Compostos organofosforados pentavalentes: histórico, métodos sintéticos de preparação e aplicações como inseticidas e agentes antitumorais

Santos, Viviane Martins Rebello dos; Donnici, Cláudio Luis; DaCosta, João Batista Neves; Caixeiro, Janaína Marques Rodrigues

doi:10.1590/s0100-40422007000100028

Cited by 56 publications

(46 citation statements)

References 58 publications

(70 reference statements)

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“…The aging process occurs at different times, depending on the nature of the organophosphorus compound. 1,[21][22][23][24][25] An understanding of the processes and mechanisms behind the reactivation of the inhibited AChE (11) is required to develop new drugs for the treatment of intoxication with neurotoxic organophosphorus agents. 10 The most effective reported reactivation compounds are cationic oximes prepared from pyridine aldehydes.…”

Section: Introductionmentioning

confidence: 99%

The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon

Ribeiro¹,

Prates²,

Alves³

et al. 2012

J. Braz. Chem. Soc.

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Importantes agentes para defesa contra armas de guerra química são reativadores da acetilcolinesterase humana (huAChE) inibida por compostos organofosforados neurotóxicos (OP), e precisam de uma permeabilidade razoável pela barreira hematoencefálica (HB). Neste trabalho, oximas neutras, que penetram HB melhor do que as oximas catiônicas atualmente utilizadas como agentes de defesa, foram testadas como reativadores da huAChE inibida com paraoxon usando o método de Ellman modificado e pralidoxima (2-PAM) como padrão positivo. A oxima neutra mais ativa foi a 2-tiofenoaldoxima, que reativou 93% da huAChE inibida, sendo 12% mais eficiente do que a 2-PAM. Os resultados mostraram que oximas neutras simples possuem potencial para atuarem como antídotos para intoxicação com OPs neurotóxicos, sugerindo maior investigação no desenvolvimento de agentes de defesa neutros.Important defense agents against chemical warfare weapons, which are reactivators of human acetylcholinesterase (huAChE) inhibited by neurotoxic organophosphorus compounds (OP), need a reasonable permeation of the hematoencephalic barrier (HB). In this work, neutral oximes, which permeate HB better than the cationic oximes currently used as defense agents, were tested as reactivators of huAChE inhibited with paraoxon using the modified Ellman test with pralidoxime (2-PAM) as positive standard. The most active neutral oxime was (thiophen-2-yl)aldoxime, which reactivated 93% of the inhibited huAChE and was 12% more effective than 2-PAM. The results showed that simple neutral oximes have potential to function as antidotes for intoxication with neurotoxic OPs, suggesting further research on the development of neutral defense agents.Keywords: neutral oximes, huAChE reactivation, paraoxon, chemical warfare, (thiophen-2-yl)aldoxime IntroductionIntoxication with neurotoxic organophosphorus compounds is a serious problem caused by some pesticides used in agriculture, such as paraoxon (1) and malathion (2) ( Figure 1) and chemical warfare agents. [1][2][3][4][5][6][7][8][9][10][11] According to the World Health Organization, there are about 220,000 intoxications with organophosphorus pesticides throughout the world every year, leading to approximately 20,000 deaths. 1,[12][13][14] The most dangerous neurotoxic compounds are the chemical warfare agents soman (3), sarin (4), tabun (5) and VX (6) ( Figure 1). Though their use is prohibited by the United Nations, these agents have been employed as weapons by terrorist groups and by countries that did not sign the Chemical Weapon Convention administered by the Organization for the Prohibition of Chemical Weapons (OPCW).The principal target for the action of neurotoxic organophosphorus compounds is the enzyme acetylcholinesterase (AChE), a serine hydrolase that controls the nerve impulses at the cholinergic receptors in the central and peripheral nervous systems. 1,15-20 As shown in Ribeiro et al. 1217 Vol. 23, No. 7, 2012 Figure 2, the function of AChE (7) is the hydrolysis of the nerve impulse transmitter acetylcholine...

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Section: Introductionmentioning

confidence: 99%

The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon

Ribeiro¹,

Prates²,

Alves³

et al. 2012

J. Braz. Chem. Soc.

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“…It is common for insect species to use different resistance mechanisms to adapt to the pressure exerted by continuous use of an insecticide or to single molecules, and one mechanism of resistance that insects develop is the modifi cation of the target protein of the insecticide, although the use of selective insecticides is a major factor in insect control (17) .…”

Section: Discussionmentioning

confidence: 99%

In vitro evaluation of the effect of botanical formulations used in the control of Aedes aegypti L. (Diptera: Culicidae) on liver enzymes.

Porto

Motti

Machado

et al. 2016

Rev. Soc. Bras. Med. Trop.

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Introduction: Dengue fever is a viral disease transmitted by the Aedes aegypti Linn. (1792) (Diptera: Culicidae) mosquito, which is endemic in several regions of Brazil. Alternative methods for the control of the vector include botanical insecticides, which offer advantages such as lower environmental contamination levels and less likelihood of resistant populations. Thus, in this study, the ability of botanical insecticide formulations to inhibit the activity of the liver enzymes serum cholinesterase and malate dehydrogenase was evaluated. Methods: Inhibition profi les were assessed using in vitro assays for cholinesterase and malate dehydrogenase activity and quantitated by ultraviolet-visible spectroscopy at 410nm to 340nm. Results: Insecticide products formulated from cashew nutshell liquid [A] and ricinoleic acid [B] showed cholinesterase activity levels of 6.26IU/mL and 6.61IU/mL, respectively, while the control level for cholinesterase was 5-12IU/mL. The products did not affect the level of 0.44IU/mL established for malate dehydrogenase, as the levels produced by [A] and [B] were 0.43IU/mL and 0.45IU/mL, respectively. Conclusions: Our fi ndings show that in vitro testing of the formulated products at concentrations lethal to A. aegypti did not affect the activity of cholinesterase and malate dehydrogenase, indicating the safety of these products.

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“…Organophosphates have a high biological activity, relative instability and a half-life in plants from two to 10 days, but in general, they are very toxic to vertebrates (Santos et al, 2007a;Santos et al, 2007b). However, despite the growth in insecticide use over the years, according to reports from producers, the damage caused by pests has also increased, probably due to selection of resistant insect populations.…”

Section: Discussionmentioning

confidence: 99%

Integrated management of tomato fruit borer (Neoleucinodes elegantalis)

FranÃ§a¹,

Oliveira²,

Badji³

et al. 2015

Afr. J. Agric. Res.

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The management of Neoleucinodes elegantalis (Guenée) (Lepidoptera: Crambidae) with neem-based and registered insecticides most applied on tomato crops in the Agreste region on N. elegantalis (eggs, pre-pupae and pupae) were evaluated in this study; methomyl, chlorpyrifos, lambda-cyhalothrin, betacypermethrin, deltamethrin, etofenprox, chlorantraniliprole and the neem-based insecticides (azadirachtin A/B and emulsifiable neem oil) were used for studying the repellent effect on oviposition. Lufenuron, deltamethrin and indoxacarb associated with 2.5% sucrose were used as toxic baits on tomato plants. Regarding the ovicidal effect, etofenprox and methomyl had the highest egg mortality, reducing larval survival and fruit damage. Etofenprox had the highest average mortality: 50% in pupae and 38% in pre-pupae. As for repellency, all insecticides tested reduced significantly the number of eggs when compared to the control, except for azadirachtin and chlorantraniliprole. Lufenuron and deltamethrin decreased the number of eggs, showing great potential for use in toxic baits, while indoxacarb stimulated oviposition, thus not being recommended for this purpose. The appropriate use of synthetic insecticides can maximize their potential of control, as long as their use is directed to the stage of the pest that causes higher damage to the crop, or exploring their potential as oviposition deterrent, as well as their use in toxic baits.

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Compostos organofosforados pentavalentes: histórico, métodos sintéticos de preparação e aplicações como inseticidas e agentes antitumorais

Cited by 56 publications

References 58 publications

The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon

The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon

In vitro evaluation of the effect of botanical formulations used in the control of Aedes aegypti L. (Diptera: Culicidae) on liver enzymes.

Integrated management of tomato fruit borer (Neoleucinodes elegantalis)

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