Acetylcholinesterase Inhibition by Sulphur and Selenium Heterosubstituted Isomers of<i>N</i>,<i>N</i>-Diethylcarbamyl Choline and Carbaryl

Lindgren, Björn; Lindgren, Gerd; Artursson, Elisabeth; Puu, Gertrud; Fredriksson, Jan; Andersson, Maine

doi:10.3109/14756368509031277

Cited by 15 publications

(6 citation statements)

References 16 publications

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“…The nature of directly bonded residues at carbamyl compounds (Se and S derivatives of 1-naphthyl-N-methyl carbamates, Fig. S18) is similar to previous carbamyl derivatives, which is probably the reason why these two derivatives have similar inhibitory activity towards electric eel acetylcholinesterase (0.2-0.3 mM) (Lindgren et al, 1985).…”

Section: Discussionsupporting

confidence: 66%

“…It is evident that the search results only offer a better insight into compounds that bind only non-polar residues. Sulfur and selenium derivatives of N,N-diethylcarbamylcholine have shown similar and only marginal inhibitory activity towards electric eel acetylcholinesterase (0.2-0.3 mM) (Lindgren et al, 1985). Residues directly bonded to an S or Se atom in this case (alkyl and carbonyl group) do not have the ability to make classical hydrogen bonds as an H-atom donor (Fig.…”

Section: Discussionmentioning

confidence: 96%

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Supramolecular insight into the substitution of sulfur by selenium, based on crystal structures, quantum-chemical calculations and biosystem recognition

Đorđević

Popadić

Sarvan

et al. 2020

Acta Crystallogr Sect B

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Statistical analysis of data from crystal structures extracted from the Cambridge Structural Database (CSD) has shown that S and Se atoms display a similar tendency towards specific types of interaction if they are part of a fragment that corresponds to the side chains of cysteine (Cys), methionine (Met) selenocysteine (Sec) and selenomethionine (Mse). The most numerous are structures with C-HÁ Á ÁSe and C-HÁ Á ÁS interactions ($80%), notably less numerous are structures with SeÁ Á ÁSe and SÁ Á ÁS interactions ($5%), and SeÁ Á Á and SÁ Á Á interactions are the least numerous. The results of quantum-chemical calculations have indicated that C-HÁ Á ÁSe ($À0.8 kcal mol À1 ) and C-HÁ Á ÁS interactions are weaker than the most stable parallel interaction ($À3.3 kcal mol À1 ) and electrostatic interactions of / type ($À2.6 kcal mol À1 ). Their significant presence can be explained by the abundance of CH groups compared with the numbers of Se and S atoms in the crystal structures, and also by the influence of substituents bonded to the Se or S atom that further reduce their possibilities for interacting with species from the environment. This can also offer an explanation as to why O-HÁ Á ÁSe ($À4.4 kcal mol À1 ) and N-HÁ Á ÁSe interactions ($À2.2 kcal mol À1 ) are less numerous. Docking studies revealed that S and Se rarely participate in interactions with the amino acid residues of target enzymes, mostly because those residues preferentially interact with the substituents bonded to Se and S. The differences between Se and S ligands in the number and positions of their binding sites are more pronounced if the substituents are polar and if there are more Se/S atoms in the ligand.

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Section: Discussionsupporting

confidence: 66%

Section: Discussionmentioning

confidence: 96%

Supramolecular insight into the substitution of sulfur by selenium, based on crystal structures, quantum-chemical calculations and biosystem recognition

Đorđević

Popadić

Sarvan

et al. 2020

Acta Crystallogr Sect B

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confidence: 99%

“…The biological properties of thiolcarbamates have received much attention, including their use in herbicides, 4b-f pesticides, 4g-i antifertility agents,4j and antivirals 4k. The cleavage of the acyl−S bond of thiolcarbamates by protic solvents and nucleophiles is well-known ,7a and may be related to the biological activity of these compounds 4k. Early routes to thiolcarbamates included acid-mediated addition of alcohols to thiocyanates, the Newman−Kwart rearrangement, and various procedures involving phosgene 8 or other highly energetic reagents .…”

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confidence: 99%

Expanded Chemistry of Formamidine Ureas

Díaz

Finn

2003

Org. Lett.

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“…Selenophosphorus compounds have been introduced as powerful cholinesterase inhibitors 13–16 . Some compounds bearing selenium are toxic chemicals and capable of forming covalent bonds with biological molecules through their active sites 17,18 .…”

Section: Introductionmentioning

confidence: 99%

Structural characterization of Chemical Weapons Convention‐related phosphonoselenoates by electron ionization and electrospray ionization mass spectrometry

Hosseini¹,

Faraz²,

Naseri³

et al. 2021

Rapid Comm Mass Spectrometry

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Rationale Organophosphorus compounds with phosphorus atom bonded to one methyl, ethyl or propyl (normal or iso) group are listed in Schedule 2 of the Chemical Weapons Convention (CWC). Selenophosphorus compounds, listed in Schedule 2.B.4, have very limited representation in mass spectral libraries and the open literature. Methods Members of a new category of selenophosphorus compounds were prepared via microsynthetic protocols and their fragmentation pathways were investigated using electron ionization (EI) and positive electrospray ionization (ESI) mass spectrometry. The EI and ESI fragmentation pathways were suggested and supported by acquired fragment ions of deuterated analogs and density functional theory calculations. Results Mass spectrometric investigations showed some interesting fragmentation pathways, such as McLafferty‐type, selenono–selenolo rearrangements, intramolecular electrophilic aromatic substitution reaction and α‐cleavage. Conclusions Efficient microsynthesis was conducted, and EI‐MS spectra and ESI‐MS/MS spectra of a series of selenophosphorus compounds were collected and studied with the purpose of identifying CWC‐related chemicals during on‐site inspection and/or off‐site analysis.

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Acetylcholinesterase Inhibition by Sulphur and Selenium Heterosubstituted Isomers ofN,N-Diethylcarbamyl Choline and Carbaryl

Cited by 15 publications

References 16 publications

Supramolecular insight into the substitution of sulfur by selenium, based on crystal structures, quantum-chemical calculations and biosystem recognition

Supramolecular insight into the substitution of sulfur by selenium, based on crystal structures, quantum-chemical calculations and biosystem recognition

Expanded Chemistry of Formamidine Ureas

Structural characterization of Chemical Weapons Convention‐related phosphonoselenoates by electron ionization and electrospray ionization mass spectrometry

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