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Article ; Online: Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study.

Kadela-Tomanek, Monika / Krzykawski, Kamil / Halama, Adrianna / Kubina, Robert

2023 Volume 28, Issue 18

Abstract: One of the most essential health problems is cancer, the first or second cause of death worldwide. Head and neck cancers are hard to detect due to non-specific symptoms. The treatment often relies on a combination of radio and chemotherapy. For this ... ...

Abstract	One of the most essential health problems is cancer, the first or second cause of death worldwide. Head and neck cancers are hard to detect due to non-specific symptoms. The treatment often relies on a combination of radio and chemotherapy. For this reason, the research of new anticancer compounds is fundamental. The natural and synthetic compounds with 1,4-naphthoquinone scaffold is characterized by high anticancer activity. The study aimed to evaluate the synthesis and anticancer activity of hybrids 1,4-naphthoquinone with thymidine derivatives. The series of compounds allows us to check the influence of the substituent in the C3' position of the thymidine moiety on the cytotoxicity against squamous cancer cell lines (SCC-9 and SCC-25) and submandibular gland cancer (A-253). An annexin V/propidium iodide (PI) co-staining assay shows that derivatives cause the apoptotic in SCC-25 and A-253 cell lines. The molecular docking study examined the interaction between the active site of the BCL-2 protein and the hybrids.
MeSH term(s)	Humans ; Molecular Docking Simulation ; Antineoplastic Agents/chemistry ; Thymidine/pharmacology ; Head and Neck Neoplasms ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Cell Proliferation ; Molecular Structure ; Apoptosis ; Structure-Activity Relationship
Chemical Substances	1,4-naphthoquinone (RBF5ZU7R7K) ; Antineoplastic Agents ; Thymidine (VC2W18DGKR)
Language	English
Publishing date	2023-09-15
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28186644
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Article ; Online: 28- O -Acetyl-3- O ′-(prop-2-enoyl)betulin

Ewa Bębenek / Elwira Chrobak / Monika Kadela-Tomanek

Molbank, Vol 2023, Iss M1696, p M

2023 Volume 1696

Abstract: 28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions ... ...

Abstract	28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions produced a new 3-alkenyl betulin derivative. The structure of the obtained compound was confirmed based on the analysis of NMR, IR, EI MS, and HRMS spectra. Selected pharmacokinetic parameters related to the absorption and distribution were calculated for the new betulin derivative using in silico methods.
Keywords	betulin ; synthesis ; ADME ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2023-07-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: 3- O -But-2-ynoyl-28- O ′-acetylbetulin

Elwira Chrobak / Ewa Bębenek / Monika Kadela-Tomanek

Molbank, Vol 2023, Iss M1686, p M

2023 Volume 1686

Abstract: The aim of the work was the synthesis of a new 28-acetylbetulin derivative containing an ester group with a carbon–carbon triple bond in the C3 position. To obtain the title compound, a reaction of 28-acetylbetulin with but-2-ynoic acid was carried out ... ...

Abstract	The aim of the work was the synthesis of a new 28-acetylbetulin derivative containing an ester group with a carbon–carbon triple bond in the C3 position. To obtain the title compound, a reaction of 28-acetylbetulin with but-2-ynoic acid was carried out according to the Steglich method. The synthetized compound was fully characterized by analyzing the nuclear magnetic resonance spectra ( 1 H-NMR, 13 C-NMR), as well as the heteronuclear single quantum coherence (HSQC), and by conducting a heteronuclear multiple bond coherence (HMBC) experiment. Infrared (IR) spectroscopy and high-resolution mass spectrometry (HRMS) were also performed. Additionally, pharmacokinetic parameters and drug similarity of the studied molecule were calculated using in silico methods.
Keywords	betulin ; NMR spectroscopy ; ADME ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2023-07-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Modification of 6,7-Dichloro-5,8-Quinolinedione at C2 Position

Monika Kadela-Tomanek / Ewa Bębenek / Elwira Chrobak

Applied Sciences, Vol 13, Iss 1530, p

Synthesis, Quantum Chemical Properties, and Activity against DT-Diaphorase Enzyme

2023 Volume 1530

Abstract: This research presents a synthesis and characterization of new 6,7-dichloro-5,8-quinolinedione derivatives with various groups at the C2 position. Chemical structures were examined by the spectroscopic methods. The quantum chemical parameters calculated ... ...

Abstract	This research presents a synthesis and characterization of new 6,7-dichloro-5,8-quinolinedione derivatives with various groups at the C2 position. Chemical structures were examined by the spectroscopic methods. The quantum chemical parameters calculated using the DFT method showed that these derivatives are highly reactive towards the nucleophilic target. The molecular electrostatic potential map (MEP) showed that nucleophilic regions are localized near the nitrogen atom and the formyl group. Introduction of the hydroxyl or formyl groups at the C2 position led to the formation of an additional nucleophilic region. New compounds were tested as substrates for the NQO1 protein. An enzymatic study showed that derivatives are a good substrate for the NQO1 enzyme. Moreover, it was shown that the enzymatic conversion rates depend on the type of substituent at the C2 position of the 5,8-quinolinedione scaffold. A molecular docking study was used to study the interaction between new derivatives and the NQO1 protein. The arrangement and type of interactions between derivatives and the NQO1 enzyme depended on the type of substituent at the C2 position. A derivative with the hydroxyl group at this position was found to form an additional hydrogen bond between the formyl group and the tyrosine.
Keywords	5,8-quinolinedione ; DFT ; NQO1 ; DT-diaphorase ; molecular docking ; Technology ; T ; Engineering (General). Civil engineering (General) ; TA1-2040 ; Biology (General) ; QH301-705.5 ; Physics ; QC1-999 ; Chemistry ; QD1-999
Subject code	540
Language	English
Publishing date	2023-01-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: New Propargyloxy Derivatives of Galangin, Kaempferol and Fisetin-Synthesis, Spectroscopic Analysis and In Vitro Anticancer Activity on Head and Neck Cancer Cells.

Kubina, Robert / Krzykawski, Kamil / Sokal, Arkadiusz / Madej, Marcel / Dziedzic, Arkadiusz / Kadela-Tomanek, Monika

Cells

2023 Volume 12, Issue 18

Abstract: Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in ... ...

Abstract	Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in water, are unstable and have low bioavailability, they are subjected to chemical modification to obtain new derivatives with better properties. This study aimed to synthesize and analyze new propargyloxy derivatives of galangin, kaempferol and fisetin, and to evaluate their anticancer activity against selected HNC cell lines. The obtained derivatives were assessed by spectroscopic analysis; next, their anticancer activity was evaluated using a flow cytometer and real-time cell analysis. The results showed that only the fisetin derivative was suitable for further analysis, due to the lack of crystal formation of the compound. The fisetin derivative statistically significantly increases the number of cells in the G2/M phase (
MeSH term(s)	Humans ; Kaempferols/pharmacology ; Flavonoids/pharmacology ; Head and Neck Neoplasms/drug therapy
Chemical Substances	fisetin (OO2ABO9578) ; galangin (142FWE6ECS) ; Kaempferols ; Flavonoids
Language	English
Publishing date	2023-09-15
Publishing country	Switzerland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2661518-6
ISSN	2073-4409 ; 2073-4409
ISSN (online)	2073-4409
ISSN	2073-4409
DOI	10.3390/cells12182288
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Lipophilicity and ADMET Analysis of Quinoline-1,4-quinone Hybrids.

Kadela-Tomanek, Monika / Jastrzębska, Maria / Chrobak, Elwira / Bębenek, Ewa

Pharmaceutics

2022 Volume 15, Issue 1

Abstract: Lipophilicity is one of the basic properties of a potential drug determining its solubility in non-polar solvents and, consequently, its ability to passively penetrate the cell membrane, as well as the occurrence of various pharmacokinetic processes, ... ...

Abstract	Lipophilicity is one of the basic properties of a potential drug determining its solubility in non-polar solvents and, consequently, its ability to passively penetrate the cell membrane, as well as the occurrence of various pharmacokinetic processes, including adsorption, distribution, metabolism, excretion, and toxicity (ADMET). Heterocyclic compounds containing a nitrogen atom play a significant role in the search for new drugs. In this study, lipophilicity as well as other physicochemical, pharmacokinetic and toxicity properties affecting the bioavailability of the quinolone-1,4-quinone hybrids are presented. Lipophilicity was determined experimentally as well as theoretically using various computer programs. The tested compounds showed low values of experimental lipophilicity and its relationship with the type of 1,4-quinone moiety. Introduction of the nitrogen atom reduced the lipophilicity depending on the position at the 5,8-quinolinedione moiety. The bioavailability of the tested compounds was determined in silico using the ADMET parameters. The obtained parameters showed that most of the hybrids can be used orally and do not exhibit neurotoxic effects. Similarity analysis was used to examine the relationship between the ADMET parameters and experimental lipophilicity. The ability of hybrids to interact with biological targets was characterized by global reactivity descriptors. The molecular docking study showed that the hybrids can inhibit the BCL-2 protein.
Language	English
Publishing date	2022-12-22
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527217-2
ISSN	1999-4923
ISSN	1999-4923
DOI	10.3390/pharmaceutics15010034
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Article ; Online: 28- O -Acetyl-3- O ’-(Phenylpropynoyl)Betulin

Ewa Bębenek / Monika Kadela-Tomanek / Beata Filip-Psurska / Elwira Chrobak

Molbank, Vol 2023, Iss 4, p M

2023 Volume 1741

Abstract: New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1 H NMR, 13 C NMR, IR, EI MS and HRMS. The antiproliferative ... ...

Abstract	New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1 H NMR, 13 C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28- O -acetyl-3- O ’-(phenylpropynoyl)betulin were evaluated against three human cancer cell lines: T47D (breast cancer), CCRF/CEM (leukemia), SW707 (colorectal adenocarcinoma) and murine cell line P388 (leukemia). The synthesized compound exhibited moderate antiproliferative activity against P388 cells (IC 50 = 35.51 µM). The in silico analysis showed that the title compound meets the criteria of Veber’s rule.
Keywords	triterpenes ; synthesis ; anticancer activity ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2023-10-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives

Monika Kadela-Tomanek / Kamil Krzykawski / Adrianna Halama / Robert Kubina

Molecules, Vol 28, Iss 6644, p

Synthesis, Anticancer Activity, and Molecular Docking Study

2023 Volume 6644

Abstract	One of the most essential health problems is cancer, the first or second cause of death worldwide. Head and neck cancers are hard to detect due to non-specific symptoms. The treatment often relies on a combination of radio and chemotherapy. For this reason, the research of new anticancer compounds is fundamental. The natural and synthetic compounds with 1,4-naphthoquinone scaffold is characterized by high anticancer activity. The study aimed to evaluate the synthesis and anticancer activity of hybrids 1,4-naphthoquinone with thymidine derivatives. The series of compounds allows us to check the influence of the substituent in the C3′ position of the thymidine moiety on the cytotoxicity against squamous cancer cell lines (SCC-9 and SCC-25) and submandibular gland cancer (A-253). An annexin V/propidium iodide (PI) co-staining assay shows that derivatives cause the apoptotic in SCC-25 and A-253 cell lines. The molecular docking study examined the interaction between the active site of the BCL-2 protein and the hybrids.
Keywords	1,4-naphthoquinone ; AZT ; apoptotic ; head and neck cancers ; Organic chemistry ; QD241-441
Subject code	540
Language	English
Publishing date	2023-09-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Hybrids of 1,4-Quinone with Quinoline Derivatives: Synthesis, Biological Activity, and Molecular Docking with DT-Diaphorase (NQO1).

Kadela-Tomanek, Monika / Jastrzębska, Maria / Chrobak, Elwira / Bębenek, Ewa / Latocha, Małgorzata

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 19

Abstract: Hybrids 1,4-quinone with quinoline were obtained by connecting two active structures through an oxygen atom. This strategy allows to obtain new compounds with a high biological activity and suitable bioavailability. Newly synthesized compounds were ... ...

Abstract	Hybrids 1,4-quinone with quinoline were obtained by connecting two active structures through an oxygen atom. This strategy allows to obtain new compounds with a high biological activity and suitable bioavailability. Newly synthesized compounds were characterized by various spectroscopic methods. The enzymatic assay used showed that these compounds were a suitable DT-diaphorase (NQO1) substrates as evidenced by increasing enzymatic conversion rates relative to that of streptonigrin. Hybrids were tested in vitro against a panel of human cell lines including melanoma, breast, and lung cancers. They showed also a high cytotoxic activity depending on the type of 1,4-quinone moiety and the applied tumor cell lines. It was found that cytotoxic activity of the studied hybrids was increasing against the cell lines with higher NQO1 protein level, such as breast (MCF-7 and T47D) and lung (A549) cancers. Selected hybrids were tested for the transcriptional activity of the gene encoding a proliferation marker (H3 histone), cell cycle regulators (p53 and p21) and the apoptosis pathway (BCL-2 and BAX). The molecular docking was used to examine the probable interaction between the hybrids and NQO1 protein.
MeSH term(s)	Antineoplastic Agents/chemistry ; Apoptosis ; Benzoquinones ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Histones ; Humans ; Hydroxyquinolines/pharmacology ; Molecular Docking Simulation ; NAD(P)H Dehydrogenase (Quinone)/metabolism ; Oxygen/metabolism ; Quinolines/chemistry ; Quinones/metabolism ; Quinones/pharmacology ; Streptonigrin ; Tumor Suppressor Protein p53 ; bcl-2-Associated X Protein/metabolism
Chemical Substances	Antineoplastic Agents ; Benzoquinones ; Histones ; Hydroxyquinolines ; Quinolines ; Quinones ; Tumor Suppressor Protein p53 ; bcl-2-Associated X Protein ; Streptonigrin (261Q3JB310) ; quinone (3T006GV98U) ; NAD(P)H Dehydrogenase (Quinone) (EC 1.6.5.2) ; NQO1 protein, human (EC 1.6.5.2) ; Oxygen (S88TT14065)
Language	English
Publishing date	2022-09-21
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27196206
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: 3′-[4-({[3β,28-Bis(acetyloxy)lup-20(29)-en-30-yl]oxy}carbonyl)-1 H -1,2,3-triazol-1-yl]-3′-deoxythymidine

Ewa Bębenek / Monika Kadela-Tomanek / Elwira Chrobak / Małgorzata Latocha

Molbank, Vol 2022, Iss M1370, p M

2022 Volume 1370

Abstract: The reaction of the azidothymidine (AZT) with the 30-propynoylated derivative of 3,28- O , O ′-diacetylbetulin gave a 1,4-disubstituted 1,2,3-triazole. The chemical structure of new derivative was characterized by 1 H NMR, 13 C NMR and HR-MS. The ... ...

Abstract	The reaction of the azidothymidine (AZT) with the 30-propynoylated derivative of 3,28- O , O ′-diacetylbetulin gave a 1,4-disubstituted 1,2,3-triazole. The chemical structure of new derivative was characterized by 1 H NMR, 13 C NMR and HR-MS. The triterpene-AZT conjugate was tested against a human cancer cell lines such as glioblastoma (SNB-19), amelanotic melanoma (C-32), ovarian adenocarcinoma (SKOV-3) and breast cancer (T47D, and MCF-7). 3′-[4-({[3β,28-Bis(acetyloxy)lup-20(29)-en-30-yl]oxy}carbonyl)-1 H -1,2,3-triazol-1-yl]-3′-deoxythymidine shown significant activity against MCF-7 cells, with an IC 50 value of 4.37 µM.
Keywords	triterpene ; 1,2,3-triazole ; 1,3 dipolar cycloaddition (CuAAC) ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2022-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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