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Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]

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2016
2628.pdf (290.9Kb)
Authors
Basić, Jasmina V.
Ivković, Branka
Stevanović, Slavica
Lazarević, Andelka
Vujić, Zorica
Article (Published version)
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Abstract
Lipophilicity of twelve synthesized chalcones, whose ring B is a ortho, meta or para monosubstituted with alkyl, oxyalkyl groups or halogens was determined by reverse phase liquid chromatography, using octadecyl-functionalized (RP-18) silica gel as a stationary phase and two-component mixture of methanol/water as a mobile phase. Linear dependence of log k' values of the volume fraction of methanol in the mobile phase was determined for all analyzed compounds, with high coefficient of correlation (r > 0.99). Extrapolation of the line to 0% methanol concentration resulted in the capacity factor of chromatographic system where water is the mobile phase (log k(w)). For five standard substances, chemically similar to chalcones, log kw values were determined under experimental conditions and they were correlated with logP values of those compounds available in the literature. log P-EXP values of synthesized chalcones were calculated on the basis of the created standard curve. In order to est...imate the relevance of the experimentally obtained log P values for chalcones, correlation of log P-EXP values with the log P values obtained through various computational procedures was performed using linear regression analysis. Statistical parameters of dependence showed that the best matching of the results had been achieved with ChemOffice program, suggesting that this program is suitable for calculating logP values of newly-synthesized chalcones, as well as of compounds structurally similar to chalcones.

Source:
Hemijska industrija, 2016, 70, 5, 511-518
Publisher:
  • Savez hemijskih inženjera, Beograd
Funding / projects:
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.2298/HEMIND150426057B

ISSN: 0367-598X

WoS: 000388029800003

Scopus: 2-s2.0-84995449840
[ Google Scholar ]
1
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2630
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Basić, Jasmina V.
AU  - Ivković, Branka
AU  - Stevanović, Slavica
AU  - Lazarević, Andelka
AU  - Vujić, Zorica
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2630
AB  - Lipophilicity of twelve synthesized chalcones, whose ring B is a ortho, meta or para monosubstituted with alkyl, oxyalkyl groups or halogens was determined by reverse phase liquid chromatography, using octadecyl-functionalized (RP-18) silica gel as a stationary phase and two-component mixture of methanol/water as a mobile phase. Linear dependence of log k' values of the volume fraction of methanol in the mobile phase was determined for all analyzed compounds, with high coefficient of correlation (r > 0.99). Extrapolation of the line to 0% methanol concentration resulted in the capacity factor of chromatographic system where water is the mobile phase (log k(w)). For five standard substances, chemically similar to chalcones, log kw values were determined under experimental conditions and they were correlated with logP values of those compounds available in the literature. log P-EXP values of synthesized chalcones were calculated on the basis of the created standard curve. In order to estimate the relevance of the experimentally obtained log P values for chalcones, correlation of log P-EXP values with the log P values obtained through various computational procedures was performed using linear regression analysis. Statistical parameters of dependence showed that the best matching of the results had been achieved with ChemOffice program, suggesting that this program is suitable for calculating logP values of newly-synthesized chalcones, as well as of compounds structurally similar to chalcones.
PB  - Savez hemijskih inženjera, Beograd
T2  - Hemijska industrija
T1  - Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]
VL  - 70
IS  - 5
SP  - 511
EP  - 518
DO  - 10.2298/HEMIND150426057B
UR  - conv_3706
ER  - 
@article{
author = "Basić, Jasmina V. and Ivković, Branka and Stevanović, Slavica and Lazarević, Andelka and Vujić, Zorica",
year = "2016",
abstract = "Lipophilicity of twelve synthesized chalcones, whose ring B is a ortho, meta or para monosubstituted with alkyl, oxyalkyl groups or halogens was determined by reverse phase liquid chromatography, using octadecyl-functionalized (RP-18) silica gel as a stationary phase and two-component mixture of methanol/water as a mobile phase. Linear dependence of log k' values of the volume fraction of methanol in the mobile phase was determined for all analyzed compounds, with high coefficient of correlation (r > 0.99). Extrapolation of the line to 0% methanol concentration resulted in the capacity factor of chromatographic system where water is the mobile phase (log k(w)). For five standard substances, chemically similar to chalcones, log kw values were determined under experimental conditions and they were correlated with logP values of those compounds available in the literature. log P-EXP values of synthesized chalcones were calculated on the basis of the created standard curve. In order to estimate the relevance of the experimentally obtained log P values for chalcones, correlation of log P-EXP values with the log P values obtained through various computational procedures was performed using linear regression analysis. Statistical parameters of dependence showed that the best matching of the results had been achieved with ChemOffice program, suggesting that this program is suitable for calculating logP values of newly-synthesized chalcones, as well as of compounds structurally similar to chalcones.",
publisher = "Savez hemijskih inženjera, Beograd",
journal = "Hemijska industrija",
title = "Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]",
volume = "70",
number = "5",
pages = "511-518",
doi = "10.2298/HEMIND150426057B",
url = "conv_3706"
}
Basić, J. V., Ivković, B., Stevanović, S., Lazarević, A.,& Vujić, Z.. (2016). Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]. in Hemijska industrija
Savez hemijskih inženjera, Beograd., 70(5), 511-518.
https://doi.org/10.2298/HEMIND150426057B
conv_3706
Basić JV, Ivković B, Stevanović S, Lazarević A, Vujić Z. Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]. in Hemijska industrija. 2016;70(5):511-518.
doi:10.2298/HEMIND150426057B
conv_3706 .
Basić, Jasmina V., Ivković, Branka, Stevanović, Slavica, Lazarević, Andelka, Vujić, Zorica, "Determination of the lipophilicity of 2҆'-Hydroxychalcones by RP-HPLC method [Određivanje lipofilnosti 2'-hidroksihalkona primenom RP-HPLC metode]" in Hemijska industrija, 70, no. 5 (2016):511-518,
https://doi.org/10.2298/HEMIND150426057B .,
conv_3706 .

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