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Volume 12
Issue 7
10.3390/vaccines12070707
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Article

Modeling 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP) Chemistry to Design Glycoconjugate Vaccines with Desired Structural and Immunological Characteristics

by
Rebecca Nappini
1,2,
Renzo Alfini
2,
Salvatore Durante
2,
Laura Salvini
3,
Maria Michelina Raso
2,
Elena Palmieri
2,
Roberta Di Benedetto
2,
Martina Carducci
2,
Omar Rossi
2,
Paola Cescutti
1,
Francesca Micoli
2 and
Carlo Giannelli
2,*
1
Dipartimento di Scienze della Vita, Università Degli Studi di Trieste, Via L Giorgieri 1, Ed. C11, 34127 Trieste, Italy
2
GSK Vaccines Institute for Global Health (GVGH), 53100 Siena, Italy
3
Fondazione Toscana Life Sciences (TLS), 53100 Siena, Italy
*
Author to whom correspondence should be addressed.
Vaccines 2024, 12(7), 707; https://doi.org/10.3390/vaccines12070707
Submission received: 17 April 2024 / Revised: 14 June 2024 / Accepted: 17 June 2024 / Published: 24 June 2024
(This article belongs to the Special Issue Advances in Glycoconjugate Vaccines and Nanovaccines)
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Abstract

Glycoconjugation is a well-established technology for vaccine development: linkage of the polysaccharide (PS) antigen to an appropriate carrier protein overcomes the limitations of PS T-independent antigens, making them effective in infants and providing immunological memory. Glycoconjugate vaccines have been successful in reducing the burden of different diseases globally. However, many pathogens still require a vaccine, and many of them display a variety of glycans on their surface that have been proposed as key antigens for the development of high-valency glycoconjugate vaccines. CDAP chemistry represents a generic conjugation strategy that is easily applied to PS with different structures. This chemistry utilizes common groups to a large range of PS and proteins, e.g., hydroxyl groups on the PS and amino groups on the protein. Here, new fast analytical tools to study CDAP reaction have been developed, and reaction conditions for PS activation and conjugation have been extensively investigated. Mathematical models have been built to identify reaction conditions to generate conjugates with wanted characteristics and successfully applied to a large number of bacterial PSs from different pathogens, e.g., Klebsiella pneumoniae, Salmonella Paratyphi A, Salmonella Enteritidis, Salmonella Typhimurium, Shighella sonnei and Shigella flexneri. Furthermore, using Salmonella Paratyphi A O-antigen and CRM197 as models, a design of experiment approach has been used to study the impact of conjugation conditions and conjugate features on immunogenicity in rabbits. The approach used can be rapidly extended to other PSs and accelerate the development of high-valency glycoconjugate vaccines.
Keywords: 1-cyano-4-dimethylaminopyridine tetrafluoroborate (CDAP); conjugation; design of experiment; S. Paratyphi A; 1,4-diazabicyclo[2.2.2]octane; DABCO; lutidine 1-cyano-4-dimethylaminopyridine tetrafluoroborate (CDAP); conjugation; design of experiment; S. Paratyphi A; 1,4-diazabicyclo[2.2.2]octane; DABCO; lutidine

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MDPI and ACS Style

Nappini, R.; Alfini, R.; Durante, S.; Salvini, L.; Raso, M.M.; Palmieri, E.; Di Benedetto, R.; Carducci, M.; Rossi, O.; Cescutti, P.; et al. Modeling 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP) Chemistry to Design Glycoconjugate Vaccines with Desired Structural and Immunological Characteristics. Vaccines 2024, 12, 707. https://doi.org/10.3390/vaccines12070707

AMA Style

Nappini R, Alfini R, Durante S, Salvini L, Raso MM, Palmieri E, Di Benedetto R, Carducci M, Rossi O, Cescutti P, et al. Modeling 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP) Chemistry to Design Glycoconjugate Vaccines with Desired Structural and Immunological Characteristics. Vaccines. 2024; 12(7):707. https://doi.org/10.3390/vaccines12070707

Chicago/Turabian Style

Nappini, Rebecca, Renzo Alfini, Salvatore Durante, Laura Salvini, Maria Michelina Raso, Elena Palmieri, Roberta Di Benedetto, Martina Carducci, Omar Rossi, Paola Cescutti, and et al. 2024. "Modeling 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP) Chemistry to Design Glycoconjugate Vaccines with Desired Structural and Immunological Characteristics" Vaccines 12, no. 7: 707. https://doi.org/10.3390/vaccines12070707

APA Style

Nappini, R., Alfini, R., Durante, S., Salvini, L., Raso, M. M., Palmieri, E., Di Benedetto, R., Carducci, M., Rossi, O., Cescutti, P., Micoli, F., & Giannelli, C. (2024). Modeling 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate (CDAP) Chemistry to Design Glycoconjugate Vaccines with Desired Structural and Immunological Characteristics. Vaccines, 12(7), 707. https://doi.org/10.3390/vaccines12070707

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