Metal Ion Chelating Research Articles

Fractionation and characterization of antioxidant peptides from rice bran protein hydrolysates stimulated by in vitro gastrointestinal digestion

AbstractBackground and objectiveRice bran protein concentrate was prepared and hydrolyzed by using pepsin–pancreatin. The obtained result was further filtered through 5‐kDa membranes. A permeate was collected and sequentially fractionated by different chromatographic techniques. The peptide fractions were determined for the antioxidant activities.FindingsThree peptide fractions were derived after separating the crude protein hydrolysates by anion‐exchange chromatography. Due to its highest ABTS radical scavenging and metal chelating activities (p < .05), fraction F2‐A was pooled and separated further by size‐exclusion chromatography (SEC). Among the SEC fractions, F1‐S showed strongest antioxidant activities; thus, it was collected for reverse‐phase HPLC purification. Subsequently, the peptide fractions were successfully separated and F4‐H had the greatest ABTS‐scavenging activities (214.61 µmol Trolox/g sample, respectively). In addition, it displayed the strongest ability to reduce ferric to ferrous ions (104.80 µmol FeSO4/g sample) (p < .05), while F1‐H showed the highest ability to chelate metal ions (266.40 µmol EDTA/g sample) (p < .05).ConclusionThese results demonstrate that hydrophobic amino acids play a major role in scavenging free radicals, whereas polar amino acids are responsible for reducing and chelating metal ions.Significance and noveltyRice bran protein composes of high ratio of hydrophobic amino acid. It is a suitable source of antioxidant peptides that might be produced during gastrointestinal digestion. Separation and purification using chromatographic techniques showed promising results for selectively fractionate antioxidant peptides with specific activity.

A novel approach for obtaining α,β-diaminophosphonates bearing structurally diverse side chains and their interactions with transition metal ions studied by ITC.

Aminophosphonates are an important group of building blocks in medicinal and pharmaceutical chemistry. Novel representatives of this class of compounds containing nontypical side chains are still needed. The aza-Michael-type addition of amines to phosphonodehydroalanine derivatives provides a simple and effective approach for synthesizing N′-substituted α,β-diaminoethylphosphonates and thus affords general access to aminophosphonates bearing structurally diverse side chains. Thermodynamic analysis of the chosen aminophosphonates at physiological pH proves that they serve as potent chelators for copper(ii) ions and moderate chelators for nickel(ii) ions.

Naturally present metal ions in plants could interfere with common antioxidant assays

Most of the commonly applied assays used to assess antioxidant properties of plant extracts exploit the ability of some biologically active metabolites to participate in oxidation-reduction reactions with metal ions. On the other hand, most plants contain different chelated metal ions whose levels depend on the geographic origin, soil, and environmental pollutions. In this study the levels of redox-active metal ions in three plant sources were measured and extracts of these botanicals were treated with ChelexⓇ – an ion exchanger that is noteworthy for its ability to bind transition metal ions. The original and chelated extracts were subjected to three antioxidant assays based on single electron transfer. The results obtained showed statistically significant differences between the original and Chelex-treated extracts suggesting that the naturally present metal ions could interfere with the results of the three most commonly applied antioxidant methods.•The proposed pre-analytical procedure is simple and does not require special instrumental equipment.•Preliminary depletion of redox active metal ions, namely iron and copper ions could improve reproducibility of the analytical methods.•The method allows a more reliable comparison of antioxidant properties of particular botanical species from different geographic regions.

Leveraging synthetic chlorins for bio-imaging applications.

Synthetic chlorins are not only fluorescent, the modulation of the tetrapyrrole system can also chelate metal ions. Conjugation of linkers at their pyrrolidines allows for conjugation to bio-molecules to create target specificity. By altering these chemo-photophysical properties, this work facilitates the use of chlorins in fluorescent imaging and positron emission tomography (PET).

Antioxidant activitiy of Lactobacillus plantarum , Lactobacillus sake and Lactobacillus curvatus strains isolated from fermented Turkish Sucuk.

In recent years, it is very important to find more safe and natural antioxidants than biological sources to replace synthetic antioxidants. The antioxidant properties of 22 lactic acid bacteria were investigated in vitro in the present study. The conducted in vitro antioxidant assays included scavenging the 2,2-diphenyl-1-picrylhydrazil (DPPH) free radical, metal (Fe+2) ion chelation, hydroxyl radical and superoxide radical scavenging properties, and anti-lipid peroxidation. Analysis of DPPH free radical scavenging property of microorganisms demonstrated that Lactobacillus plantarum IH14L (90.34 ± 0.40%) strain exhibited the highest activity. The highest Fe+2 chelation activity was observed with Lactobacillus curvatus GH5L (75.98 ± 5.35%), while the lowest chelation activity was observed with L. plantarum IH14L (19.80 ± 0,05). The highest and lowest hydroxyl radical scavenging strains were L. plantarum IH16L (82.25 ± 1.60%) and L. plantarum IH26L (35.60 ± 4.50) strains, respectively. Comparison of superoxide radical scavenging activities of the microorganisms demonstrated that these activities ranged between 21.63 ± 1.32% and 7.22 ± 0.04%. A positive correlation was identified between the hydroxyl radical scavenging activity of the microorganisms and the anti-lipid peroxidation property. It was found that they had the potential for use in nutritional and probiotic applications as protective and natural antioxidants.

ОЦІНЮВАННЯ АНТИОКСИДАНТНИХ ВЛАСТИВОСТЕЙ ЕКСПЕРИМЕНТАЛЬНИХ ПОЛІКОМПОНЕНТНИХ КОМПЛЕКСІВ

The involvement of free radicals appears to be the feature of most human diseases. The general mechanism of cell damage involves the excessive uncontrolled production of reactive oxygen species resulting in the intensification of lipid peroxidation processes and damaging of macromolecules. These processes are generally accompanied by a decrease in the concentration and/or activity of natural antioxidants. Moreover, the exhaustion of the antioxidant capacity of the organism is among the key reasons leading to the development of pathological states. The maintenance of the prooxidant-antioxidant balance by the systematic use of products or dietary supplements, the components of which exhibit antioxidant activity, can be considered as a part of a strategy for the prevention and control of diseases associated with oxidative stress. The current work aims to study the free radical scavenging activity of two experimental poly-component complexes. Antioxidant properties of complexes were determined in experiments in vitro. The estimation of total antioxidant activity, nitric oxide, hydrogen peroxide radical, and superoxide anion scavenging activity was performed. The results revealed that both complexes have the potentials to prevent the formation of free radicals and can be used as agents with antioxidant properties. It was established that the effect of complex 1 and 2 is complex and first of all aimed at the prevention of the formation of dangerous free radicals by reducing the level of hydrogen peroxide. The additional mechanism involves the chelating of metal ions, in particular ferrous iron. The antioxidant ability exhibited by complex 1 was found to be higher than the total antioxidant activity of complex 2. Complex 1 was more effective in the ability to neutralize superoxide anion-radicals while complex 2 showed a high percentage inhibition of Fe2+-induced lipid peroxidation.

S-adenosylmethionine tRNA modification: unexpected/unsuspected implications of former/new players.

S-adenosylmethionine supplies methyl groups to many acceptors, including lipids, proteins, RNA, DNA, and a wide range of small molecules. It acts as the precursor in the biosynthesis of metal ion chelating compounds, such as nicotianamine and phytosiderophores, of the polyamines spermidine and spermine and of some plant hormones. Finally, it is the source of catalytic 5′-deoxyadenosyl radicals.Radical S-adenosylmethionine (SAM) enzymes (RS) represent one of the most abundant groups (more than 100,000) of enzymes, exerting a plethora of biological functions, some of which are still unknown.In this work, we will focus on two RS: CDK5RAP1 and CDKAL1, both of which are involved in tRNA modifications that result in important tRNA folding and stability and in maintaining high translational fidelity. Based on this crucial role, their impairment can be important in the development of different human diseases.

Structural properties of the chelating agent 2,6-bis(1-(3-hydroxypropyl)-1,2,3-triazol-4-yl)pyridine: a combined XRD and DFT structural study.

The conformational isomerism of the chelating agent 2,6-bis(1-(3-hydroxypropyl)-1,2,3-triazol-4-yl)pyridine (PTD), exploited in fuel reprocessing in spent nuclear waste, has been studied by single crystal X-ray diffraction analysis in combination with an extensive DFT conformational investigation. In the solid-state, the elucidated crystal structure (i.e., not yet published) shows that by thermal treatment (DSC) no other phases are observed upon crystallization from the melt, indicating that the conformation observed by X-ray data is rather stable. Mapping of intermolecular and intramolecular noncovalent interactions has been used to elucidate the unusual arrangement of the asymmetric unit. Considerations relating to the stability of different conformational isomers in aqueous and non-aqueous solutions are also presented. The accurate structural description reported here might open various research topics such as the potential of PTD to act as an outer sphere ligand in the formation of second sphere coordination complexes and their interconversion by mechanochemical means.

Comparative assessment of physicochemical and antioxidative properties of mung bean protein hydrolysates.

Two commercial plant proteases namely ficin and bromelain, were acquired to hydrolyze mung bean protein over 300 min hydrolysis, and the physicochemical and antioxidative properties of the obtained hydrolysates were investigated. Bromelain-treated mung bean protein hydrolysates presented a higher degree of hydrolysis in comparison with ficin-treated hydrolysates, further modifying their physicochemical and emulsifying properties. All mung bean protein hydrolysates exhibited 50% scavenging of DPPH radical (IC50) in the concentration range from 8.67 to 16.22 μg mL−1. Our results also showed that strong metal ion-chelating activity was found in the ficin- (higher activity) and bromelain-treated protein hydrolysates. In addition, oxidative stability of linoleic acid was significantly enhanced by two selected protein hydrolysates, particularly the bromelain-treated hydrolysate with the highest inhibition effect of linoleic acid oxidation (94.55 ± 0.10%). Interestingly, both of these two hydrolysates could effectively retard lipid oxidation of sunflower oil and sunflower oil-in-water emulsion, while the ficin-treated hydrolysate showed slightly better performance. Therefore, mung bean protein hydrolysates showed potential to inhibit lipid oxidation, which could be advantageous in the food industry for producing fortified food.

Effects of partial hydrolysis on the structural, functional and antioxidant properties of oat protein isolate.

The degree of hydrolysis (DH) plays important roles in the characteristics of food proteins. Herein, in order to explore the effects of partial hydrolysis on the structural, functional and antioxidant characteristics of hydrolysates, oat protein isolate was partially hydrolyzed with alcalase at different DHs (2%, 4%, 6%, 8%, 12%, and 16%). Our results showed that hydrolysis could induce significant structural changes in oat protein, mainly reflecting at the amino acid pattern, molecular weight profile and protein conformation. Alcalase hydrolysis also resulted in hydrolysates with the emulsifying activity index of at least 19.83 m2 g-1, and the highest emulsion stability was observed in the hydrolysate with a DH of 6%, possibly due to its suitable molecular weight, exposed hydrophobic amino acid residues and high surface net charge. Besides, all hydrolysates exerted excellent DPPH radical scavenging activity with an IC50 value ranging from 19.23 to 30.32 μg mL-1, which was closely correlated with DH. The oat protein isolate with moderate alcalase hydrolysis (DH 6%) exhibited the strongest metal ion-chelating activity and possessed the maximum amount of hydrophilic amino acids. More importantly, the oat protein hydrolysate with a DH of 6% not only prolonged the induction period of sunflower oil, but also improved the stability of the sunflower oil-in-water emulsion, as evidenced by the reduced TBARS production and the homogeneous droplet size. Therefore, partial hydrolysis can be advantageous for improving the functional and antioxidant characteristics of oat protein isolate, particularly the hydrolysate with a DH of 6%.

Bioproducts from forest biomass: Essential oils and hydrolates from wastes of Cupressus lusitanica Mill. and Cistus ladanifer L.

Unattended forest wastes are, among others, a potential source of wildfires, as well as a growth media for forest pests. As a way of lowering the detrimental effect of these wastes, it is important to convert these under-valued resources into a value-generating market forest wastes use. Essential oils (EOs) and hydrolates (Hs) from Cupressus lusitanica and Cistus ladanifer waste products, resulting from forest landscaping in Portugal, were evaluated for chemical composition and biological activity. Essential oils and Hs were obtained by steam-distillation (SD) and hydrodistillation (HD). Essential oils and Hs volatiles were analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC–MS). The antimicrobial activity of EOs was studied by disk agar diffusion method against Escherichia coli, Staphylococcus aureus and Candida albicans. Antioxidant activity of EOs and Hs was evaluated by 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) free radical, superoxide anion radical formation, xanthine oxidase and chelating metal ions assays. Anti-inflammatory activity of Hs was assessed by albumin denaturation assay. Monoterpene hydrocarbons and oxygen-containing monoterpenes dominated C. lusitanica EO (SD, 82–86 %, HD, 80–85 %) and Hs volatiles (SD, 93–94 %; HD 64–81 %), respectively. α-Pinene (14–36 %), limonene (8–21 %), δ-3-carene (8–19 %) and sabinene (6–18 %) were the main EO constituents. Hydrolates volatiles were dominated by cis-3-hexen-1-ol (0.1–13 %), camphor (1–11 %), umbellulone (t-48 %), p-cymene-8-ol (11–16 %) and terpinen-4-ol (21–31 %). C. ladanifer EOs were dominated by monoterpene hydrocarbons (SD, 48–80 % and HD, 29 %) and Hs by oxygen-containing monoterpenes (SD, 38–43 %, HD, 39 %). The EO major constituents were α-pinene (13–28 %) and camphene (5–25 %), whereas 2,6,6-trimethyl cyclohexanone (2–12 %) and trans-pinocarveol (5–13 %) dominated the Hs volatiles. This study reports for the first time the chemical composition of the hydrolate volatiles of these two species and their anti-inflammatory properties. Among the studied biological activities, the EOs showed the best antioxidant properties while Hs demonstrated higher anti-inflammatory activity.

57 Carnosine prevents oxidative damage in myoblast cells derived from porcine skeletal muscle

Abstract Carnosine (β-alanyl-L-histidine) is a molecule naturally and exclusively present in muscle food with the highest concentrations found in skeletal muscles and brain of the animal. Among its numerous biochemical properties, carnosine has antioxidant activity which include metal ion chelation and free radical scavenging. We have recently reported that high muscle carnosine content in pig is associated with better meat quality. Moreover, supplementing pigs with β-alanine reduced oxidative damage to Longissimus muscle (LM) lipids and proteins. Among previously reported antioxidant activities, carnosine was found to limit the production of reactive oxygen species (ROS) and increase antioxidant enzyme activities. However, these studies were mainly conducted in rodents and cell lines and mechanisms in play remain to be characterized. To determine the effect of carnosine in preventing oxidative damage and characterize the mechanisms in play, we have undertaken experiments using the progeny (myoblasts) of satellite cells isolated from the LM of newborn piglets. Cells were treated with carnosine (0, 10, 25 and 50 mM) for 48 h and were then either collected immediately or treated with H2O2 (0.3 mM, 1 h) to induce an oxidative stress. Our results showed that carnosine prevents oxidative stress through the reduction of total intracellular ROS and by modulating the antioxidant system in myoblasts.Carnosine increased the mRNA abundance of NEF2L2, a transcription factor activated by oxidative stress, and several of its downstream regulated antioxidant genes. Western blot analyses further suggest that the protective effect of carnosine on H2O2-induced oxidative stress is mediated through the p38 MAPK intracellular pathway. Finally, the addition of carnosine to H2O2-treated myoblasts increased the basal cellular oxygen consumption rate (OCR), the ATP-linked OCR and proton leaks, thus suggesting an effect of carnosine on mitochondrial functions. Taken together, these findings demonstrate the important role of carnosine in preventing oxidative damage in porcine muscle cells.

Expanding the Toolbox of Metal–Phenolic Networks via Enzyme‐Mediated Assembly

AbstractFunctional coatings are of considerable interest because of their fundamental implications for interfacial assembly and promise for numerous applications. Universally adherent materials have recently emerged as versatile functional coatings; however, such coatings are generally limited to catechol, (ortho‐diphenol)‐containing molecules, as building blocks. Here, we report a facile, biofriendly enzyme‐mediated strategy for assembling a wide range of molecules (e.g., 14 representative molecules in this study) that do not natively have catechol moieties, including small molecules, peptides, and proteins, on various surfaces, while preserving the molecule's inherent function, such as catalysis (≈80 % retention of enzymatic activity for trypsin). Assembly is achieved by in situ conversion of monophenols into catechols via tyrosinase, where films form on surfaces via covalent and coordination cross‐linking. The resulting coatings are robust, functional (e.g., in protective coatings, biological imaging, and enzymatic catalysis), and versatile for diverse secondary surface‐confined reactions (e.g., biomineralization, metal ion chelation, and N‐hydroxysuccinimide conjugation).

Expanding the Toolbox of Metal-Phenolic Networks via Enzyme-Mediated Assembly.

Functional coatings are of considerable interest because of their fundamental implications for interfacial assembly and promise for numerous applications. Universally adherent materials have recently emerged as versatile functional coatings; however, such coatings are generally limited to catechol, (ortho-diphenol)-containing molecules, as building blocks. Here, we report a facile, biofriendly enzyme-mediated strategy for assembling a wide range of molecules (e.g., 14 representative molecules in this study) that do not natively have catechol moieties, including small molecules, peptides, and proteins, on various surfaces, while preserving the molecule's inherent function, such as catalysis (≈80 % retention of enzymatic activity for trypsin). Assembly is achieved by in situ conversion of monophenols into catechols via tyrosinase, where films form on surfaces via covalent and coordination cross-linking. The resulting coatings are robust, functional (e.g., in protective coatings, biological imaging, and enzymatic catalysis), and versatile for diverse secondary surface-confined reactions (e.g., biomineralization, metal ion chelation, and N-hydroxysuccinimide conjugation).

Modification of Polyacrylonitrile Fibers by Coupling to Thiosemicarbazones.

This work reports the modification of Polyacrylonitrile (PAN) fibers by coupling to thiosemicarbazones to achieve the biological activity for the applications in the food product packaging. After modification, seven thiosemicarbazone compounds were synthesized. The as-synthesized thiosemicarbazone compounds were bonded to PAN fibers via covalent coupling, which was confirmed using Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and scanning electron microscopy. The mean graft efficiency of the compounds was about 1.92%, and the antibacterial efficiency was 88.6% and 45.1% against Staphylococcus aureus (S-aureus) bacteria. All the seven thiosemicarbazone compounds exerted excellent tyrosinase activity, low cytotoxicity, excellent metal ion chelation ability, and anti-bacterial behavior against both gram-positive and negative bacteria. The mechanical properties of the fibers have been maintained without significant damage after the chemical modification. The break strength test and elongation at the break test were done to measure the fracture strength of the modified fibers. Overall, the promising properties of the modified PAN fibers show potential applications in food packaging materials for fruits and vegetables, which require long-term anti-browning effects during their transportation and storage.

Structure-activity of chelating collectors for flotation: A DFT study

Based on density functional theory calculations, the molecular frontier orbital of six types of chelating collector were studied, including S-S, S-N, N-N, S-O, N-O and O-O types, and mercaptobenzothiazole, ethyl xanthate, diethyldithiophosphate, and diethyldithiocarbamate, dithizone (keto form and enol form), dimethylglyoxime, thiocarboxylic acid, 8-hydroxyquinoline, salicylaldoxime, salicylhydroxamic acid, oleic acid, and cupferron were selected as representatives. The calculation results of the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and the orbital coefficients show that the chelating atoms of the collectors have great activity and large coefficient. For S-S type of collectors, the interactions of Cu, Fe Pb and Zn metal ions with double bond S, single-coordinated S and two-coordinated S are different. Moreover, mercaptobenzothiazole is more likely to chelate metal ions by means of S-N but not S-S. In S-N type, the interactions of Cu, Fe Pb and Zn metal ions with N atom are weaker than with S atom. For dimethylglyoxime (N-N type), the interactions of metal with the two N atom are nearly the same. For N-O type, the activity of N atom in a benzene ring is weaker than in a strain chain. The metal-O interactions are also different in S-O, N-O and O-O types of chelating collectors. Calculated results suggest that the electronic structure and spatial structure of an atom are very important to its interaction with metals and minerals.

Antidiabetic and Antioxidant Activity of Green Synthesized Starch Nanoparticles: An In Vitro Study

This study was aimed to assess the antidiabetic and antioxidant activity of starch nanoparticles (StNPs) synthesized by green synthesis through in vitro model. Several organic solvents were used for the extraction of active compounds from Gymnema sylvestre. The methanolic extract was used for the synthesis of StNPs from dried potato starch. The characterization studies such as GC–MS, FT-IR, SEM, EDS and XRD were performed to analyze the sample. The StNPs were found to be ellipsoidal in nature with the average particle size of 19.8 nm. The StNPs showed highest DPPH radical scavenging activity with 74.41 ± 0.54% at 100 µg/mL concentration. Besides, the IC50 values were found to be 66.69 µg/mL and 61.99 µg/mL for the StNPs and standard (ascorbic acid), respectively. The StNPs showed the highest metal ion chelating activity of 66.71 ± 0.34% at a concentration of 100 µg/mL. The highest reducing power of StNPs was found to be 0.385 ± 0.002 at 100 µg/mL. Moreover, in vitro antidiabetic activity was studied using alpha-amylase inhibition assay and the highest inhibition activity of StNPs was 58.56 ± 0.44% at a concentration of 100 µg/mL. The present study provided preliminary evidence indicated that the StNPs synthesized using methanolic extract of G. sylvestre had potential activity against diabetes.

Characterization of Single Amino Acid Variations in an EDTA-Tolerating Non-specific Nuclease from the Ice-Nucleating Bacterium Pseudomonas syringae.

Non-specific nuclease (NSN) can be applied in industrial downstream processing to remove nucleic acids from crude protein extracts or in cell-sorting systems to degrade nucleic acids derived from lysed cells. PsNuc from the ice-nucleating bacterium Pseudomonas syringae has the ability to decompose double- and single-stranded DNA in linear or circular form and RNA. It is not affected by the presence of metal-ion chelators such as EDTA and tolerates several protease inhibitors and reducing agents. A multiple sequence alignment of PsNuc with closely related enzymes (97-99% identity on the protein level) within the family Pseudomonaceae revealed the presence of only six amino acid residues that are variable in putative NSN from different members of the genus Pseudomonas. Single amino acid variants were produced in recombinant form in Escherichia coli, purified, and characterized. They showed similar activity compared to PsNuc, but a single variant even displayed an improved performance with an activity of > 20,000U/mg at 35°C, while amino acid residues S148 and V161 were found to be essential for enzymatic functionality. These results suggest that homologous nucleases from Pseudomonaceae display high activity levels in a metal-ion-independent manner and are therefore of interest for applications in biotechnology.

In vitro gastrointestinal digestion of crisphead lettuce: Changes in bioactive compounds and antioxidant potential

In this study, the potential health benefits of crisphead lettuce (Lactuca sativa L.) before and after digestion were represented by the recovery, bioaccessibility, and change of bioactive compounds including total phenolic (TPC) and total flavonoids content (TFC), and bioactivities [in vitro antioxidant activities including 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2, 2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging activities, ferric reducing antioxidant power (FRAP) and metal ion chelating activity (MIC)]. The release of bioactive compounds as well as bioactivities increased during gastric and intestinal digestion for 1 h and subsequently decreased when digestion was completed. The bioaccessibility of TPC and TFC at after digestion was 56–73 and 75–79%, respectively. Among all bioactivities, crisphead lettuce showed a residual activity of ABTS (61–95%) followed by FRAP (70–86%), DPPH (24–52%) and MIC (32–73%) during the digestion. Our study suggested that crisphead lettuce maintains stability in both bioactive compounds and bioactivities during the digestion.

8-Hydroxyquinoline Glycoconjugates: Modifications in the Linker Structure and Their Effect on the Cytotoxicity of the Obtained Compounds.

Small molecule nitrogen heterocycles are very important structures, widely used in the design of potential pharmaceuticals. Particularly, derivatives of 8-hydroxyquinoline (8-HQ) are successfully used to design promising anti-cancer agents. Conjugating 8-HQ derivatives with sugar derivatives, molecules with better bioavailability, selectivity, and solubility are obtained. In this study, 8-HQ derivatives were functionalized at the 8-OH position and connected with sugar derivatives (D-glucose or D-galactose) substituted with different groups at the anomeric position, using copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC). Glycoconjugates were tested for inhibition of the proliferation of cancer cell lines (HCT 116 and MCF-7) and inhibition of β-1,4-galactosyltransferase activity, which overexpression is associated with cancer progression. All glycoconjugates in protected form have a cytotoxic effect on cancer cells in the tested concentration range. The presence of additional amide groups in the linker structure improves the activity of glycoconjugates, probably due to the ability to chelate metal ions present in many types of cancers. The study of metal complexing properties confirmed that the obtained glycoconjugates are capable of chelating copper ions, which increases their anti-cancer potential.