VII Simposio Internacional de Química 2019 "SIQ 2019" -VII Conferencia "Ciencias Químicas"

VII Simposio Internacional de Química 2019

SIQ 2019

Synthesis and caracterization of Streptococcus Pneumoniae capsular polysacharide glycoconjugates obtained by oxidation with TEMPO/NaBr/NaClO

Resumen [ES]

Streptococcus pneumoniae is a Gram-positive bacterium responsible for multiple invasive and non-invasive diseases in humans. According to the World Health Organization this is one of the leading causes of death in children under 5 years. Carbohydrate-protein conjugate vaccines protect infants; since they induce a powerful immune response and generate immunological memory against the capsular polysaccharide of the bacteria. Union between polysaccharide and protein requires sufficient complementary functional groups, which must be introduced without affecting the antigenic, immunogenic and chemical-physical properties of antigen. The present work established a method of Streptococcus pneumoniae capsular polysaccharides serotype 14, 19A and 19F oxidation by oxidation with TEMPO / NaClO / NaBr to generate carboxyl acids in defined primary alcohols of each capsular polysaccharide. The oxidation level was controlled by the initial concentration of NaClO. Undesired fragmentation can be prevented by increasing the molar ratio TEMPO / NaClO. The oxidation site was determined by 1H-NMR and TOCSY. The conjugates to tetanus toxoid were obtained by a carbodiimide or Ugi-4c. The oxidized polysaccharides and the conjugates were characterized by high performance liquid chromatography, colorimetric assay, ELISA, dot blot and 1H-NMR. The conjugates were immunogenic in BALB / c mice and NZW rabbits. Oxidation with TEMPO is a useful method to obtain conjugated carbohydrate-protein vaccines.

Resumen [EN]

Streptococcus pneumoniae is a Gram-positive bacterium responsible for multiple invasive and non-invasive diseases in humans. According to the World Health Organization this is one of the leading causes of death in children under 5 years. Carbohydrate-protein conjugate vaccines protect infants; since they induce a powerful immune response and generate immunological memory against the capsular polysaccharide of the bacteria. Union between polysaccharide and protein requires sufficient complementary functional groups, which must be introduced without affecting the antigenic, immunogenic and chemical-physical properties of antigen. The present work established a method of Streptococcus pneumoniae capsular polysaccharides serotype 14, 19A and 19F oxidation by oxidation with TEMPO / NaClO / NaBr to generate carboxyl acids in defined primary alcohols of each capsular polysaccharide. The oxidation level was controlled by the initial concentration of NaClO. Undesired fragmentation can be prevented by increasing the molar ratio TEMPO / NaClO. The oxidation site was determined by 1H-NMR and TOCSY. The conjugates to tetanus toxoid were obtained by a carbodiimide or Ugi-4c. The oxidized polysaccharides and the conjugates were characterized by high performance liquid chromatography, colorimetric assay, ELISA, dot blot and 1H-NMR. The conjugates were immunogenic in BALB / c mice and NZW rabbits. Oxidation with TEMPO is a useful method to obtain conjugated carbohydrate-protein vaccines.

Sobre el ponente

Abel Zanuy

Lic. Abel Zanuy

FInlay Institute of Vaccines Flag of Cuba
Información Práctica
English (US)
No definido
30 minutos
No definido
Autores
Janoi chang calderón
Lic. Abel Zanuy
Laura rodriguez noda
Aldrin vasco milan
Raine garrido arteaga
Daniel garcía rivera
Dagmar garcía rivera
Jean pierre soubal
Bárbara baró bicet
Jessy pedroso fernández
Vicente vérez bencomo
Darielys santana mederos
Abel zanuy reguera
Palabras clave
conjugated vaccine
edc
glycoconjugation
s. pneumoniae
tempo oxidation
ugi 4c