Rational design of imidazolium based salts as anthelmintic agents

Ranjan, Prabodh; Athar, Mohd; Rather, Hilal; Vijayakrishna, Kari; Vasita, Rajesh; Jha, Prakash C.

doi:10.1016/j.molliq.2018.02.001

Cited by 5 publications

(7 citation statements)

References 67 publications

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“…As reported, the vermicidal activity increases with the alkyl chain length and IL‐OH analogs were found to be more active than IL−Br . Therefore, in continuation of our prior studies, we hereby aimed to screen 1‐butylimidazolium derived ILs for vermicidal activities and cytotoxicity (on normal cell line MC3T3‐L1, mouse embryonic fibroblasts) to check the combined effects of extended hydrophobic factors (as alkyl chain) with different anions. Further, quantitative‐structure‐activity‐relationship (QSAR / or SAR) and molecular docking studies were performed to render the mechanistic insight for governing factors,,, and molecular basis of ILs vermicidal activities, respectively ,,.…”

Section: Resultsmentioning

confidence: 80%

“…The previous studies have suggested that the variable hydrophobic factors (changes with alkyl chains) and two different counter anions (

{B r}^{-} {a n d O H}^{-})

influence the vermicidal activities of 1‐methylimidazolium derived ILs 4pt Considering the facts, herein we have evaluate the vermicidal activities of 1‐butylimidazolium derived ILs, with extended alkyl chains (n‐C 4 H 9 , n‐C 6 H 13 and n‐C 10 H 21 , substituted at N‐3 position of 1‐butylimidazolium ring) and different possible cationic and anionic (

{B r}^{-} {, O H}^{-}, {B F}_{4}^{-}

) combinations to check the effects of extended hydrophobic factors and different anion on vermicidal activities and cytotoxicity.…”

Section: Resultsmentioning

confidence: 99%

“…Inspired from our previous results,, we have tested the vermicidal (or anthelmintic) activities of the synthesized ILs and Albendazole sulfoxides (ABZSO) against the Pheretima posthuma (P. posthuma) . The vermicidal activities (VAs) were reported as a function of percentage paralysis and mortality (Figure S16).…”

Section: Resultsmentioning

confidence: 99%

“… Comparison of percentage paralysis (a) and mortality (b) of 1‐butyl‐3‐alkylimidazolium and 1‐methyl‐3‐alkylimidazolium derivatives, (IL‐Br/ or BF 4 / or OH) containing three different anions and Albendazole sulfoxides (as reference). The percentage paralysis and percentage mortality of 1‐butyl‐3‐alkylimidazolium, 1‐methyl‐3‐alkylimidazolium derivatives and Albendazole sulfoxides (ABZSO) are given in navy blue, orange, and green colors, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Further, in order to explicate the effect of extended n‐alkyl chain present at N1 position of the 1‐butylimidazolium derived ILs (Figure ). Threfore, we compared the activiites of 1‐butylimidazolium derived ILs with our previously published work (which advocates the VAs of 1‐methyl‐3‐alkylimidazolium derived ILs) (details can be found in Figure a and 3b). Details of the vermicidal activities of 1‐methylimidazolium derived ILs can be found in ESI Figure S22 to S29 .…”

Section: Resultsmentioning

confidence: 99%

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Appraisal of 1‐Butylimidazole‐Derived Ionic Liquids as Anthelmintic Agents: An Experimental and In Silico Approach

et al. 2018

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We have synthesized and characterized 1‐butyl‐3‐alkylimidazolium derived ionic liquids (ILs) functionalized with various alkyl groups (‐C2H5, ‐C4H9, ‐C6H13, ‐C8H17, and ‐C10H21) and counter anions (OH-,Br-andBF4- ). Further, these ILs were tested for the vermicidal activity and cell‐viability study against the Pheretima posthuma (Indian earthworm) and MC3T3‐L1 cells, respectively. IL‐OH with higher alkyl chains (‐C10H21) displayed promising vermicidal activity as compared to other counterparts (IL−Br and IL‐BF4). Further, quantitative‐structure‐activity‐relationships (QSAR) modelling was carried out using density functional theory (DFT) derived quantum mechanical descriptors to assess the factors responsible for the biological activities. Based on the QSAR study it was found that LUMO of the anion and polar surface area of the cation possess significant correlation (r2, 0.85; RMSE, 0.06). Also, receptor‐binding based molecular docking was carried out to study the binding patterns of the tested IL. Introduction In past few decades, ionic liquids (ILs) have generated paramount interest in several field of chemistry, i.e., catalysis, electrochemistry,, biotechnology, biomass energy and pharmaceutical applications–, and many others. This wide range of applications are due to their characteristic tunable nature of ILs which facilitate desired biochemical properties via varying their counter anions and alkyl chain length., Subsequent tailoring of biologically active cations or anions can add substantial potential to their therapeutic implication and administration as active pharmaceutical ingredients (APIs)., Efforts are made to probe the effects of various anions, alkyl chains and charge on the quaternary nitrogen atom. It has been articulated that medicinal aspect of ILs is greatly impeded by their toxicity; however, attempts are in the progress to afford a balance between toxicity and biochemical/ biopharmaceutical properties. In particular, the maxim “poison is in the dose”, encouraged to develop ILs as useful therapeutics. Earlier, we have screened the imidazolium derived ILs for their vermicidal activity with varying alkyl chains (R= ‐C2H5, ‐C4H9, ‐C6H13, ‐C8H17) and Br−/OH− as counter anions.

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