TY  - JOUR
AU  - Đaković-Sekulić, Tatjana
AU  - Smolinski, Adam
AU  - Mandić, Anamarija
AU  - Lazić, Anita
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3992
AB  - Lipophilicity has, for a long time, been recognized as a meaningful parameter in structure-activity relationships. It is also the single most informative physicochemical property that reveals a wealth of information on intermolecular forces, intramolecular interactions, and molecular structure in the broadest sense. In this paper, a total of 14 chromatographic measures of lipophilicity (thin-layer chromatography and high-performance liquid chromatography) and 11 computationally estimated logP-s for 21 newly synthesized 3-(4-substituted benzyl)-cycloalkylspiro-5-hidantoin derivatives have been investigated. Similarities among the investigated compounds as well as lipophilicity measures were examined by the multivariate exploratory analysis, principal component analysis, hierarchical cluster analysis, and sum of ranking differences. These chemometric approaches reveal the arrangement of investigated compounds into clusters according to lipophilicity. Chemometric consideration of lipophilicity renders principal component scores as entirely unsuitable lipophilicity measures. Furthermore, the logP values estimated from calibration graph by using a set of standard reference compounds were equivalent to the corresponding chromatographic descriptors of hydantoins extrapolated from linear relationship between retention parameters and mobile phase composition. Comparison of the 2 chromatographic techniques places high-performance liquid chromatography lipophilicity indices slightly ahead of thin-layer chromatography.
PB  - Wiley, Hoboken
T2  - Journal of Chemometrics
T1  - Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity
IS  - 4
VL  - 32
DO  - 10.1002/cem.2991
ER  - 

@article{
author = "Đaković-Sekulić, Tatjana and Smolinski, Adam and Mandić, Anamarija and Lazić, Anita",
year = "2018",
abstract = "Lipophilicity has, for a long time, been recognized as a meaningful parameter in structure-activity relationships. It is also the single most informative physicochemical property that reveals a wealth of information on intermolecular forces, intramolecular interactions, and molecular structure in the broadest sense. In this paper, a total of 14 chromatographic measures of lipophilicity (thin-layer chromatography and high-performance liquid chromatography) and 11 computationally estimated logP-s for 21 newly synthesized 3-(4-substituted benzyl)-cycloalkylspiro-5-hidantoin derivatives have been investigated. Similarities among the investigated compounds as well as lipophilicity measures were examined by the multivariate exploratory analysis, principal component analysis, hierarchical cluster analysis, and sum of ranking differences. These chemometric approaches reveal the arrangement of investigated compounds into clusters according to lipophilicity. Chemometric consideration of lipophilicity renders principal component scores as entirely unsuitable lipophilicity measures. Furthermore, the logP values estimated from calibration graph by using a set of standard reference compounds were equivalent to the corresponding chromatographic descriptors of hydantoins extrapolated from linear relationship between retention parameters and mobile phase composition. Comparison of the 2 chromatographic techniques places high-performance liquid chromatography lipophilicity indices slightly ahead of thin-layer chromatography.",
publisher = "Wiley, Hoboken",
journal = "Journal of Chemometrics",
title = "Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity",
number = "4",
volume = "32",
doi = "10.1002/cem.2991"
}

Đaković-Sekulić, T., Smolinski, A., Mandić, A.,& Lazić, A.. (2018). Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity. in Journal of Chemometrics
Wiley, Hoboken., 32(4).
https://doi.org/10.1002/cem.2991

Đaković-Sekulić T, Smolinski A, Mandić A, Lazić A. Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity. in Journal of Chemometrics. 2018;32(4).
doi:10.1002/cem.2991 .

Đaković-Sekulić, Tatjana, Smolinski, Adam, Mandić, Anamarija, Lazić, Anita, "Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity" in Journal of Chemometrics, 32, no. 4 (2018),
https://doi.org/10.1002/cem.2991 . .

TY  - CONF
AU  - Đaković-Sekulić, Tatjana
AU  - Smolinski, Adam
AU  - Tot, Kristina
AU  - Lazić, Anita
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7464
AB  - In this poster presentation the retention data of new cycloalkane-5-spirohydantoins bearing a substituted benzyl group in position 3 of the heterocyclic ring have been examined (Figure 1). Previously the intermolecular interactions of the crystal structures of

cycloalkane-S-spirohydantoins with halo-

In

geno substituted benzyl group (R = Cl and

Br) in position 3 had been studied [1].

Besides, the eflect of R substituent on the absorption UV-Vis spectra of cyclopen-tanespiro-S-hydantoins (2] had been studied,

100.
PB  - Budapest : Research Centre for Natural Sciences, Institute of Excellence, Hungarian Academy of Sciences
C3  - Book of Abstracts / Conferentia Chemometrica 2017, Gyöngyös-Farkasmály, Hungary, September 03-06, 2017
T1  - Lipophilicity assessment and chromatographic characterization of new spirohydantoin derivatives potential anticonvulsant agents
SP  - P09
UR  - https://hdl.handle.net/21.15107/rcub_technorep_7464
ER  - 

@conference{
author = "Đaković-Sekulić, Tatjana and Smolinski, Adam and Tot, Kristina and Lazić, Anita",
year = "2017",
abstract = "In this poster presentation the retention data of new cycloalkane-5-spirohydantoins bearing a substituted benzyl group in position 3 of the heterocyclic ring have been examined (Figure 1). Previously the intermolecular interactions of the crystal structures of

cycloalkane-S-spirohydantoins with halo-

In

geno substituted benzyl group (R = Cl and

Br) in position 3 had been studied [1].

Besides, the eflect of R substituent on the absorption UV-Vis spectra of cyclopen-tanespiro-S-hydantoins (2] had been studied,

100.",
publisher = "Budapest : Research Centre for Natural Sciences, Institute of Excellence, Hungarian Academy of Sciences",
journal = "Book of Abstracts / Conferentia Chemometrica 2017, Gyöngyös-Farkasmály, Hungary, September 03-06, 2017",
title = "Lipophilicity assessment and chromatographic characterization of new spirohydantoin derivatives potential anticonvulsant agents",
pages = "P09",
url = "https://hdl.handle.net/21.15107/rcub_technorep_7464"
}

Đaković-Sekulić, T., Smolinski, A., Tot, K.,& Lazić, A.. (2017). Lipophilicity assessment and chromatographic characterization of new spirohydantoin derivatives potential anticonvulsant agents. in Book of Abstracts / Conferentia Chemometrica 2017, Gyöngyös-Farkasmály, Hungary, September 03-06, 2017
Budapest : Research Centre for Natural Sciences, Institute of Excellence, Hungarian Academy of Sciences., P09.
https://hdl.handle.net/21.15107/rcub_technorep_7464

Đaković-Sekulić T, Smolinski A, Tot K, Lazić A. Lipophilicity assessment and chromatographic characterization of new spirohydantoin derivatives potential anticonvulsant agents. in Book of Abstracts / Conferentia Chemometrica 2017, Gyöngyös-Farkasmály, Hungary, September 03-06, 2017. 2017;:P09.
https://hdl.handle.net/21.15107/rcub_technorep_7464 .

Đaković-Sekulić, Tatjana, Smolinski, Adam, Tot, Kristina, Lazić, Anita, "Lipophilicity assessment and chromatographic characterization of new spirohydantoin derivatives potential anticonvulsant agents" in Book of Abstracts / Conferentia Chemometrica 2017, Gyöngyös-Farkasmály, Hungary, September 03-06, 2017 (2017):P09,
https://hdl.handle.net/21.15107/rcub_technorep_7464 .

TY  - JOUR
AU  - Đaković-Sekulić, Tatjana
AU  - Smolinski, Adam
AU  - Trišović, Nemanja
AU  - Ušćumlić, Gordana
AU  - Božić, Biljana
PY  - 2015
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3114
AB  - Cancer is the major health problem affecting the mankind of today. Most of the drugs used in traditional chemotherapy are very limited and the discovery of novel, more active, more selective and less toxic ones is still very intensive. A chemometric approach was applied in the study of antiproliferative activity against human colon cancer and breast cancer as well as in the study of lipophilicity of 3-(4-substitutedbenzyl)-5-ethyl-5-phenyl- and 3-(4-substituted benzyl)-5,5-diphenylhydantoins. Hierarchical clustering analysis (HCA) shows that the investigated hydantoins have higher antiproliferative activity against human breast cancer cells than against human colon cancer cells. However, some hydantoins at the highest applied concentration reverse antiproliferative effect, higher against the human colon cancer cells and lower against human breast cancer cells. Principal component analysis (PCA) gives better insight into the activity of hydantoins related to their structural changes. It distinguishes more active compounds from the less active ones according to various criteria. Generally, more lipophilic 5,5-diphenylhydantoins exhibit a higher antiproliferative activity comparing to less lipophilic 5-ethyl-5-phenylhydantoins. Also, a substituent attached to benzyl moieties affects the activity additionally. The activity is particularly pronounced for compounds with cyano, methyl, chloro and bromo group. Halogen substituent were superior in antiproliferative capacity particularly in the series of 5,5-diphenylhydantoins.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - Chemometric Study of the Antiproliferative Activity of Some New Hydantoin Derivatives: Assessment of Activity and Chromatographic Lipophilicity Data
EP  - 1386
IS  - 7
SP  - 1379
VL  - 26
DO  - 10.5935/0103-5053.20150106
ER  - 

@article{
author = "Đaković-Sekulić, Tatjana and Smolinski, Adam and Trišović, Nemanja and Ušćumlić, Gordana and Božić, Biljana",
year = "2015",
abstract = "Cancer is the major health problem affecting the mankind of today. Most of the drugs used in traditional chemotherapy are very limited and the discovery of novel, more active, more selective and less toxic ones is still very intensive. A chemometric approach was applied in the study of antiproliferative activity against human colon cancer and breast cancer as well as in the study of lipophilicity of 3-(4-substitutedbenzyl)-5-ethyl-5-phenyl- and 3-(4-substituted benzyl)-5,5-diphenylhydantoins. Hierarchical clustering analysis (HCA) shows that the investigated hydantoins have higher antiproliferative activity against human breast cancer cells than against human colon cancer cells. However, some hydantoins at the highest applied concentration reverse antiproliferative effect, higher against the human colon cancer cells and lower against human breast cancer cells. Principal component analysis (PCA) gives better insight into the activity of hydantoins related to their structural changes. It distinguishes more active compounds from the less active ones according to various criteria. Generally, more lipophilic 5,5-diphenylhydantoins exhibit a higher antiproliferative activity comparing to less lipophilic 5-ethyl-5-phenylhydantoins. Also, a substituent attached to benzyl moieties affects the activity additionally. The activity is particularly pronounced for compounds with cyano, methyl, chloro and bromo group. Halogen substituent were superior in antiproliferative capacity particularly in the series of 5,5-diphenylhydantoins.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "Chemometric Study of the Antiproliferative Activity of Some New Hydantoin Derivatives: Assessment of Activity and Chromatographic Lipophilicity Data",
pages = "1386-1379",
number = "7",
volume = "26",
doi = "10.5935/0103-5053.20150106"
}

Đaković-Sekulić, T., Smolinski, A., Trišović, N., Ušćumlić, G.,& Božić, B.. (2015). Chemometric Study of the Antiproliferative Activity of Some New Hydantoin Derivatives: Assessment of Activity and Chromatographic Lipophilicity Data. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 26(7), 1379-1386.
https://doi.org/10.5935/0103-5053.20150106

Đaković-Sekulić T, Smolinski A, Trišović N, Ušćumlić G, Božić B. Chemometric Study of the Antiproliferative Activity of Some New Hydantoin Derivatives: Assessment of Activity and Chromatographic Lipophilicity Data. in Journal of the Brazilian Chemical Society. 2015;26(7):1379-1386.
doi:10.5935/0103-5053.20150106 .

Đaković-Sekulić, Tatjana, Smolinski, Adam, Trišović, Nemanja, Ušćumlić, Gordana, Božić, Biljana, "Chemometric Study of the Antiproliferative Activity of Some New Hydantoin Derivatives: Assessment of Activity and Chromatographic Lipophilicity Data" in Journal of the Brazilian Chemical Society, 26, no. 7 (2015):1379-1386,
https://doi.org/10.5935/0103-5053.20150106 . .

TY  - JOUR
AU  - Đaković-Sekulić, Tatjana
AU  - Smolinski, Adam
AU  - Trišović, Nemanja
AU  - Ušćumlić, Gordana
PY  - 2012
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2190
AB  - Molecular properties relevant to pharmacokinetics of two sets of newly synthesized hydantoin derivatives based on two well-known drugs (Nirvanol and Phenytoin) were studied. Properties under consideration were either determined empirically by reversed-phase high-performance thin-layer chromatography or calculated by the use of established theoretical medicinal chemistry/drug design software. These properties represent selected structural features of analytes, which affect their processes of absorption, distribution, metabolism, excretion, and toxicity. Principal component analysis was used to visualize the differences between six mobile phase modifiers used as well as similarities between 24 analyzed compounds. To find appropriate quantitative relationships between RM, W for the tested compounds and molecular descriptors, stepwise regression, partial least squares (PLS), and robust PLS were used. The best results were obtained with robust PLS.
PB  - Wiley-Blackwell, Malden
T2  - Journal of Chemometrics
T1  - Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs
EP  - 107
IS  - 3-4
SP  - 95
VL  - 26
DO  - 10.1002/cem.1421
ER  - 

@article{
author = "Đaković-Sekulić, Tatjana and Smolinski, Adam and Trišović, Nemanja and Ušćumlić, Gordana",
year = "2012",
abstract = "Molecular properties relevant to pharmacokinetics of two sets of newly synthesized hydantoin derivatives based on two well-known drugs (Nirvanol and Phenytoin) were studied. Properties under consideration were either determined empirically by reversed-phase high-performance thin-layer chromatography or calculated by the use of established theoretical medicinal chemistry/drug design software. These properties represent selected structural features of analytes, which affect their processes of absorption, distribution, metabolism, excretion, and toxicity. Principal component analysis was used to visualize the differences between six mobile phase modifiers used as well as similarities between 24 analyzed compounds. To find appropriate quantitative relationships between RM, W for the tested compounds and molecular descriptors, stepwise regression, partial least squares (PLS), and robust PLS were used. The best results were obtained with robust PLS.",
publisher = "Wiley-Blackwell, Malden",
journal = "Journal of Chemometrics",
title = "Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs",
pages = "107-95",
number = "3-4",
volume = "26",
doi = "10.1002/cem.1421"
}

Đaković-Sekulić, T., Smolinski, A., Trišović, N.,& Ušćumlić, G.. (2012). Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs. in Journal of Chemometrics
Wiley-Blackwell, Malden., 26(3-4), 95-107.
https://doi.org/10.1002/cem.1421

Đaković-Sekulić T, Smolinski A, Trišović N, Ušćumlić G. Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs. in Journal of Chemometrics. 2012;26(3-4):95-107.
doi:10.1002/cem.1421 .

Đaković-Sekulić, Tatjana, Smolinski, Adam, Trišović, Nemanja, Ušćumlić, Gordana, "Multivariate evaluation of the correlation between retention data and molecular descriptors of antiepileptic hydantoin analogs" in Journal of Chemometrics, 26, no. 3-4 (2012):95-107,
https://doi.org/10.1002/cem.1421 . .