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A Monocarbonyl Curcuminoid Derivative Inhibits the Activity of Human Glutathione Transferase A4-4 and Chemosensitizes Glioblastoma Cells to Temozolomide.

التفاصيل البيبلوغرافية
العنوان: A Monocarbonyl Curcuminoid Derivative Inhibits the Activity of Human Glutathione Transferase A4-4 and Chemosensitizes Glioblastoma Cells to Temozolomide.
المؤلفون: Tsouri S; Laboratory of Enzyme Technology, Department of Biotechnology, School Applied Biology and Biotechnology, Agricultural University of Athens, 75 Iera Odos Street, 11855 Athens, Greece., Tselo E; Laboratory of Enzyme Technology, Department of Biotechnology, School Applied Biology and Biotechnology, Agricultural University of Athens, 75 Iera Odos Street, 11855 Athens, Greece., Premetis GE; Laboratory of Enzyme Technology, Department of Biotechnology, School Applied Biology and Biotechnology, Agricultural University of Athens, 75 Iera Odos Street, 11855 Athens, Greece., Furlan V; Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova 17, SI-2000 Maribor, Slovenia., Pantiora PD; Laboratory of Enzyme Technology, Department of Biotechnology, School Applied Biology and Biotechnology, Agricultural University of Athens, 75 Iera Odos Street, 11855 Athens, Greece., Mavroidi B; Institute of Biosciences & Applications, National Centre for Scientific Research 'Demokritos', 15310 Athens, Greece., Matiadis D; Institute of Biosciences & Applications, National Centre for Scientific Research 'Demokritos', 15310 Athens, Greece.; Department of Biomedical Sciences, University of West Attica, Egaleo Park Campus, 12243 Athens, Greece., Pelecanou M; Institute of Biosciences & Applications, National Centre for Scientific Research 'Demokritos', 15310 Athens, Greece., Papageorgiou AC; Turku Bioscience Centre, University of Turku and Åbo Akademi University, 20521 Turku, Finland., Bren U; Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova 17, SI-2000 Maribor, Slovenia.; Faculty of Mathematics, Natural Sciences and Information Technologies, University of Primorska, Glagoljaška 8, SI-6000 Koper, Slovenia.; Institute of Environmental Protection and Sensors, Beloruska Ulica 7, SI-2000 Maribor, Slovenia., Sagnou M; Institute of Biosciences & Applications, National Centre for Scientific Research 'Demokritos', 15310 Athens, Greece., Labrou NE; Laboratory of Enzyme Technology, Department of Biotechnology, School Applied Biology and Biotechnology, Agricultural University of Athens, 75 Iera Odos Street, 11855 Athens, Greece.
المصدر: Pharmaceuticals (Basel, Switzerland) [Pharmaceuticals (Basel)] 2024 Mar 11; Vol. 17 (3). Date of Electronic Publication: 2024 Mar 11.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 101238453 Publication Model: Electronic Cited Medium: Print ISSN: 1424-8247 (Print) Linking ISSN: 14248247 NLM ISO Abbreviation: Pharmaceuticals (Basel) Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c2004-
مستخلص: Human glutathione transferase A4-4 (hGSTA4-4) displays high catalytic efficiency towards 4-hydroxyalkenals and other cytotoxic and mutagenic products of radical reactions and lipid peroxidation. Its role as a target for the chemosensitization of cancer cells has not been investigated so far. In this study, the inhibitory potency of twelve selected natural products and ten monocarbonyl curcumin derivatives against hGSTA4-4 was studied. Among natural products, ellagic acid turned out to be the strongest inhibitor with an IC 50 value of 0.44 ± 0.01 μM. Kinetic analysis using glutathione (GSH) and 1-chloro-2,4-dinitrobenzene (CDNB) as variable substrates showed that ellagic acid behaved as a competitive inhibitor towards both GSH and CDNB, with K i values of 0.39 ± 0.02 and 0.63 ± 0.03 μM, respectively. Among the curcumin derivatives studied, three proved to be the most potent inhibitors, in the order DM151 > DM101 > DM100, with IC 50 values of 2.4 ± 0.1 μM, 12.7 ± 1.1 μΜ and 16.9 ± 0.4 μΜ, respectively. Further kinetic inhibition analysis of the most active derivative, DM151, demonstrated that this compound is a mixed inhibitor towards CDNB with inhibition constants of K i = 4.1 ± 0.5 μM and K i' = 0.536 ± 0.034 μM, while it is a competitive inhibitor towards GSH with a K i = 0.98 ± 0.11 μM. Molecular docking studies were performed to interpret the differences in binding of ellagic acid and curcumin derivatives to hGSTA4-4. The in silico measured docking scores were consistent with the obtained experimental data. Hydrogen bonds appear to be the main contributors to the specific binding of monocarbonyl curcumin derivatives, while π-π stacking interactions play a key role in the enzyme-ellagic acid interaction. In vitro cytotoxicity assessment of the worst (DM148) and the best (DM151) inhibitors was performed against glioblastoma cell lines U-251 MG and U-87 MG. The results revealed that DM151 displays considerably higher cytotoxicity against both glioblastoma cell lines, while the glioblastoma cytotoxicity of DM148 was very limited. Furthermore, low and non-toxic doses of DM151 sensitized U-251 MG cells to the first-line glioblastoma chemotherapeutic temozolomide (TMZ), allowing us to propose for the first time that hGSTA4-4 inhibitors may be attractive therapeutic partners for TMZ to optimize its clinical effect in glioblastoma chemotherapy.
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معلومات مُعتمدة: P2-0046, P2-0438, L2-3175, J1-4398, L2-4430, J3-4498, J7-4638, J1-4414, J3-4497, J4-4633, I0-E015, and J1-2471 Slovenian Research and Innovation Agency (ARIS) program; NOO Slovenian Ministry of Science and Education
فهرسة مساهمة: Keywords: GST inhibition; chemoresistance; chemosensitization; curcumin; ellagic acid; glioblastoma; human glutathione transferase A4-4; monocarbonyl curcumin derivatives; temozolomide sensitization
تواريخ الأحداث: Date Created: 20240328 Latest Revision: 20240330
رمز التحديث: 20240330
مُعرف محوري في PubMed: PMC10974579
DOI: 10.3390/ph17030365
PMID: 38543151
قاعدة البيانات: MEDLINE
الوصف
تدمد:1424-8247
DOI:10.3390/ph17030365