Protected Sugar Research Articles

Deletion of the transcription factors Hsf1, Msn2 and Msn4 in yeast uncovers transcriptional reprogramming in response to proteotoxic stress.

The response to proteotoxic stresses such as heat shock allows organisms to maintain protein homeostasis under changing environmental conditions. We asked what happens if an organism can no longer react to cytosolic proteotoxic stress. To test this, we deleted or depleted, either individually or in combination, the stress-responsive transcription factors Msn2, Msn4, and Hsf1 in Saccharomyces cerevisiae. Our study reveals a combination of survival strategies, which together protect essential proteins. Msn2 and 4 broadly reprogram transcription, triggering the response to oxidative stress, as well as biosynthesis of the protective sugar trehalose and glycolytic enzymes, while Hsf1 mainly induces the synthesis of molecular chaperones and reverses the transcriptional response upon prolonged mild heat stress (adaptation).

Multi-omics data provide insight into the adaptation of the glasshouse plant Rheum nobile to the alpine subnival zone

Subnival glasshouse plants provide a text-book example of high-altitude adaptation with reproductive organs enclosed in specialized semi-translucent bracts, monocarpic reproduction and continuous survival under stress. Here, we present genomic, transcriptomic and metabolomic analyses for one such plant, the Noble rhubarb (Rheum nobile). Comparative genomic analyses show that an expanded number of genes and retained genes from two recent whole-genome duplication events are both relevant to subnival adaptation of this species. Most photosynthesis genes are downregulated within bracts compared to within leaves, and indeed bracts exhibit a sharp reduction in photosynthetic pigments, indicating that the bracts no longer perform photosynthesis. Contrastingly, genes related to flavonol synthesis are upregulated, providing enhanced defense against UV irradiation damage. Additionally, anatomically abnormal mesophyll combined with the downregulation of genes related to mesophyll differentiation in bracts illustrates the innovation and specification of the glass-like bracts. We further detect substantial accumulation of antifreeze proteins (e.g. AFPs, LEAs) and various metabolites (e.g. Proline, Protective sugars, procyanidins) in over-wintering roots. These findings provide new insights into subnival adaptation and the evolution of glasshouse alpine plants.

Loss of preferential access to the protected EU sugar market: Fiji's response

AbstractThe Fijian government's response since 2010 to the loss of preferential access to the European Union's previously highly protected sugar market has been to increasingly support its cane growers and millers. That support is now much higher than most other countries' assistance to the sugar industry. This study provides detailed estimates of the changing extent of those transfers to producers from both taxpayers and consumers during 2010–22. In doing so, it estimates for the first time an annual time series of nominal rates of assistance to producers and consumer tax equivalent rates (NRAs and CTEs, but they are also converted to producer and consumer support estimates as defined by the OECD). Those NRA and CTE estimates have been approaching 100%. The level of support was equivalent to 10% of Fiji's agricultural value added in 2018–21 and is around 5% of its government's consolidated revenue—at a time when the government has a very high debt‐to‐GDP ratio (90% in 2022). Since the nature of the support is economically inefficient, inequitable, environmentally damaging and fiscally unsustainable given foreseeable market prospects, suggestions are made as to how that support might be repurposed to provide better economic, social and environmental outcomes for Fiji.

How sustainable is the growth of assistance to Fijian sugar producers?

Following the loss of preferential access to the European Union’s previously highly protected sugar market, Fiji’s Government has been increasingly supporting its producers since 2010. That support is now much higher than most other countries’ assistance to the sugar sector. This study summarizes estimates of the changing extent of those transfers to producers from taxpayers and consumers. It does so by expressing them as nominal rates of assistance to producers and consumer tax equivalent rates (NRAs and CTEs). Those NRA and CTE estimates may well now exceed 100%. The level of support is around 5% of the government’s consolidated revenue. The nature of the support is not only economically inefficient and inequitable but also environmentally damaging and fiscally unsustainable given foreseeable market prospects. This suggests the need for that support to be re-purposed to provide better economic, social and environmental outcomes. Several suggestions as to how to do that conclude the paper.

Selective silver (I)-catalyzed four-component gram-scale synthesis of novel 1,4-disubstituted 1,2,3-triazole-sulfonamides under heterogeneous catalysis and microwave irradiation in water

The Ag3PO4-MEA catalyst was successfully prepared and proved to be an efficient and selective catalyst of the multicomponent synthesis of a new library of 1,4-disubstituted 1,2,3-triazole-sulfonamides 5a-n. This new methodology cleanly proceeded in water under microwave activation using N-propargyl saccharin, NaN3 or SO2(N3)2, substituted benzyl chloride or protected sugar and non-conjugated primary amines, using Ag(I) in a method-comparison study to Cu(I) as conventional Sharpless catalyst. The proposed strategy allows a simple, rapid and scalable route to 1,2,3-triazoles sulfonamides derivatives 5 through in-situ ring-opening of saccharin system with primary amine. All compounds have been fully characterized by NMR, mass spectrometry and X-ray crystallography analysis. The catalyst has been prepared via a green Sol-Gel methodology and fully analyzed by X-ray Diffraction (XRD), Fourier Transform Infrared (FTIR) Spectroscopy and Scanning Electron Microscopy (SEM) coupled to Energy Dispersive X-ray Spectroscopy (EDX), and Brunauer-Emmett-Teller (BET) method. The catalyst is easily recovered during the process and showed high recyclability.

Impact of protectant uptake on the shelf-life of dried Lacticaseibacillusrhamnosus

To improve the survival of dried probiotics, it is advised to expose the bacteria to protectants prior to processing, allowing equilibration of internal solutes. However, optimal conditions for this exposure remain unclear.This study examined solute uptake by Lacticaseibacillus rhamnosus HN001 (formally known as Lactobacillus rhamnosus HN001) at 4 °C and 20 °C, over exposure times of 0–240 min. The cells were exposed to hyperosmotic solutions of glucose and sucrose, two potential protective sugars, which are metabolisable and have different molecular weights. Sugar uptake was analysed through HPLC, while the impact on cell viability after freeze-drying was examined at 30 °C and 40 °C. The interactions between cell biomolecules and sugars were examined using Nano DSC.Results showed that the sugars were rapidly taken up by the cells, independent of temperature. At 20 °C, glucose was readily metabolised, eventually resulting in loss of cell viability during storage. Conversely, the Nano DSC study revealed interactions between the cells and sucrose, potentially providing some explanation as to the stability of the cells.In conclusion, sugar type and exposure temperature were shown to exert a significant effect on the viability of Lacticaseibacillus rhamnosus. Nano DSC is a promising technique to understand the protectant and cells’ interactions.

Regulation of secondary antioxidants and carbohydrates by gamma-aminobutyric acid under salinity-alkalinity stress in rice (Oryza sativa L.).

Gamma-aminobutyric acid (GABA) is known to improve tolerance against abiotic stresses but less studied for salinity-alkalinity stress (SAS). In the present study, GABA regulation of secondary antioxidants and carbohydrates was studied in rice in the presence and absence of SAS. About 1.5mM GABA, 200mM SAS, GABA + SAS were applied to 5-day old seedlings, and thereafter measurements were done in shoots and roots at 24, 48, 72h in rice cultivars CSR 43 (tolerant) and Pusa 44 (susceptible). SAS was applied in molar ratio of 1:9:9:1 of NaCl:Na2SO4:NaHCO3:Na2CO3. Peroxidases (POX), polyphenol oxidases (PPO), lignin, flavonoids and phenolics from secondary metabolism and invertases, hexoses, sucrose and starch from carbohydrate metabolism were studied. Pusa 44 increased soluble POX, lignin, flavonoids in shoots but deficient in roots during stress period but improved under GABA + SAS. CSR 43 increased soluble POX, lignin, flavonoids in roots consistently throughout the stress period and also improved under GABA + SAS. Early increase in cell wall POX/PPO under SAS was seen in CSR 43 only, while Pusa 44 improved this under GABA + SAS. During stress period, CSR 43 showed an increasing trend of cell wall invertase activity, sucrose, sucrose-to-hexose ratio and starch in roots but Pusa 44 showed poor such response but Pusa 44 improved starch, sucrose, sucrose-to-hexose ratio by significant amount in both shoots and roots under GABA + SAS. The overall study indicated GABA as an important regulator of secondary and carbohydrate metabolisms. Besides improving secondary antioxidants, GABA under stress may improve cellular reserves like starch and protective sugars like sucrose.

Towards Functional Fluorous Surfactants. Synthesis and Spectroscopic Features of Systematically Modified Sugar-Substituted Fluorous 1,2,3-Triazoles

ABSTRACT A library of 10 series of homologous compounds making up a total of 30 new, fluorous 1-substituted 1,2,3-triazol-4-ylmethyl(and ethyl) ether surfactant candidates, with highly systematic variations in substituent position and type, have been synthesised in consistently good yields by processes involving copper(I)-accelerated Huisgen-Meldal dipolar cycloaddition reactions. Each series contains a perfluorobutylethyl, perfluorohexylethyl or perfluorooctylethyl substituents at triazole position N(1) or attached through the triazole ether oxygen, and either a 1-β-D-glucosyl or 6-α-D-galactosyl substituent at the alternative triazole position. Half the library was prepared directly with the sugar components in a protected form (peracetylated glucose derivatives and 1,2:3,4-bisacetonide galactose derivatives) while the other series with unprotected sugars were obtained following a secondary deprotection step by trans-esterification using sodium methoxide or acid catalysed acetal solvation. All the triazoles are candidates for study as fluorous surfactants that are switchable between amphiphilic partner states, hydrophobic in the case of protected sugars and hydrophilic in unprotected sugars. As a prelude to surfactant studies, the NMR spectroscopic characteristics of the newly establish library of compounds were examined. Data were compared and contrasted within and between each series with reference to related literature analogues. Analysis of unprotected 6-galactosyl derivatives was complicated by the well known generation of inseparable, epimeric mixtures of hemiacetal pyranose and furanose products and the general paucity in the literature of NMR spectroscopic data assignments of signals from 1-β-hydroxygalactopyranose compounds. These matters have been addressed in this paper and the comparisons include analyses of unprotected 1'-α- and 1'-β-hydroxy-pyranose derivatives.

A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.

Synthesis of a Fluorescent Cytidine TNA Triphosphate Analogue.

Threose nucleic acid (TNA) is refractory to nuclease digestion and capable of undergoing Darwinian evolution, which together make it a promising system for diagnostic and therapeutic applications that require high biological stability. Expanding the sequence/chemical diversity of TNA would enable the development of functional TNA molecules with enhanced physicochemical properties. Recently, we have reported the synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue (1,3-diaza-2-oxo-phenothiazine, tCfTP) that maintains Watson-Crick base pairing with guanine. It not only improves TNA synthesis by enabling an engineered TNA polymerase to read through sequential G-repeats in a DNA template but it also introduces new physicochemical properties, such as increased hydrophobic character and fluorescence. Here, we describe the synthesis protocol for tCfTP, which includes three silica gel purifications, two precipitations, and one HPLC purification. Starting from protected threofuranosyl sugar, desired TNA nucleoside was obtained in a Vorbrüggen glycosylation reaction. After deprotection, nucleoside was further converted to 3'-monophosphate, activated by 2-methylimidazole, and subsequently treated with pyrophosphate to afford the desired 3'-triphosphate (tCfTP).

Novel Position-Specific 18O/16O Measurement of Carbohydrates. I. O-3 of Glucose and Confirmation of 18O/16O Heterogeneity at Natural Abundance Levels in Glucose from Starch in a C4 Plant.

The 18O/16O ratio at both molecular and positional levels in the carbohydrates of higher plants is a reliable proxy for the plant growth environment, and a potential indicator of the plant photosynthetic carbon assimilation mode, and its physiological, biochemical and metabolic status. The lack of exploitable nuclear resonance in 18O and 16O and the extremely low 17O abundance make the NMR-based PSIA (position-specific isotopic analysis) a significant challenge. In this Article, an alternative three-step wet chemistry based method for accessing the 18O/16O of glucose O-3 is presented. The O atoms (OH groups) at positions 1, 2, 5, and 6 were first protected by acetonation (converting glucose to 1,2;5,6-di- O-isopropylidene-glucofuranose). The protected glucose was then esterified at O-3 by thionoformylation. Subsequent Barton-McCombie deoxygenation quantitatively removed the O-3 from the protected sugar. Mass balance was then applied to calculate the 18O/16O of O-3 using the isotopic values of the protected sugar before and after the deoxygenation step. The method is innovative in that (i) isolation and purification of individual compounds for 18O by EA/Pyrolysis/IRMS analysis is unnecessary as the reaction mixture can be analyzed on a GC/Pyrolysis/IRMS; (ii) sample quantity is dramatically reduced; and (iii) the approach to access the O-3 isotopic signal can be easily expanded to other positions within glucose and other sugars. It was shown that O-3 is enriched by 12 mUr relative to the molecular average (O-2-O-6) for a glucose of C4 photosynthetic origin. We highlighted the potential applications of the intramolecular O isotopic heterogeneity of glucose this method revealed.

About the Sterilization of Chitosan Hydrogel Nanoparticles.

In the last years, nanostructured biomaterials have raised a great interest as platforms for delivery of drugs, genes, imaging agents and for tissue engineering applications. In particular, hydrogel nanoparticles (HNP) associate the distinctive features of hydrogels (high water uptake capacity, biocompatibility) with the advantages of being possible to tailor its physicochemical properties at nano-scale to increase solubility, immunocompatibility and cellular uptake. In order to be safe, HNP for biomedical applications, such as injectable or ophthalmic formulations, must be sterile. Literature is very scarce with respect to sterilization effects on nanostructured systems, and even more in what concerns HNP. This work aims to evaluate the effect and effectiveness of different sterilization methods on chitosan (CS) hydrogel nanoparticles. In addition to conventional methods (steam autoclave and gamma irradiation), a recent ozone-based method of sterilization was also tested. A model chitosan-tripolyphosphate (TPP) hydrogel nanoparticles (CS-HNP), with a broad spectrum of possible applications was produced and sterilized in the absence and in the presence of protective sugars (glucose and mannitol). Properties like size, zeta potential, absorbance, morphology, chemical structure and cytotoxicity were evaluated. It was found that the CS-HNP degrade by autoclaving and that sugars have no protective effect. Concerning gamma irradiation, the formation of agglomerates was observed, compromising the suspension stability. However, the nanoparticles resistance increases considerably in the presence of the sugars. Ozone sterilization did not lead to significant physical adverse effects, however, slight toxicity signs were observed, contrarily to gamma irradiation where no detectable changes on cells were found. Ozonation in the presence of sugars avoided cytotoxicity. Nevertheless, some chemical alterations were observed in the nanoparticles.

New insights into the interaction of proteins and disaccharides-The effect of pH and concentration.

To gain new insights into the interaction of proteins and disaccharides, we investigated the hydrodynamic radii, RhProt, of lysozyme molecules in solution and in a ternary protein-sugar-water system by PFG-NMR. Our approach is based on the assumption that the anhydrobiotic properties of disaccharides like trehalose are based on aggregation of sugar molecules to the proteins, i.e., accumulation of sugar molecules close to the protein, and that this process can be investigated by the experimentally detectable RhProt value of the protein. The Rh values are calculated from the experimentally determined diffusion coefficients and the application of a viscosity correction using the inert molecule dioxane as an internal viscosity reference. The experiments were performed as a function of sugar concentration, the overall particle concentration and the pH value. We investigated the disaccharides trehalose and sucrose, mainly for the reason that trehalose has well know cryptobiotic properties while sucrose, which is similar in size and structure, lacks these properties. The results show the formation of a protective sugar shell around the proteins over a wider range of concentrations and pH values in the case of trehalose.

Masked fungal toxins in our food

When fungi attack agricultural crops, they don’t just decrease yield, they can also leave behind poisonous compounds on the harvest. Although food safety scientists have long monitored these fungal products, known as mycotoxins, in recent years they’ve discovered that plants can chemically modify the compounds for their own survival, say, by adding a protective sugar group. However, food safety tests don’t currently look for these masked mycotoxins. Furthermore, the masked mycotoxins “may be hydrolyzed in the [human] digestive tract, thereby releasing the parental form and increasing the total exposure to the toxin,” notes a research team led by Sabine E. Kulling of the German Federal Research Institute of Nutrition & Food (J. Agric. Food Chem. 2016, DOI: 10.1021/acs.jafc.6b03120). Kulling and her colleagues report that when Alternaria alternata infects tomato cells, the fungus first decorates its toxins—including alternariol (shown)—with a sulfate group and then the tomato’s enzymes add a glucoside. Because

Synthesis of three different galactose-based methacrylate monomers for the production of sugar-based polymers

Glycopolymers, synthetic sugar-containing macromolecules, are attracting ever-increasing interest from the chemistry community. Glycidyl methacrylate (GMA) is an important building block for the synthesis of sugar based methacrylate monomers and polymers. Normally, glycidyl methacrylate shows some advantages such as reactivity against nucleophiles or milder synthetic conditions such as other reactive methacrylate monomers. However, condensation reactions of glycidyl methacrylate with for instance protected galactose monomer leads to a mixture of two products due to a strong competition between the two possible pathways: epoxide ring opening or transesterification. In this paper, we propose two alternative routes to synthesize regiospecific galactose-based methacrylate monomers using the epoxy-ring opening reaction. In the first alternative route, the protected galactose is first oxidized to the acid in order to make it more reactive against the epoxide of GMA. In the second route, the protected sugar was first treated with epichlorohydrin followed by the epoxy ring opening reaction with methacrylic acid, to create an identical analogue of the ring-opening product of GMA. These two monomers were polymerized using conventional radical polymerization and were compared to the previously known galactose-methacrylate one. The new polymers show similar thermal stability but lower glass transition temperature (Tg) with respect to the known galactose methacrylate polymer.

Chitosan nanogels for biomedical applications: Choosing a suitable sterilization method

Event Abstract Back to Event Chitosan nanogels for biomedical applications: Choosing a suitable sterilization method Raquel Galante1, 2, Irene Satiko1, Nádia A. Bou-Chacra1, Rogério Colaço2, Ana P. Serro2, 3 and Terezinha J. Pinto1 1 Faculdade de Ciências Farmacêuticas - Universidade de São Paulo, Departamento de Farmácia, Brazil 2 Instituto Superior Técnico - Universidade de Lisboa, Centro de Química Estrutural, Portugal 3 Instituto Superior de Ciências da Saúde Egas Moniz, Centro De Investigação Interdisciplinar Egas Moniz, Portugal Introduction: Nanostructured hydrogels have been subject of detailed studies aiming a wide range of biomedical and pharmaceutical applications. Sterilization is a crucial step in the development of this type of materials[1]. Although often effective, the conventional sterilization methods may change the physico-chemical properties of the gels and their biocompatibility, compromising their functionality[1],[2]. The main goal of this work is to study the effect of different sterilization methods on the intrinsic properties of chitosan nanogels. In addition to conventional methods (autoclave and gamma radiation) a recent and promising ozone-based method of sterilization, still in the development phase, was also evaluated to assess its applicability to the studied material. Method: A model chitosan-based nanostructured hydrogel (nanogel), with broad spectrum of possible applications was produced by ionic gelation, using sodium tripolyphosphate (TPP) as a crosslinking agent. The nanogel was sterilized by autoclave, gamma irradiation and by ozone gas in the absence and in the presence of protective sugars (dextrose and mannitol). Sterilization parameters, such as temperature, time of exposure and irradiation dose, were varied in order to study their effect. A complete characterization protocol was carried out, before and after each sterilization method, as follows: size, dispersion and zeta potential alterations where analyzed by Zetasizer measurements; surface topography and morphology were studied by Scanning Electronic Microscopy and physicochemical alterations were monitored by Fourier Transform Infrared Spectroscopy analysis. In order to ensure the effectiveness of the ozone method, sterility efficacy tests were carried out by purposely contaminating the samples with different loads of a microorganism known to be resistant to the technique. Results and Discussion: Exposing the nanogel, as it is, to gamma rays, let to the immediately visible formation of sediments. Although the UV-Vis spectra data did not show significant alterations, the size and zeta potential measurements displayed significant effects on Z-average size, PDI and zeta potential values, thus resulting in a degraded nanogel.Upon the sugar addition (D-glucose and mannitol) to the nanogel suspension, the results showed a substantial increase of the resistance to irradiation.The variation of average particle due to gamma rays irradiation can be observed in Figure 1, for all the studied conditions. In both cases, size, PDI, and zeta potential values variations were significantly reduced.Concerning the ozone gas method, the nanogel revealed a promising resistance to the ozonation, having shown no major sings of alteration in size, zeta potential and PDI..The variation of average particle due to ozonation can be observed in Figure 2, for all the studied conditions. Conclusions: Sterilization of soft polymeric biomaterials such as nanogels is a challenging task. The information available in the literature about the sterilization of chitosan nanogels is scarce, which reinforces the importance of this work. It was found that the nanogel resistance to irradiation increases considerably in the presence of protective sugars. The results obtained are also promising with regard to the possible applicability of the ozone sterilization since the nanogel seems to withstand the method without displaying significant adverse effects. Figure 1: Average particle size before and after sterilization by gamma irradiation Figure 2: Average particle size before and after sterilization by ozone gas. Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES); Fundação para a Ciência e Tecnologia (FCT), Project SurfLenses - MERA-NET; A special thanks to Dr. Pablo Vásquez from IPEN (Instituto de Pesquisas Energéticas e Nucleares)

ChemInform Abstract: Efficient and Selective Azidation of per‐O‐Acetylated Sugars Using Ultrasound Activation: Application to the One‐Pot Synthesis of 1,2,3‐Triazole Glycosides.

AbstractAn inexpensive, simple, and highly efficient process is developed for the selective anomeric azidation of protected sugars using ultrasound activation and an of iron catalyst.

Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected d-Ribose

New, improved methods to access nucleosides are of general interest not only to organic chemists but to the greater scientific community as a whole due their key implications in life and disease. Current synthetic methods involve multistep procedures employing protected sugars in the glycosylation of nucleobases. Using modified Mitsunobu conditions, we report on the first direct glycosylation of purine and pyrimidine nucleobases with unprotected D-ribose to provide β-pyranosyl nucleosides and a one-pot strategy to yield β-furanosides from the heterocycle and 5-O-monoprotected D-ribose.

Cryopreservation of hepatocyte (HepG2) cell monolayers: Impact of trehalose

A simple method to cryogenically preserve hepatocyte monolayers is currently not available but such a technique would facilitate numerous applications in the field of biomedical engineering, cell line development, and drug screening. We investigated the effect of trehalose and dimethyl sulfoxide (Me2SO) in cryopreservation of human hepatocellular carcinoma (HepG2) cells in suspension and monolayer formats. HepG2 cell monolayers were incubated for 24h at varying concentrations of trehalose (50–150mM) prior to cryopreservation to identify the optimum concentration for such preincubation. When trehalose alone was used as the cryoprotective agent (CPA), cells in monolayer format did not survive freezing while cells in suspension demonstrated 14% viability 24h after thawing. Only 6–13% of cells in monolayers survived freezing in cell culture medium supplemented with 10% Me2SO, but 42% of cells were recovered successfully if monolayers were preincubated with 100mM trehalose prior to freezing in the Me2SO supplemented medium. Interestingly, for cells frozen in suspension in presence of 10% Me2SO, metabolic activity immediately following thawing did not change appreciably compared to unfrozen control cells. Finally, Raman spectroscopy techniques were employed to evaluate ice crystallization in the presence and absence of trehalose in freezing solutions without cells because crystallization may alter the extent of injury observed in cell monolayers. We speculate that biomimetic approaches of using protective sugars to preserve cells in monolayer format will facilitate the development of techniques for long-term preservation of human tissues and organs in the future.

Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety

Twelve novel 8-hydroxyquinoline derivatives were synthesized with good yields by performing copper-catalyzed Huisgen 1,3-dipolar cycloaddition (“click” reaction) between an 8-O-alkylated-quinoline containing a terminal alkyne and various aromatic or protected sugar azides. These compounds were evaluated in vitro for their antiproliferative activity on various cancer cell types. Protected sugar derivative 16 was the most active compound in the series, exhibiting potent antiproliferative activity and high selectivity toward ovarian cancer cells (OVCAR-03, GI50 < 0.25 μg mL−1); this derivative was more active than the reference drug doxorubicin (OVCAR-03, GI50 = 0.43 μg mL−1). In structure–activity relationship (SAR) studies, the physico-chemical parameters of the compounds were evaluated and docking calculations were performed for the α-glucosidase active site to predict the possible mechanism of action of this series of compounds.