962-39-0Relevant articles and documents
Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis
Rodrigues, Débora Munhoz,Portapilla, Gisele Bulh?es,Silva, Guilherme Martins,Duarte, Andressa,Rotta, Cristiana Gon?alez,da Silva, Carlos Henrique Tomich de Paula,de Albuquerque, Sérgio,Bastos, Jairo Kenupp,Campo, Vanessa Leiria
, (2021/08/30)
Breast cancer has the highest incidence and mortality in females, while prostate cancer has the second-highest incidence in males. Studies have shown that compounds from Brazilian green propolis have antitumor activities and can selectively inhibit the AKR1C3 enzyme, overexpressed in hormone-dependent prostate and breast tumors. Thus, in an attempt to develop new cytotoxic inhibitors against these cancers, three prenylated compounds, artepillin C, drupanin and baccharin, were isolated from green propolis to synthesize new derivatives via coupling reactions with different amino acids. All obtained derivatives were submitted to antiproliferative assays against four cancer cells (MCF-7, MDA MB-231, PC-3, and DU145) and two normal cell lines (MCF-10A and PNT-2) to evaluate their cytotoxicity. In general, the best activity was observed for compound 6e, derived from drupanin, which exhibited half-maximal inhibitory concentration (IC50) of 9.6 ± 3 μM and selectivity index (SI) of 5.5 against MCF-7 cells. In silico studies demonstrated that these derivatives present coherent docking interactions and binding modes against AKR1C3, which might represent a possible mechanism of inhibition in MCF-7 cells.
Probe compounds for fluorescence recognition of amino acid enantiomers and synthesis and applications thereof
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Paragraph 0030, (2019/01/05)
The invention provides probe compounds for fluorescence recognition of amino acid enantiomers. Probe compounds (a, b, c) are prepared by following steps: dissolving dimethyl squarate into anhydrous methanol, dropwise adding methanol solutions of phenylalanine ethyl ester, phenylalanine benzyl ester, and phenylalanine tert-butyl ester, after addition, stirring the solution for 20 to 24 hours at a room temperature, filtering the solution, and finally washing the filter residues by ethyl acetate several times. When D-proline is added into ethanol-water solutions of chiral probe compounds (a, c),the fluorescence strength of the solutions is reduced; when L-proline is added into the solutions, the fluorescence strength of the solutions is enhanced obviously; and thus the probe compounds (a,c)have a good recognition effect on two enantiomers of proline. When L-valine is added into ethanol-water solutions of the probe compound (b), the fluorescence strength of the solution is obviously reduced; when D-valine is added into the solution, the fluorescence strength of the solution is not changed; and thus the probe compound (b) has a good recognition effect on two enantiomers of valine.
A novel route towards cycle-tail peptides using oxime resin: Teaching an old dog a new trick
Bérubé, Christopher,Borgia, Alexandre,Voyer, Normand
, p. 9117 - 9123 (2019/01/03)
Two anabaenopeptins, Schizopeptin 791 and anabaenopeptin NZ825, have similar structural features and have been synthesized via a novel acid-catalyzed head-to-side-chain concomitant cyclization/cleavage reaction on oxime resin. The methodology gave rapid access to the anabaenopeptin scaffold by taking advantage of a combined solid-phase/solution-phase synthetic strategy. Also, as side-products of the synthesis, large C2-symmetric 38-member cyclic peptides ring bearing two endocyclic lysine side-chains were isolated, constituting a novel cyclic peptide scaffold.