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1.
J Ethnopharmacol ; 250: 112471, 2020 Mar 25.
Artículo en Inglés | MEDLINE | ID: mdl-31837414

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Ocimum basilicum L. is a perennial herb that has been used in traditional Asian Indian medicine for thousands of years as a natural anti-inflammatory, antibiotic, diuretic, and analgesic. AIM OF THE STUDY: The present study was conducted to investigate the analgesic effects of basil essential oil (BEO) in inflammatory pain models and identify underlying mechanisms. We further investigated whether BEO affects physiological pain and motor coordination. MATERIALS AND METHODS: The analgesic effects of BEO were assessed in various mouse experimental pain models using formalin, acetic acid, heat, and carrageenan as stimuli. BEO was administered by intraperitoneal injection or inhalation. The involvement of various pathways in the analgesic effect of BEO was assessed by pretreating mice with selective pharmacological inhibitors, administered intraperitoneally. Opioid pathways were tested using the κ-opioid antagonist 5'-guanidinonaltrindole (GNTI; 0.3 mg/kg), δ-opioid antagonist naltrindole (NTD; 5 mg/kg) and µ-opioid antagonist naloxone (NAL; 8 mg/kg); nitric oxide (NO) pathways were tested using the NO synthase inhibitor N-nitro l-arginine methyl ester (L-NAME; 37.5 mg/kg) and NO precursor L-arginine (L-Arg; 600 mg/kg); and KATP channel pathways were tested using the ATP-sensitive K+ channel blocker, glibenclamide-hippuric acid (GHA, 2 mg/kg). Potential effects of BEO on motor coordination were assessed using a rotarod test. RESULTS: BEO exerted analgesic effects in all pain models. Notably, pretreatment with naltrindole, naloxone, or L-arginine significantly reduced the analgesic effects of BEO in the formalin test. BEO increased mean withdrawal latencies in a thermal plantar test at a high dose, but not at lower doses. BEO had no effect on motor coordination. CONCLUSIONS: Our findings indicate that the analgesic effects of BEO are primarily mediated by delta- and mu-opioid pathways and further suggest that BEO has potential for development as an analgesic agent for the relief of inflammatory pain.


Asunto(s)
Analgésicos/farmacología , Ocimum basilicum/química , Aceites Volátiles/farmacología , Dolor/tratamiento farmacológico , Analgésicos/administración & dosificación , Analgésicos/aislamiento & purificación , Animales , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Inflamación/tratamiento farmacológico , Inflamación/patología , Masculino , Ratones , Ratones Endogámicos C57BL , Aceites Volátiles/administración & dosificación , Aceites Volátiles/aislamiento & purificación , Dolor/fisiopatología , Receptores Opioides delta/efectos de los fármacos , Receptores Opioides delta/metabolismo , Receptores Opioides mu/efectos de los fármacos , Receptores Opioides mu/metabolismo
2.
Org Lett ; 8(24): 5533-6, 2006 Nov 23.
Artículo en Inglés | MEDLINE | ID: mdl-17107065

RESUMEN

We have demonstrated that one-dimensional supramolecular dye assemblies with a uniform diameter can be created by utilizing schizophyllan (SPG) as a one-dimensional host. In the supramolecular nanofibers, the dye molecules are assembled into the different aggregation modes depending on the preparation procedures. The findings establish that SPG is useful for creating the supramolecular nanofibers, where temporal superstructures can be stabilized by the SPG-specific helical higher-order structure. [structure: see text].

3.
Carbohydr Res ; 341(1): 35-40, 2006 Jan 16.
Artículo en Inglés | MEDLINE | ID: mdl-16289495

RESUMEN

(1-->3)-beta-D-Glucans having various functional appendages (lactoside, ferrocene, pyrene, and porphyrin) can be prepared in an convenient, quantitative, and regioselective manner through regioselective bromination-azidation of curdlan to afford 6-azido-6-deoxycurdlan followed by chemoselective [3+2]-cycloadditions with various functional modules bearing a terminal alkyne group. The ability to monitor reaction conversions is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides; the reaction can be readily monitored based on the intensity of azido peaks in the in situ attenuated total reflection infrared spectra.


Asunto(s)
beta-Glucanos/síntesis química , Alquinos/química , Azidas/química , Resonancia Magnética Nuclear Biomolecular , Proteoglicanos , Espectroscopía Infrarroja por Transformada de Fourier , beta-Glucanos/química
4.
Org Biomol Chem ; 3(24): 4321-8, 2005 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-16327892

RESUMEN

Schizophyllan interacts with various 1,4-diphenylbutadiyne derivatives to induce their chirally-twisted packing. A series of referential experiments using other polysaccharides (amylose, pullulan, dextran, etc.) and a carbohydrate-appended detergent (dodecyl-beta-d-glucopyranoside) indicates that these 1,4-diphenylbutadiyne derivatives are accommodated within a tubular cavity constructed by a helical superstructure of schizophyllan. In these 1,4-diphenylbutadiyne derivatives, 1,4-bis(p-propionamidophenyl)butadiyne can be easily polymerized through UV-irradiation, in which schizophyllan acts as a one-dimensional mold to produce the corresponding poly(diacetylene)s with fibrous morphologies. Detailed investigations on this unique approach to prepare the nanofibers revealed that it includes two individual processes, that is, 1) UV-mediated polymerization of encapsulated 1,4-bis(p-propionamidophenyl)butadiyne to produce immature nanofibers and 2) their reorganization through hydrophobic interfiber interactions into ordered nanofibers. The other 1,4-diphenylbutadiyne derivatives could not be polymerized through UV-irradiation, indicating that the p-propionamido-functionalities play substantial roles for a suitable packing of the monomer for the polymerization. The other 1,4-diphenylbutadiyne derivatives, however, can be also polymerized through gamma-ray irradiation in the presence of schizophyllan to give the corresponding poly(diacetylene)-nanofibers, emphasizing the wide applicability of the schizophyllan-based strategy for polymerization of various 1,4-diphenylbutadiyne derivatives.


Asunto(s)
Acetileno/análogos & derivados , Nanoestructuras/efectos de la radiación , Polímeros/química , Sizofirano/química , Acetileno/química , Butadienos/síntesis química , Butadienos/química , Microscopía Electrónica de Transmisión , Estructura Molecular , Nanoestructuras/ultraestructura , Polímero Poliacetilénico , Poliinos , Análisis Espectral , Estereoisomerismo
5.
Chem Commun (Camb) ; (37): 4655-7, 2005 Oct 07.
Artículo en Inglés | MEDLINE | ID: mdl-16175282

RESUMEN

We have demonstrated that the creation of novel silica nanofibers with a uniform diameter is possible by utilizing beta-1,3-glucan polysaccharide as a one-dimensional host for monoalkoxysilane; the finding establishes that beta-1,3-glucan can act not only as a novel one-dimensional host for metal alkoxide polycondensation but also as an interface between inorganic nanofibers and functional organic molecules.

6.
J Am Chem Soc ; 127(16): 5875-84, 2005 Apr 27.
Artículo en Inglés | MEDLINE | ID: mdl-15839686

RESUMEN

We have found that single-chain schizophyllan and curdlan (s-SPG and s-curdlan, respectively) can dissolve as-grown and cut single-walled carbon nanotubes (ag-SWNTs and c-SWNTs, respectively) in aqueous solution. The vis-NIR spectra of the composites suggest that c-SWNTs are dissolved as a bundle, whereas ag-SWNTs exist as one or only a few pieces in the tubular hollow constructed by the helical structure inherent to these beta-1,3-glucans. EDX and CLSM measurements and TEM observation established that the distribution map of these polysaccharides overlaps well with the image of SWNTs, indicating that these two components form a composite. Very interestingly, when c-SWNTs were dissolved with the aid of s-SPG or s-curdlan in water, a clear periodical structure with inclined stripes, as detected by AFM, appeared on the fibrous composite surface. Because this periodical structure has never been recognized for the composites with other water-soluble polymers, one can regard that s-SPG or s-curdlan wraps c-SWNTs constructing a helically twined structure. High-resolution TEM observation of an ag-SWNTs/s-SPG composite gave a clearer image in that two s-SPG chains twine one ag-SWNT and the helical motif is right-handed. When this sample was subjected to the AFM measurement, the composite showed the 2-3 nm height. This height implies that one piece of ag-SWNT is included in the s-SPGs helical structure. As a summary, it has been established that beta-1,3-glucans such as s-SPG and s-curdlan not only dissolve SWNTs but also create a novel superstructure on the surface.


Asunto(s)
Nanotubos de Carbono/química , Sizofirano/química , beta-Glucanos/química , Secuencia de Carbohidratos , Microscopía de Fuerza Atómica , Modelos Moleculares , Datos de Secuencia Molecular , Soluciones , Espectroscopía Infrarroja Corta , Espectrometría Raman , Agua/química
8.
J Am Chem Soc ; 127(13): 4548-9, 2005 Apr 06.
Artículo en Inglés | MEDLINE | ID: mdl-15796500

RESUMEN

Supramolecular chiral insulated molecular wire was constructed by self-assembly of a neutral one-dimensional schizophyllan host and a water-soluble polythiophene guest. The work presented here will not only open a door to a new application of polysaccharides but also provide an important clue to prepare stable supramolecular insulated molecular wires with one-handed helical structure.


Asunto(s)
Polímeros/química , Sizofirano/química , Tiofenos/química , Secuencia de Carbohidratos , Microscopía de Fuerza Atómica , Modelos Moleculares , Datos de Secuencia Molecular , Polímeros/síntesis química , Sizofirano/síntesis química , Solubilidad , Estereoisomerismo , Tiofenos/síntesis química , Agua/química
9.
Chemistry ; 10(20): 5067-75, 2004 Oct 11.
Artículo en Inglés | MEDLINE | ID: mdl-15372647

RESUMEN

The morphology of conjugate polymers (such as poly(ethylenedioxythiophene), poly(pyrrole), and poly(aniline)) can be controlled in their polymerization processes, by applying the concept of the templating method to oxidative polymerization. As oxidative polymerization of these monomers produces cationic intermediates, the anionic assemblies can act as potential templates due to the mutual electrostatic attractive force. Oxidative polymerization of ethylenedioxythiophene (EDOT), pyrrole, and aniline was carried out using helical superstructures of synthetic lipid assemblies as templates. Interestingly, we have found that oxidative polymerization of these monomers results in novel polymeric aggregates, such as a helical-tape structure and an intertwined helical structure, and that both the right-handed and left-handed helical structures can be created by a change in the hydrophilic head groups. This is the first example of helical superstructures composed of conjugate polymers that have been designed utilizing a convenient templating method.

10.
Org Biomol Chem ; 2(8): 1139-44, 2004 Apr 21.
Artículo en Inglés | MEDLINE | ID: mdl-15064789

RESUMEN

It was found that single-walled carbon nanotubes (SWNTs) solubilized into water by complexation with DNA (salmon testes) can be readily deposited on the ITO electrode by electrochemical oxidative polymerization of ethylenedioxythiophene (EDOT). The driving force for this novel deposition is an electrostatic interaction between the anionic charges of wrapping DNA and the cationic charges of poly(EDOT) formed in the oxidative polymerization process. The presence of poly(EDOT), SWNTs and DNA in the composite was confirmed by measurements of UV-Vis, IR, resonance Raman spectra, cyclic voltammetry (CV) and confocal laser scanning microscopy (CLSM). The composite adsorbed a DNA intercalator (ethidium bromide: EB) very efficiently, which is regarded to be further evidence for inclusion of DNA. The surface morphology, characterized by CLSM, SEM and AFM, featured the network structure consisting of 0.5-ca. 10 microm nanorods. Very interestingly, we found that photoexcitation of EB bound to the DNA generates the photocurrent, indicating that the excited energy of EB is injected into SWNTs, which is collected by the electroconductive poly(EDOT) film on the ITO electrode. We believe, therefore, that the present system is a very convenient method to explore new materials related to redox and photochemical functions.


Asunto(s)
Técnicas Biosensibles , Compuestos Bicíclicos Heterocíclicos con Puentes/química , ADN/química , Nanotecnología , Nanotubos de Carbono/química , Polímeros/química , Electroquímica , Microelectrodos , Microscopía Confocal , Oxidación-Reducción , Fotoquímica , Reproducibilidad de los Resultados , Análisis Espectral , Factores de Tiempo
12.
Carbohydr Res ; 339(2): 251-8, 2004 Jan 22.
Artículo en Inglés | MEDLINE | ID: mdl-14698883

RESUMEN

Microscopic studies of the complex between poly(C) and schizophyllan (SPG), employing both AFM and SEM, revealed that the complex takes the same rod-like architecture on the mica surface as those of the renatured SPG and the original triple helix of SPG, indicating that the complex also has a helical structure. The SEM observations showed the helical pattern on the rod surface, only when the sample was metal shadowed. The pitch evaluated from the image is comparable with that obtained from crystallographic data. The ability to visualize the helical structure can be explained from the hypothesis that the platinum grains may assemble on the sample using the molecular surface of the SPG (or complex) as the template.


Asunto(s)
Microscopía de Fuerza Atómica , Poli C/química , Sizofirano/química , Sizofirano/ultraestructura , Conformación de Carbohidratos , Microscopía Electrónica de Rastreo , Modelos Moleculares , Estructura Molecular
13.
Org Biomol Chem ; 1(13): 2343-7, 2003 Jul 07.
Artículo en Inglés | MEDLINE | ID: mdl-12945707

RESUMEN

It was found that [60]fullerene encapsulated in p-sulfonatocalix[8]arene and single-walled carbon nanotubes (SWNTs) solubilized by sodium dodecylsulfate can be readily deposited on the ITO electrode by electrochemical oxidative polymerization of ethylenedioxythiophene (EDOT) without chemical modification of these carbon clusters. The driving force for the deposition is an electrostatic interaction between the anionic complexes and the cationic charges of poly(EDOT) formed in the oxidative polymerization process. The surface morphology was thoroughly characterized by scanning electron micrograph: the [60]fullerene/poly(EDOT) film is covered by nano-particles with 20-100 nm diameters whereas the SWNTs/poly(EDOT) film is covered by nanorods with several microm length and ca. 100 nm diameter. The results indicate that the anionic complexes act as nuclei for the polymer growth in the oxidation polymerization. Interestingly, when these modified ITO electrodes were photoirradiated, the appearance of a photocurrent wave was observed. The action spectra showed that the photoexcited energy of [60]fullerene or SWNTs is efficiently collected by the electroconductive poly(EDOT) film and transferred to the ITO electrode.

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