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The antibacterial and anti-inflammatory effect of thioglycosides has already been established. This study investigates the effects of thioglycosides extracted from white mustard, specifically the “Bamberka” variety, in the context of oral hygiene. The aim of the study is to clarify an evidence-based link between the documented antibacterial and anti-inflammatory effects attributed to thioglycosides and their practical application in oral care. A randomized, single-blinded (patient-blinded) clinical study was performed on 66 patients using mustard-based toothpaste for oral hygiene. The patients were examined at baseline and after 6 and 12 months. The values of the Approximal Plaque Index (API), the Plaque Index (PI), and Bleeding on probing (BOP) were taken into consideration. The results show a significant reduction in plaque accumulation, especially after 6 months of using mustard-based toothpaste in all examined parameters. This suggests that thioglycosides from mustard contribute to a considerable decrease in dental plaque accumulation, confirming their potential in natural oral care solutions, which is indicated in the main conclusions or interpretations.

New 1-thia-azaspiro[4.5]decane derivatives, their derived thiazolopyrimidine and 1,3,4-thiadiazole compounds were synthesized. The thioglycoside derivatives of the synthesized (1,3,4-thiadiazolyl)thiaazaspiro[4.5]decane and thiazolopyrimidinethione compounds were synthesized by glycosylation reactions using acetylated glycosyl bromides. The anticancer activity of synthesized compounds was studied against the cell culture of HepG-2 (human liver hepatocellular carcinoma), PC-3 (human prostate adenocarcinoma) and HCT116 (human colorectal carcinoma) cell lines and a number of compounds showed moderate to high inhibition activities.

New 1,3,4-thiadiazole thioglycosides linked to substituted arylidine systems were synthesized via glycosylation of the prepared 1,3,4-thiadiazole thiol compounds. Click strategy was also used for the synthesis of new 1,3,4-thiadiazole and 1,2,3-triazole hybrid glycosides by reaction of the acetylenic derivatives with different glycosyl azids followed by deacetylation process. The cytotoxic activities of the prepared compounds were studied against HCT-116 (human colorectal carcinoma) and MCF-7 (human breast adenocarcinoma) cell lines using the MTT assay. The results showed that the key thiadiazolethione compounds 2 and 3, the triazole glycosides linked to p-methoxyarylidine derivatives 14 and 15 in addition to the free hydroxyl glycoside 20 were found potent in activity comparable to the reference drug doxorubicin against MCF-7 human cancer cells. The acetylenic derivative 2 and glycoside 20 were also found highly active against HCT-116 cell lines.

The growing prevalence of multidrug-resistant Gram-negative pathogens highlights the urgent need for therapeutic strategies that complement traditional antibiotics by targeting essential virulence pathways. Glycosyltransferase LgtC, a key enzyme in lipooligosaccharide (LOS) biosynthesis, represents an attractive target for antivirulence approaches because of its essential role in bacterial immune evasion and pathogenicity. In this work, we employed an integrated in silico pipeline to identify thioglycoside analogs structurally related to the metabolic decoys FucSBn and BacSBn, evaluating their potential to hit the UDP-galactose donor pocket of LgtC. A similarity-based screening in PubChem, followed by ADME–Tox filtering yield 18 candidate analogs. Molecular docking using AutoDock-GPU revealed several candidates, most notably C-5 (− 8.36 kcal/mol) and C-18 (− 8.13 kcal/mol), to bind favorably within the donor site, showing more negative mean scoring values than natural donor UDP-α-D-galactose (− 6.74 kcal/mol). Redocking of the natural ligand reproduced the crystallographic pose, supporting the reliability of the docking protocol. To assess dynamic behavior, 100 ns molecular dynamics simulations (AMBER14) were performed for each complex. The top-scoring analogs maintained stable binding poses, with RMSD values of ~ 2.0–3.0 Å and preserved donor-like hydrogen-bond networks complemented by π-stacking and sulfur-mediated contacts. These interaction patterns suggest that the thioglycoside analogs may occupy the donor site in a manner compatible with competitive binding. While docking and MD describe different aspects of ligand recognition, several trends observed in docking, such as the favorable binding scores of C-5 and C-18, are broadly consistent with their ability to maintain stable poses during MD. Based on this consistency and scoring, the thioglycoside scaffolds C-5, C-14, and C-18 emerge as computationally prioritized candidates for subsequent biochemical testing against LgtC. Furthermore, these scaffolds offer a mechanistic basis and putative starting points for future structure-based optimization of thioglycoside analogs aimed at disrupting LOS biosynthesis in multidrug-resistant Gram-negative bacteria.

Sugars with heteroatoms other than oxygen have attained considerable importance in glycobiology and in drug design since they are often more stable in blood plasma due to their resistance to enzymes, such as glycosidases, phosphorylases and glycosyltransferases. The replacement of oxygen atoms in sugars with sulfur forms thio-sugars, which are potentially useful for the treatment of diabetes and some bacterial and viral infections. Here, we evaluated the antibacterial activity of thio-functionalized carbohydrate derivatives. A set of 21 compounds was screened against acid-fast Mycobacterium tuberculosis (Mtb), gram-negative Escherichia coli and gram-positive Staphylococcus aureus. The tested carbohydrate derivatives were most effective against tubercle bacilli, with as many as five compounds (thioglycoside 6, thiosemicarbazone 16A, thiosemicarbazone 20, aminothiadiazole 23, and thiazoline 26) inhibiting its growth with MIC50 ≤ 50 µM/CFU. Only two compounds (aminothiadiazole 23 and thiazoline 26) were able to inhibit the growth of E. coli at concentrations below 1 mM, and one of them, aminothiadiazole 23, inhibited the growth of S. aureus at a concentration ≤1 mM. The five compounds affecting the growth of mycobacteria were either thiodisaccharides (6, 16A, and 20) or thioglycosides (23 and 26). All of these compounds (6, 16A, 20, 23, and 26) were able to inhibit the growth of Mtb deposited within human macrophages. However, three of the five selected compounds (6, 23, and 26) exhibited relatively high cytotoxicity in mouse fibroblasts at micromolar concentrations. The selected thio-sugars are very promising compounds, thus making them candidates for further modifications that would decrease their cytotoxicity against eukaryotic cells without affecting their antimycobacterial potential.

A series of novel pyrazolopyrimidine and pyrazololpyridine thioglycosides were synthesized and confirmed via their spectral analyses. To evaluate the effect of these anti-metabolic compounds against proliferation of Huh-7 and Mcf-7 as in vitro models of human liver and breast cancers, respectively. Vero cells were used as an example of normal green monkey kidney cells. The most promising compound was subjected to a nanoformulation by its encapsulation into chitosan nanoparticles to increase its anti-cancerous activity. Nanoformulation was confirmed by TEM and FT-IR to ensure encapsulation and screened for their cytotoxicity against Huh-7 and Mcf-7 cells using MTT colorimetric assay and morphological examination. Genotoxic effect was performed by cellular DNA fragmentation assay. Simulated CompuSyn software (linear interaction effect) was conducted to predict the possible synergistic effect of nanocomposite as anticancerous activity. Apoptotic effect was further analyzed by detection of apoptotic proteins using ELISA assay. The nano preparation was successfully prepared by encapsulation of compound 14 into chitosan nanoparticles, controlled to a size at 105 nm and zeta charges at 40.2 mV. Treatment of Huh-7 and Mcf-7 showed that compound 14 was the most cytotoxic compound on both cancer cell lines where IC was 24.59 (9.836 μg/mL) and 12.203 (4.8812 μg/mL) on Huh-7 and Mcf-7 respectively. But IC of the nano preparation was 37.19 and 30.68 μg/mL on Huh-7 and Mcf-7, respectively, indicating its aggressiveness on human breast cancer cells as confirmed by DNA fragmentation assay and theoretically by CompuSyn tool. A novel series of pyrazolopyrimidine thioglycosides and pyrazolopyridine thioglycosides were synthesized. Nanoformulation of compound 14 into chitosan nanoparticles demonstrated anticancer activity and can be used as a drug delivery system, but further studies are still required.

A novel series of uridine glycoconjugates, derivatives of 4-aminophenyl 1-thioglycosides, was designed and synthesized. All compounds were evaluated in vitro for their antiviral activity against hepatitis C virus (HCV) and classical swine fever virus (CSFV), two important human and animal viral pathogens for which new or improved therapeutic options are needed. The antiviral activity of all synthesized compounds was confirmed using pseudo-plaque reduction assays in which a significant arrest of CSFV and HCV growth was observed in the presence of these compounds. Two of the synthesized compounds, 9 and 12, displayed a significant inhibitory effect on HCV and CSFV propagation with IC50 values of 4.9 and 13.5 µM for HCV and 4.2 and 4 µM for CSFV, respectively, with low cytotoxicity. Using various infection and replication models, we have shown that both compounds were able to significantly reduce viral genome replication by up to 90% with IC50 values in the low micromolar range. A structure activity analysis of the synthesized compounds showed that the high antiviral activity was attributed to the hydrophobicity of glycoconjugates and the introduction of elements capable to coordinate metal ions into the spacer connecting the sugar and uridine moiety, which can be useful in the development of new antiviral compounds in the future.

Thiosugars, containing a sulfur atom as heteroatom or a disaccharide linked via a sulfur bridge, possess unique physicochemical properties such as water solubility, which differs from conventional functionalized monosaccharides. The differences in biological activities between thiosugars and their oxygen analogs depend on geometric, conformational, and flexibility differences. They depend also on their electronic differences, the sulfide function being less electronegative and more polarizable than the ethereal moiety. Many functionalized thiosugars occur naturally and are potential targets for the development of carbohydrate-based therapeutics. Among the few new examples of the potential new targets are salacinol and kotalanol, tagetitoxin, thiolactomycin and analogues, mycothiol and analogues, and S-nitrosothiols. These new developments and representative examples of functionalized thiosugar prototypes as potential new targets are presented in this mini review.[PUBLICATION ABSTRACT]