Structure-Activity Relationship Studies with Mosquito Repellent Amides

Suryanarayana, M.; Pandey, K. S.; Prakash, S.; Raghuveeran, C. D.; Dangi, R. S.; Swamy, Raji; Rao, K. M.

doi:10.1002/jps.2600801111

Cited by 39 publications

(17 citation statements)

References 7 publications

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“…Another 3D (three-dimensional) QSAR model defined an optimal structural pattern that consists of two oxygen atoms (one of which belongs to an amide group) positioned a certain distance from each other and joined by a lipophilic moiety [10]. Predictive models have also been derived by using multi-linear QSAR based on experimental [11] and theoretical [12] descriptors. Protection times of a large set of carboxamides and N-acylpiperidines were qualitatively analyzed using artificial neural networks and multiple linear regression [13,14].…”

Section: Introductionmentioning

confidence: 99%

Promising Aedes aegypti Repellent Chemotypes Identified through Integrated QSAR, Virtual Screening, Synthesis, and Bioassay

Oliferenko

Poda

et al. 2013

PLoS ONE

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Molecular field topology analysis, scaffold hopping, and molecular docking were used as complementary computational tools for the design of repellents for Aedes aegypti, the insect vector for yellow fever, chikungunya, and dengue fever. A large number of analogues were evaluated by virtual screening with Glide molecular docking software. This produced several dozen hits that were either synthesized or procured from commercial sources. Analysis of these compounds by a repellent bioassay resulted in a few highly active chemicals (in terms of minimum effective dosage) as viable candidates for further hit-to-lead and lead optimization effort.

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Section: Introductionmentioning

confidence: 99%

Promising Aedes aegypti Repellent Chemotypes Identified through Integrated QSAR, Virtual Screening, Synthesis, and Bioassay

Oliferenko

Poda

et al. 2013

PLoS ONE

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Section: Structural Diversity Of Chemical Repellentsmentioning

confidence: 99%

“…In addition to these early studies on chemical structure, there have been more recent efforts to identify specific physical‐chemical and electronic descriptors that can predict mosquito repellency of the diethylbenzamides 73–75. One of the first attempts at a quantitative structure–activity relationship approach was made by Suryanarayana et al 74 and yielded a model containing log lipophilicity ( P ), log vapor pressure (VP) and log molecular length (ML). Although the predictive value of this model was not high ( R 2 = 0.304), it provided a quantitative approach to measuring the importance of selected physical‐chemical properties that were reported in the repellents literature, including vapor pressure 76.…”

Section: Structural Diversity Of Chemical Repellentsmentioning

confidence: 99%

Mosquito repellents: a review of chemical structure diversity and olfaction

2010

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Research on mosquito chemical repellents continues to advance, along with knowledge of mosquito olfaction and behavior, mosquito-host interactions and chemical structure. New tools and technologies have revealed information about insect olfactory mechanisms and processing, providing a more complex approach for the interpretation of how chemical repellents influence host-seeking and feeding behavior. Even with these advances, there is still a large amount of information contained in the early works on insect repellents. Many of the standard test methods and chemicals that are still used for evaluating active repellents were developed in the 1940s. These studies contain valuable references to the activity of different structural classes of chemicals, and serve as a guide to optimization of select compounds for insect repellency effects.

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“…Although experimental studies have confirmed that DEETrelated toxicity is minimal, 3,[18][19][20] there are a few reports of toxicity associated with the use of DEET in humans and animals, especially if the chemical is misused or the patients are more susceptible after absorption of large quantities of DEET systemically. [21][22][23] Currently available preparations of DEET are contained in vehicles that inevitably increase the absorption of DEET through the skin.…”

Section: Discussionmentioning

confidence: 99%

“…3 Even though DEET is highly effective, the duration of action of DEET appears to be short lived. Once applied to the skin, DEET has an insect repellent activity ranging from 30 min to 6 hr, 4,5 whereas its antiparasitic effect is even shorter.…”

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confidence: 99%

Development and evaluation of LIPODEET, a new long-acting formulation of N, N-diethyl-m-toluamide (DEET) for the prevention of schistosomiasis.

Salafsky

Kalyanasundaram

He³

et al. 1999

The American Journal of Tropical Medicine and Hygiene

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Abstract. N, N-diethyl-m-toluamide (DEET) is a common and fairly safe active ingredient in many insect repellents. Our recent studies showed that when applied to the skin, DEET has a potent anti-parasitic effect against Schistosoma mansoni. However, the beneficial effects of DEET lasted only for a few minutes, presumably due to its rapid absorption through the skin. In this study, we evaluated different carrier formulations that prolong the activity of DEET in the skin. Among the various formulations analyzed, DEET incorporated into liposomes (LIPODEET) appeared to prolong the activity of DEET for more than 48 hr after a single application. Furthermore, LIPODEET was found to be minimally absorbed through the skin and loss due to washing off was limited. These findings thus suggest LIPODEET is a safe and long-acting formulation of DEET that is quite effective against schistosomiasis. N, N-diethyl-m-toluamide (DEET) is a relative safe, broad spectrum insect repellent that is used extensively against both human and animal pests worldwide.1,2 Although chemical research has produced a number of DEET analogs and other related compounds, none have consistently enjoyed as widespread use as DEET. 3 Even though DEET is highly effective, the duration of action of DEET appears to be short lived. Once applied to the skin, DEET has an insect repellent activity ranging from 30 min to 6 hr, 4,5 whereas its antiparasitic effect is even shorter.6 To obtain a longer duration of activity, there is a need to reapply DEET, often repeatedly with concentrations as high as 70%. 5 This is due to the fact that DEET is absorbed through the skin relatively quickly and is thus rapidly cleared from the skin.7,8 Therefore, any agent that retards the absorption of DEET through the skin will potentially prolong the repellency, or in this case the anti-parasitic action of DEET in the superficial layers of the skin. Furthermore, a reduced absorption will potentially decrease any systemic toxicity associated with DEET. We therefore tested various formulations that prolonged the effect of DEET against schistosomiasis in the skin. MATERIALS AND METHODSRadio-labeling of snails and collection of radiolabeled cercariae. Biomphalaria glabrata species of snails infected with S. mansoni were obtained from Dr. Fred Lewis (Biomedical Research Institute, Rockville, MD). The infected snails were maintained under controlled conditions of light at 85-87ЊF. Snails were checked individually for the presence of the parasite by observing the emergence of cercariae from them by exposing to a bright light source for 1 hr. Once determining that the snails are releasing cercariae, they were radiolabeled with 35 S-methionine as described previously. 9 Snails suspended in distilled water (0. 5 ml/snail) were exposed to 35 S-methionine (Tran 35 S-label, specific activity ϭ 1,047 Ci/mmol, catalog # 51006; ICN Pharmaceuticals, Inc., Irvine, CA) at a concentration of 20 Ci/ml at 37ЊC in the dark. After 16 hr of exposure to the radioisotope, the snails were rinsed, moved to ...

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Structure-Activity Relationship Studies with Mosquito Repellent Amides

Cited by 39 publications

References 7 publications

Promising Aedes aegypti Repellent Chemotypes Identified through Integrated QSAR, Virtual Screening, Synthesis, and Bioassay

Promising Aedes aegypti Repellent Chemotypes Identified through Integrated QSAR, Virtual Screening, Synthesis, and Bioassay

Mosquito repellents: a review of chemical structure diversity and olfaction

Development and evaluation of LIPODEET, a new long-acting formulation of N, N-diethyl-m-toluamide (DEET) for the prevention of schistosomiasis.

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