Peter Kis

@savba.sk

Department of Glycochemistry, Slovak Academy of Sciences
Research Associate

Peter Kis


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https://researchid.co/peter.kis
9

Scopus Publications

71

Scholar Citations

6

Scholar h-index

4

Scholar i10-index

Scopus Publications

  • Manipulation and quantification of the levels of Autoinducer-2 quorum sensing signal in the mouse gut
    Miguel V. Rodrigues, António Ferreira, Maria Ramirez-Montoya, Rita A. Oliveira, Raphaël Defaix, Peter Kis, Vitor Cabral, M. Rosário Bronze, Karina B. Xavier, M. Rita Ventura
    Bioorganic Chemistry, 2025
    Quorum Sensing is a signalling mechanism used by bacteria to regulate gene expression as a function of population density, enabling them to engage in group behaviours. Autoinducer-2 (AI-2) is the most ubiquitously produced quorum sensing signal among bacterial species and it is unique in its capability of fostering cell-cell signalling across species from different phyla in multispecies communities. Alterations of AI-2 levels in the mouse gut can change the composition of the major gut microbiota phyla, but given the chemical instability of this signal, its quantification in intestinal samples and in vivo manipulation are challenging. Here, we optimised a Gas Chromatography - Mass Spectrometry (GC-MS) method to detect and quantify AI-2 in intestinal samples. Using a newly synthesised deuterated AI-2 molecule as the internal standard for AI-2 quantification, we quantified the levels of AI-2 in the cecum of conventionally raised mice with a complex microbiota. Moreover, we used a commensal Klebsiella sp. with probiotic potential to manipulate AI-2 levels in the mouse gut. We showed that mice colonised with mutants of this commensal Klebsiella sp. can be used to manipulate the levels of AI-2 in the mouse gut in both mono-colonised animals and those with a complex microbiota following recovery from antibiotic treatment. Overall, our results show that the analytical approach proposed here allows for robust and specific direct measurements of AI-2 in mouse caecal samples and can also be applied to other complex biological samples containing AI-2 aiming to study the role of quorum sensing signalling in microbiota communities.
  • Environmentally Friendly Degradation and Detoxification of Rifampicin by a Bacterial Laccase and Hydrogen Peroxide
    Paulo Durão, Peter Kis, Ivo M. Chelo, M. Rita Ventura, Lígia O. Martins
    Chembiochem, 2024
    Antibiotics are micropollutants accumulating in our rivers and wastewaters, potentially leading to bacterial antibiotic resistance, a worldwide problem to which there is no current solution. Here, we have developed an environmentally friendly two‐step process to transform the antibiotic rifampicin (RIF) into non‐antimicrobial compounds. The process involves an enzymatic oxidation step by the bacterial CotA‐laccase and a hydrogen peroxide bleaching step. NMR identified rifampicin quinone as the main product of the enzymatic oxidation. Growth of Escherichia coli strains in the presence of final degradation products (FP) and minimum inhibitory concentration (MIC) measurements confirmed that FP are non‐anti‐microbial compounds, and bioassays suggest that FP is not toxic to eukaryotic organisms. Moreover, competitive fitness assays between susceptible and RIF‐resistant bacteria show that susceptible bacteria is strongly favoured in the presence of FP. Our results show that we have developed a robust and environmentally friendly process to effectively remediate rifampicin from antibiotic contaminated environments.
  • Synthesis and Potential of Autoinducer-2 and Analogs to Manipulate Inter-Species Quorum Sensing
    Miguel V. Rodrigues, Peter Kis, Karina B. Xavier, M. Rita Ventura
    Israel Journal of Chemistry, 2023
    Abstract Quorum sensing (QS) is enabled by the production of signalling molecules called autoinducers, whose presence in the environment modulates the behavior of bacterial populations. Autoinducer‐2 (AI‐2) is unique as it is recognized by different species of bacteria and fosters signalling across different species. To further understand QS mechanisms and to discover potential novel therapeutics based on the modulation of bacterial behavior many analogs have been synthesized. This review aims to provide a critical analysis of the state‐of‐the‐art of the synthesis of AI‐2 and its analogs. It serves as a non‐exhaustive consolidation of previous studies of analogs, focusing on the synthetic approaches and the structure‐activity relationship conclusions drawn after the analysis of the chemical libraries of the research groups involved in the field. This article is intended to be a strong foundation for the rational planning of synthetic strategies of analogs with specific bioactivities.
  • Acuminosylation of Tyrosol by a Commercial Diglycosidase
    Peter Haluz, Peter Kis, Matej Cvečko, Mária Mastihubová, Vladimír Mastihuba
    International Journal of Molecular Sciences, 2023
    A commercial glycosidase mixture obtained from Penicillium multicolor (Aromase H2) was found to comprise a specific diglycosidase activity, β-acuminosidase, alongside undetectable levels of β-apiosidase. The enzyme was tested in the transglycosylation of tyrosol using 4-nitrophenyl β-acuminoside as the diglycosyl donor. The reaction was not chemoselective, providing a mixture of Osmanthuside H and its counterpart regioisomer 4-(2-hydroxyethyl)phenyl β-acuminoside in 58% yield. Aromase H2 is therefore the first commercial β-acuminosidase which is also able to glycosylate phenolic acceptors.
  • A sustainable approach to phenylethanoid glycopyranosides: Study of glycosylations promoted by zinc salts
    Peter Kis, Mária Mastihubová
    Sustainable Chemistry and Pharmacy, 2021
  • Synthesis of tyrosol and hydroxytyrosol glycofuranosides and their biochemical and biological activities in cell-free and cellular assays
    Peter Kis, Eva Horváthová, Eliška Gálová, Andrea Ševčovičová, Veronika Antalová, Elena Karnišová Potocká, Vladimír Mastihuba, Mária Mastihubová
    Molecules, 2021
    Tyrosol (T) and hydroxytyrosol (HOT) and their glycosides are promising candidates for applications in functional food products or in complementary therapy. A series of phenylethanoid glycofuranosides (PEGFs) were synthesized to compare some of their biochemical and biological activities with T and HOT. The optimization of glycosylation promoted by environmentally benign basic zinc carbonate was performed to prepare HOT α-L-arabino-, β-D-apio-, and β-D-ribofuranosides. T and HOT β-D-fructofuranosides, prepared by enzymatic transfructosylation of T and HOT, were also included in the comparative study. The antioxidant capacity and DNA-protective potential of T, HOT, and PEGFs on plasmid DNA were determined using cell-free assays. The DNA-damaging potential of the studied compounds for human hepatoma HepG2 cells and their DNA-protective potential on HepG2 cells against hydrogen peroxide were evaluated using the comet assay. Experiments revealed a spectrum of different activities of the studied compounds. HOT and HOT β-D-fructofuranoside appear to be the best-performing scavengers and protectants of plasmid DNA and HepG2 cells. T and T β-D-fructofuranoside display almost zero or low scavenging/antioxidant activity and protective effects on plasmid DNA or HepG2 cells. The results imply that especially HOT β-D-fructofuranoside and β-D-apiofuranoside could be considered as prospective molecules for the subsequent design of supplements with potential in food and health protection.
  • Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
    Eva Horvathova, Maria Mastihubova, Elena Karnisova Potocka, Peter Kis, Eliska Galova, Andrea Sevcovicova, Martina Klapakova, Luba Hunakova, Vladimir Mastihuba
    Toxicology in Vitro, 2019
    The study focused on protective potential of phytochemicals applicable in prevention and health protection is of great importance. Various structures of these compounds and a wide range of their biological activities have inspired organic chemists to sythesize their effective analogues in order to further increase their efficacy. The aims of our study were (i) to synthesize phenylethanoid glycopyranosides: salidroside (SALI - tyrosol β-d-glucopyranoside), tyrosol β-d-galactopyranoside (TYBGAL), tyrosol α-d-galactopyranoside (TYAGAL), tyrosol α-d-mannopyranoside (TYAMAN), hydroxytyrosol α-d-mannopyranoside (HOTAMA), homosyringyl β-d-glucopyranoside (HSYGLU), hydroxytyrosol β-d-xylopyranoside (HOTXYL) and hydroxysalidroside (HOSALI); (ii) to determine their antioxidant capacities (cell-free approaches); (iii) to evaluate their cytotoxicity (MTT test), protectivity against hydrogen peroxide (H2O2; comet assay) and effect on the intracellular glutathione level (iGSH; flow cytometry) in experimental system utilizing human hepatoma HepG2 cells. HOSALI, HOTAMA, HOTXYL and HSYGLU manifested the highest antioxidant capacity in cell-free assays and they were most active in protection of HepG2 cells against H2O2. On the other hand, pre-treatment of HepG2 cells with SALI had protective effects even though SALI displayed almost no activity in cell-free assays. Differences in the efficacy of the analogues revealed that structures of their molecules in terms of aglycone combined with sugar moiety affect their activities.
  • Reaction mechanism of β-apiosidase from Aspergillus aculeatus
    Vladimír Mastihuba, Elena Karnišová Potocká, Iveta Uhliariková, Peter Kis, Stanislav Kozmon, Mária Mastihubová
    Food Chemistry, 2019
    Apiosidases are glycosidases relevant for aroma development during fermentation of wines and black tea. Reaction mechanism of apiosidase from Aspergillus aculeatus in commercial glycanase Viscozyme L was studied by 1H NMR technique. Study of hydrolysis of 4-nitrophenyl β-D-apiofuranoside revealed that this reaction proceeds with inversion of hydroxyl group in the anomeric center, which confirms inverting mechanism of the enzyme and its inability to catalyze transapiosylation in syntheses of apiosides.
  • Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
    Peter Kis, Elena Potocká, Vladimír Mastihuba, Mária Mastihubová
    Carbohydrate Research, 2016
    4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step-benzoylation of primary hydroxyl of 2,3-isopropylidene-α,β-d-apiofuranose catalysed by Lipolase 100T and stereoselective β-d-apiofuranosylation of p-nitrophenol using BF3⋅OEt2/Et3N. The product was used for screening of β-d-apiofuranosidase activity in 61 samples of crude commercial enzymes and plant materials. Fifteen enzyme preparations originating from different strains of genera Aspergillus display β-d-apiofuranosidase activity. The highest activity was found in Rapidase AR 2000 (78.27 U/g) and lyophilized Viscozyme L (64,36 U/g).

RECENT SCHOLAR PUBLICATIONS

  • Synthesis of autoinducer-2 prodrugs and analogues as a new antimicrobial strategy
    P Kis, MV Rodrigues, KB Xavier, MR Ventura
    Phytochemistry Letters 69, 103446 , 2025
    2025.0
  • Manipulation and quantification of the levels of Autoinducer-2 quorum sensing signal in the mouse gut
    MV Rodrigues, A Ferreira, M Ramirez-Montoya, RA Oliveira, R Defaix, ...
    Bioorganic Chemistry 157, 108274 , 2025
    2025.0
    Citations: 6
  • Environmentally friendly degradation and detoxification of rifampicin by a bacterial laccase and hydrogen peroxide
    P Durão, P Kis, IM Chelo, MR Ventura, LO Martins
    ChemBioChem 25 (2), e202300627 , 2024
    2024.0
    Citations: 6
  • Synthesis and Potential of Autoinducer‐2 and Analogs to Manipulate Inter‐Species Quorum Sensing
    MV Rodrigues, P Kis, KB Xavier, MR Ventura
    Israel Journal of Chemistry 63 (5-6), e202200091 , 2023
    2023.0
    Citations: 11
  • Acuminosylation of tyrosol by a commercial diglycosidase
    P Haluz, P Kis, M Cvečko, M Mastihubová, V Mastihuba
    International Journal of Molecular Sciences 24 (6), 5943 , 2023
    2023.0
    Citations: 8
  • Synthesis of tyrosol and hydroxytyrosol glycofuranosides and their biochemical and biological activities in cell-free and cellular assays
    P Kis, E Horváthová, E Gálová, A Ševčovičová, V Antalová, ...
    Molecules 26 (24), 7607 , 2021
    2021.0
    Citations: 4
  • A sustainable approach to phenylethanoid glycopyranosides: Study of glycosylations promoted by zinc salts
    P Kis, M Mastihubová
    Sustainable Chemistry and Pharmacy 24, 100537 , 2021
    2021.0
    Citations: 2
  • Apiin-induction of β-apiosidase production by Aspergillus sp. strains
    K Karkeszová, V Illeová, P Kis, V Mastihuba, M Polakovič
    Acta Chimica Slovaca 13 (1), 72-76 , 2020
    2020.0
    Citations: 3
  • Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
    E Horvathova, M Mastihubova, EK Potocka, P Kis, E Galova, ...
    Toxicology in Vitro 61, 104646 , 2019
    2019.0
    Citations: 10
  • Reaction mechanism of β-apiosidase from Aspergillus aculeatus
    V Mastihuba, EK Potocká, I Uhliariková, P Kis, S Kozmon, M Mastihubová
    Food Chemistry 274, 543-546 , 2019
    2019.0
    Citations: 11
  • Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
    P Kis, E Potocká, V Mastihuba, M Mastihubová
    Carbohydrate research 430, 48-53 , 2016
    2016.0
    Citations: 10
  • SYNTHESIS OF CHROMOGENIC PROBES FOR DETECTION AND ASSAY OF DIGLYCOSIDASES
    M Cvečko, P Kis, M Mastihubová, V Mastihuba

MOST CITED SCHOLAR PUBLICATIONS

  • Synthesis and Potential of Autoinducer‐2 and Analogs to Manipulate Inter‐Species Quorum Sensing
    MV Rodrigues, P Kis, KB Xavier, MR Ventura
    Israel Journal of Chemistry 63 (5-6), e202200091 , 2023
    2023.0
    Citations: 11
  • Reaction mechanism of β-apiosidase from Aspergillus aculeatus
    V Mastihuba, EK Potocká, I Uhliariková, P Kis, S Kozmon, M Mastihubová
    Food Chemistry 274, 543-546 , 2019
    2019.0
    Citations: 11
  • Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
    E Horvathova, M Mastihubova, EK Potocka, P Kis, E Galova, ...
    Toxicology in Vitro 61, 104646 , 2019
    2019.0
    Citations: 10
  • Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
    P Kis, E Potocká, V Mastihuba, M Mastihubová
    Carbohydrate research 430, 48-53 , 2016
    2016.0
    Citations: 10
  • Acuminosylation of tyrosol by a commercial diglycosidase
    P Haluz, P Kis, M Cvečko, M Mastihubová, V Mastihuba
    International Journal of Molecular Sciences 24 (6), 5943 , 2023
    2023.0
    Citations: 8
  • Manipulation and quantification of the levels of Autoinducer-2 quorum sensing signal in the mouse gut
    MV Rodrigues, A Ferreira, M Ramirez-Montoya, RA Oliveira, R Defaix, ...
    Bioorganic Chemistry 157, 108274 , 2025
    2025.0
    Citations: 6
  • Environmentally friendly degradation and detoxification of rifampicin by a bacterial laccase and hydrogen peroxide
    P Durão, P Kis, IM Chelo, MR Ventura, LO Martins
    ChemBioChem 25 (2), e202300627 , 2024
    2024.0
    Citations: 6
  • Synthesis of tyrosol and hydroxytyrosol glycofuranosides and their biochemical and biological activities in cell-free and cellular assays
    P Kis, E Horváthová, E Gálová, A Ševčovičová, V Antalová, ...
    Molecules 26 (24), 7607 , 2021
    2021.0
    Citations: 4
  • Apiin-induction of β-apiosidase production by Aspergillus sp. strains
    K Karkeszová, V Illeová, P Kis, V Mastihuba, M Polakovič
    Acta Chimica Slovaca 13 (1), 72-76 , 2020
    2020.0
    Citations: 3
  • A sustainable approach to phenylethanoid glycopyranosides: Study of glycosylations promoted by zinc salts
    P Kis, M Mastihubová
    Sustainable Chemistry and Pharmacy 24, 100537 , 2021
    2021.0
    Citations: 2
  • Synthesis of autoinducer-2 prodrugs and analogues as a new antimicrobial strategy
    P Kis, MV Rodrigues, KB Xavier, MR Ventura
    Phytochemistry Letters 69, 103446 , 2025
    2025.0
  • SYNTHESIS OF CHROMOGENIC PROBES FOR DETECTION AND ASSAY OF DIGLYCOSIDASES
    M Cvečko, P Kis, M Mastihubová, V Mastihuba