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  1. Article ; Online: Hierarchical peroxiredoxin assembly through orthogonal pH-response and electrostatic interactions.

    Anaya-Plaza, Eduardo / Özdemir, Zulal / Wimmer, Zdenek / Kostiainen, Mauri A

    Journal of materials chemistry. B

    2023  Volume 11, Issue 48, Page(s) 11544–11551

    Abstract: Morpheeins are proteins that adapt their morphology and function to the environment. Therefore, their use in nanotechnology opens up the bottom-up preparation of anisotropic metamaterials, based on the sequential use of different stimuli. A prominent ... ...

    Abstract Morpheeins are proteins that adapt their morphology and function to the environment. Therefore, their use in nanotechnology opens up the bottom-up preparation of anisotropic metamaterials, based on the sequential use of different stimuli. A prominent member of this family of proteins is peroxiredoxins (Prx), with dual peroxidase and chaperone function, depending on the pH of the media. At high pH, they show a toroidal morphology that turns into tubular stacks upon acidification. While the toroidal conformers have been explored as building blocks to yield 1D and 2D structures, the obtention of higher ordered materials remain unexplored. In this research, the morpheein behaviour of Prx is exploited to yield columnar aggregates, that are subsequently self-assembled into 3D anisotropic bundles. This is achieved by electrostatic recognition between the negatively charged protein rim and a positively charged porphyrin acting as molecular glue. The subsequent and orthogonal input lead to the alignment of the monodimensional stacks side-by-side, leading to the precise assembly of this anisotropic materials.
    MeSH term(s) Peroxiredoxins/chemistry ; Peroxiredoxins/metabolism ; Static Electricity ; Peroxidase/metabolism ; Nanotechnology ; Hydrogen-Ion Concentration
    Chemical Substances Peroxiredoxins (EC 1.11.1.15) ; Peroxidase (EC 1.11.1.7)
    Language English
    Publishing date 2023-12-13
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2702241-9
    ISSN 2050-7518 ; 2050-750X
    ISSN (online) 2050-7518
    ISSN 2050-750X
    DOI 10.1039/d3tb00369h
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues.

    Kazakova, Oxana / Giniyatullina, Gulnara / Babkov, Denis / Wimmer, Zdenek

    International journal of molecular sciences

    2022  Volume 23, Issue 3

    Abstract: This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their ... ...

    Abstract This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.
    MeSH term(s) Angiogenesis Inhibitors/chemical synthesis ; Angiogenesis Inhibitors/chemistry ; Angiogenesis Inhibitors/pharmacology ; Anti-Infective Agents/chemical synthesis ; Anti-Infective Agents/chemistry ; Anti-Infective Agents/pharmacology ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Aquatic Organisms/chemistry ; Biological Products/chemistry ; Biological Products/pharmacology ; Cholestanes/chemistry ; Cholestanols/chemistry ; Humans ; Neuroprotective Agents/chemical synthesis ; Neuroprotective Agents/chemistry ; Neuroprotective Agents/pharmacology ; Spermine/analogs & derivatives ; Spermine/chemistry ; Steroids/chemical synthesis ; Steroids/chemistry ; Steroids/pharmacology ; Triterpenes/chemical synthesis ; Triterpenes/chemistry ; Triterpenes/pharmacology
    Chemical Substances 3-N-1(spermine)-7, 24-dihydroxy-5-cholestane 24-sulfate ; Angiogenesis Inhibitors ; Anti-Infective Agents ; Antineoplastic Agents ; Biological Products ; Cholestanes ; Cholestanols ; Neuroprotective Agents ; Steroids ; Triterpenes ; ceragenins ; claramine ; Spermine (2FZ7Y3VOQX) ; squalamine (F8PO54Z4V7)
    Language English
    Publishing date 2022-01-19
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms23031075
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: From Marine Metabolites to the Drugs of the Future

    Oxana Kazakova / Gulnara Giniyatullina / Denis Babkov / Zdenek Wimmer

    International Journal of Molecular Sciences, Vol 23, Iss 1075, p

    Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

    2022  Volume 1075

    Abstract: This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their ... ...

    Abstract This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.
    Keywords squalamine ; trodusquemine ; ceragenine ; claramine ; triterpenoids ; antibiotic ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Subject code 540
    Language English
    Publishing date 2022-01-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  4. Article ; Online: Selected plant triterpenoids and their amide derivatives in cancer treatment: A review.

    Özdemir, Zulal / Wimmer, Zdeněk

    Phytochemistry

    2022  Volume 203, Page(s) 113340

    Abstract: Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted ... ...

    Abstract Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted frequently to be food and nutrition plants and producing pharmacologically important secondary metabolites. Triterpenoids represent an important group of plant secondary metabolites displaying emerging pharmacological importance. This review article sheds light on four selected triterpenoids, oleanolic, ursolic, betulinic and platanic acid, and on their amide derivatives as important natural or semisynthetic agents in cancer treatment, and, in part, in pathogenic microbe treatment. A literature search was made in the Web of Science for the given key words covering the required area of secondary plant metabolites and their amide derivatives. The most recently published findings on the biological activity of the selected triterpenoids, and on the structures and biological activity of their relevant amide derivatives have been summarized therein. Mainly anti-cancer effects, and, in part, antimicrobial and other effects of the four selected triterpenoids and their amide derivatives have also been reviewed. A comparison of the effects of the parent plant products and those of their amide derivatives has been made.
    MeSH term(s) Amides/pharmacology ; Amides/therapeutic use ; Humans ; Neoplasms/drug therapy ; Oleanolic Acid/chemistry ; Plants, Medicinal/metabolism ; Triterpenes/chemistry ; Triterpenes/pharmacology ; Triterpenes/therapeutic use
    Chemical Substances Amides ; Triterpenes ; Oleanolic Acid (6SMK8R7TGJ)
    Language English
    Publishing date 2022-08-17
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 208884-8
    ISSN 1873-3700 ; 0031-9422
    ISSN (online) 1873-3700
    ISSN 0031-9422
    DOI 10.1016/j.phytochem.2022.113340
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Selected Plant Triterpenoids and Their Derivatives as Antiviral Agents.

    Wimmerová, Martina / Bildziukevich, Uladzimir / Wimmer, Zdeněk

    Molecules (Basel, Switzerland)

    2023  Volume 28, Issue 23

    Abstract: The results of the most recent investigation of triterpenoid-based antiviral agents namely in the HIV-1 and HSV-1 treatment were reviewed and summarized. Several key historical achievements are included to stress consequences and continuity in this ... ...

    Abstract The results of the most recent investigation of triterpenoid-based antiviral agents namely in the HIV-1 and HSV-1 treatment were reviewed and summarized. Several key historical achievements are included to stress consequences and continuity in this research. Most of the agents studied belong to a series of compounds derived from betulin or betulinic acid, and their synthetic derivative is called bevirimat. A termination of clinical trials of bevirimat in Phase IIb initiated a search for more successful compounds partly derived from bevirimat or designed independently of bevirimat structure. Surprisingly, a majority of bevirimat mimics are derivatives of betulinic acid, while other plant triterpenoids, such as ursolic acid, oleanolic acid, glycyrrhetinic acid, or other miscellaneous triterpenoids, are relatively rarely involved in a search for a novel antiviral agent. Therefore, this review article is divided into three parts based on the leading triterpenoid core structure.
    MeSH term(s) Triterpenes/pharmacology ; Triterpenes/chemistry ; Antiviral Agents/pharmacology ; Betulinic Acid ; Pentacyclic Triterpenes/pharmacology ; Plants
    Chemical Substances Triterpenes ; bevirimat (S125DW66N8) ; Antiviral Agents ; Betulinic Acid (4G6A18707N) ; Pentacyclic Triterpenes
    Language English
    Publishing date 2023-11-22
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules28237718
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: Saponins of Selected Triterpenoids as Potential Therapeutic Agents: A Review.

    Bildziukevich, Uladzimir / Wimmerová, Martina / Wimmer, Zdeněk

    Pharmaceuticals (Basel, Switzerland)

    2023  Volume 16, Issue 3

    Abstract: Saponins represent important natural derivatives of plant triterpenoids that are secondary plant metabolites. Saponins, also named glycoconjugates, are available both as natural and synthetic products. This review is focused on saponins of the oleanane, ... ...

    Abstract Saponins represent important natural derivatives of plant triterpenoids that are secondary plant metabolites. Saponins, also named glycoconjugates, are available both as natural and synthetic products. This review is focused on saponins of the oleanane, ursane, and lupane types of triterpenoids that include several plant triterpenoids displaying various important pharmacological effects. Additional convenient structural modifications of naturally-occurring plant products often result in enhancing the pharmacological effects of the parent natural structures. This is an important objective for all semisynthetic modifications of the reviewed plant products, and it is included in this review paper as well. The period covered by this review (2019-2022) is relatively short, mainly due to the existence of previously published review papers in recent years.
    Language English
    Publishing date 2023-03-02
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2193542-7
    ISSN 1424-8247
    ISSN 1424-8247
    DOI 10.3390/ph16030386
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  7. Article ; Online: Saponins of Selected Triterpenoids as Potential Therapeutic Agents

    Uladzimir Bildziukevich / Martina Wimmerová / Zdeněk Wimmer

    Pharmaceuticals, Vol 16, Iss 386, p

    A Review

    2023  Volume 386

    Abstract: Saponins represent important natural derivatives of plant triterpenoids that are secondary plant metabolites. Saponins, also named glycoconjugates, are available both as natural and synthetic products. This review is focused on saponins of the oleanane, ... ...

    Abstract Saponins represent important natural derivatives of plant triterpenoids that are secondary plant metabolites. Saponins, also named glycoconjugates, are available both as natural and synthetic products. This review is focused on saponins of the oleanane, ursane, and lupane types of triterpenoids that include several plant triterpenoids displaying various important pharmacological effects. Additional convenient structural modifications of naturally-occurring plant products often result in enhancing the pharmacological effects of the parent natural structures. This is an important objective for all semisynthetic modifications of the reviewed plant products, and it is included in this review paper as well. The period covered by this review (2019–2022) is relatively short, mainly due to the existence of previously published review papers in recent years.
    Keywords oleanane ; ursane ; lupane ; saponin ; glycoconjugate ; pharmacological effects ; Medicine ; R ; Pharmacy and materia medica ; RS1-441
    Subject code 580
    Language English
    Publishing date 2023-03-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  8. Article ; Online: Selected Plant Triterpenoids and Their Derivatives as Antiviral Agents

    Martina Wimmerová / Uladzimir Bildziukevich / Zdeněk Wimmer

    Molecules, Vol 28, Iss 23, p

    2023  Volume 7718

    Abstract: The results of the most recent investigation of triterpenoid-based antiviral agents namely in the HIV-1 and HSV-1 treatment were reviewed and summarized. Several key historical achievements are included to stress consequences and continuity in this ... ...

    Abstract The results of the most recent investigation of triterpenoid-based antiviral agents namely in the HIV-1 and HSV-1 treatment were reviewed and summarized. Several key historical achievements are included to stress consequences and continuity in this research. Most of the agents studied belong to a series of compounds derived from betulin or betulinic acid, and their synthetic derivative is called bevirimat. A termination of clinical trials of bevirimat in Phase IIb initiated a search for more successful compounds partly derived from bevirimat or designed independently of bevirimat structure. Surprisingly, a majority of bevirimat mimics are derivatives of betulinic acid, while other plant triterpenoids, such as ursolic acid, oleanolic acid, glycyrrhetinic acid, or other miscellaneous triterpenoids, are relatively rarely involved in a search for a novel antiviral agent. Therefore, this review article is divided into three parts based on the leading triterpenoid core structure.
    Keywords plant triterpenoid ; structure modifier ; antiviral activity ; HIV-1 ; HSV-1 ; maturation inhibitor ; Organic chemistry ; QD241-441
    Subject code 540
    Language English
    Publishing date 2023-11-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  9. Article ; Online: Nano-assembly of cytotoxic amides of moronic and morolic acid.

    Bildziukevich, Uladzimir / Šlouf, Miroslav / Rárová, Lucie / Šaman, David / Wimmer, Zdeněk

    Soft matter

    2023  Volume 19, Issue 39, Page(s) 7625–7634

    Abstract: Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, ... ...

    Abstract Moronic acid and morolic acid, less frequently studied plant triterpenoids, were subjected to derivation with several structural modifiers, namely, piperazine-, pyrazine-, 1
    Language English
    Publishing date 2023-10-11
    Publishing country England
    Document type Journal Article
    ZDB-ID 2191476-X
    ISSN 1744-6848 ; 1744-683X
    ISSN (online) 1744-6848
    ISSN 1744-683X
    DOI 10.1039/d3sm01035j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Selected plant triterpenoids and their amide derivatives in cancer treatment: A review

    Özdemir, Zulal / Wimmer, Zdeněk

    Phytochemistry. 2022 Nov., v. 203 p.113340-

    2022  

    Abstract: Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted ... ...

    Abstract Medicinal plants have been used to treat different diseases throughout the human history namely in traditional medicine. Most of the plants mentioned in this review article belong among them, including those that are widely spread in the nature, counted frequently to be food and nutrition plants and producing pharmacologically important secondary metabolites. Triterpenoids represent an important group of plant secondary metabolites displaying emerging pharmacological importance. This review article sheds light on four selected triterpenoids, oleanolic, ursolic, betulinic and platanic acid, and on their amide derivatives as important natural or semisynthetic agents in cancer treatment, and, in part, in pathogenic microbe treatment. A literature search was made in the Web of Science for the given key words covering the required area of secondary plant metabolites and their amide derivatives. The most recently published findings on the biological activity of the selected triterpenoids, and on the structures and biological activity of their relevant amide derivatives have been summarized therein. Mainly anti-cancer effects, and, in part, antimicrobial and other effects of the four selected triterpenoids and their amide derivatives have also been reviewed. A comparison of the effects of the parent plant products and those of their amide derivatives has been made.
    Keywords bioactive properties ; cancer therapy ; humans ; nutrition ; plant biochemistry ; secondary metabolites ; traditional medicine ; triterpenoids ; Medicinal plant ; Secondary metabolite ; Pentacyclic triterpenoid ; Amide ; Cytotoxicity ; Antimicrobial activity ; Hepatitis a virus ; Antimalarial activity
    Language English
    Dates of publication 2022-11
    Publishing place Elsevier Ltd
    Document type Article ; Online
    ZDB-ID 208884-8
    ISSN 1873-3700 ; 0031-9422
    ISSN (online) 1873-3700
    ISSN 0031-9422
    DOI 10.1016/j.phytochem.2022.113340
    Database NAL-Catalogue (AGRICOLA)

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