| Title: | QM-CSA: a novel quantum mechanics-based protocol for evaluation of the carcinogen-scavenging activity of polyphenolic compounds |
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| Authors: | ID Furlan, Veronika (Author)
ID Tošović, Jelena (Author)
ID Bren, Urban (Author) |
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| Files: |  foods-13-02708.pdf (10,13 MB)
MD5: 389D8EB592F3EC06891FE242405C5E4C
 https://www.mdpi.com/2304-8158/13/17/2708
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| Language: | English |
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| Work type: | Article |
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| Typology: | 1.01 - Original Scientific Article |
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| Organization: | FKKT - Faculty of Chemistry and Chemical Engineering
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| Abstract: | In this study, a novel quantum mechanics-based protocol for the evaluation of carcinogenscavenging activity (QM-CSA) is developed. The QM-CSA protocol represents a universal and
quantitative approach to evaluate and compare the activation-free energies for alkylation reactions
between individual polyphenolic compounds and chemical carcinogens of the epoxy type at physiological conditions by applying two scales: the absolute scale allowing for the comparison with
guanine and the relative scale allowing the comparison with glutathione as a reference compound.
The devised quantum mechanical methodology was validated by comparing the activation-free
energies calculated with 14 DFT functionals in conjunction with two implicit solvation models (SMD
and CPCM) and the experimental activation-free energies for reactions between nine investigated
chemical carcinogens and guanine. According to the obtained results, the best agreement with experimental data was achieved by applying DFT functionals M11-L and MN12-L in conjunction with the
flexible 6-311++G(d,p) basis set and implicit solvation model SMD, and the obtained uncertainties
were proven to be similar to the experimental ones. To demonstrate the applicability of the QM-CSA
protocol, functionals M11-L, and MN12-L in conjunction with the SMD implicit solvation model were
applied to calculate activation-free energies for the reactions of nine investigated chemical carcinogens
of the epoxy type with three catechins, namely EGCG, EGC, and (+)-catechin. The order of CSA in
this series of catechins in comparison to guanine and glutathione was determined as (+)-catechin >
EGC > EGCG. The obtained results, for the first time, demonstrated the evaluation and comparison
of CSA in a series of selected catechins with respect to glutathione and guanine. Moreover, the
presented results provide valuable insights into the reaction mechanisms and configurations of the
corresponding transition states. The novel QM-CSA protocol is also expected to expand the kinetic
data for alkylation reactions between various polyphenolic compounds and chemical carcinogens of
the epoxy type, which is currently lacking in the scientific literature |
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| Keywords: | activation-free energies, chemical carcinogens, polyphenols, guanine, glutathione, quantum mechanical calculations, M11-L and MN12-L DFT functionals |
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| Publication status: | Published |
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| Publication version: | Version of Record |
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| Submitted for review: | 25.07.2024 |
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| Article acceptance date: | 22.08.2024 |
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| Publication date: | 27.08.2024 |
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| Publisher: | MDPI |
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| Year of publishing: | 2024 |
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| Number of pages: | 27 str. |
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| Numbering: | Vol. 13, iss. 17, [article no.] 2708 |
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| PID: | 20.500.12556/DKUM-90449-1024ecc7-fd83-cc8a-463f-7c965df76129  |
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| UDC: | 547.56 |
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| ISSN on article: | 2304-8158 |
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| COBISS.SI-ID: | 206227459 |
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| DOI: | 10.3390/foods13172708 |
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| Copyright: | © 2024 by the authors
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| Publication date in DKUM: | 04.09.2024 |
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| Views: | 192 |
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| Downloads: | 31 |
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| Metadata: |    |
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| Categories: | Misc.
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