Non-enzyme-catalyzed thiol addition onto the α,β-unsaturated carbonyl system is associated with several biological effects. Kinetics and diastereoselectivity of non-enzyme catalyzed nucleophilic addition of reduced glutathione (GSH) and N-acetylcysteine (NAC) to the six-membered cyclic chalcone analogs and were investigated at different pH values (pH 3.2, 7.4 and 8.0). The selected compounds displayed in vitro cancer cell cytotoxicity (IC) of different orders of magnitude. The chalcones intrinsically reacted with both thiols under all incubation conditions. The initial rates and compositions of the final mixtures depended both on the substitution and the pH. The stereochemical outcome of the reactions was evaluated using high-pressure liquid chromatography with UV detection (HPLC-UV). The structures of the formed thiol-conjugates and the retro-Michael products ()- and ()- were confirmed by high-pressure liquid chromatography-mass spectrometry (HPLC-MS). Frontier molecular orbitals and the Fukui function calculations were carried out to investigate their effects on the six-membered cyclic analogs. Data were compared with those obtained with the open-chain () and the seven-membered () analogs. The observed reactivities do not directly relate to the difference in in vitro cancer cell cytotoxicity of the compounds.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11277078PMC
http://dx.doi.org/10.3390/ijms25147773DOI Listing

Publication Analysis

Top Keywords

cyclic analogs
8
six-membered cyclic
8
vitro cancer
8
cancer cell
8
cell cytotoxicity
8
high-pressure liquid
8
-2-benzylidenecyclanones xix
4
xix reaction
4
reaction -2-4'-x-benzylidene-1-tetralones
4
-2-4'-x-benzylidene-1-tetralones cellular
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!