Journal
GLYCOCONJUGATE JOURNAL
Volume 20, Issue 6, Pages 407-414Publisher
SPRINGER
DOI: 10.1023/B:GLYC.0000033997.01760.b9
Keywords
carbohydrate; sialic acid; N-acylneuraminic acid; glycoconjugate; immunogenicity; cancer vaccine
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Funding
- NATIONAL CANCER INSTITUTE [R01CA095142] Funding Source: NIH RePORTER
- NCI NIH HHS [R01 CA095142-01, R01 CA095142-04, R01 CA095142, R01 CA095142-02, 1R01 CA95142, R01 CA095142-03] Funding Source: Medline
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The overexpression of N-acetylneuraminic acid (Neu5Ac) is closely correlated with malignant transformations. Thus, Neu5Ac is an important target in the design of cancer vaccines. To study the influence of chemical modifications of Neu5Ac on its immunological properties, the alpha-allyl glycosides of five differently N-acylated neuraminic acid derivatives were prepared. Following selective ozonolysis of their allyl group to form an aldehyde functionality, they were coupled to keyhole limpet hemocyanin (KLH) via reductive amination. Resultant glycoconjugates were studied in C57BL/6 mice. The N-propionyl, N-iso-butanoyl and N-phenylacetyl derivatives of neuraminic acid provoked robust immune responses of various antibody isotypes, including IgM, IgG1, IgG2a and IgG3, whereas N-trifluoropropionylneuraminic acid and natural Neu5Ac were essentially nonimmunogenic. Moreover, the N-phenylacetyl and N-iso-butanoyl derivatives mainly induced IgG responses that are desirable for antitumor applications. These results raise the promise of formulating effective glycoconjugate cancer vaccines via derivatizing sialic acid residues of sialooligosaccharides. Published in 2004.
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