Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• Freund's adjuvant-induced arthritis in rats [12]. However, the molecular mechanisms of these anti-inflammatory effects have not been investigated. In our ongoing search for bioactive natural products, we have isolated three new spiroketals – breynin J (1), epibreynin J (2), and probreynogenin (3) – and

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• University Munich, Lichtenbergstraße 4, D-85748 Garching, Germany Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia 10.3762/bjoc.15.174 Abstract Muramyl dipeptide is the minimal structure of peptidoglycan with adjuvant properties. Replacement of the N-acetylmuramyl moiety

• present the design, synthesis and biological evaluation of novel mannosylated desmuramyl peptide derivatives. Mannose was coupled to dipeptides containing a lipophilic adamantane on N- or C-terminus through a glycolyl or hydroxyisobutyryl linker. Adjuvant activities of synthesized compounds were

• investigated in the mouse model using ovalbumin as an antigen. Their activities were compared to the previously described mannosylated adamantane-containing desmuramyl peptide and peptidoglycan monomer. Tested compounds exhibited adjuvant activity and the strongest enhancement of IgG production was stimulated

A chemically contiguous hapten approach for a heroin–fentanyl vaccine

• Yoshihiro Natori,
• Candy S. Hwang,
• Lucy Lin,
• Lauren C. Smith,
• Bin Zhou and
• Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

• that, when formulated with an adjuvant, would present us with a vaccine capable of generating antibodies to both drugs. Based on this idea, a series of nine vaccines were prepared that enabled us to detect subtle influences on antibody response to each drug. In sum, we found little traction with each

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• recognition by pathogen-recognition receptors during L. major-induced leishmaniasis. Keywords: adjuvant; carbohydrates; L. major; microparticle; PAMP; Introduction Recognition of parasite cell surface molecules by host immune cells initiates the first step in the immune response [1][2]. The host’s immune

• administration to L. major infected mice (Figure 4). Results and Discussion To further probe the biological mechanisms responsible for L. major immune regulation, a new adjuvant-like pathogen-associated molecular probe was designed to promote pathogen recognition receptor (PRR)-mediated internalization and slow

• microparticle allows for investigation into the mechanisms of pathogen-recognition via MR and TLR2/4 and antigen presentation by APCs. Furthermore, it is anticipated that the glycodendrimer microparticles could provide spared dose vaccination or adjuvant therapy against L. major leishmaniasis, which will be

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• towards oligosaccharides, which would also contribute to the identification and development of drug candidates. For example, cancer immunotherapy based on vaccines derived from carbohydrate antigen–adjuvant combinations has received much attention in recent years [75][76][77]. However, the difficulties

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• adjuvant monophosphoryl lipid A, MPLA – leads to the induction of a different cytokine profile that weakens toxicity but preserves the beneficial adjuvant effects of endotoxin. Other Gram-negative bacteria can produce lipid A variants which are either less endotoxic or inactive (e.g., cannot be recognised

• infection and persistent inflammation. 2.2. Synthesis of monophosphoryl lipid A (MPLA) as potential vaccine adjuvant In contrast to the attenuated or whole killed vaccines which contain bacterial cell wall components and nucleic acids serving as naturally occurring adjuvants, the subunit vaccines lack these

• was shown to greatly enhance the adaptive immune responses [100]. Monophosphoryl lipid A (MPLA), an efficient and safe vaccine adjuvant registered for the use in Europe [59] is derived from the LPS of Salmonella minnesota R595 by following chemical modifications: elimination of the core

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• , since Listeria protection is largely dependent on T-cells activation [103]. The presence of glucose ensures a biocompatible and water dispersible highly efficacious DC targeting system. DC loaded in vitro with GAuNPs-LLO, co-formulated with an adjuvant, provided better protection against listeriosis

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• group [17]. Immunological evaluation of the BSA/TTox conjugates In order to evaluate the immunological properties of the vaccine candidate 18b, three female Balb/cj mice of 6–8 weeks were immunized subcutaneously with 18b in the presence of complete Freund’s adjuvant (CFA). Two booster immunizations

• with incomplete Freund’s adjuvant (IFA) were performed by intraperitoneal applications at intervals of 21 days. Five days following the final immunization, serum antibody levels were determined by an enzyme-linked immunosorbent assay (ELISA). Therefore, blood was drawn from tail veins of the mice and

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• dose to evaluate the effect of dose variation. The conjugates were formulated with aluminum phosphate, an adjuvant commonly used for vaccines in the market or in preclinical development [38]. As a control, the CRM197 conjugate with MenX fragments having an average degree of polymerization (avDP) of 15

• received PBS with adjuvant. ELISA analysis. The antibody response induced by the glycoconjugates against the MenX polysaccharide and the HSA conjugates (see Supporting Information File 1) were measured by ELISA. Similarly as described in [27], plates were coated with the polysaccharide by adding 100 μL

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

• Vincent Fagan,
• Istvan Toth and
• Pavla Simerska

Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

• absence of other important immuno-stimulatory components, known as adjuvants [4]. Adjuvant development has advanced slowly and for many decades, aluminium salts were the only adjuvants approved for clinical use [5]. Recently, research efforts have focused on the development of adjuvants which activate

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents. Keywords: Acanthophyllum gypsophiloides; adjuvant; hemolysis; NMR; saponin

• investigations into saponins, particularly concerning the study of the relationships between their structure, adjuvant activity and toxicity [5][7]. In this paper we report the isolation and structural assessment of two saponins from the roots of A. gypsophiloides Rgl. (Turkestan soap root) with the further

• investigation of their toxicity, hemolytic activity, anti-inflammatory, antifungal and adjuvant properties. The roots of A. gypsophiloides Rgl. are an easily available raw material, which was reported [18] to comprise a saponin with a structure that is close to that of the extremely efficient adjuvant QS-21. A

Acid- mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

• Katsunori Tanaka and
• Koichi Fukase

Beilstein J. Org. Chem. 2009, 5, No. 40, doi:10.3762/bjoc.5.40

• known to induce tumorigenesis in mice and arthritis and lupus nephritis in rats, and has been widely used as an adjuvant for monoclonal antibody production in mouse ascites [57][58][59]. However, in 2002, the basking shark was listed on Article II of the Washington Convention (Convention on