Structure-Activity Relationship of Metabolic Sialic Acid Inhibitors and Labeling Reagents.
ACS Chem Biol
; 17(3): 590-597, 2022 03 18.
Article
em En
| MEDLINE
| ID: mdl-35179348
ABSTRACT
Sialic acids cap the glycans of cell surface glycoproteins and glycolipids. They are involved in a multitude of biological processes, and aberrant sialic acid expression is associated with several pathologies, such as cancer. Strategies to interfere with the sialic acid biosynthesis can potentially be used for anticancer therapy. One well-known class of sialylation inhibitors is peracetylated 3-fluorosialic acids. We synthesized 3-fluorosialic acid derivatives modified at the C-4, C-5, C-8, and C-9 position and tested their inhibitory potency in vitro. Modifications at C-5 lead to increased inhibition, compared to the natural acetamide at this position. These structure-activity relationships could also be applied to improve the efficiency of sialic acid metabolic labeling reagents by modification of the C-5 position. Hence, these results improve our understanding of the structure-activity relationships of sialic acid glycomimetics and their metabolic processing.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ácidos Siálicos
/
Ácido N-Acetilneuramínico
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article