42381-62-4Relevant articles and documents
Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their in Vivo Adjuvant Activity
Guzelj, Samo,Nabergoj, Sanja,Gobec, Martina,Pajk, Stane,Klan?i?, Veronika,Slütter, Bram,Frkanec, Ru?a,?timac, Adela,?ket, Primo?,Plavec, Janez,Mlinari?-Ra??an, Irena,Jakopin, ?iga
, p. 7809 - 7838 (2021/06/28)
We report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds had immunostimulatory effects on peripheral blood mononuclear cells at the protein and transcriptional levels, and augmented dendritic-cell-mediated activation of T cells, while 75 additionally enhanced the cytotoxic activity of peripheral blood mononuclear cells against malignant cells. The C18 lipophilic tail of 75 is identified as a pivotal structural element that confers in vivo adjuvant activity in conjunction with a liposomal delivery system. Accordingly, liposome-encapsulated 75 showed promising adjuvant activity in mice, surpassing that of muramyl dipeptide, while achieving a more balanced Th1/Th2 immune response, thus highlighting its potential as a vaccine adjuvant.
New multifunctional surfactants from natural phenolic acids
Centini, Marisanna,Rossato, Maria Sole,Sega, Alessandro,Buonocore, Anna,Stefanoni, Sara,Anselmi, Cecilia
experimental part, p. 74 - 80 (2012/04/10)
Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.
Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities
Wei, Qing-Yi,Jiang, Hong,Zhang, Jian-Xun,Guo, Peng-Fei,Wang, Huan
, p. 1905 - 1911,7 (2020/07/30)
Hydroxycinnamic acids have a variety of biological activities, including antioxidant activity. To find more active antioxidants with hydroxycinnamoyl moiety, we synthesized a series of N-hydroxycinnamoyl amino acid esters and evaluated their antioxidative activities by 2,2- diphenyl-1-picryl hydrazyl (DPPH) radical scavenging and human red blood cells (RBCs) haemolysis methods. It was found that N-caffeoyl amides exhibited the highest DPPHscavenging activities, whereas N-feruloyl amides demonstrated the highest antihaemolysis activities among the three different hydroxycinnamamides (caffeoyl, feruloyl, and p-coumaroyl), and that hydroxycinnamoyl amides were more effective than their corresponding free acid and ester compounds in both DPPH and RBC haemolysis tests.
