Relationship between lipophilicity and antitumor activity of molecule library of Mannich ketones determined by high-performance liquid chromatography, clogP calculation and cytotoxicity test

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Abstract

A series of Mannich ketones were synthesized in order to study the relative importance of structure and specific substitutions in relation to their lipophilicity and antitumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl and tetrahydro-isoquinolyl groups in various positions on three different skeletons. Lipophilicity of Mannich ketones was characterised by chromatography data (log k′) and by software calculated parameters (clogP). Compounds were tested on their ability to inhibit the proliferation of the A431 human adenocarcinoma cell line evaluated by MTT and apoptosis assays. The results suggest that the higher the lipophilicity values (log k′ and clogP), the higher the antitumor and apoptotic activity of Mannich ketones. Determination of lipophilicity by measuring the log k′ or by calculating the clogP values of the compounds may help to predict their biological activities.

Original languageEnglish
Pages (from-to)361-368
Number of pages8
JournalJournal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Volume768
Issue number2
DOIs
Publication statusPublished - Mar 5 2002

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High performance liquid chromatography
Cytotoxicity
Ketones
Libraries
High Pressure Liquid Chromatography
Molecules
Substitution reactions
Chromatography
Bioactivity
Skeleton
Assays
Adenocarcinoma
Thermodynamic properties
Software
Cells
Apoptosis
Cell Line

Keywords

  • Hydrophobicity
  • Mannich ketones

ASJC Scopus subject areas

  • Biochemistry

Cite this

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title = "Relationship between lipophilicity and antitumor activity of molecule library of Mannich ketones determined by high-performance liquid chromatography, clogP calculation and cytotoxicity test",
abstract = "A series of Mannich ketones were synthesized in order to study the relative importance of structure and specific substitutions in relation to their lipophilicity and antitumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl and tetrahydro-isoquinolyl groups in various positions on three different skeletons. Lipophilicity of Mannich ketones was characterised by chromatography data (log k′) and by software calculated parameters (clogP). Compounds were tested on their ability to inhibit the proliferation of the A431 human adenocarcinoma cell line evaluated by MTT and apoptosis assays. The results suggest that the higher the lipophilicity values (log k′ and clogP), the higher the antitumor and apoptotic activity of Mannich ketones. Determination of lipophilicity by measuring the log k′ or by calculating the clogP values of the compounds may help to predict their biological activities.",
keywords = "Hydrophobicity, Mannich ketones",
author = "F. Holl{\'o}sy and T. L{\'o}r{\'a}nd and L. Őrfi and D{\'a}niel Er{\"o}s and G. K{\'e}ri and M. Idei",
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T1 - Relationship between lipophilicity and antitumor activity of molecule library of Mannich ketones determined by high-performance liquid chromatography, clogP calculation and cytotoxicity test

AU - Hollósy, F.

AU - Lóránd, T.

AU - Őrfi, L.

AU - Erös, Dániel

AU - Kéri, G.

AU - Idei, M.

PY - 2002/3/5

Y1 - 2002/3/5

N2 - A series of Mannich ketones were synthesized in order to study the relative importance of structure and specific substitutions in relation to their lipophilicity and antitumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl and tetrahydro-isoquinolyl groups in various positions on three different skeletons. Lipophilicity of Mannich ketones was characterised by chromatography data (log k′) and by software calculated parameters (clogP). Compounds were tested on their ability to inhibit the proliferation of the A431 human adenocarcinoma cell line evaluated by MTT and apoptosis assays. The results suggest that the higher the lipophilicity values (log k′ and clogP), the higher the antitumor and apoptotic activity of Mannich ketones. Determination of lipophilicity by measuring the log k′ or by calculating the clogP values of the compounds may help to predict their biological activities.

AB - A series of Mannich ketones were synthesized in order to study the relative importance of structure and specific substitutions in relation to their lipophilicity and antitumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl and tetrahydro-isoquinolyl groups in various positions on three different skeletons. Lipophilicity of Mannich ketones was characterised by chromatography data (log k′) and by software calculated parameters (clogP). Compounds were tested on their ability to inhibit the proliferation of the A431 human adenocarcinoma cell line evaluated by MTT and apoptosis assays. The results suggest that the higher the lipophilicity values (log k′ and clogP), the higher the antitumor and apoptotic activity of Mannich ketones. Determination of lipophilicity by measuring the log k′ or by calculating the clogP values of the compounds may help to predict their biological activities.

KW - Hydrophobicity

KW - Mannich ketones

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