Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides.
José Brango-VanegasLuan A MartinhoLucinda J BessaAndreanne G VasconcelosAlexandra PlácidoAlex L PereiraJosé Roberto de Souza de Almeida LeiteAngelo Henrique Lira MachadoPublished in: Beilstein journal of organic chemistry (2019)
Eight new sulfide-based cyclic peptidomimetic analogues of solonamides A and B have been synthesized via solid-phase peptide synthesis and SN2' reaction on a Morita-Baylis-Hillman (MBH) residue introduced at the N-terminal of a tetrapeptide. This last step takes advantage of the electrophilic feature of the MBH residue and represents a new cyclization strategy occurring. The analogues were prepared in moderate overall yields and did not show toxic effects on Staphylococcus aureus growth and were not toxic to human fibroblasts. Two of them inhibited the hemolytic activity of S. aureus, suggesting an interfering action in the bacterial quorum sensing similar to the one already reported for solonamides.
Keyphrases
- molecular docking
- staphylococcus aureus
- structure activity relationship
- endothelial cells
- machine learning
- high intensity
- deep learning
- induced pluripotent stem cells
- amino acid
- biofilm formation
- pluripotent stem cells
- cystic fibrosis
- methicillin resistant staphylococcus aureus
- escherichia coli
- pseudomonas aeruginosa
- neural network