126151-67-5Relevant academic research and scientific papers
Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic
Papi, Francesco,Paris, Arnaud,Lafite, Pierre,Daniellou, Richard,Nativi, Cristina
supporting information, p. 7366 - 7372 (2020/10/13)
The monosaccharide Tn and the disaccharide STn are tumor antigens with similar structures and common biosynthetic pathways. Both are always over-expressed simultaneously on tumor cell surfaces. We report herein the efficient synthesis of the STnThr antigen analogue 2, featuring the immunogenic TnThr mimetic 1 aglycon. Analogously to the native STn, 2 is recognized by the influenza N1 neuraminidase. A model of the N1·2 complex showed the sialyl moiety of 2 well nested in the active site pocket, with docking unaffected by the rigid aglycon. The analogue 2 is, therefore, in association with mimetic 1, a good determinant for the design of new multiantigen cancer vaccines.
Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity
Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst
, p. 1142 - 1146 (2018/10/21)
The endothelial glycoprotein MUC1 is known to underlie alterations in cancer by means of aberrant glycosylation accompanied by changes in morphology. The heavily shortened glycans induce a collapse of the peptide backbone and enable accessibility of the latter to immune cells, rendering it a tumor-associated antigen. Synthetic vaccines based on MUC1 tandem repeat motifs, comprising tumor-associated 2,3-sialyl-T antigen, conjugated to the immunostimulating tetanus toxoid, are reported herein. Immunization with these vaccines in a simple water/oil emulsion produced a strong immune response in mice to which stimulation with complete Freund’s adjuvant (CFA) was not superior. In both cases, high levels of IgG1 and IgG2a/b were induced in C57BL/6 mice. Additional glycosylation in the immunodominant PDTRP domain led to improved binding of the induced antisera to MCF-7 breast tumor cells, compared with that of the monoglycosylated peptide vaccine.
Solution phase synthesis of (1→5)-amide linked sugar amino acid dimers derived from sialic acids
Gervay, Jacquelyn,Flaherty, Terrence M.,Nguyen, Can
, p. 1493 - 1496 (2007/10/03)
Carboxy-protected amino derivatives and amino-protected carboxy derivatives of three different C-2 analogs as well as a 2,3-dehydro NeuAc were prepared. These monomers were coupled in solution using BOP activation of the carboxy terminus to form (1→5)-amide linked dimers of sialyl amino acid derivatives.
