Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity
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 lipophil...icity 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.
Keywords:
HCA / PCA / spirohydantoins / SRDSource:
Journal of Chemometrics, 2018, 32, 4Publisher:
- Wiley, Hoboken
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
DOI: 10.1002/cem.2991
ISSN: 0886-9383
WoS: 000430668000002
Scopus: 2-s2.0-85039159223
Institution/Community
Inovacioni centarTY - 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 . .