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[PMID]:29240785
[Au] Autor:Lu W; Hwang JK; Zeng F; Leal WS
[Ad] Endereço:Department of Molecular and Cellular Biology, University of California Davis, Davis, CA, United States of America.
[Ti] Título:DEET as a feeding deterrent.
[So] Source:PLoS One;12(12):e0189243, 2017.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The insect repellent N,N-diethyl-3-methylbenzamide (DEET), is a multimodal compound that acts as a spatial repellent as well as an irritant (contact repellent), thus being perceived by the insect's olfactory and gustatory systems as an odorant and a tastant, respectively. Soon after DEET was developed, almost 6 decades ago, it was reported that it reduced mosquito feeding on blood mixed with this repellent. It is now known that the mosquito proboscis senses contact repellents with the tips (labella) of the labium, which remain in direct contact with the outer layers of the skin, while the stylets, including the feeding deterrent sensor (labrum), penetrate the skin. We designed a behavioral assay that allowed us to measure feeding deterrence without complications from contact or spatial repellency. Using the southern house mosquito, Culex quinquefasciatus, we demonstrate here that when DEET was mixed with blood and covered by Parafilm® layers, the mean number of landings and duration of contacts with surfaces covering blood mixed with DEET or blood plus solvent (dimethyl sulfoxide) did not differ significantly thus implying that DEET did not leak to the outer surface. The feeding times, however, were significantly different. When blood was mixed either with 0.1 or 1% DEET, female southern house mosquitoes spent significantly (P<0.0001) less time feeding than the time spent feeding on blood mixed only with the solvent. By contrast, significant differences in the mean times of feeding on blood containing 1% picaridin and blood plus solvent were significant at 5%, but not at 1% level. Like DEET, the contact repellent and insecticide, permethrin, caused a significant (P<0.0001) reduction in feeding time. We, therefore, concluded, that in this context, DEET, permethrin, and, to a lesser extent, picaridin, act as feeding deterrents.
[Mh] Termos MeSH primário: Culex/efeitos dos fármacos
DEET/farmacologia
Comportamento Alimentar/efeitos dos fármacos
Repelentes de Insetos/farmacologia
[Mh] Termos MeSH secundário: Animais
Culex/fisiologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 134-62-3 (DEET)
[Em] Mês de entrada:1801
[Cu] Atualização por classe:180307
[Lr] Data última revisão:
180307
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171215
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0189243


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[PMID]:28774603
[Au] Autor:Aghdam E; Xiang Y; Sun J; Shang C; Yang X; Fang J
[Ad] Endereço:Department of Civil and Environmental Engineering, Hong Kong University of Science and Technology, Kowloon, Hong Kong, China.
[Ti] Título:DBP formation from degradation of DEET and ibuprofen by UV/chlorine process and subsequent post-chlorination.
[So] Source:J Environ Sci (China);58:146-154, 2017 Aug.
[Is] ISSN:1001-0742
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The formation of disinfection by-products (DBPs) from the degradation of N,N-diethyl-3-methyl benzoyl amide (DEET) and ibuprofen (IBP) by the ultraviolet irradiation (UV)/chlorine process and subsequent post-chlorination was investigated and compared with the UV/H O process. The pseudo first-order rate constants of the degradation of DEET and IBP by the UV/chlorine process were 2 and 3.1 times higher than those by the UV/H O process, respectively, under the tested conditions. This was due to the significant contributions of both reactive chlorine species (RCS) and hydroxyl radicals (HO) in the UV/chlorine process. Trichloromethane, 1,1,1-trichloro-2-propanone and dichloroacetic acid were the major known DBPs formed after 90% of both DEET and IBP that were degraded by the UV/chlorine process. Their yields increased by over 50% after subsequent 1-day post-chlorination. The detected DBPs after the degradation of DEET and IBP comprised 13.5% and 19.8% of total organic chlorine (TOCl), respectively, and the proportions increased to 19.8% and 33.9% after subsequent chlorination, respectively. In comparison to the UV/H O process accompanied with post-chlorination, the formation of DBPs and TOCl in the UV/chlorine process together with post-chlorination was 5%-63% higher, likely due to the generation of more DBP precursors from the attack of RCS, in addition to HO.
[Mh] Termos MeSH primário: DEET/química
Desinfetantes/análise
Ibuprofeno/química
Poluentes Químicos da Água/análise
Purificação da Água/métodos
[Mh] Termos MeSH secundário: Desinfetantes/química
Desinfecção
Halogenação
Peróxido de Hidrogênio
Radical Hidroxila
Raios Ultravioleta
Poluentes Químicos da Água/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Disinfectants); 0 (Water Pollutants, Chemical); 134-62-3 (DEET); 3352-57-6 (Hydroxyl Radical); BBX060AN9V (Hydrogen Peroxide); WK2XYI10QM (Ibuprofen)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170811
[Lr] Data última revisão:
170811
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170805
[St] Status:MEDLINE


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Borges, Ligia Miranda Ferreira
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[PMID]:28495195
[Au] Autor:Ferreira LL; Oliveira Filho JG; Mascarin GM; León AAP; Borges LMF
[Ad] Endereço:Escola de Veterinária e Zootecnia. Universidade Federal de Goiás, Campus II, Samambaia, Cx. Postal 131, CEP: 74001-970, Goiânia, Goiás, Brazil.
[Ti] Título:In vitro repellency of DEET and ß-citronellol against the ticks Rhipicephalus sanguineus sensu lato and Amblyomma sculptum.
[So] Source:Vet Parasitol;239:42-45, 2017 May 30.
[Is] ISSN:1873-2550
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Rhipicephalus sanguineus sensu lato and Amblyomma sculptum can parasite humans and domestic animals and are vectors of pathogens, including zoonoses. Repellents are an important tool of tick control. This study aimed to compare the efficacy of N,N-diethyl- 3-methylbenzamide (DEET), a standard repellent, versus ß-citronellol in a Petri dish bioassay. A semicircle of filter paper (31.8cm ) was treated with 87µl of one of four concentrations (0.200, 0.100, 0.050 and 0.025mg/cm ) of ß-citronellol, DEET or solvent (ethanol). A head-to-head test was developed treating one side with increasing concentrations of ß-citronellol as above mentioned, against the highest concentration of DEET. Besides that a blank assay was performed. Three males and three females were placed in the middle of the plate and their location was evaluated 5, 10 and 30min after the test was initiated. As a result, the time had no significant effect on repellency response of the ticks exposed to both compounds and their concentrations. The repellency response raised according with the increase of concentration. Additionally, our findings indicate that the tick A. sculptum was more sensitive to the compounds tested and ß-citronellol showed a higher efficacy than DEET. In addition, ß-citronellol could be formulated to protect humans and other animals from R. sanguineus s. l. and A. sculptum infestation, as well as the diseases transmitted by these species.
[Mh] Termos MeSH primário: DEET/farmacologia
Repelentes de Insetos/farmacologia
Ixodidae/efeitos dos fármacos
Monoterpenos/farmacologia
[Mh] Termos MeSH secundário: Animais
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 0 (Monoterpenes); 134-62-3 (DEET); P01OUT964K (citronellol)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171031
[Lr] Data última revisão:
171031
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170513
[St] Status:MEDLINE


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[PMID]:28419272
[Au] Autor:Boonyuan W; Sathantriphop S; Tainchum K; Muenworn V; Prabaripai A; Bangs MJ; Chareonviriyaphap T
[Ad] Endereço:Department of Entomology, Faculty of Agriculture, Kasetsart University, Bangkok 10900, Thailand.
[Ti] Título:Insecticidal and Behavioral Avoidance Responses of Anopheles minimus and Culex quinquefasciatus (Diptera: Culicidae) to Three Synthetic Repellents.
[So] Source:J Med Entomol;54(5):1312-1322, 2017 Sep 01.
[Is] ISSN:1938-2928
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Escape responses, knockdown (KD), and toxicity of laboratory strains of Anopheles minimus Theobald and Culex quinquefasciatus Say to three synthetic mosquito repellents, DEET (N, N-diethyl-3-methylbenzamide), IR3535, or picaridin, at 5% v/v concentrations, were evaluated using repellent-treated papers in standard WHO tube assays and an excito-repellency (ER) test chamber system. The tube assays recorded knockdown effects of each repellent immediately after 30-min exposure and the final morality following a 24-h holding period. DEET showed 100% KD at 30 min and complete toxicity at 24 h against both species. Both actions were either minimal or absent for IR3535 and picaridin, respectively. Culex quinquefasciatus showed significantly greater escape with DEET compared with the other compounds in both contact irritancy (excitation) and noncontact spatial repellency trials. Anopheles minimus showed much more pronounced irritancy and repellency flight escape to IR3535 than picaridin. DEET was the most active irritant and repellent compound against Cx. quinquefasciatus. When adjusting contact test responses based on paired noncontact repellency assays, DEET and IR3535 showed much stronger spatial repellent properties than irritancy with An. minimus. Picaridin performed poorly as an irritant or repellent against both species. We conclude that DEET, followed by IR3535, act as strong spatial repellents at 5% concentration. DEET also performs as a strong toxicant. Our findings show that different mosquitoes can respond contrastingly to repellents, thus the importance to test a wider range of species and populations to assess the full range of chemical action.
[Mh] Termos MeSH primário: Anopheles
Culex
DEET
Repelentes de Insetos
Piperidinas
Propionatos
[Mh] Termos MeSH secundário: Animais
Feminino
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 0 (Piperidines); 0 (Propionates); 134-62-3 (DEET); 65GQA237EH (ethyl-3-(N-n-butyl-N-acetyl)aminopropionate); N51GQX0837 (picaridin)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170922
[Lr] Data última revisão:
170922
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170419
[St] Status:MEDLINE
[do] DOI:10.1093/jme/tjx081


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[PMID]:28334229
[Au] Autor:Hughes DT; Pelletier J; Rahman S; Chen S; Leal WS; Luetje CW
[Ad] Endereço:Department of Molecular and Cellular Pharmacology, University of Miami Miller School of Medicine, R-189, PO Box 016189, Miami, FL 33101, USA and.
[Ti] Título:Functional and Nonfunctional Forms of CquiOR91, an Odorant Selectivity Subunit of Culex quinquefasciatus.
[So] Source:Chem Senses;42(4):333-341, 2017 May 01.
[Is] ISSN:1464-3553
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:In Culex quinquefasciatus, CquiOR91 is the ortholog of 2 larvae-specific odorant receptors (ORs) from Anopheles gambiae (Agam\Or40, previously shown to respond to several odorant ligands including the broad-spectrum repellent N,N-diethyl-3-methylbenzamide, DEET) and Aedes aegypti (Aaeg\Or40). When we cloned full-length CquiOR91 from a Culex quinquefasciatus larval head RNA sample, we found 2 alleles of this OR, differing at 9 residues. Functional analysis using the Xenopus oocyte expression system and 2-electrode voltage clamp electrophysiology revealed one allele (CquiOR91.1) to be nonfunctional, whereas the other allele (CquiOR91.2) was functional. Receptors formed by CquiOR91.2 and Cqui\Orco responded to (-)-fenchone, (+)-fenchone, and DEET, similar to what has been reported for Agam\Or40. We also identified 5 novel odorant ligands for the CquiOR91.2 + Cqui\Orco receptor: 2-isobutylthiazole, veratrole, eucalyptol, d-camphor, and safranal, with safranal being the most potent. To explore possible reasons for the lack of function for CquiOR91.1, we generated a series of mutant CquiOR91.2 subunits, in which the residue at each of the 9 polymorphic residue positions was changed from what occurs in CquiOR91.2 to what occurs in CquiOR91.1. Eight of the 9 mutant versions of CquiOR91.2 formed functional receptors, responding to (-)-fenchone. Only the CquiOR91.2 Y183C mutant was nonfunctional. The reverse mutation (C183Y) conferred function on CquiOR91.1 , which became responsive to (-)-fenchone and safranal. These results indicate that the "defect" in CquiOR91.1 that prevents function is the cysteine at position 183.
[Mh] Termos MeSH primário: Culicidae/química
Proteínas de Insetos/genética
Receptores Odorantes/genética
[Mh] Termos MeSH secundário: Alelos
Animais
DEET/metabolismo
Proteínas de Insetos/metabolismo
Ligantes
Mutação
Norbornanos/metabolismo
Subunidades Proteicas
Receptores Odorantes/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Proteins); 0 (Ligands); 0 (Norbornanes); 0 (Protein Subunits); 0 (Receptors, Odorant); 1195-79-5 (fenchone); 134-62-3 (DEET)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:170623
[Lr] Data última revisão:
170623
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170324
[St] Status:MEDLINE
[do] DOI:10.1093/chemse/bjx011


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[PMID]:28202077
[Au] Autor:Kimutai A; Ngeiywa M; Mulaa M; Njagi PG; Ingonga J; Nyamwamu LB; Ombati C; Ngumbi P
[Ad] Endereço:Department of Biological Sciences, University of Kabianga, P.O. Box 2030-20200, Kericho, Kenya. kimutaialbert@yahoo.com.
[Ti] Título:Repellent effects of the essential oils of Cymbopogon citratus and Tagetes minuta on the sandfly, Phlebotomus duboscqi.
[So] Source:BMC Res Notes;10(1):98, 2017 Feb 15.
[Is] ISSN:1756-0500
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: The sandfly, Phlebotomus duboscqi is a vector of zoonotic cutaneous leishmaniasis (ZCL) that is an important public health problem in Eastern Africa. Repellents have been used for protection of humans against vectors of ZCL and other vectors that transmit killer diseases including malaria, Rift Valley fever, dengue, and yellow fever. The repellent effects of different doses of the essential oils from the lemon grass, Cymbopogon citratus and Mexican marigold, Tagetes minuta were evaluated in a two-chamber bioassay against 3- to 7-day-old unfed females of P. duboscqi in the laboratory. The results were compared with those that were obtained when test animals were treated with an equivalent dose of diethyl-3-methylbenzamide, which is a repellent that is commonly used as a positive control. RESULTS: Overall, percentage repellency increased with increasing doses of the essential oils while biting rates decreased with increasing concentrations of the oils. Further, the oil of C. citratus was more potent than that of T. minuta with regard to protection time and biting deterrence. The effective doses at 50% (ED ) and at 90% (ED ) for the oil of C. citratus, were 0.04 and 0.79 mg/ml, respectively. Those of the oil of T. minuta were 0.10 and 12.58 mg/ml. In addition, the percentage repellency of 1 mg/ml of the essential oils of C. citratus and T. minuta against sandflies was 100% and 88.89%, respectively. A lower dose of 0.5 mg/ml of the oils, elicited 89.13% repellency for C. citratus and 52.22% for T. minuta. CONCLUSION: The laboratory tests showed that the essential oils of the two plants were highly repellent to adult sand flies, P. duboscqi. Thus, the two essential oils are candidate natural repellents that can be used against P. duboscqi due to their high efficacy at very low doses, hence, the envisaged safety in their use over chemical repellents. It remains to carry out clinical studies on human subjects with appropriate formulations of the oils prior to recommending their adoption for use against the sandflies.
[Mh] Termos MeSH primário: Cymbopogon/química
Repelentes de Insetos/farmacologia
Óleos Voláteis/farmacologia
Phlebotomus/fisiologia
Óleos Vegetais/farmacologia
Tagetes/química
[Mh] Termos MeSH secundário: Animais
Bioensaio/métodos
Cricetinae
DEET/farmacologia
Relação Dose-Resposta a Droga
Feminino
Cromatografia Gasosa-Espectrometria de Massas
Seres Humanos
Controle de Insetos/métodos
Insetos Vetores/efeitos dos fármacos
Insetos Vetores/fisiologia
Óleos Voláteis/isolamento & purificação
Óleos Vegetais/isolamento & purificação
Especificidade da Espécie
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 0 (Oils, Volatile); 0 (Plant Oils); 134-62-3 (DEET)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170227
[Lr] Data última revisão:
170227
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170217
[St] Status:MEDLINE
[do] DOI:10.1186/s13104-017-2396-0


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[PMID]:28055518
[Au] Autor:Phillips J
[Ad] Endereço:1 University of Alabama at Birmingham.
[Ti] Título:Rocky Mountain Spotted Fever.
[So] Source:Workplace Health Saf;65(1):48, 2017 Jan.
[Is] ISSN:2165-0969
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The tick-borne disease Rocky Mountain spotted fever (RMSF) can have deadly outcomes unless treated appropriately, yet nonspecific flu-like symptoms complicate diagnosis. Occupational health nurses must have a high index of suspicion with symptomatic workers and recognize that recent recreational or occupational activities with potential tick exposure may suggest RMSF.
[Mh] Termos MeSH primário: Enfermagem do Trabalho/métodos
Febre Maculosa das Montanhas Rochosas/diagnóstico
Picadas de Carrapatos
[Mh] Termos MeSH secundário: Doença Aguda
Antibacterianos/uso terapêutico
DEET/uso terapêutico
Doxiciclina/uso terapêutico
Seres Humanos
Fatores de Risco
Febre Maculosa das Montanhas Rochosas/tratamento farmacológico
Febre Maculosa das Montanhas Rochosas/epidemiologia
Picadas de Carrapatos/prevenção & controle
Picadas de Carrapatos/terapia
Estados Unidos/epidemiologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 134-62-3 (DEET); N12000U13O (Doxycycline)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:170614
[Lr] Data última revisão:
170614
[Sb] Subgrupo de revista:N
[Da] Data de entrada para processamento:170106
[St] Status:MEDLINE
[do] DOI:10.1177/2165079916683711


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[PMID]:28025109
[Au] Autor:Flunker LK; Nutter TJ; Johnson RD; Cooper BY
[Ad] Endereço:Division of Neuroscience, Dept. of Oral and Maxillofacial Surgery, Box 100416, JHMHC, University of Florida College of Dentistry, Gainesville, FL 32610, USA. Electronic address: lflunker@dental.ufl.edu.
[Ti] Título:DEET potentiates the development and persistence of anticholinesterase dependent chronic pain signs in a rat model of Gulf War Illness pain.
[So] Source:Toxicol Appl Pharmacol;316:48-62, 2017 Feb 01.
[Is] ISSN:1096-0333
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Exposure to DEET (N,N-diethyl-meta-toluamide) may have influenced the pattern of symptoms observed in soldiers with GWI (Gulf War Illness; Haley and Kurt, 1997). We examined how the addition of DEET (400mg/kg; 50% topical) to an exposure protocol of permethrin (2.6mg/kg; topical), chlorpyrifos (CP; 120mg/kg), and pyridostigmine bromide (PB;13mg/kg) altered the emergence and pattern of pain signs in an animal model of GWI pain (Nutter et al., 2015). Rats underwent behavioral testing before, during and after a 4week exposure: 1) hindlimb pressure withdrawal threshold; 2) ambulation (movement distance and rate); and 3) resting duration. Additional studies were conducted to assess the influence of acute DEET (10-100µM) on muscle and vascular nociceptor K 7, K , Na 1.8 and Na 1.9. We report that a 50% concentration of DEET enhanced the development and persistence of pain-signs. Rats exposed to all 4 compounds exhibited ambulation deficits that appeared 5-12weeks post-exposure and persisted through weeks 21-24. Rats exposed to only three agents (CP or PB excluded), did not fully develop ambulation deficits. When PB was excluded, rats also developed rest duration pain signs, in addition to ambulation deficits. There was no evidence that physiological doses of DEET acutely modified nociceptor K 7, K , Na 1.8 or Na 1.9 activities. Nevertheless, DEET augmented protocols decreased the conductance of K 7 expressed in vascular nociceptors harvested from chronically exposed rats. We concluded that DEET enhanced the development and persistence of pain behaviors, but the anticholinesterases CP and PB played a determinant role.
[Mh] Termos MeSH primário: Inibidores da Colinesterase/toxicidade
Dor Crônica/induzido quimicamente
DEET/toxicidade
Modelos Animais de Doenças
Repelentes de Insetos/toxicidade
Síndrome do Golfo Pérsico/induzido quimicamente
[Mh] Termos MeSH secundário: Animais
Inibidores da Colinesterase/administração & dosagem
Dor Crônica/patologia
Sinergismo Farmacológico
Repelentes de Insetos/administração & dosagem
Masculino
Medição da Dor/efeitos dos fármacos
Medição da Dor/métodos
Síndrome do Golfo Pérsico/patologia
Ratos
Ratos Sprague-Dawley
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Cholinesterase Inhibitors); 0 (Insect Repellents); 134-62-3 (DEET)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170531
[Lr] Data última revisão:
170531
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161228
[St] Status:MEDLINE


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[PMID]:27838022
[Au] Autor:Fink P; Moelzner J; Berghahn R; von Elert E
[Ad] Endereço:University of Cologne, Cologne Biocenter, Workgroup Aquatic Chemical Ecology, Zülpicher Strasse 47b, 50674 Koeln, Germany. Electronic address: fink@limno.net.
[Ti] Título:Do insect repellents induce drift behaviour in aquatic non-target organisms?
[So] Source:Water Res;108:32-38, 2017 Jan 01.
[Is] ISSN:1879-2448
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Synthetic insect repellents are compounds applied to surfaces to discourage insects, mainly mosquitoes, from landing on those surfaces. As some of these repellents have repeatedly been detected in surface waters at significant concentrations, they may also exert repellent effects on aquatic non-target organisms. In running water systems, aquatic invertebrates actively enter downstream drift in order to avoid unfavourable environmental conditions. We thus tested the hypothesis that the widely used insect repellents DEET (N,N-Diethyl-m-toluamide), EBAAP (3-[N-butyl-N-acetyl]-aminopropionic acid ethyl ester) and Icaridin (1-piperidinecarboxylic acid 2-(2-hydroxyethyl)-1-methylpropyl ester) induce downstream drift behaviour in the aquatic invertebrates Gammarus pulex (Crustacea, Amphipoda) and Cloeon dipterum (Insecta, Ephemeroptera), using a laboratory-scale drift assay. We found no clear increase in the drift behaviour of both invertebrate species across a concentration gradient of eight orders of magnitude and even beyond maximum environmental concentrations for any of the three repellents. We found no evidence for a direct drift-inducing activity of insect repellents on aquatic non-target organisms.
[Mh] Termos MeSH primário: DEET
Repelentes de Insetos
[Mh] Termos MeSH secundário: Animais
Organismos Aquáticos
Água
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 059QF0KO0R (Water); 134-62-3 (DEET)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170505
[Lr] Data última revisão:
170505
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161114
[St] Status:MEDLINE


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[PMID]:27535661
[Au] Autor:Drakou CE; Tsitsanou KE; Potamitis C; Fessas D; Zervou M; Zographos SE
[Ad] Endereço:Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, 48 Vassileos Constantinou Avenue, 11635, Athens, Greece.
[Ti] Título:The crystal structure of the AgamOBP1•Icaridin complex reveals alternative binding modes and stereo-selective repellent recognition.
[So] Source:Cell Mol Life Sci;74(2):319-338, 2017 Jan.
[Is] ISSN:1420-9071
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Anopheles gambiae Odorant Binding Protein 1 in complex with the most widely used insect repellent DEET, was the first reported crystal structure of an olfactory macromolecule with a repellent, and paved the way for OBP1-structure-based approaches for discovery of new host-seeking disruptors. In this work, we performed STD-NMR experiments to directly monitor and verify the formation of a complex between AgamOBP1 and Icaridin, an efficient DEET alternative. Furthermore, Isothermal Titration Calorimetry experiments provided evidence for two Icaridin-binding sites with different affinities (Kd = 0.034 and 0.714 mM) and thermodynamic profiles of ligand binding. To elucidate the binding mode of Icaridin, the crystal structure of AgamOBP1•Icaridin complex was determined at 1.75 Å resolution. We found that Icaridin binds to the DEET-binding site in two distinct orientations and also to a novel binding site located at the C-terminal region. Importantly, only the most active 1R,2S-isomer of Icaridin's equimolar diastereoisomeric mixture binds to the AgamOBP1 crystal, providing structural evidence for the possible contribution of OBP1 to the stereoselectivity of Icaridin perception in mosquitoes. Structural analysis revealed two ensembles of conformations differing mainly in spatial arrangement of their sec-butyl moieties. Moreover, structural comparison with DEET indicates a common recognition mechanism for these structurally related repellents. Ligand interactions with both sites and binding modes were further confirmed by 2D H- N HSQC NMR spectroscopy. The identification of a novel repellent-binding site in AgamOBP1 and the observed structural conservation and stereoselectivity of its DEET/Icaridin-binding sites open new perspectives for the OBP1-structure-based discovery of next-generation insect repellents.
[Mh] Termos MeSH primário: Anopheles/metabolismo
Repelentes de Insetos/química
Repelentes de Insetos/metabolismo
Piperidinas/química
Receptores Odorantes/química
Receptores Odorantes/metabolismo
[Mh] Termos MeSH secundário: Animais
Calorimetria
Cristalografia por Raios X
DEET/química
DEET/metabolismo
Fluorescência
Ligações de Hidrogênio
Modelos Moleculares
Piperidinas/metabolismo
Ligação Proteica
Multimerização Proteica
Espectroscopia de Prótons por Ressonância Magnética
Soluções
Eletricidade Estática
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insect Repellents); 0 (Piperidines); 0 (Receptors, Odorant); 0 (Solutions); 134-62-3 (DEET); N51GQX0837 (picaridin)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160819
[St] Status:MEDLINE
[do] DOI:10.1007/s00018-016-2335-6



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