New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations

Hmuda, Sleem F.; Trišović, Nemanja; Rogan, Jelena; Poleti, Dejan; Vitnik, Željko J.; Vitnik, Vesna D.; Valentić, Nataša V.; Božić, Biljana; Ušćumlić, Gordana S.

doi:10.1007/s00706-013-1149-6

Cited by 17 publications

(18 citation statements)

References 26 publications

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“…The substituents and numbering of the hydantoins are listed in Table . Hydantoins were synthesized by the procedure published previously (Hmuda et al, ; Naydenova et al, ; Suzuki et al, ).…”

Section: Methodsmentioning

confidence: 99%

“…The antiproliferative activities of 3‐(4‐substituted benzyl)‐5‐ethyl‐5‐phenyl‐ and 3‐(4‐substituted benzyl)‐5,5‐diphenylhydantoins against human colon cancer adenocarcinoma cell line HCT‐116 were tested previously (Hmuda et al, ). The antiproliferative effect of the investigated compounds on HCT‐116 cell line is given in Table S2 in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

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QSAR characterization of new synthesized hydantoins with antiproliferative activity

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Lazić

Božić

et al. 2019

Biomedical Chromatography

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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-(4substituted 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.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

QSAR characterization of new synthesized hydantoins with antiproliferative activity

Tot

Lazić

Božić

et al. 2019

Biomedical Chromatography

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“…The goal of this study was to examine the cumulative effect of a hydantoin structure, selenium and palladium on cancer cells. Hydantoins are widely used compounds in cancer studies (Mudit et al 2009;Hmuda et al 2014). Moreover, bicyclic hydantoins are also studied (Ananda Kumar et al 2009;Basappa et al 2009).…”

Section: Introductionmentioning

confidence: 99%

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

Živanović

Košarić²,

Šmit³

et al. 2017

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Selenium and palladium containing compounds separately exert multifunctional effects on cells. While selenium containing compounds usually exert antioxidative properties, palladium(II) containing compounds are cytotoxic and prooxidative. Here we investigated biological effects of bicyclic seleno-hydantoin cis-7a-ethyl-5-methyl-5-phenylselanylmethyl-tetrahydro-pyrrolo[1,2-c] imidazole-1,3-dione (Hid-Se), and its palladium(II) complex, trans-bis-(cis-7a-ethyl-5-methyl-5-phenylselanylmethyl-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dionato) palladium(II) chloride ((Hid-Se) 2 Pd) on human colon HCT-116 and breast MDA-MB-231 cancer cell lines. Hid-Se and (Hid-Se) 2 Pd showed prooxidative and cytotoxic character. In all performed experiments (Hid-Se) 2 Pd proved to be more active, i.e. this substance exerted greater prooxidative effect, cytotoxicity and influence on cell migration potential. Even though Hid-Se and (Hid-Se) 2 Pd enhanced migration of HCT-116 cells, very important feature of these substances is the strong antimigratory potential on metastatic MDA-MB-231 cells.

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“…As part of our previous research on the structural characterization and biological activity of 3,5‐disubstituted‐5‐phenylhydantoins, 4 series of such compounds were synthesized and their anticonvulsant and antiproliferative activity described . In this work, new cycloalkyl‐5‐spirohydantoins bearing a substituted benzyl group in position 3 were synthesized.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity

Sekulić

Smoliński

Mandić

et al. 2017

Journal of Chemometrics

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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-(4substituted 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.

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New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations

Cited by 17 publications

References 26 publications

QSAR characterization of new synthesized hydantoins with antiproliferative activity

QSAR characterization of new synthesized hydantoins with antiproliferative activity

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

Chromatographic and in silico assessment of logP measures for new spirohydantoin derivatives with anticancer activity

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