The action of two ethyl carbamates on acetylcholinesterase and reproductive organs of Rhipicephalus microplus

Prado-Ochoa, M.G.; Ramírez-Noguera, Patricia; Díaz-Torres, Roberto; Fariña, Germán Isauro Garrido; Vázquez-Valadez, V.H.; Velázquez-Sánchez, A.M.; Ángeles, Enrique; Arenzana-Seisdedos, Fernando

doi:10.1016/j.vetpar.2013.10.028

Cited by 19 publications

(12 citation statements)

References 24 publications

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“…Nevertheless, plasma cholinesterase levels did not decrease in treated rats. Furthermore, in vitro observations made by our group showed that the carbamates used in this study are weak inhibitors with a low affinity for acetylcholinesterase in R. microplus [5]. In light of this finding, we associate the clinical signs observed in treated rats with the weak inhibitor effect on acetylcholinesterase of the carbamates that were evaluated in this study.…”

Section: Discussionmentioning

confidence: 60%

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Assessment of Acute Oral and Dermal Toxicity of 2 Ethyl-Carbamates with Activity againstRhipicephalus microplusin Rats

Prado-Ochoa

Gutiérrez-Amezquita

Abrego-Reyes

et al. 2014

BioMed Research International

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The acute oral and dermal toxicity of two new ethyl-carbamates (ethyl-4-bromophenyl-carbamate and ethyl-4-chlorophenyl-carbamate) with ixodicide activity was determined in rats. The oral LD50 of each carbamate was 300 to 2000 mg/kg, and the dermal LD50 of each carbamate was >5000 mg/kg. Clinically, the surviving rats that had received oral doses of each carbamate showed decreased weight gain (P < 0.05) and had slight nervous system manifestations. These clinical signs were evident from the 300 mg/kg dose and were reversible, whereas the 2000 mg/kg dose caused severe damage and either caused their death or was motive for euthanasia. At necropsy, these rats had dilated stomachs and cecums with diffuse congestion, as well as moderate congestion of the liver. Histologically, the liver showed slight degenerative lesions, binucleated hepatocytes, focal coagulative necrosis, and congestion areas; the severity of the lesions increased with dosage. Furthermore, an slight increase in gamma-glutamyltransferase, lactate dehydrogenase, and creatinine was observed in the plasma. The dermal application of the maximum dose (5000 mg/kg) of each carbamate did not cause clinical manifestations or liver and skin alterations. This finding demonstrates that the carbamates under study have a low oral hazard and low acute dermal toxicity.

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Section: Discussionmentioning

confidence: 60%

“…These carbamates caused alterations in the reproductive organs, vitellogenesis, and the viability of the ovarian cells, and these effects were found to be independent of acetylcholinesterase inhibition [5]. …”

Section: Introductionmentioning

confidence: 99%

Assessment of Acute Oral and Dermal Toxicity of 2 Ethyl-Carbamates with Activity againstRhipicephalus microplusin Rats

Prado-Ochoa

Gutiérrez-Amezquita

Abrego-Reyes

et al. 2014

BioMed Research International

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“…The evaluated carbamates have inhibitory effects on the development of ovary cells in R. microplus ticks [4], which prompted study of the effects of these carbamates on mammalian ovaries. Histological examinations of the ovaries of the rats exposed to either carbamate did not reveal any apparent pathological changes; we believe that the single deposits of hemosiderin observed in the organs of some of the rats were unrelated to any direct damage to this organ.…”

Section: Discussionmentioning

confidence: 99%

“…The new carbamates (designed and synthesized in FES-Cuautitlan-UNAM), ethyl-4-bromophenyl-carbamate (LQM 919) and ethyl-4-chlorophenyl-carbamate (LQM 996), inhibit ovogenesis, damage ovary cells, and, therefore, affect the reproduction of the cattle tick Rhipicephalus microplus (effective doses LQM 919 = 0.687 mg/mL and LQM 996 = 0.279 mg/mL; [2, 3]). These effects occur in both strains that are susceptible and strains that are resistant to the commercial ixodicides that are used in Mexico [2–4]. Thus, these carbamates have been suggested as an option for tick control.…”

Section: Introductionmentioning

confidence: 99%

Subchronic Toxicity Study in Rats of Two New Ethyl-Carbamates with Ixodicidal Activity

Prado-Ochoa

Abrego-Reyes

Velázquez-Sánchez

et al. 2014

BioMed Research International

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Female and male Wistar rats were used to determine the subchronic oral toxicities of two new ethyl-carbamates with ixodicidal activities (ethyl-4-bromphenyl-carbamate and ethyl-4-chlorphenyl-carbamate). The evaluated carbamates were administered in the drinking water (12.5, 25 and 50 mg/kg/day) for 90 days. Exposure to the evaluated carbamates did not cause mortality or clinical signs and did not affect food consumption or weight gain. However, exposure to these carbamates produced alterations in water consumption, hematocrit, percentages of reticulocytes, plasma proteins, some biochemical parameters (aspartate aminotransferase, gamma-glutamyl transpeptidase, cholinesterase, and creatinine activities), thiobarbituric acid reactive substances, and the relative weight of the spleen. Histologically, slight pathological alterations were found in the liver that were consistent with the observed biochemical alterations. The nonobserved adverse effect levels (NOAELs) of the evaluated carbamates were 12.5 mg/kg/day for both the female and male rats. The low severity and reversibility of the majority of the observed alterations suggest that the evaluated carbamates have low subchronic toxicity.

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“…All calculations for the new compounds (described in Table 2) were carried out using Gaussian 09 [10] and GaussView 5.0. [11] The atomic and molecular properties were determined for the geometric optimization of the carbamates structures through the basis functions: HF/6-31+G(d), B3LYP/6-31+G(d), B3LYP/6-311+G(d,p), BVP86/6-31+G(d) and PBEPBE/6-31+G(d) [12] [13] [14] [15]. The molecules were initially minimize using the semi empiric method PM3, followed by the full optimization with the theory levels: HF/6-31+G(d), B3LYP/6-31+G(d), B3LYP/6-311+G(d,p), BVP86/6-31+G(d) and PBEPBE/6-31+G(d).…”

Section: Molecular Modeling Of the New Lqm9000 Seriesmentioning

confidence: 99%

Molecular Modeling and Synthesis of Ethyl Benzyl Carbamates as Possible Ixodicide Activity

Hugo¹,

Alejandro²,

María³

et al. 2019

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Carbamates are molecules that have different types of biological activities and provide a particular chemical control against ticks. The new structures of the proposed compounds were optimized and synthetized respectively, through a molecular model using the methods:PM3, HF and DFT applying the B3LYP functional, with the basis 6-31+G(d) and 6-311+G(d,p), BVP86 and PBEPBE with 6-31+G(d) and the vibrational frequencies computed. These calculated frequencies were compared with the experimental ones to determine the most accurate level of theory for the prediction of vibrational frequencies of the compounds. The best results were obtained through HF/631+G(d). Additionally, we report a modification to obtain this type of compounds, and based on the amino-dehalogenation of ethyl chloroformate, different benzyl ethyl carbamates were synthesized modifying the base molecule. The performances obtained were compared to others already reported. The methodology used allowed us to synthesize new carbamates using benzylamine derivatives through a modification on the basic catalysis of the addition-elimination reaction.

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The action of two ethyl carbamates on acetylcholinesterase and reproductive organs of Rhipicephalus microplus

Cited by 19 publications

References 24 publications

Assessment of Acute Oral and Dermal Toxicity of 2 Ethyl-Carbamates with Activity againstRhipicephalus microplusin Rats

Assessment of Acute Oral and Dermal Toxicity of 2 Ethyl-Carbamates with Activity againstRhipicephalus microplusin Rats

Subchronic Toxicity Study in Rats of Two New Ethyl-Carbamates with Ixodicidal Activity

Molecular Modeling and Synthesis of Ethyl Benzyl Carbamates as Possible Ixodicide Activity

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