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Article ; Online: Approaches Towards Better Immunosuppressive Agents.

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

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.
Language	English
Publishing date	2024-03-29
Publishing country	United Arab Emirates
Document type	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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Article ; 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 Volume 189, Page(s) 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 term(s)	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
Chemical Substances	Amino Acids ; Enzyme Inhibitors ; Immunosuppressive Agents ; Peptide Fragments ; IMP Dehydrogenase (EC 1.1.1.205) ; Mycophenolic Acid (HU9DX48N0T)
Language	English
Publishing date	2020-01-24
Publishing country	France
Document type	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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Article ; 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 Volume 16, Issue 1, Page(s) 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 term(s)	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
Chemical Substances	Minocycline (FYY3R43WGO)
Language	English
Publishing date	2021-09-08
Publishing country	England
Document type	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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Article ; 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 Volume 37, Issue 1, Page(s) 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 term(s)	Amides/pharmacology ; Amines ; Anhydrides ; Benzoxazoles ; Enzyme Inhibitors/pharmacology ; IMP Dehydrogenase ; Immunosuppressive Agents/chemistry ; Inosine ; Mycophenolic Acid/chemistry ; Solvents
Chemical Substances	Amides ; Amines ; Anhydrides ; Benzoxazoles ; Enzyme Inhibitors ; Immunosuppressive Agents ; Solvents ; Inosine (5A614L51CT) ; IMP Dehydrogenase (EC 1.1.1.205) ; Mycophenolic Acid (HU9DX48N0T)
Language	English
Publishing date	2022-10-03
Publishing country	England
Document type	Journal Article
ZDB-ID	2082578-X
ISSN	1475-6374 ; 1475-6366
ISSN (online)	1475-6374
ISSN	1475-6366
DOI	10.1080/14756366.2022.2127701
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Article ; 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 Volume 21, Issue 4, Page(s) 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 term(s)	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
Chemical Substances	Amino Acids ; Antineoplastic Agents ; Peptides ; Mycophenolic Acid (HU9DX48N0T)
Language	English
Publishing date	2020-05-07
Publishing country	Netherlands
Document type	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
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Zs.A 5583: Show issues

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Article ; 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.
Language	English
Publishing date	2017-07-25
Publishing country	Netherlands
Document type	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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Article ; 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 Volume 116, Page(s) 318–319

Language	English
Publishing date	2016-06-30
Publishing country	France
Document type	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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Article ; 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 Volume 143, Page(s) 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 term(s)	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
Chemical Substances	Amino Acids ; Anti-Bacterial Agents ; Peptides ; Mycophenolic Acid (HU9DX48N0T)
Keywords	covid19
Language	English
Publishing date	2017-12-01
Publishing country	France
Document type	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
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Article ; 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 Volume 21, Issue 2, Page(s) 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 term(s)	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
Chemical Substances	Immunosuppressive Agents ; Mycophenolic Acid (HU9DX48N0T) ; Adenosine (K72T3FS567)
Language	English
Publishing date	2018-04-02
Publishing country	England
Document type	Journal Article
ZDB-ID	2077926-4
ISSN	1477-2213 ; 1028-6020
ISSN (online)	1477-2213
ISSN	1028-6020
DOI	10.1080/10286020.2018.1451521
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Article ; Online: New Analogues of Mycophenolic Acid.

Siebert, Agnieszka / Prejs, Michal / Cholewinski, Grzegorz / Dzierzbicka, Krystyna

Mini reviews in medicinal chemistry

2017 Volume 17, Issue 9, Page(s) 734–745

Abstract: Background: Mycophenolic acid (MPA) possesses antibacterial, antifungal, antiviral, immunosuppressive and anticancer properties. It is a non-competitive and reversible inhibitor of dehydrogenase inosine-5'-monophosphate (IMPDH). This compound belongs to ...

Abstract	Background: Mycophenolic acid (MPA) possesses antibacterial, antifungal, antiviral, immunosuppressive and anticancer properties. It is a non-competitive and reversible inhibitor of dehydrogenase inosine-5'-monophosphate (IMPDH). This compound belongs to the immunosuppressive drugs used for the prevention of both acute and chronic transplant rejection. Until now, two derivatives of MPA have been used clinically: mycophenolate mofetil (MMF, CellCept) and mycophenolate sodium (MPS, Myfortic). They cause, similar to MPA, although at lower degree, the side effects such as vomiting, abdominal pain, diarrhea, nausea, gastrointestinal, urogenital tract, blood or nervous system disorders. These drawbacks and glucuronidation of MPA in vivo limit the use of these compounds as pharmaceuticals. Therefore, research is still going on for more effective analogs that are less toxic to the organism and could improve the quality of life of patients. Conclusion: In this review article, the authors present the synthesis of novel derivatives of mycophenolic acid, together with their initial biological investigations.
MeSH term(s)	Graft Rejection/drug therapy ; Humans ; Immunosuppressive Agents/adverse effects ; Immunosuppressive Agents/chemistry ; Immunosuppressive Agents/therapeutic use ; Molecular Structure ; Mycophenolic Acid/adverse effects ; Mycophenolic Acid/chemistry ; Mycophenolic Acid/therapeutic use
Chemical Substances	Immunosuppressive Agents ; Mycophenolic Acid (HU9DX48N0T)
Language	English
Publishing date	2017
Publishing country	Netherlands
Document type	Journal Article ; Review
ZDB-ID	2104081-3
ISSN	1875-5607 ; 1389-5575
ISSN (online)	1875-5607
ISSN	1389-5575
DOI	10.2174/1389557516666161129160001
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