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Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids

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2017
1566.pdf (2.186Mb)
Authors
Cvijetic, Ilija N.
Verbic, Tatjana Z.
Drakulić, Branko J.
Stanković, Dalibor M.
Juranic, Ivan O.
Manojlović, Dragan D.
Zloh, Mire
Article (Published version)
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Abstract
Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values... was determined from the experimentally obtained pK(a) values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.

Keywords:
aryldiketo acids (ADKs) / redox properties / structure-property relationship / acidity constants
Source:
Journal of the Serbian Chemical Society, 2017, 82, 3, 303-316
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials (EU-621375)
Related info:
  • Referenced by
    https://vinar.vin.bg.ac.rs/handle/123456789/8851

DOI: 10.2298/JSC161118021C

ISSN: 0352-5139

WoS: 000401126100006

Scopus: 2-s2.0-85018278992
[ Google Scholar ]
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URI
https://vinar.vin.bg.ac.rs/handle/123456789/1570
Collections
  • WoS Import
Institution/Community
Vinča
TY  - JOUR
AU  - Cvijetic, Ilija N.
AU  - Verbic, Tatjana Z.
AU  - Drakulić, Branko J.
AU  - Stanković, Dalibor M.
AU  - Juranic, Ivan O.
AU  - Manojlović, Dragan D.
AU  - Zloh, Mire
PY  - 2017
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1570
AB  - Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values was determined from the experimentally obtained pK(a) values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.
T2  - Journal of the Serbian Chemical Society
T1  - Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids
VL  - 82
IS  - 3
SP  - 303
EP  - 316
DO  - 10.2298/JSC161118021C
ER  - 
@article{
author = "Cvijetic, Ilija N. and Verbic, Tatjana Z. and Drakulić, Branko J. and Stanković, Dalibor M. and Juranic, Ivan O. and Manojlović, Dragan D. and Zloh, Mire",
year = "2017",
abstract = "Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values was determined from the experimentally obtained pK(a) values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.",
journal = "Journal of the Serbian Chemical Society",
title = "Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids",
volume = "82",
number = "3",
pages = "303-316",
doi = "10.2298/JSC161118021C"
}
Cvijetic, I. N., Verbic, T. Z., Drakulić, B. J., Stanković, D. M., Juranic, I. O., Manojlović, D. D.,& Zloh, M.. (2017). Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids. in Journal of the Serbian Chemical Society, 82(3), 303-316.
https://doi.org/10.2298/JSC161118021C
Cvijetic IN, Verbic TZ, Drakulić BJ, Stanković DM, Juranic IO, Manojlović DD, Zloh M. Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids. in Journal of the Serbian Chemical Society. 2017;82(3):303-316.
doi:10.2298/JSC161118021C .
Cvijetic, Ilija N., Verbic, Tatjana Z., Drakulić, Branko J., Stanković, Dalibor M., Juranic, Ivan O., Manojlović, Dragan D., Zloh, Mire, "Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids" in Journal of the Serbian Chemical Society, 82, no. 3 (2017):303-316,
https://doi.org/10.2298/JSC161118021C . .

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