trained cognitive tasks. We aimed to further examine potential transfer effects of this training paradigm and to determine which cognitive functions might predict training gains. Fifty-one older adults were assigned to either recollection training (n = 30) or an active control condition (n = 21) for six sessions over 2 weeks. Afterward, the recollection training group showed a greatly enhanced ability to reject the repeated foils. Surprisingly, however, the training and the control groups improved to the same degree in recognition accuracy (d') on their respective training tasks. Further, despite the recollection group's significant improvement in rejecting the repeated foils, we observed little evidence of transfer to non-trained tasks (including a temporal source memory test). Younger age and higher baseline scores on a measure of global cognitive function (as measured by the Montreal Cognitive Assessment tool) and working memory (as measured by Digit Span Backward) predicted gains made by the recollection training group members.
- Published
- 2014
- Full Text
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31. Iron-catalyzed C(sp²)-H alkylation of carboxamides with primary electrophiles.
- Author
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Monks BM, Fruchey ER, and Cook SP
- Subjects
- Alkylation, Aminoquinolines chemistry, Bromides chemistry, Carbon chemistry, Catalysis, Hydrogen chemistry, Amides chemistry, Iron chemistry
- Published
- 2014
- Full Text
- View/download PDF
32. Iron-catalyzed coupling of aryl sulfamates and aryl/vinyl tosylates with aryl Grignards.
- Author
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Agrawal T and Cook SP
- Abstract
The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3·3H2O and the N-heterocyclic carbene ligand IPr·HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.
- Published
- 2014
- Full Text
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33. A unified strategy for iron-catalyzed ortho-alkylation of carboxamides.
- Author
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Fruchey ER, Monks BM, and Cook SP
- Subjects
- Alkylation, Bromides chemistry, Catalysis, Furans chemistry, Iodides chemistry, Organophosphorus Compounds chemistry, Amides chemistry, Aminoquinolines chemistry, Iron chemistry
- Abstract
Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenylphosphino)ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5-10 min.
- Published
- 2014
- Full Text
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34. Iron-catalyzed borylation of alkyl electrophiles.
- Author
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Atack TC, Lecker RM, and Cook SP
- Subjects
- Boronic Acids chemistry, Catalysis, Esters chemistry, Molecular Structure, Boronic Acids chemical synthesis, Esters chemical synthesis, Ferric Compounds chemistry, Hydrocarbons, Halogenated chemistry
- Abstract
The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.
- Published
- 2014
- Full Text
- View/download PDF
35. Iron-catalyzed arene alkylation reactions with unactivated secondary alcohols.
- Author
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Jefferies LR and Cook SP
- Abstract
A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.
- Published
- 2014
- Full Text
- View/download PDF
36. Palladium-catalyzed intramolecular iodine-transfer reactions in the presence of β-hydrogen atoms.
- Author
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Monks BM and Cook SP
- Published
- 2013
- Full Text
- View/download PDF
37. Lifestyle Matters for maintenance of health and wellbeing in people aged 65 years and over: study protocol for a randomised controlled trial.
- Author
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Sprange K, Mountain GA, Brazier J, Cook SP, Craig C, Hind D, Walters SJ, Windle G, Woods R, Keetharuth AD, Chater T, and Horner K
- Subjects
- Age Factors, Aged, Cost-Benefit Analysis, England, Geriatric Assessment, Health Care Costs, Humans, Quality of Life, Quality-Adjusted Life Years, Surveys and Questionnaires, Time Factors, Wales, Aging psychology, Community Health Services economics, Health Services for the Aged economics, Life Style, Mental Health, Occupational Therapy economics, Research Design
- Abstract
Background: Healthy, active ageing is strongly associated with good mental wellbeing which in turn helps to prevent mental illness. However, more investment has been made into research into interventions to prevent mental illness than into those designed to improve mental wellbeing. This applied research programme will provide high quality evidence for an intervention designed to improve and sustain mental wellbeing in older adults., Methods/design: This study was a multi-centre, pragmatic, two-arm, parallel group, individually randomised controlled trial to determine the population benefit of an occupational therapy based intervention for community living people aged 65 years or older. Participants (n = 268) will be identified in one city in the North of England and in North Wales through GP mail-outs, signposting by local authority, primary care staff and voluntary sector organisations and through community engagement. Participants will be randomised to one of two treatment arms: an intervention (Lifestyle Matters programme); or control (routine access to health and social care). All participants will be assessed at baseline, 6 and 24 months post-randomisation. The primary outcome, which is a person reported outcome, is the SF-36 Mental Health dimension at six months post randomisation. Secondary outcome measures have been selected to measure psychosocial, physical and mental health outcomes. They include other dimensions of the SF36, EQ-5D-3L, Brief Resilience Scale, General Perceived Self Efficacy Scale, PHQ-9, de Jong Gierveld Loneliness Scale, Health and Social Care Resource Use and the wellbeing question of the Integrated Household Survey 2011. A cost effectiveness analysis will investigate the incremental cost per Quality Adjusted Life Years (QALYs) of the Lifestyle Matters intervention compared with treatment as usual., Discussion: The questions being posed through this research are important given the increasing numbers of older people, pressure on the public purse and the associated need to support good health in the extended lifespan. The proposed trial will determine the clinical and cost effectiveness of the intervention delivered in a UK context. The results will support commissioners and providers with decisions about implementation., Trial Registration: Current Controlled Trials ISRCTN67209155.
- Published
- 2013
- Full Text
- View/download PDF
38. Palladium-catalyzed alkyne insertion/reduction route to trisubstituted olefins.
- Author
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Fruchey ER, Monks BM, Patterson AM, and Cook SP
- Abstract
A new route to trisubstituted olefins through a palladium-catalyzed alkyne insertion/reduction reaction with unactivated alkyl iodides is reported. The reaction proceeds under mild conditions and tolerates a range of functional groups and substitution patterns. Preliminary mechanistic inquiry suggests that the transformation may proceed through a hybrid radical/organometallic pathway.
- Published
- 2013
- Full Text
- View/download PDF
39. Source memory in normal aging and Parkinson's disease.
- Author
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Davidson PS, Cook SP, McGhan L, Bouchard T, and Camicioli R
- Subjects
- Adult, Aged, Aging pathology, Case-Control Studies, Executive Function, Female, Hippocampus pathology, Humans, Male, Neuroimaging, Parkinson Disease pathology, Aging psychology, Memory, Parkinson Disease psychology
- Abstract
Several theorists have described memory in Parkinson's disease (PD) as involving an amplification of the deficits seen in normal aging, and drawn parallels between PD and frontal lesion patients. Both normal aging and frontal lobe damage impair memory for the context in which one has encountered information (i.e., source memory). We thus sought to determine whether PD patients would show especially poor source memory. We assessed memory for perceptual (voice), spatial (location of loudspeaker), and temporal (list) source memory in 18 PD patients, 23 healthy older adults, and 35 young people. Although both the healthy aged and PD groups performed more poorly than the young on most of the memory tests, the PD patients failed to show significantly greater impairments than the healthy older adults. The PD patients did perform more poorly, however, on a measure of executive function (the Wisconsin Card Sorting Test [WCST]). We discuss potential reasons why PD had a surprisingly minimal effect on source memory in our study, and relate our data to broader theories of memory impairment in Parkinson's disease., (© 2013 The British Psychological Society.)
- Published
- 2013
- Full Text
- View/download PDF
40. The quest for affordable artemisinin.
- Author
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Cook SP
- Subjects
- Animals, Antimalarials chemistry, Antimalarials isolation & purification, Antimalarials therapeutic use, Artemisinins chemistry, Artemisinins isolation & purification, Artemisinins therapeutic use, Chemistry Techniques, Synthetic economics, Humans, Malaria epidemiology, Antimalarials chemical synthesis, Artemisia annua chemistry, Artemisinins chemical synthesis, Drug Costs, Malaria drug therapy, Plasmodium drug effects
- Published
- 2013
- Full Text
- View/download PDF
41. Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.
- Author
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DeLuca RJ, Edwards JL, Steffens LD, Michel BW, Qiao X, Zhu C, Cook SP, and Sigman MS
- Subjects
- Artemisinins chemistry, Catalysis, Ketones chemical synthesis, Ligands, Molecular Structure, Oxidation-Reduction, Alkenes chemistry, Artemisinins chemical synthesis, Ketones chemistry, Organometallic Compounds chemistry, Oxazoles chemistry, Palladium chemistry, Quinolines chemistry
- Abstract
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.
- Published
- 2013
- Full Text
- View/download PDF
42. Learner-to-learner visual acuity screening: a solution for early identification of visual acuity disabilities.
- Author
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Cook SP and Pasio SC
- Subjects
- Cost-Benefit Analysis, Humans, Disability Evaluation, Disabled Persons rehabilitation, Vision Disorders diagnosis, Vision Disorders economics, Vision Disorders rehabilitation, Vision Screening organization & administration, Visual Acuity
- Abstract
Background: The National School Health Policy guidelines (2002) stipulate that primary school learners should have their vision, speech, hearing, mental health, teeth, nutrition and development screened annually. In reality, especially in under-resourced areas such as the Eastern Cape, many learners with disabilities are not identified, with profound consequences for their ability to learn., Method: This article describes a cost-effective and community-empowering solution, Learner-to-Learner Visual Acuity Screening, whereby secondary school learners were trained to conduct basic visual acuity (VA) eye screening for foundation-phase learners., Results: Of a group of Grade R learners, 30% were identified as having impaired VA and referred for ophthalmic or optometric evaluation., Conclusions: This project created greater awareness among learners, parents and teachers regarding abnormal VA and increased interaction between secondary and primary school learners. This simple and cost-effective strategy could be easily and effectively replicated in other schools, helping to address the need for basic eye care.
- Published
- 2013
- Full Text
- View/download PDF
43. Iron-catalyzed cross-coupling reactions of alkyl Grignards with aryl sulfamates and tosylates.
- Author
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Agrawal T and Cook SP
- Subjects
- Catalysis, Combinatorial Chemistry Techniques, Molecular Structure, Palladium chemistry, Temperature, Ferric Compounds chemistry, Fluorides chemistry, Sulfonic Acids chemistry, Tosyl Compounds chemistry
- Abstract
The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and β-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF(3)•3H(2)O was critical to minimize nucleophile isomerization.
- Published
- 2013
- Full Text
- View/download PDF
44. Palladium-catalyzed alkyne insertion/Suzuki reaction of alkyl iodides.
- Author
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Monks BM and Cook SP
- Abstract
A palladium-catalyzed alkyne insertion/Suzuki reaction with unactivated alkyl iodides is described. Under the reaction conditions, selective migratory insertion of alkynes avoids β-hydride elimination and provides a facile synthesis of stereodefined, tetrasubstituted olefins. The transformation offers broad substrate scope for both the alkyl iodide and boron nucleophile. Mechanistic studies have revealed inversion of the stereocenter for the carbon bearing the iodide.
- Published
- 2012
- Full Text
- View/download PDF
45. A concise synthesis of (+)-artemisinin.
- Author
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Zhu C and Cook SP
- Subjects
- Antimalarials chemistry, Artemisinins chemistry, Humans, Malaria drug therapy, Stereoisomerism, Antimalarials chemical synthesis, Artemisia annua chemistry, Artemisinins chemical synthesis
- Abstract
Malaria represents one of the most medically and economically debilitating diseases present in the world today. Fortunately, there exists a highly effective treatment based on the natural product artemisinin. Despite the development of several synthetic approaches to the natural product, a streamlined synthesis that utilizes low-cost chemical inputs has yet to materialize. Here we report an efficient, cost-effective approach to artemisinin. Key to the success of the strategy was the development of mild, complexity-building reaction cascades that allowed the use of readily available, affordable cyclohexenone as the key starting material.
- Published
- 2012
- Full Text
- View/download PDF
46. A reductive-Heck approach to the hydroazulene ring system: a formal synthesis of the englerins.
- Author
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Gao P and Cook SP
- Subjects
- Molecular Structure, Oxidation-Reduction, Sesquiterpenes, Guaiane chemistry, Stereoisomerism, Azulenes chemistry, Sesquiterpenes, Guaiane chemical synthesis
- Abstract
The reduction of a palladium enolate prior to β-hydride elimination provides a unique reaction for the synthesis of the hydroazulene ring system. When combined with a transannular epoxide rearrangement cascade, the reductive-Heck reaction allows rapid entry to the oxo-bridged guaiane core of the englerins.
- Published
- 2012
- Full Text
- View/download PDF
47. A point mutation at F1737 of the human Nav1.7 sodium channel decreases inhibition by local anesthetics.
- Author
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Panigel J and Cook SP
- Subjects
- Amino Acid Substitution genetics, Binding Sites drug effects, Binding Sites genetics, Binding, Competitive genetics, HEK293 Cells, Humans, Ion Channel Gating drug effects, Ion Channel Gating genetics, NAV1.7 Voltage-Gated Sodium Channel, Neural Inhibition drug effects, Neural Inhibition genetics, Nociceptors physiology, Sodium Channels physiology, Anesthetics, Local pharmacology, Drug Resistance genetics, Nociceptors drug effects, Point Mutation genetics, Sodium Channel Blockers pharmacology, Sodium Channels genetics
- Abstract
Voltage-gated sodium channels (VGSC) contribute to the initiation and propagation of action potentials within the nervous system. These channels are important targets for inhibition by several classes of drugs, including antiarrhythmics and local anesthetics. Structural and pharmacological studies have localized the binding of these drugs to a common site near the channel's intracellular pore region. Point mutations within this region disrupt local anesthetic inhibition of cardiac, CNS, and skeletal muscle VGSC subtypes. This study was designed to test whether a similar structural requirement for drug binding exists on the peripheral neuronal VGSC subtype; Na(v)1.7. In support of this hypothesis, an alanine substitution for phenylalanine at position 1737 (F1737A) in the pore lining S6 segment of domain IV in human Na(v)1.7 reduced both use- and state- dependent inhibition of the local anesthetics, lidocaine and tetracaine, by 8-21-fold. We also saw a 2-3-fold reduction in tonic inhibition with the F1737A mutant. The voltage dependence of both activation and inactivation were unaffected by the F1737A mutation, however, fast inactivation kinetics were impaired, such that a significant portion of inward current remained at the end of a 20-ms depolarization. These data suggest that F1737 forms a part of the high affinity binding of local anesthetics as well as mediating inactivation processes of neuronal Na(v)1.7 channels.
- Published
- 2011
- Full Text
- View/download PDF
48. Adaptation of continuous-flow cavity ring-down spectroscopy for batch analysis of δ13C of CO2 and comparison with isotope ratio mass spectrometry.
- Author
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Berryman EM, Marshall JD, Rahn T, Cook SP, and Litvak M
- Subjects
- Animals, Breath Tests methods, Calibration, Carbon Dioxide chemistry, Carbon Dioxide metabolism, Coleoptera metabolism, Least-Squares Analysis, Pinus, Reproducibility of Results, Statistics, Nonparametric, Carbon Dioxide analysis, Carbon Isotopes analysis, Mass Spectrometry methods, Soil chemistry
- Abstract
Measurements of δ(13)C in CO(2) have traditionally relied on samples stored in sealed vessels and subsequently analyzed using magnetic sector isotope ratio mass spectrometry (IRMS), an accurate but expensive and high-maintenance analytical method. Recent developments in optical spectroscopy have yielded instruments that can measure δ(13)CO(2) in continuous streams of air with precision and accuracy approaching those of IRMS, but at a fraction of the cost. However, continuous sampling is unsuited for certain applications, creating a need for conversion of these instruments for batch operation. Here, we present a flask (syringe) adaptor that allows the collection and storage of small aliquots (20-30 mL air) for injection into the cavity ring-down spectroscopy (CRDS) instrument. We demonstrate that the adaptor's precision is similar to that of traditional IRMS (standard deviation of 0.3‰ for 385 ppm CO(2) standard gas). In addition, the concentration precision (±0.3% of sample concentration) was higher for CRDS than for IRMS (±7% of sample concentration). Using the adaptor in conjunction with CRDS, we sampled soil chambers and found that soil-respired δ(13)C varied between two different locations in a piñon-juniper woodland. In a second experiment, we found no significant discrimination between the respiration of a small beetle (~5 mm) and its diet. Our work shows that the CRDS system is flexible enough to be used for the analysis of batch samples as well as for continuous sampling. This flexibility broadens the range of applications for which CRDS has the potential to replace magnetic sector IRMS., (Copyright © 2011 John Wiley & Sons, Ltd.)
- Published
- 2011
- Full Text
- View/download PDF
49. Identification of non-amidine inhibitors of acid-sensing ion channel-3 (ASIC3).
- Author
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Kuduk SD, Chang RK, Di Marco CN, Dipardo RM, Cook SP, Cato MJ, Jovanovska A, Urban MO, Leitl M, Spencer RH, Kane SA, Hartman GD, and Bilodeau MT
- Subjects
- Acid Sensing Ion Channels, Amidines chemistry, Amiloride chemistry, Animals, Nerve Tissue Proteins metabolism, Rats, Sodium Channel Blockers pharmacology, Sodium Channels metabolism, Structure-Activity Relationship, Nerve Tissue Proteins antagonists & inhibitors, Sodium Channel Blockers chemistry
- Abstract
A series of benzothiophene methyl amines were examined in an effort to identify non-amidine chemotypes with reduced polypharmacology from existing leads with the goal of finding potent ASIC3 channel blockers to advance the therapeutic evaluation of ASIC3 inhibition., (Copyright © 2011 Elsevier Ltd. All rights reserved.)
- Published
- 2011
- Full Text
- View/download PDF
50. High concentration electrophysiology-based fragment screen: discovery of novel acid-sensing ion channel 3 (ASIC3) inhibitors.
- Author
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Wolkenberg SE, Zhao Z, Mulhearn JJ, Harrison ST, Sanders JM, Cato MJ, Jovanovska A, Panigel J, Cook SP, Henze DA, Kane SA, Hartman GD, and Barrow JC
- Subjects
- Acid Sensing Ion Channels, Animals, Molecular Structure, Peptide Fragments, Rats, Small Molecule Libraries, Sodium Channels, Drug Discovery, Electrophysiological Phenomena, Nerve Tissue Proteins antagonists & inhibitors
- Abstract
The Merck Fragment Library was screened versus acid-sensing ion channel 3 (ASIC3), a novel target for the treatment of pain. Fragment hits were optimized using two strategies, and potency was improved from 0.7 mM to 3 μM with retention of good ligand efficiency and incorporation of reasonable physical properties, off-target profile, and rat pharmacokinetics., (Copyright © 2011 Elsevier Ltd. All rights reserved.)
- Published
- 2011
- Full Text
- View/download PDF
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