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1.
Int J Biol Macromol ; 193(Pt A): 672-680, 2021 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-34710478

RESUMO

In this study, we investigated the interaction between myofibrillar proteins (MPs) and selected alcohols (1-pentanol, 1-hexanol, and 1-heptanol). Only 1-heptanol exhibited the binding ability to MPs, and the binding ability significantly increased with increasing protein concentration (p < 0.05). In addition, both static and dynamic quenching occurred during the interaction, with a red shift of the maximum absorption peak in the synchronous fluorescence spectra indicating a change in the microenvironment of the MPs. The results of circular dichroism measurements suggested that the interaction between MPs and 1-heptanol altered the secondary structure of the MPs. Furthermore, thermodynamic analysis showed that hydrogen bonding and van der Waals forces dominated the interaction between MPs and 1-heptanol, which was confirmed by the results of molecular docking/dynamics simulations. This study provides an in-depth understanding of the interaction between MPs and alcohols, which can help to improve the flavor control in meat.


Assuntos
Proteínas de Transporte/química , Heptanol/química , Simulação de Acoplamento Molecular , Proteínas Musculares/química , Miofibrilas/química , Sítios de Ligação , Fenômenos Biofísicos , Dicroísmo Circular , Fluorescência , Ligação de Hidrogênio , Simulação de Dinâmica Molecular , Ligação Proteica , Estrutura Secundária de Proteína , Termodinâmica
2.
Chem Senses ; 45(7): 513-521, 2020 10 09.
Artigo em Inglês | MEDLINE | ID: mdl-32609815

RESUMO

Probing the neural mechanisms that underlie each sensory system requires the presentation of perceptually appropriate stimulus concentrations. This is particularly relevant in the olfactory system as additional odorant receptors typically respond with increasing stimulus concentrations. Thus, perceptual measures of olfactory sensitivity provide an important guide for functional experiments. This study focuses on aliphatic alcohols because they are commonly used to survey neural activity in a variety of olfactory regions, probe the behavioral limits of odor discrimination, and assess odor-structure activity relationships in mice. However, despite their frequent use, a systematic study of the relative sensitivity of these odorants in mice is not available. Thus, we assayed the ability of C57BL/6J mice to detect a homologous series of primary aliphatic alcohols (1-propanol to 1-heptanol) using a head-fixed Go/No-Go operant conditioning assay combined with highly reproducible stimulus delivery. To aid in the accessibility of our data, we report the animal's threshold to each odorant according to the 1) ideal gas condition, 2) nonideal gas condition (factoring in the activity of the odorant in the solvent), and 3) the liquid dilution of the odorant in the olfactometer. Of the odorants tested, mice were most sensitive to 1-hexanol and least sensitive to 1-butanol. These updated measures of murine sensitivity will hopefully guide experimenters in choosing appropriate stimulus concentrations for experiments using these odorants.


Assuntos
Álcoois Graxos/química , Limiar Sensorial/fisiologia , Olfato/fisiologia , 1-Butanol/química , 1-Butanol/farmacologia , 1-Propanol/química , 1-Propanol/farmacologia , Animais , Comportamento Animal/efeitos dos fármacos , Álcoois Graxos/farmacologia , Feminino , Gases/química , Heptanol/química , Heptanol/farmacologia , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Limiar Sensorial/efeitos dos fármacos
3.
J Biol Chem ; 294(44): 16164-16171, 2019 11 01.
Artigo em Inglês | MEDLINE | ID: mdl-31511325

RESUMO

The self-labeling protein HaloTag has been used extensively to determine the localization and turnover of proteins of interest at the single-cell level. To this end, halogen-substituted alkanes attached to diverse fluorophores are commercially available that allow specific, irreversible labeling of HaloTag fusion proteins; however, measurement of protein of interest half-life by pulse-chase of HaloTag ligands is not widely employed because residual unbound ligand continues to label newly synthesized HaloTag fusions even after extensive washing. Excess unlabeled HaloTag ligand can be used as a blocker of undesired labeling, but this is not economical. In this study, we screened several inexpensive, low-molecular-weight haloalkanes as blocking agents in pulse-chase labeling experiments with the cell-permeable tetramethylrhodamine HaloTag ligand. We identified 7-bromoheptanol as a high-affinity, low-toxicity HaloTag-blocking agent that permits protein turnover measurements at both the cell population (by blotting) and single-cell (by imaging) levels. We show that the HaloTag pulse-chase approach is a nontoxic alternative to inhibition of protein synthesis with cycloheximide and extend protein turnover assays to long-lived proteins.


Assuntos
Bioensaio/métodos , Análise de Célula Única/métodos , Coloração e Rotulagem/métodos , Corantes Fluorescentes/metabolismo , Meia-Vida , Heptanol/análogos & derivados , Heptanol/química , Ligantes , Estabilidade Proteica , Proteínas , Proteólise , Rodaminas/química , Rodaminas/metabolismo
4.
J Sep Sci ; 42(2): 566-573, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30371989

RESUMO

In this study, the application of a mixture of organic solvents as a supported liquid membrane for improving the efficiency of the electromembrane extraction procedure was investigated. The extraction process was followed by high-performance liquid chromatography analysis of two model drugs (verapamil and riluzole). In this research, four organic solvents, including 1-heptanol, 1-octanol, 2-nitrophenyl octyl ether, and 2-ethyl hexanol, were selected as model solvents and different binary mixtures (v/v 2:1, 1:1 and 1:2) were used as the supported liquid membrane. The mixture of 2-ethyl hexanol and 1-otanol (v/v, 2:1) improved the extraction efficiency of model drugs by 1.5 to 12 times. It was found that extraction efficiency is greatly influenced by the level of electric current. In this study, for various mixtures of organic solvents, the electric current fluctuated between 50 and 2500 µA, and the highest extraction efficiencies were obtained with low and stable electric currents. Finally, the optimized extraction condition was validated and applied for the determination of model drugs in urine and wastewater samples.


Assuntos
Técnicas Eletroquímicas , Riluzol/isolamento & purificação , Verapamil/isolamento & purificação , Águas Residuárias/química , Poluentes Químicos da Água/isolamento & purificação , 1-Octanol/química , Éteres/química , Heptanol/química , Hexanóis/química , Riluzol/química , Riluzol/urina , Solventes/química , Verapamil/química , Verapamil/urina , Poluentes Químicos da Água/química , Poluentes Químicos da Água/urina
5.
J Agric Food Chem ; 65(47): 10250-10257, 2017 Nov 29.
Artigo em Inglês | MEDLINE | ID: mdl-29108415

RESUMO

2-Mercapto-4-heptanone, 4-mercapto-2-heptanone, and the corresponding mercaptoalcohols, previously identified in cooked red bell pepper (Capsicum annuum), were used as examples to determine the distributions of stereoisomers of naturally occurring polyfunctional thiols. The thiols were isolated using simultaneous distillation-extraction and enriched by affinity chromatography. Enantioselective analysis was performed via multidimensional gas chromatography. For the studied cultivar California Wonder, the investigation of different batches of cooked red bell pepper revealed consistent ratios of the stereoisomers independent of origin and date of purchase. Quantitative estimations showed that the stereoisomers were present in cooked red bell peppers at concentrations in the range of 0.04-10.2 µg/kg. Lower concentrations were observed in cooked green bell peppers. The change from green to red color was also accompanied by shifts in the proportions of stereoisomers in favor of the (S)-enantiomers of the mercaptoheptanones and of the (4S)-configured stereoisomers of 4-mercapto-2-heptanol.


Assuntos
Capsicum/química , Heptanol/química , Extratos Vegetais/química , Culinária , Estereoisomerismo
6.
J Sci Food Agric ; 97(1): 182-190, 2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26970416

RESUMO

BACKGROUND: Six corn starch inclusion complexes were synthesized using small nonpolar or weak polar aroma compounds (heptanolide, carvone and menthone) and small polar aroma compounds (linalool, heptanol and menthol). The objectives of this study were to (a) investigate the ability of corn starch to form inclusion complexes with these aroma compounds and (b) characterize the structure of the corn starch inclusion complexes. RESULTS: The resulting inclusion ratios were 75.6, 36.9, 43.8, 91.9, 67.2 and 54.7% for heptanolide, carvone, menthone, linalool, heptanol and menthol respectively. The inclusion complexes had laminated structures with a certain amount of holes or blocky constructions. Compared with gelatinized corn starch, the transition temperatures, peak temperatures and enthalpies of the inclusion complexes were significantly different. The major peak of CO at 1771 cm-1 and significant peak shifts revealed the formation of inclusion complexes. X-ray diffractometry (XRD) analyses revealed that the crystallinity of corn starch-polar aroma compound inclusion complexes increased. Based on cross-polarization magic angle spinning 13 C nuclear magnetic resonance (CP-MAS 13 C NMR) results, novel peaks and chemical shifts were attributed to the presence of small aroma compounds, thereby confirming the formation of corn starch inclusion complexes. CONCLUSION: Small nonpolar and polar aroma compounds can be complexed to corn starch. © 2016 Society of Chemical Industry.


Assuntos
Amido/química , Monoterpenos Acíclicos , Varredura Diferencial de Calorimetria , Cristalização , Monoterpenos Cicloexânicos , Estabilidade de Medicamentos , Tecnologia de Alimentos , Heptanol/química , Ligação de Hidrogênio , Espectroscopia de Ressonância Magnética , Mentol/química , Microscopia Eletrônica de Varredura , Monoterpenos/química , Sensação , Espectroscopia de Infravermelho com Transformada de Fourier , Amido/ultraestrutura , Termodinâmica , Difração de Raios X
7.
J Chromatogr A ; 1425: 81-7, 2015 Dec 18.
Artigo em Inglês | MEDLINE | ID: mdl-26632516

RESUMO

The first part of the current work systematically described the screening of different types of organic solvents as the supported liquid membrane (SLM) for electromembrane extraction (EME) of acidic drugs, including different alcohols, ketones, and ethers. Seven acidic drugs with a wide logP range (1.01-4.39) were selected as model substances. For the first time, the EME recovery of acidic drugs and system-current across the SLM with each organic solvent as SLM were investigated and correlated to relevant solvent properties such as viscosity and Kamlet and Taft solvatochromic parameters. Solvents with high hydrogen bonding acidity (α) and dipolarity-polarizability (π*) were found to be successful SLMs, and 1-heptanol was the most efficient candidate, which provided EME recovery in the range of 94-110%. Both hydrogen bonding interactions, dipole-dipole interactions, and hydrophobic interactions were involved in stabilizing the deprotonated acidic analytes (with high hydrogen bonding basicity and high dipole moment) during mass transfer across the SLM. The efficiency of the extraction normally decreased with increasing hydrocarbon chain length of the SLM, which was mainly due to increasing viscosity and decreasing α and π* values. The system-current during EME was found to be dependent on the type and the volume of the SLM. In contact with human plasma, an SLM of pure 1-heptanol was unstable, and to improve stability, 1-heptanol was mixed with 2-nitrophenyl octyl ether (NPOE). With this SLM, exhaustive EME was performed from diluted human plasma, and the recoveries of five out of seven analytes were over 91% after 10min EME. This approach was evaluated using HPLC-UV, and the evaluation data were found to be satisfactory.


Assuntos
Membranas Artificiais , Preparações Farmacêuticas/sangue , Solventes/química , Cromatografia Líquida de Alta Pressão , Técnicas Eletroquímicas , Éteres/química , Heptanol/química , Humanos , Ligação de Hidrogênio
8.
Insect Mol Biol ; 24(5): 528-38, 2015 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-26152502

RESUMO

Odorant-binding proteins (OBPs) play an important role in insect olfactory processes and are thought to be responsible for the transport of pheromones and other semiochemicals across the sensillum lymph to the olfactory receptors within the antennal sensilla. As an important general odorant binding protein in the process of olfactory recognition, LstiGOBP1 of Loxostege sticticalis L. has been shown to have good affinity to various plant volatiles. However, the binding specificity of LstiGOBP1 should be further explored in order to better understand the olfactory recognition mechanism of L. sticticalis. In this study, real-time PCR experiments indicated that LstiGOBP1 was expressed primarily in adult antennae. Homology modelling and molecular docking were then conducted on the interactions between LstiGOBP1 and 1-heptanol to understand the interactions between LstiGOBP1 and their ligands. Hydrogen bonds formed by amino acid residues might be crucial for the ligand-binding specificity on molecular docking, a hypothesis that was tested by site-directed mutagenesis. As predicted binding sites for LstiGOBP1, Thr15, Trp43 and Val14 were replaced by alanine to determine the changes in binding affinity. Finally, fluorescence assays revealed that the mutants Thr15 and Trp43 had significantly decreased binding affinity to most odours; in mutants that had two-site mutations, the binding to the six odours that were tested was completely abolished. This result indicates that Thr15 and Trp43 were involved in binding these compounds, possibly by forming multiple hydrogen bonds with the functional groups of the ligands. These results provide new insights into the detailed chemistry of odours' interactions with proteins.


Assuntos
Proteínas de Artrópodes/metabolismo , Mariposas/genética , Odorantes , Receptores Odorantes/genética , Sequência de Aminoácidos , Animais , Antenas de Artrópodes/metabolismo , Proteínas de Artrópodes/química , Feminino , Perfilação da Expressão Gênica , Heptanol/química , Masculino , Simulação de Acoplamento Molecular , Dados de Sequência Molecular , Mariposas/metabolismo , Mutagênese Sítio-Dirigida , Ligação Proteica , Receptores Odorantes/química , Receptores Odorantes/metabolismo
9.
J Food Sci ; 80(7): C1476-89, 2015 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-26087889

RESUMO

UNLABELLED: Enzymatic extrusion, instead of traditional steam cooking, to treat rice is an efficient and alternative pretreatment for Chinese rice wine fermentation. In order to determine the formation of volatiles in enzymatic extrusion-processed rice wine (EE), and to confirm its characteristic flavor compounds, headspace solid-phase micro-extraction followed by GC-MS was used. A total of 66 volatile compounds were identified in EE. During fermentation, most volatiles generated from enzymatic extruded rice had the similar trends with those from steam-cooked rice, but the differences in the concentration of volatiles indicated a changed balance of flavors release caused by enzymatic extrusion. Besides, the concentrations and sorts of volatiles in EEs fermented from different rice particle sizes, were not dramatically different. By principal component analysis, EE could be distinctly separated from other traditional Chinese rice wines according to its characteristic volatiles, namely, 2-heptanol, 1-octen-3-ol, ethyl 4-hydroxybenzoate, methylpentyl 2-propenoate, γ-hexalactone, and 4-vinylguaiacol. PRACTICAL APPLICATION: Enzymatic extrusion liquefaction has been a popular thermal treatment for cereals, and gradually being applied in fermentation and liquor-making industry all over the world. The characterization of volatile flavor compounds in Chinese rice wine processed by enzymatic extrusion liquefaction pretreatment, might be made use not only for a better understanding of this new-type rice wine, but for the further utilization of enzymatic extrusion in other wine or alcohol production as well.


Assuntos
Fermentação , Aromatizantes/análise , Oryza , Vinho/análise , Culinária , Cromatografia Gasosa-Espectrometria de Massas , Guaiacol/análogos & derivados , Guaiacol/química , Heptanol/química , Hidroxibenzoatos/química , Lactonas/química , Octanóis/química , Parabenos/química , Tamanho da Partícula , Extração em Fase Sólida , Microextração em Fase Sólida , Paladar , Compostos Orgânicos Voláteis/análise
10.
Environ Sci Technol ; 49(13): 7717-25, 2015 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-26010217

RESUMO

A kinetic study of the gas-phase reactions of OH radicals with three unsaturated biogenic alcohols, (E)-3-hexen-1-ol, (Z)-3-hepten-1-ol, and (Z)-3-octen-1-ol, has been performed. The rate coefficients obtained are (in units of 10(-10) cm(3) molecule(-1) s(-1)) k1 (OH + (E)-CH2(OH)CH2CH═CHCH2CH3) = (1.14 ± 0.14), k2 (OH + (Z)-CH2(OH)CH2CH═CHCH2CH2CH3) = (1.28 ± 0.23), and k3 (OH + (Z)-CH2(OH)CH2CH═CHCH2CH2CH2CH3) = (1.49 ± 0.35). In addition, a product study on the reactions of OH with (E)-3-hexen-1-ol and (Z)-3-hepten-1-ol is reported. All the experiments were performed at (298 ± 2) K and 1 atm of NOx-free air in a 1080 L photoreactor with in situ FTIR detection of organics. This work constitutes the first kinetic study of the reactions of OH radicals with (Z)-3-hepten-1-ol and (Z)-3-octen-1-ol as well as the first determination of the fate of the hydroxy alkoxy radicals formed in the title reactions. An analysis of the available rates of addition of OH and Cl to the double bond of different unsaturated alcohols at 298 K has shown that they can be related by the expression log kOH = (0.29 ± 0.04) log kCl - 10.8. The atmospheric lifetimes of the alcohols studies were estimated to be around 1 h for reaction with OH radicals. The products formed in the title reactions are mainly carbonylic compounds that can contribute to the formation of ozone and PANs-type compounds in the troposphere.


Assuntos
Atmosfera/química , Heptanol/análogos & derivados , Hexanóis/química , Radical Hidroxila/química , Octanóis/química , Álcoois/química , Heptanol/química , Cinética , Relação Estrutura-Atividade , Termodinâmica
11.
Biomacromolecules ; 16(6): 1827-36, 2015 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-25961760

RESUMO

n-Heptyl α-d-mannose (HM) is a nanomolar antagonist of FimH, a virulence factor of E. coli. Herein we report on the construction of multivalent HM-based glycopolymers as potent antiadhesives of type 1 piliated E. coli. We investigate glycopolymer/FimH and glycopolymer/bacteria interactions and show that HM-based glycopolymers efficiently inhibit bacterial adhesion and disrupt established cell-bacteria interactions in vitro at very low concentration (0.1 µM on a mannose unit basis). On a valency-corrected basis, HM-based glycopolymers are, respectively, 10(2) and 10(6) times more potent than HM and d-mannose for their capacity to disrupt the binding of adherent-invasive E. coli to T84 intestinal epithelial cells. Finally, we demonstrate that the antiadhesive capacities of HM-based glycopolymers are preserved ex vivo in the colonic loop of a transgenic mouse model of Crohn's disease. All together, these results underline the promising scope of HM-based macromolecular ligands for the antiadhesive treatment of E. coli induced inflammatory bowel diseases.


Assuntos
Proteínas de Fímbrias/antagonistas & inibidores , Mucosa Intestinal/efeitos dos fármacos , Polissacarídeos Bacterianos/farmacologia , Adesinas de Escherichia coli , Animais , Adesão Celular/efeitos dos fármacos , Escherichia coli/patogenicidade , Células HeLa , Heptanol/química , Humanos , Doenças Inflamatórias Intestinais/microbiologia , Manose/química , Camundongos , Polissacarídeos Bacterianos/química
12.
Talanta ; 134: 98-104, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-25618645

RESUMO

An efficient, simple and fast low-density solvent based dispersive liquid-liquid microextraction (LDS-DLLME) followed by vortex-assisted dispersive solid phase extraction (VA-D-SPE) has been developed as a new approach for extraction and preconcentration of aflatoxin M1 in milk samples prior to its micelle enhanced spectrofluorimetic determination. In this LDS-DLLME coupled VA-D-SPE method, milk samples were first treated with methanol/water (80:20, v/v) after removing the fat layer. This solvent was directly used as the dispersing solvent in DLLME along with using 1-heptanol (as a low-density solvent with respect to water) as the extracting solvent. In VA-D-SPE approach, hydrophobic oleic acid modified Fe3O4 nanoparticles were used to retrieve the analyte from the DLLME step. It is considerably that the target of VA-D-SPE was 1-heptanol rather than the aflatoxin M1 directly. The main parameters affecting the efficiency of LDS-DLLME and VA-D-SPE procedures and signal enhancement of aflatoxin M1 were investigated and optimized. Under the optimum conditions, the method was linear in the range from 0.02 to 200 µg L(-1) with the correlation coefficient (R(2)) of 0.9989 and detection limit of 13 ng L(-1). The intra-day precision was 2.9 and 4.3% and the inter-day precision was 2.1 and 3.3% for concentration of 2 and 50 µg L(-1) respectively. The developed method was applied for extraction and preconcentration of AFM1 in three commercially available milk samples and the results were compared with the official AOAC method.


Assuntos
Aflatoxina M1/análise , Poluentes Ambientais/análise , Contaminação de Alimentos/análise , Nanopartículas de Magnetita/química , Leite/química , Adsorção , Aflatoxina M1/química , Animais , Poluentes Ambientais/química , Heptanol/química , Interações Hidrofóbicas e Hidrofílicas , Microextração em Fase Líquida , Nanopartículas de Magnetita/ultraestrutura , Micelas , Microscopia Eletrônica de Transmissão , Octoxinol/química , Ácido Oleico/química , Extração em Fase Sólida , Solventes/química , Espectrometria de Fluorescência , Tensoativos/química
13.
Chembiochem ; 16(1): 77-82, 2015 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-25477295

RESUMO

Most lipases resolve secondary alcohols in accordance with the "Kazlauskas rule" to give the R enantiomers. In a similar manner to other lipases, Candida rugosa lipase (CRL) exhibits R enantioselectivity towards heptan-2-ol, although the enantiomeric ratio (E) is low (E=1.6). However, unexpected enantioselectivity (i.e., S enantioselectivity, E=58) of CRL towards 4-(tert-butoxycarbonylamino)butan-2-ol, which has a similar chain length to heptan-2-ol, has been observed. To develop a deeper understanding of the molecular basis for this unusual enantioselectivity, we have conducted a series of molecular modeling and substrate engineering experiments. The results of these computational and experimental analyses indicated that a hydrogen bond between the Ser450 residue and the nitrogen atom of the carbamate group is critical to stabilize the transition state of the S enantiomer.


Assuntos
Amino Álcoois/química , Candida/química , Proteínas Fúngicas/química , Heptanol/química , Lipase/química , Candida/enzimologia , Ligação de Hidrogênio , Cinética , Modelos Moleculares , Proteínas Recombinantes/química , Estereoisomerismo , Relação Estrutura-Atividade , Especificidade por Substrato
14.
Phys Rev Lett ; 112(9): 098301, 2014 Mar 07.
Artigo em Inglês | MEDLINE | ID: mdl-24655283

RESUMO

Liquids composed of small-molecule monohydroxy alcohols are demonstrated to display rheological behavior typical for oligomeric chains. This observation was made possible by rheological experiments in which more than seven decades in frequency and more than five decades on the mechanical modulus scale are covered. The singly hydrogen-bonded monohydroxy alcohols were chosen because they display significant, but surprisingly poorly understood effects of intermolecular association. Based on the present shear study, one can apply theoretical concepts of polymer science to understand the anomalous physical behavior of a wide range of hydrogen-bonded liquids.


Assuntos
Heptanol/química , Hexanóis/química , Módulo de Elasticidade , Ligação de Hidrogênio , Modelos Moleculares , Reologia/métodos , Viscosidade
15.
J Oleo Sci ; 62(12): 1017-27, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-24292354

RESUMO

Two-component interactions between (perfluorooctyl) heptanol (F8H7OH) and dipalmitoylphosphatidylcholine (DPPC), which is a major component of pulmonary surfactants in mammals, were systematically elucidated using Langmuir monolayers and Langmuir-Blodgett (LB) films of the compounds. The interactions such as the miscibility of the compounds and their phase behavior were examined from thermodynamic and morphological perspectives. The surface pressure (π)-molecular area (A) and surface potential (ΔV)-A isotherms of the binary monolayers containing F8H7OH in different mole fractions (XF8H7OH) were measured simultaneously. The excess Gibbs free energy of mixing of the two components was calculated from the π-A isotherms. The resulting isotherm data were employed to construct a two-dimensional (2D) phase diagram of the system. The phase diagram revealed that the transition pressure as well as the monolayer collapse pressure change with changes in XF8H7OH. These thermodynamic analyses suggested that the miscibility of the two components and the solidification of DPPC monolayers can be induced by the addition of F8H7OH. The phase behavior upon monolayer compression was observed morphologically in situ using Brewster angle microscopy (BAM) and fluorescence microscopy (FM), as well as ex situ using atomic force microscopy (AFM). Interestingly, the AFM-based analysis revealed the formation of monodispersed 2D micelles consisting of F8H7OH at low surface pressures.


Assuntos
1,2-Dipalmitoilfosfatidilcolina/química , Álcoois Graxos/química , Fluorocarbonos/química , Heptanol/química , Surfactantes Pulmonares , Animais , Halogenação , Micelas , Microscopia , Pressão , Propriedades de Superfície , Termodinâmica
16.
Bioresour Technol ; 144: 135-40, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23863873

RESUMO

Alkyl glycosides can be synthesized by glycosidases in organic media with limited amounts of water. These systems, however, limit the solubility of the sugar substrates and decrease reaction yields. Herein we report the enzymatic synthesis of heptyl-ß-glycosides in heptanol catalyzed by a hyperthermophilic ß-glycosidase at 90°C. Our results indicate that dispersion of water in heptanol changes with time producing coalescence of water at the bottom of the reactor, playing a key role in the reaction yield. Water-soluble substrate, enzyme and products are concentrated in the aqueous phase, according to their partition coefficients, promoting side reactions that inactivate the enzyme. Reaction yield of heptyl-ß-glycosides was 35% relative to lactose, at 7% water. The increase in the water phase to 12% diminished the enzyme inactivation and increased the heptyl-ß-glycosides yield to 52%. Surface-active compounds, SDS and octyl glucoside, increased water dispersion but were unable to prevent coalescence.


Assuntos
Biocatálise , Glicosídeo Hidrolases/metabolismo , Glicosídeos/biossíntese , Temperatura , Água/química , Cor , Glicosilação , Heptanol/química , Lactose/metabolismo , Reação de Maillard , Oligossacarídeos/biossíntese , Transição de Fase , Especificidade por Substrato , Fatores de Tempo
17.
J Agric Food Chem ; 61(9): 2062-9, 2013 Mar 06.
Artigo em Inglês | MEDLINE | ID: mdl-23394583

RESUMO

4-Mercapto-2-heptanol, previously described in cooked bell pepper, was used to determine the impact of the stereochemistry on the sensory properties of a thiol with a 1,3-oxygen-sulfur functionality. In addition, the acetyl-derivatives 4-acetylthio-2-heptanol, 4-mercapto-2-heptyl acetate and 4-acetylthio-2-heptyl acetate were investigated. The synthesized stereoisomers were separated via capillary gas chromatography (GC) using chiral stationary phases. The GC orders of elution were determined by assigning the absolute configurations via NMR analysis in combination with lipase-catalyzed kinetic resolutions. Odor thresholds and odor properties were determined by means of GC/Olfactometry. The data revealed that the sensory properties of the investigated compounds are not only significantly influenced by the acetylation but also by the configurations of the two asymmetric centers.


Assuntos
Heptanol/química , Sensação , Compostos de Sulfidrila/química , Acetilação , Cromatografia Gasosa , Espectroscopia de Ressonância Magnética , Odorantes/análise , Olfato , Estereoisomerismo
18.
Stem Cell Res Ther ; 4 Suppl 1: S9, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-24565109

RESUMO

A multiorgan, functional, human in vitro assay system or 'Body-on-a-Chip' would be of tremendous benefit to the drug discovery and toxicology industries, as well as providing a more biologically accurate model for the study of disease as well as applied and basic biological research. Here, we describe the advances our team has made towards this goal, as well as the most pertinent issues facing further development of these systems. Description is given of individual organ models with appropriate cellular functionality, and our efforts to produce human iterations of each using primary and stem cell sources for eventual incorporation into this system. Advancement of the 'Body-on-a-Chip' field is predicated on the availability of abundant sources of human cells, capable of full differentiation and maturation to adult phenotypes, for which researchers are largely dependent on stem cells. Although this level of maturation is not yet achievable in all cell types, the work of our group highlights the high level of functionality that can be achieved using current technology, for a wide variety of cell types. As availability of functional human cell types for in vitro culture increases, the potential to produce a multiorgan in vitro system capable of accurately reproducing acute and chronic human responses to chemical and pathological challenge in real time will also increase.


Assuntos
Técnicas Analíticas Microfluídicas/métodos , Barreira Hematoencefálica/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Células Epiteliais/citologia , Células Epiteliais/metabolismo , Fluoroquinolonas/química , Fluoroquinolonas/toxicidade , Gases/metabolismo , Heptanol/química , Heptanol/toxicidade , Humanos , Pulmão/citologia , Técnicas Analíticas Microfluídicas/instrumentação , Modelos Biológicos , Músculo Esquelético/citologia , Miocárdio/citologia
19.
J Phys Chem A ; 116(24): 6113-26, 2012 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-22316013

RESUMO

The reactions of three unsaturated alcohols (linalool, 6-methyl-5-hepten-2-ol, and 3-methyl-1-penten-3-ol) with ozone and OH radicals have been studied using simulation chambers at T ∼ 296 K and P ∼ 760 Torr. The rate coefficient values (in cm(3) molecule(-1) s(-1)) determined for the three compounds are linalool, k(O3) = (4.1 ± 1.0) × 10(-16) and k(OH) = (1.7 ± 0.3) × 10(-10); 6-methyl-5-hepten-2-ol, k(O3) = (3.8 ± 1.2) × 10(-16) and k(OH) = (1.0 ± 0.3) × 10(-10); and 3-methyl-1-penten-3-ol, k(O3) = (5.2 ± 0.6) × 10(-18) and k(OH) = (6.2 ± 1.8) × 10(-11). From the kinetic data it is estimated that, for the reaction of O(3) with linalool, attack at the R-CH═C(CH(3))(2) group represents around (93 ± 52)% (k(6-methyl-5-hepten-2-ol)/k(linalool)) of the overall reaction, with reaction at the R-CH═CH(2) group accounting for about (1.3 ± 0.5)% (k(3-methyl-1-penten-3-ol)/k(linalool)). In a similar manner it has been calculated that for the reaction of OH radicals with linalool, attack of the OH radical at the R-CH═C(CH(3))(2) group represents around (59 ± 18)% (k(6-methyl-5-hepten-2-ol)/k(linalool)) of the total reaction, while addition of OH to the R-CH═CH(2) group is estimated to be around (36 ± 6)% (k(3-methyl-1-penten-3-ol)/k(linalool)). Analysis of the products from the reaction of O(3) with linalool confirmed that addition to the R-CH═C(CH(3))(2) group is the predominant reaction pathway. The presence of formaldehyde and hydroxyacetone in the reaction products together with compelling evidence for the generation of OH radicals in the system indicates that the hydroperoxide channel is important in the loss of the biradical [(CH(3))(2)COO]* formed in the reaction of O(3) with linalool. Studies on the reactions of O(3) with the unsaturated alcohols showed that the yields of secondary organic aerosols (SOAs) are higher in the absence of OH scavengers compared to the yields in their presence. However, even under low-NO(X) concentrations, the reactions of OH radicals with 3-methyl-1-penten-3-ol and 6-methyl-5-hepten-2-ol will make only a minor contribution to SOA formation under atmospheric conditions. Relatively high yields of SOAs were observed in the reactions of OH with linalool, although the initial concentrations of reactants were quite high. The importance of linalool in the formation of SOAs in the atmosphere requires further investigation. The impact following releases of these unsaturated alcohols into the atmosphere are discussed.


Assuntos
Heptanol/análogos & derivados , Radical Hidroxila/química , Monoterpenos/química , Ozônio/química , Pentanóis/química , Monoterpenos Acíclicos , Gases/química , Heptanol/química
20.
Electrophoresis ; 32(21): 3008-15, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-22002888

RESUMO

Electromembrane extraction (EME) and CE with capacitively coupled contactless conductivity detection (CE-C(4) D) was applied to rapid and sensitive determination of perchlorate in drinking water and environmental samples. Porous polypropylene hollow fiber impregnated with 1-heptanol acted as a supported liquid membrane (SLM) and perchlorate was transported and preconcentrated in the fiber lumen on application of electric field. High selectivity of perchlorate determination and its baseline separation from major inorganic anions was achieved in CE-C(4) D using background electrolyte solution consisting of 7.5 mM L-histidine and 40 mM acetic acid at pH 4.1. The analytical method showed excellent parameters in terms of reproducibility; RSD values for migration times and peak areas at a spiked concentration of 15 µg/L of perchlorate (US EPA recommended limit for drinking water) were below 0.2 and 8.7%, respectively, in all examined water samples. Linear calibration curves were obtained for perchlorate in the concentration range 1-100 µg/L (r(2) ≥0.999) with limits of detection at 1 µg/L for tap water and at 0.25-0.35 µg/L for environmental and bottled potable water samples. Recoveries at 15 µg/L of perchlorate were between 95.9 and 106.7% with minimum and maximum recovery values for snow and bottled potable water samples, respectively.


Assuntos
Fracionamento Químico/métodos , Eletroforese Capilar/métodos , Membranas Artificiais , Percloratos/análise , Água/química , Ácido Acético/química , Fracionamento Químico/instrumentação , Condutividade Elétrica , Eletrólitos/química , Heptanol/química , Histidina/química , Concentração de Íons de Hidrogênio , Percloratos/isolamento & purificação , Chuva/química , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
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