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  1. Artikel ; Online: Approaches Towards Better Immunosuppressive Agents.

    Walczak, Juliusz / Iwaszkiewicz-Grześ, Dorota / Cholewiński, Grzegorz

    Current topics in medicinal chemistry

    2024  

    Abstract: Several classes of compounds are applied in clinics due to their immunosuppressive properties in transplantology and the treatment of autoimmune diseases. Derivatives of mycophenolic acid, corticosteroids and chemotherapeutics bearing heterocyclic ... ...

    Abstract Several classes of compounds are applied in clinics due to their immunosuppressive properties in transplantology and the treatment of autoimmune diseases. Derivatives of mycophenolic acid, corticosteroids and chemotherapeutics bearing heterocyclic moieties like methotrexate, azathioprine, mizoribine, and ruxolitinib are active substances with investigated mechanisms of action. However, improved synthetic approaches of known drugs and novel derivatives are still being reported to attempt better accessibility and therapeutic properties. In this review article, we present the synthesis of the designed chemical structures based on recent literature reports concerning novel compounds as promising immunosuppressive drugs. Moreover, some of the discussed derivers revealed also other types of activities with prospective medicinal potential.
    Sprache Englisch
    Erscheinungsdatum 2024-03-29
    Erscheinungsland United Arab Emirates
    Dokumenttyp Journal Article
    ZDB-ID 2064823-6
    ISSN 1873-4294 ; 1568-0266
    ISSN (online) 1873-4294
    ISSN 1568-0266
    DOI 10.2174/0115680266292661240322072908
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  2. Artikel ; Online: Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid.

    Siebert, Agnieszka / Cholewiński, Grzegorz / Trzonkowski, Piotr / Rachon, Janusz

    European journal of medicinal chemistry

    2020  Band 189, Seite(n) 112091

    Abstract: Mycophenolic acid (MPA) was coupled with amino acids and biologically active peptides including derivatives of tuftsin to modify its immunosuppressive properties. Both amino acid unit in the case of simple MPA amides and modifications within peptide ... ...

    Abstract Mycophenolic acid (MPA) was coupled with amino acids and biologically active peptides including derivatives of tuftsin to modify its immunosuppressive properties. Both amino acid unit in the case of simple MPA amides and modifications within peptide moiety of MPA - tuftsin conjugates influenced the observed activity. Antiproliferative potential of the obtained conjugates was investigated in vitro and MPA amides with threonine methyl ester and conjugate of MPA with retro-tuftisin occurred to be more selective against PBMC in comparison to parent MPA. Both amino acid and peptide derivatives of MPA acted as inosine-5'-monophosphate dehydrogenaze (IMPDH) inhibitors.
    Mesh-Begriff(e) Amino Acids/chemistry ; Cell Proliferation ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Humans ; IMP Dehydrogenase/antagonists & inhibitors ; Immunosuppressive Agents/chemistry ; Immunosuppressive Agents/pharmacology ; Jurkat Cells ; Leukocytes, Mononuclear/drug effects ; Molecular Structure ; Mycophenolic Acid/chemistry ; Peptide Fragments/chemistry ; Structure-Activity Relationship
    Chemische Substanzen Amino Acids ; Enzyme Inhibitors ; Immunosuppressive Agents ; Peptide Fragments ; IMP Dehydrogenase (EC 1.1.1.205) ; Mycophenolic Acid (HU9DX48N0T)
    Sprache Englisch
    Erscheinungsdatum 2020-01-24
    Erscheinungsland France
    Dokumenttyp Journal Article
    ZDB-ID 188597-2
    ISSN 1768-3254 ; 0009-4374 ; 0223-5234
    ISSN (online) 1768-3254
    ISSN 0009-4374 ; 0223-5234
    DOI 10.1016/j.ejmech.2020.112091
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  3. Artikel ; Online: Analysis of intercondylar notch size and shape in patients with cyclops syndrome after anterior cruciate ligament reconstruction.

    Ficek, Krzysztof / Rajca, Jolanta / Cholewiński, Jerzy / Racut, Agnieszka / Gwiazdoń, Paweł / Przednowek, Krzysztof / Hajduk, Grzegorz

    Journal of orthopaedic surgery and research

    2021  Band 16, Heft 1, Seite(n) 554

    Abstract: Background: Cyclops lesion is the second most common cause of extension loss after anterior cruciate ligament reconstruction. This study focused on the correlation between the anatomy of the intercondylar notch and the incidence of cyclops lesion. To ... ...

    Abstract Background: Cyclops lesion is the second most common cause of extension loss after anterior cruciate ligament reconstruction. This study focused on the correlation between the anatomy of the intercondylar notch and the incidence of cyclops lesion. To determine whether the size and shape of the intercondylar notch are related to cyclops lesion formation following anterior cruciate ligament reconstruction according to magnetic resonance imaging (MRI) findings.
    Methods: One hundred twenty-five (125) patients were retrospectively evaluated. The notch width index (NWI) and notch shape index (NSI) were measured based on coronal and axial MRI sections in patients diagnosed with cyclops syndrome (n = 25), diagnosed with complete anterior cruciate ligament (ACL) tears (n = 50), and without cyclops lesions or ACL ruptures (n = 50).
    Results: Imaging analysis results showed that the cyclops and ACL groups had lower mean NWI and NSI values than the control group. Significant between-group differences were found in NSI (p = 0.0140) based on coronal cross-sections and in NWI (p = 0.0026) and NSI (p < 0.0001) based on axial sections.
    Conclusions: The geometry of the intercondylar notch was found to be associated with the risk of cyclops lesion formation and ACL rupture.
    Mesh-Begriff(e) Anterior Cruciate Ligament Injuries/diagnostic imaging ; Anterior Cruciate Ligament Injuries/surgery ; Anterior Cruciate Ligament Reconstruction/adverse effects ; Holoprosencephaly ; Humans ; Knee Joint/diagnostic imaging ; Knee Joint/surgery ; Magnetic Resonance Imaging ; Minocycline ; Retrospective Studies
    Chemische Substanzen Minocycline (FYY3R43WGO)
    Sprache Englisch
    Erscheinungsdatum 2021-09-08
    Erscheinungsland England
    Dokumenttyp Journal Article
    ZDB-ID 2252548-8
    ISSN 1749-799X ; 1749-799X
    ISSN (online) 1749-799X
    ISSN 1749-799X
    DOI 10.1186/s13018-021-02706-w
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  4. Artikel ; Online: Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents.

    Walczak, Juliusz Maksymilian / Iwaszkiewicz-Grześ, Dorota / Ziomkowska, Michalina / Śliwka-Kaszyńska, Magdalena / Daśko, Mateusz / Trzonkowski, Piotr / Cholewiński, Grzegorz

    Journal of enzyme inhibition and medicinal chemistry

    2022  Band 37, Heft 1, Seite(n) 2725–2741

    Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5'-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis ... ...

    Abstract The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5'-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (
    Mesh-Begriff(e) Amides/pharmacology ; Amines ; Anhydrides ; Benzoxazoles ; Enzyme Inhibitors/pharmacology ; IMP Dehydrogenase ; Immunosuppressive Agents/chemistry ; Inosine ; Mycophenolic Acid/chemistry ; Solvents
    Chemische Substanzen Amides ; Amines ; Anhydrides ; Benzoxazoles ; Enzyme Inhibitors ; Immunosuppressive Agents ; Solvents ; Inosine (5A614L51CT) ; IMP Dehydrogenase (EC 1.1.1.205) ; Mycophenolic Acid (HU9DX48N0T)
    Sprache Englisch
    Erscheinungsdatum 2022-10-03
    Erscheinungsland England
    Dokumenttyp Journal Article
    ZDB-ID 2082578-X
    ISSN 1475-6374 ; 1475-6366
    ISSN (online) 1475-6374
    ISSN 1475-6366
    DOI 10.1080/14756366.2022.2127701
    Datenquelle MEDical Literature Analysis and Retrieval System OnLINE

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  5. Artikel ; Online: Anticancer Properties of Amino Acid and Peptide Derivatives of Mycophenolic Acid.

    Siebert, Agnieszka / Deptuła, Milena / Cichorek, Mirosława / Ronowska, Anna / Cholewiński, Grzegorz / Rachon, Janusz

    Anti-cancer agents in medicinal chemistry

    2020  Band 21, Heft 4, Seite(n) 462–467

    Abstract: Background: Although Mycophenolic Acid (MPA) is applied as prodrugs in clinic as an immunosuppressant, it also possesses anticancer activity. MPA acts as Inosine-5'-Monophosphate Dehydrogenase (IMPDH) inhibitor, where the carboxylic group at the end of ... ...

    Abstract Background: Although Mycophenolic Acid (MPA) is applied as prodrugs in clinic as an immunosuppressant, it also possesses anticancer activity. MPA acts as Inosine-5'-Monophosphate Dehydrogenase (IMPDH) inhibitor, where the carboxylic group at the end of the side chain interacts with Ser 276 of the enzyme via hydrogen bonds. Therefore, MPA derivatives with other polar groups indicated high inhibition too. On the other hand, potent anticancer agents like dacarbazine and cisplatin give numerous side-effects.
    Objective: Based on the literature data, MPA derivatives should be explored towards anticancer properties. Conversion of the carboxylic group of MPA to amide could maintain antiproliferative activity. Therefore, we decided to investigate several amino acid and peptide derivatives of MPA against chosen cancer cell lines in vitro.
    Methods: Amides of MPA hold threonine and arginine amino acid unit. These amino acid derivatives were tested as L and D enantiomers and both in free acid and methyl esters forms. Additionally, MPA was modified with tuftsin or retro-tuftsin as biologically active peptides, which could act as a drug carrier.
    Results: Amino acid and peptide derivatives of MPA were investigated in vitro as potential anticancer agents on cell lines: Ab melanoma, A375 melanoma and SHSY5Y neuroblastoma. The activity of the tested compounds was compared to parent MPA and known chemotherapeutics: dacarbazine and cisplatin.
    Conclusion: Amino acid moiety and the sequence of amino acids in the peptide part influenced observed activity. The most active amino acid MPA analogues occurred to be D and L-threonine derivatives as methyl esters, probably due to better cell membrane penetration.
    Mesh-Begriff(e) Amino Acids/chemical synthesis ; Amino Acids/chemistry ; Amino Acids/pharmacology ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Cell Survival/drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Humans ; Mitochondria/drug effects ; Molecular Structure ; Mycophenolic Acid/chemical synthesis ; Mycophenolic Acid/chemistry ; Mycophenolic Acid/pharmacology ; Peptides/chemical synthesis ; Peptides/chemistry ; Peptides/pharmacology ; Structure-Activity Relationship
    Chemische Substanzen Amino Acids ; Antineoplastic Agents ; Peptides ; Mycophenolic Acid (HU9DX48N0T)
    Sprache Englisch
    Erscheinungsdatum 2020-05-07
    Erscheinungsland Netherlands
    Dokumenttyp Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2217610-X
    ISSN 1875-5992 ; 1871-5206
    ISSN (online) 1875-5992
    ISSN 1871-5206
    DOI 10.2174/1871520620666200516151456
    Datenquelle MEDical Literature Analysis and Retrieval System OnLINE

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  6. Artikel ; Online: Tuftsin - Properties and Analogs.

    Siebert, Agnieszka / Gensicka-Kowalewska, Monika / Cholewiński, Grzegorz / Dzierzbicka, Krystyna

    Current medicinal chemistry

    2017  

    Abstract: Immunomodulation is one of the significant therapeutic strategies. It includes both stimulation or suppression of the immune system by a variety of substances called immunomodulators, designed to regulate the immune response of the organism to infections ...

    Abstract Immunomodulation is one of the significant therapeutic strategies. It includes both stimulation or suppression of the immune system by a variety of substances called immunomodulators, designed to regulate the immune response of the organism to infections of varying etiology. An example of such a substance is tuftsin (TKPA) 3 (Fig. (1)). Tuftsin is an endogenous immunomodulator of a wide spectrum of biological activity. Tetrapeptide 3 provides also antitumor, antimicrobial, anticoagulant and analgesic properties. In this paper, we presented tuftsin derivatives described over the years, its biological activity and potential clinical applications.
    Sprache Englisch
    Erscheinungsdatum 2017-07-25
    Erscheinungsland Netherlands
    Dokumenttyp Journal Article
    ZDB-ID 1319315-6
    ISSN 1875-533X ; 0929-8673
    ISSN (online) 1875-533X
    ISSN 0929-8673
    DOI 10.2174/0929867324666170725140826
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  7. Artikel ; Online: Erratum to "Synthesis of functionalized new conjugates of batracylin with tuftsin/retro-tuftsin derivatives and their biological evaluation" [Eur. J. Med. Chem. 106 (2015) 85-94].

    Januchta, Wioleta / Serocki, Marcin / Dzierzbicka, Krystyna / Cholewiński, Grzegorz / Skladanowski, Andrzej

    European journal of medicinal chemistry

    2016  Band 116, Seite(n) 318–319

    Sprache Englisch
    Erscheinungsdatum 2016-06-30
    Erscheinungsland France
    Dokumenttyp Published Erratum
    ZDB-ID 188597-2
    ISSN 1768-3254 ; 0009-4374 ; 0223-5234
    ISSN (online) 1768-3254
    ISSN 0009-4374 ; 0223-5234
    DOI 10.1016/j.ejmech.2016.02.067
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  8. Artikel ; Online: Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid.

    Siebert, Agnieszka / Wysocka, Magdalena / Krawczyk, Beata / Cholewiński, Grzegorz / Rachoń, Janusz

    European journal of medicinal chemistry

    2017  Band 143, Seite(n) 646–655

    Abstract: The series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid ... ...

    Abstract The series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella pneumoniae ATCC 700603 (ESBL), Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus MRSA ATCC 43300, Staphylococcus aureus MSSA ATCC 25923. Peptide derivatives proved to be the most versatile ones, their MIC values relative to most strains was lower than MPA alone. It has been noted that the activity of amino acid derivatives depends on the configuration at the chiral center in the amino acid unit and methyl esters indicated better antimicrobial activity than analogs with free carboxylic group.
    Mesh-Begriff(e) Amino Acids/chemistry ; Amino Acids/pharmacology ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Dose-Response Relationship, Drug ; Escherichia coli/drug effects ; Klebsiella pneumoniae/drug effects ; Microbial Sensitivity Tests ; Molecular Structure ; Mycophenolic Acid/chemical synthesis ; Mycophenolic Acid/chemistry ; Mycophenolic Acid/pharmacology ; Peptides/chemistry ; Peptides/pharmacology ; Pseudomonas aeruginosa/drug effects ; Staphylococcus aureus/drug effects ; Structure-Activity Relationship
    Chemische Substanzen Amino Acids ; Anti-Bacterial Agents ; Peptides ; Mycophenolic Acid (HU9DX48N0T)
    Schlagwörter covid19
    Sprache Englisch
    Erscheinungsdatum 2017-12-01
    Erscheinungsland France
    Dokumenttyp Journal Article
    ZDB-ID 188597-2
    ISSN 1768-3254 ; 0009-4374 ; 0223-5234
    ISSN (online) 1768-3254
    ISSN 0009-4374 ; 0223-5234
    DOI 10.1016/j.ejmech.2017.11.094
    Datenquelle MEDical Literature Analysis and Retrieval System OnLINE

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  9. Artikel ; Online: Synthesis and antiproliferative activity of new mycophenolic acid conjugates with adenosine derivatives.

    Prejs, Michał / Cholewiński, Grzegorz / Trzonkowski, Piotr / Kot-Wasik, Agata / Dzierzbicka, Krystyna

    Journal of Asian natural products research

    2018  Band 21, Heft 2, Seite(n) 178–185

    Abstract: New conjugates of mycophenolic acid (MPA) and adenosine derivatives were synthesized and assessed as potential immunosuppressants on Jurkat cell line and peripheral blood mononuclear cells (PBMC) from healthy donors. As compared to MPA, all compounds ... ...

    Abstract New conjugates of mycophenolic acid (MPA) and adenosine derivatives were synthesized and assessed as potential immunosuppressants on Jurkat cell line and peripheral blood mononuclear cells (PBMC) from healthy donors. As compared to MPA, all compounds were found to be more active against Jurkat cell line. The antiproliferative activities were compared with MPA and adenosine, in both 2',3'-O-isopropylidene protected and free hydroxyl groups possessing forms. The obtained results were also discussed in terms of selectivity index, defined as SI = IC
    Mesh-Begriff(e) Adenosine/analogs & derivatives ; Adenosine/chemical synthesis ; Adenosine/chemistry ; Adenosine/pharmacology ; Cell Proliferation/drug effects ; Humans ; Immunosuppressive Agents/chemical synthesis ; Immunosuppressive Agents/pharmacology ; Jurkat Cells ; Mycophenolic Acid/analogs & derivatives ; Mycophenolic Acid/chemical synthesis ; Mycophenolic Acid/chemistry ; Mycophenolic Acid/pharmacology
    Chemische Substanzen Immunosuppressive Agents ; Mycophenolic Acid (HU9DX48N0T) ; Adenosine (K72T3FS567)
    Sprache Englisch
    Erscheinungsdatum 2018-04-02
    Erscheinungsland England
    Dokumenttyp Journal Article
    ZDB-ID 2077926-4
    ISSN 1477-2213 ; 1028-6020
    ISSN (online) 1477-2213
    ISSN 1028-6020
    DOI 10.1080/10286020.2018.1451521
    Datenquelle MEDical Literature Analysis and Retrieval System OnLINE

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  10. Artikel: Recent developments in the synthesis and biological activity of acridine/acridone analogues

    Gensicka-Kowalewska, Monika / Grzegorz Cholewiński / Krystyna Dzierzbicka

    RSC advances. 2017 Mar. 09, v. 7, no. 26

    2017  

    Abstract: Many people in the world struggle with cancer or bacterial, parasitic, viral, Alzheimer's and other diseases. Therefore, many scientists seek new, more effective, more selective and less toxic drugs. Acridine/acridone derivatives constitute a class of ... ...

    Abstract Many people in the world struggle with cancer or bacterial, parasitic, viral, Alzheimer's and other diseases. Therefore, many scientists seek new, more effective, more selective and less toxic drugs. Acridine/acridone derivatives constitute a class of compounds with a broad spectrum of biological activity and are of great interest to scientists. To date, many acridine/acridone analogues have been obtained, which, inter alia, exhibit antitumour (e.g., (1–5)), antimicrobial (e.g., (59)), and antiviral (e.g., (61)) activities and are applicable in the treatment of Alzheimer's disease (e.g., (26)). However, in many cases, their clinical application is limited and excluded because of side effects. In this survey, we describe acridine and acridone derivatives reported since 2013, methods of their synthesis and their potential clinical applications.
    Schlagwörter Alzheimer disease ; adverse effects ; drugs ; neoplasms ; surveys ; toxicity
    Sprache Englisch
    Erscheinungsverlauf 2017-0309
    Umfang p. 15776-15804.
    Erscheinungsort The Royal Society of Chemistry
    Dokumenttyp Artikel
    ISSN 2046-2069
    DOI 10.1039/c7ra01026e
    Datenquelle NAL Katalog (AGRICOLA)

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