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Dive into the research topics where Maciej Serda is active.

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Featured researches published by Maciej Serda.


Current Medicinal Chemistry | 2010

Quinoline-Based Antifungals

Robert Musiol; Maciej Serda; S. Hensel-Bielowka; Jaroslaw Polanski

Although the assortment of antifungal drugs is broad, the most commonly used agents have major drawbacks. Toxicity, serious side effects or the emergence of drug resistance are amongst them. New drugs and drug candidates under clinical trials do not guarantee better pharmacological parameters. These new medicines may appear effective; however; they may cause serious side effects. This current review is focused on the recent findings in the design of quinoline based antifungal agents. This field seems to be especially interesting as 8-hydroxyquinoline and its metal complexes have been well known as antifungals for years. Structural similarities between quinoline based antifungals and allylamines or homoallylamines, e.g. terbinafine is another interesting fact. Quinoline can be identified in a number of synthetic and natural antifungals, which indicates natures preference for this fragment and identifying it as one of the so-called privileged structures. We have discussed new trends in the design of quinolines with antifungal properties, their possible targets and the structure activity relationships within the antifungal series developed.


Current Pharmaceutical Design | 2011

Prodrugs in photodynamic anticancer therapy.

Robert Musiol; Maciej Serda; Jaroslaw Polanski

Photodynamic therapy (PDT), the concept of cancer treatment through the selective uptake of a light-sensitive agent followed by exposure to a specific wavelength, is limited by the transport of a photosensitizer (PS) to the tumor tissue. Porphyrin, an important PS class, can be used in PDT in the form of its prodrug molecule 5-aminolevulinic acid (5-ALA). Unfortunately, its poor pharmacokinetic properties make this compound difficult to administer. Two different methods for eliminating this problem can be distinguished. The first approach is to play with its formulation in order to improve the drugs applicability. The second approach, which is to find possible 5- ALA prodrugs, is an example of the double-prodrug method, a strategy often used in modern drug design. In this approach, the biological mechanisms in a long biosynthetic pathway involving several steps must be completed before the active drug appears. Recently, an idea of enhancing PDT sensitization using the so-called iron chelators seemed to increase the accumulation of protoporphyrin in cells. At the same time, iron chelators can destroy tumor cells by producing active oxygen after the formation of an active drug by chelating iron in the cancer cells. Thus, in the latter case, the therapy resembles a prodrug strategy. The mechanism can be explained by the Fenton reaction. Vitamin C is another example of a potential anticancer agent of this type.


Molecules | 2012

Investigation of the Biological Properties of (Hetero)Aromatic Thiosemicarbazones

Maciej Serda; Anna Mrozek-Wilczkiewicz; Josef Jampilek; Matus Pesko; Katarina Kralova; Marcela Vejsova; Robert Musiol; Alicja Ratuszna; Jaroslaw Polanski

Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds.


PLOS ONE | 2014

Exploring the Anti-Cancer Activity of Novel Thiosemicarbazones Generated through the Combination of Retro-Fragments: Dissection of Critical Structure-Activity Relationships

Maciej Serda; Danuta S. Kalinowski; Nathalie Rasko; Eliška Potůčková; Anna Mrozek-Wilczkiewicz; Robert Musiol; J.G. Małecki; Mieczysław Sajewicz; Alicja Ratuszna; Angelika Muchowicz; Jakub Gołąb; Tomáš Šimůnek; Des R. Richardson; Jaroslaw Polanski

Thiosemicarbazones (TSCs) are an interesting class of ligands that show a diverse range of biological activity, including anti-fungal, anti-viral and anti-cancer effects. Our previous studies have demonstrated the potent in vivo anti-tumor activity of novel TSCs and their ability to overcome resistance to clinically used chemotherapeutics. In the current study, 35 novel TSCs of 6 different classes were designed using a combination of retro-fragments that appear in other TSCs. Additionally, di-substitution at the terminal N4 atom, which was previously identified to be critical for potent anti-cancer activity, was preserved through the incorporation of an N4-based piperazine or morpholine ring. The anti-proliferative activity of the novel TSCs were examined in a variety of cancer and normal cell-types. In particular, compounds 1d and 3c demonstrated the greatest promise as anti-cancer agents with potent and selective anti-proliferative activity. Structure-activity relationship studies revealed that the chelators that utilized “soft” donor atoms, such as nitrogen and sulfur, resulted in potent anti-cancer activity. Indeed, the N,N,S donor atom set was crucial for the formation of redox active iron complexes that were able to mediate the oxidation of ascorbate. This further highlights the important role of reactive oxygen species generation in mediating potent anti-cancer activity. Significantly, this study identified the potent and selective anti-cancer activity of 1d and 3c that warrants further examination.


ACS Medicinal Chemistry Letters | 2014

Iron Chelators in Photodynamic Therapy Revisited: Synergistic Effect by Novel Highly Active Thiosemicarbazones

Anna Mrozek-Wilczkiewicz; Maciej Serda; Robert Musiol; Grzegorz Malecki; Agnieszka Szurko; Angelika Muchowicz; Jakub Golab; Alicja Ratuszna; Jaroslaw Polanski

In photodynamic therapy (PDT), a noninvasive anticancer treatment, visible light, is used as a magic bullet selectively destroying cancer cells by a photosensitizer that is nontoxic in the dark. Protoporphyrin IX (PpIX) is a natural photosensitizer synthesized in the cell, which is also a chelating agent that if bonded to Fe(2+) forms heme, a central component of hemoglobin. Therefore, xenobiotic iron chelators can disturb iron homeostasis, increasing the accumulation of PpIX, obstructing the last step of heme biosynthesis, and enhancing PDT efficiency. However, the attempts to use this promising idea have not proved to be hugely successful. Herein, we revisited this issue by analyzing the application of iron chelators highly toxic in the dark, which should have higher Fe(2+) affinity than the nontoxic chelators used so far. We have designed and prepared thiosemicarbazones (TSC) with the highest dark cellular cytotoxicity among TSCs ever reported. We demonstrate that compound 2 exerts powerful PDT enhancement when used in combination with 5-aminolevulinic acid (ALA), a precursor of PpIX.


European Journal of Medicinal Chemistry | 2016

Small molecule glycoconjugates with anticancer activity.

Gabriela Pastuch-Gawolek; Katarzyna Malarz; Anna Mrozek-Wilczkiewicz; Marta Musioł; Maciej Serda; Barbara Czaplinska; Robert Musiol

Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from small molecular quinolines and substituted gluco- and galactopyranosyl amines. Although the parent quinoline compounds were inactive in affordable concentrations, the glycoconjugates that were obtained appeared to be cytotoxic against cancer cells at the micromolar level. When combined with copper ions, their activity increased even further. Their mechanism of action is connected to the formation of reactive oxygen species and the intercalation of DNA.


Current Organic Chemistry | 2013

Microwave Assisted Synthesis of Monoazanaphthalene Scaffolds

Wioleta Cieslik; Maciej Serda; Agata Kurczyk; Robert Musiol

Current achievements in the microwave-assisted synthesis of quinoline and isoquinoline are discussed in this review. Monoazanaphthalenes are important scaffolds in organic synthesis and especially in drug design. Due to their frequent appearance in bio- logically active compounds, drugs and natural products, they are claimed to be privileged structures. Synthetic routes to these compounds have been known for more than one hundred years but their availability is still the main limiting factor. Conventional methods are labori- ous, time consuming and do not offer satisfactory yields or purity of the products. On the other hand, microwave-assisted protocols do not provide enough versatility in designing a molecular scaffold, i.e. substitution pattern. Most of the known microwave-assisted synthe- ses consist of the modification of monoazanaphthalene rings and as such are limited to several easily available scaffolds.


Journal of Cancer | 2017

Iron Chelators and Exogenic Photosensitizers. Synergy through Oxidative Stress Gene Expression

Anna Mrozek-Wilczkiewicz; Katarzyna Malarz; Marzena Rams-Baron; Maciej Serda; Daniela Bauer; Franz-Peter Montforts; Alicja Ratuszna; Thomas A. Burley; Jaroslaw Polanski; Robert Musiol

In non-invasive anticancer photodynamic therapy (PDT), a nontoxic photosensitizer (PS), which is activated by visible light, is used as a magic bullet that selectively destroys cancer cells. Recently, we described the combined therapy of 5-aminolevulinic acid (ALA-PDT) with thiosemicarbazone (TSC), i.e. an iron-chelating agent. This resulted in a strong synergistic effect. Herein, we investigated a novel strategy using a combination of PDT consist of the xenobiotic-porphyrin type PS with TSC. We observed a synergistic effect for all of the pairs of TSC-PS. This approach can be rationalized by the fact that both chlorin and TSC can affect the generation of reactive oxygen species (ROS). In order to elucidate the plausible mechanism of action, we also combined the investigated PSs with DFO, which forms complexes that are redox inactive. We detected a slight antagonism or additivity for this combination. This may suggest that the ability of an iron chelator (IC) to participate in the production of ROS and the generation of oxidative stress is important.


Oncotarget | 2018

The role of oxidative stress in activity of anticancer thiosemicarbazones

Katarzyna Malarz; Anna Mrozek-Wilczkiewicz; Maciej Serda; Marta Rejmund; Jaroslaw Polanski; Robert Musiol

Thiosemicarbazones are chelators of transition metals such as iron or copper whose anticancer potency is intensively investigated. Although two compounds from this class have entered clinical trials, their precise mechanism of action is still unknown. Recent studies have suggested the mobilization of the iron ions from a cell, as well as the inhibition of ribonucleotide reductase, and the formation of reactive oxygen species. The complexity and vague nature of this mechanism not only impedes a more rational design of novel compounds, but also the further development of those that are highly active that are already in the preclinical phase. In the current work, a series of highly active thiosemicarbazones was studied for their antiproliferative activity in vitro. Our experiments indicate that these complexes have ionophoric properties and redox activity. They appeared to be very effective generating reactive oxygen species and deregulating the antioxidative potential of a cell. Moreover, the genes that are responsible for antioxidant capacity were considerably deregulated, which led to the induction of apoptosis and cell cycle arrest. On the other hand, good intercalating properties of the studied compounds may explain their ability to cleave DNA strands and to also poison related enzymes through the formation of reactive oxygen species. These findings may help to explain the particularly high selectivity that they have over normal cells, which generally have a stronger redox equilibrium.


Bioorganic & Medicinal Chemistry Letters | 2012

Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy

Maciej Serda; Danuta S. Kalinowski; Anna Mrozek-Wilczkiewicz; Robert Musiol; Agnieszka Szurko; Alicja Ratuszna; Namfon Pantarat; Zaklina Kovacevic; Angelica M. Merlot; Des R. Richardson; Jaroslaw Polanski

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Jaroslaw Polanski

University of Silesia in Katowice

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Robert Musiol

University of Silesia in Katowice

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Anna Mrozek-Wilczkiewicz

University of Silesia in Katowice

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J.G. Małecki

University of Silesia in Katowice

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Alicja Ratuszna

University of Silesia in Katowice

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Anna Maroń

University of Silesia in Katowice

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Katarzyna Malarz

University of Silesia in Katowice

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Agnieszka Szurko

University of Silesia in Katowice

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Angelika Muchowicz

Medical University of Warsaw

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