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Article

Preparation, Supramolecular Aggregation and Immunological Activity of the Bona Fide Vaccine Adjuvant Sulfavant S

1
Bio-Organic Chemistry Unit, CNR-Institute of Biomolecular Chemistry, Via Campi Flegrei 34, 80078 Pozzuoli, Italy
2
Consorzio Italbiotec, Via Fantoli, 16/15, 20138 Milano, Italy
3
BioSearch Srl., Villa Comunale c/o Stazione Zoologica “A.Dohrn”, 80121 Napoli, Italy
4
Institute for Polymers, Composites and Biomaterials (IPCB), CNR, 80125 Naples, Italy
5
Medicina Interna, Immunologia Clinica e Medicina Traslazionale, Università di Genova and IRCCS-Ospedale S. Martino, 16131 Genova, Italy
*
Authors to whom correspondence should be addressed.
These authors contributed equally.
Mar. Drugs 2020, 18(9), 451; https://doi.org/10.3390/md18090451
Received: 20 July 2020 / Revised: 21 August 2020 / Accepted: 26 August 2020 / Published: 29 August 2020
(This article belongs to the Special Issue Sulfur-Containing Marine Bioactives)
In aqueous conditions, amphiphilic bioactive molecules are able to form self-assembled colloidal structures modifying their biological activity. This behavior is generally neglected in preclinical studies, despite its impact on pharmacological development. In this regard, a significative example is represented by a new class of amphiphilic marine-inspired vaccine adjuvants, collectively named Sulfavants, based on the β-sulfoquinovosyl-diacylglyceride skeleton. The family includes the lead product Sulfavant A (1) and two epimers, Sulfavant R (2) and Sulfavant S (3), differing only for the stereochemistry at C-2 of glycerol. The three compounds showed a significant difference in immunological potency, presumably correlated with change of the aggregates in water. Here, a new synthesis of diastereopure 3 was achieved, and the study of the immunomodulatory behavior of mixtures of 2/3 proved that the bizarre in vitro response to 13 effectively depends on the supramolecular aggregation states, likely affecting the bioavailability of agonists that can effectively interact with the cellular targets. The evidence obtained with the mixture of pure Sulfavant R (2) and Sulfavant S (3) proves, for the first time, that supramolecular organization of a mixture of active epimers in aqueous solution can bias evaluation of their biological and pharmacological potential. View Full-Text
Keywords: sulfavants; adjuvant; immunomodulatory activity; colloid; aggregates sulfavants; adjuvant; immunomodulatory activity; colloid; aggregates
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MDPI and ACS Style

Manzo, E.; Fioretto, L.; Gallo, C.; Ziaco, M.; Nuzzo, G.; D’Ippolito, G.; Borzacchiello, A.; Fabozzi, A.; De Palma, R.; Fontana, A. Preparation, Supramolecular Aggregation and Immunological Activity of the Bona Fide Vaccine Adjuvant Sulfavant S. Mar. Drugs 2020, 18, 451. https://doi.org/10.3390/md18090451

AMA Style

Manzo E, Fioretto L, Gallo C, Ziaco M, Nuzzo G, D’Ippolito G, Borzacchiello A, Fabozzi A, De Palma R, Fontana A. Preparation, Supramolecular Aggregation and Immunological Activity of the Bona Fide Vaccine Adjuvant Sulfavant S. Marine Drugs. 2020; 18(9):451. https://doi.org/10.3390/md18090451

Chicago/Turabian Style

Manzo, Emiliano, Laura Fioretto, Carmela Gallo, Marcello Ziaco, Genoveffa Nuzzo, Giuliana D’Ippolito, Assunta Borzacchiello, Antonio Fabozzi, Raffaele De Palma, and Angelo Fontana. 2020. "Preparation, Supramolecular Aggregation and Immunological Activity of the Bona Fide Vaccine Adjuvant Sulfavant S" Marine Drugs 18, no. 9: 451. https://doi.org/10.3390/md18090451

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