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QSAR characterization of new synthesized hydantoins with antiproliferative activity

Authorized Users Only
2019
Authors
Tot, Kristina
Lazić, Anita
Božić, Biljana
Mandić, Anamarija
Đaković-Sekulić, Tatjana
Article (Published version)
Metadata
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Abstract
Hydantois have been identified as constituents of a number of pharmacologically active molecules. In the present study, we have examined in vitro antiproliferative activity against human colon cancer cell lines HCT-116 of three series of 3-(4-substituted benzyl)-hydantoins with various substituent attached in position 5 of the hydantoin ring. Since the investigated compounds have recently been synthesized and show antiproliferative activity, a good understanding of the properties of the potential drug responsible for their pharmacokinetics is an important goal for their further development. One of the important properties is lipophilicity. Lipophilicity has been assessed by reversed-phase liquid chromatography (high-performance thin-layer chromatography and high-pressure liquid chromatography) by means of direct and indirect (using calibration curve) methods. Chromatographic lipophilicity indices in addition to calculated logP values were compared by hierarchical cluster analysis. The ...linear solvation energy relationship approach was used to understand and compare the types and relative strength of the molecular interactions that occur in the chromatographic as well as in the n-octanol-water partitioning systems. Finally, correlation between in silico pharmacokinetic predictors and antiproliferative activity was examined. Preliminary quantitative structure-activity relationship modeling indicates that pharmacokinetic predictors capture only one-quarter of all chemical features that are important for antiproliferative activity itself. Among selected descriptors are chromatographic lipophilicity indices.

Keywords:
ADMET / human colon cancer / lipophilicity / LSER / QSAR
Source:
Biomedical Chromatography, 2019, 33, 8
Publisher:
  • Wiley, Hoboken
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)

DOI: 10.1002/bmc.4539

ISSN: 0269-3879

PubMed: 30927290

WoS: 000502987000001

Scopus: 2-s2.0-85064487637
[ Google Scholar ]
1
1
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4111
Collections
  • Radovi istraživača (Inovacioni centar) / Researchers’ publications (Innovation Centre)
Institution/Community
Inovacioni centar
TY  - JOUR
AU  - Tot, Kristina
AU  - Lazić, Anita
AU  - Božić, Biljana
AU  - Mandić, Anamarija
AU  - Đaković-Sekulić, Tatjana
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4111
AB  - Hydantois have been identified as constituents of a number of pharmacologically active molecules. In the present study, we have examined in vitro antiproliferative activity against human colon cancer cell lines HCT-116 of three series of 3-(4-substituted benzyl)-hydantoins with various substituent attached in position 5 of the hydantoin ring. Since the investigated compounds have recently been synthesized and show antiproliferative activity, a good understanding of the properties of the potential drug responsible for their pharmacokinetics is an important goal for their further development. One of the important properties is lipophilicity. Lipophilicity has been assessed by reversed-phase liquid chromatography (high-performance thin-layer chromatography and high-pressure liquid chromatography) by means of direct and indirect (using calibration curve) methods. Chromatographic lipophilicity indices in addition to calculated logP values were compared by hierarchical cluster analysis. The linear solvation energy relationship approach was used to understand and compare the types and relative strength of the molecular interactions that occur in the chromatographic as well as in the n-octanol-water partitioning systems. Finally, correlation between in silico pharmacokinetic predictors and antiproliferative activity was examined. Preliminary quantitative structure-activity relationship modeling indicates that pharmacokinetic predictors capture only one-quarter of all chemical features that are important for antiproliferative activity itself. Among selected descriptors are chromatographic lipophilicity indices.
PB  - Wiley, Hoboken
T2  - Biomedical Chromatography
T1  - QSAR characterization of new synthesized hydantoins with antiproliferative activity
IS  - 8
VL  - 33
DO  - 10.1002/bmc.4539
UR  - conv_6010
ER  - 
@article{
author = "Tot, Kristina and Lazić, Anita and Božić, Biljana and Mandić, Anamarija and Đaković-Sekulić, Tatjana",
year = "2019",
abstract = "Hydantois have been identified as constituents of a number of pharmacologically active molecules. In the present study, we have examined in vitro antiproliferative activity against human colon cancer cell lines HCT-116 of three series of 3-(4-substituted benzyl)-hydantoins with various substituent attached in position 5 of the hydantoin ring. Since the investigated compounds have recently been synthesized and show antiproliferative activity, a good understanding of the properties of the potential drug responsible for their pharmacokinetics is an important goal for their further development. One of the important properties is lipophilicity. Lipophilicity has been assessed by reversed-phase liquid chromatography (high-performance thin-layer chromatography and high-pressure liquid chromatography) by means of direct and indirect (using calibration curve) methods. Chromatographic lipophilicity indices in addition to calculated logP values were compared by hierarchical cluster analysis. The linear solvation energy relationship approach was used to understand and compare the types and relative strength of the molecular interactions that occur in the chromatographic as well as in the n-octanol-water partitioning systems. Finally, correlation between in silico pharmacokinetic predictors and antiproliferative activity was examined. Preliminary quantitative structure-activity relationship modeling indicates that pharmacokinetic predictors capture only one-quarter of all chemical features that are important for antiproliferative activity itself. Among selected descriptors are chromatographic lipophilicity indices.",
publisher = "Wiley, Hoboken",
journal = "Biomedical Chromatography",
title = "QSAR characterization of new synthesized hydantoins with antiproliferative activity",
number = "8",
volume = "33",
doi = "10.1002/bmc.4539",
url = "conv_6010"
}
Tot, K., Lazić, A., Božić, B., Mandić, A.,& Đaković-Sekulić, T.. (2019). QSAR characterization of new synthesized hydantoins with antiproliferative activity. in Biomedical Chromatography
Wiley, Hoboken., 33(8).
https://doi.org/10.1002/bmc.4539
conv_6010
Tot K, Lazić A, Božić B, Mandić A, Đaković-Sekulić T. QSAR characterization of new synthesized hydantoins with antiproliferative activity. in Biomedical Chromatography. 2019;33(8).
doi:10.1002/bmc.4539
conv_6010 .
Tot, Kristina, Lazić, Anita, Božić, Biljana, Mandić, Anamarija, Đaković-Sekulić, Tatjana, "QSAR characterization of new synthesized hydantoins with antiproliferative activity" in Biomedical Chromatography, 33, no. 8 (2019),
https://doi.org/10.1002/bmc.4539 .,
conv_6010 .

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