Novel functionally substituted esters based on sodium diethyldithiocarbamate derivatives: Synthesis, characterization, biological activity and molecular docking studies.
Acetylcholinesterase
/ metabolism
Animals
Butyrylcholinesterase
/ metabolism
Carbonic Anhydrases
/ metabolism
Ditiocarb
/ chemical synthesis
Dose-Response Relationship, Drug
Electrophorus
Enzyme Inhibitors
/ chemical synthesis
Esters
/ chemical synthesis
Glycoside Hydrolases
/ antagonists & inhibitors
Horses
Humans
Hypoglycemic Agents
/ chemical synthesis
Molecular Docking Simulation
Molecular Structure
Saccharomyces cerevisiae
/ enzymology
Structure-Activity Relationship
Alkylations
Enzyme inhibition
Metabolic enzymes
Molecular docking
Sodium diethyldithiocarbamate
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
06 2020
06 2020
Historique:
received:
19
02
2020
revised:
12
03
2020
accepted:
13
03
2020
pubmed:
1
4
2020
medline:
24
2
2021
entrez:
1
4
2020
Statut:
ppublish
Résumé
Alkylation of sodium diethyldithiocarbamate with allyl-2-chloroacetate, allyl-3-chloropropionate, chloromethyl-2-(tetrahydrofuran-2-yl)acetate, and 4-(chloromethyl)-1,3-dioxolane in the aqueous medium synthesized functionally substituted esters of N, N-dietyleditiocarbamic acid (M1-M4). Most active compounds were docked into the catalytic active site of the enzyme. We identified that acetate moiety for inhibition of hCA I, hCA II, and α-glycosidase and dioxolane and thiocarbamic acid moieties for inhibition of AChE and BChE enzymes are very important. The hCA I isoform was inhibited by these novel functionally substituted esters based on sodium diethyldithiocarbamate derivatives (M1-M4) in low micromolar levels, the Ki of which differed between 48.03 ± 9.77 and 188.42 ± 46.08 µM. Against the physiologically dominant isoform hCA II, the novel compounds demonstrated K
Identifiants
pubmed: 32224335
pii: S0045-2068(20)30400-4
doi: 10.1016/j.bioorg.2020.103762
pii:
doi:
Substances chimiques
Enzyme Inhibitors
0
Esters
0
Hypoglycemic Agents
0
Ditiocarb
99Z2744345
Acetylcholinesterase
EC 3.1.1.7
Butyrylcholinesterase
EC 3.1.1.8
Glycoside Hydrolases
EC 3.2.1.-
Carbonic Anhydrases
EC 4.2.1.1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103762Informations de copyright
Copyright © 2020 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declared that there is no conflict of interest.