Evaluation of hydrophobicity and antitumor activity of a molecule library of Mannich ketones of cycloalkanones

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Abstract

A series of Mannich ketones of cycloalkanones were synthesized to study the relative importance of structure and specific substitutions in relation to their hydrophobicity and anti-tumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl, and tetrahydro-isoquinolyl groups in various position on four different base structures. Hydrophobicity of Mannich ketones was characterized by chromatography data fhollosy@puskin.sote.hu (log k′) and by software calculated parameters (c log P). Cell proliferation inhibitory activity of cycloalkanones was evaluated by MTT and apoptosis assays on A431 human adenocarcinoma cells. Our results suggest that the higher the hydrophobicity values (log k′ and c log P) the higher the antitumor- and apoptotic activity of Mannich ketones. Determination of hydrophobicity by measuring the log k′ or by calculating the c log P values of the compounds may help to predict their biological activities.

Original languageEnglish
Pages (from-to)1129-1143
Number of pages15
JournalJournal of Liquid Chromatography and Related Technologies
Volume25
Issue number7
DOIs
Publication statusPublished - 2002

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Hydrophobicity
Ketones
Hydrophobic and Hydrophilic Interactions
Libraries
Molecules
Substitution reactions
Cell proliferation
Chromatography
Bioactivity
Tumors
Assays
Adenocarcinoma
Software
Cell Proliferation
Apoptosis
Neoplasms

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Biochemistry
  • Clinical Biochemistry

Cite this

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title = "Evaluation of hydrophobicity and antitumor activity of a molecule library of Mannich ketones of cycloalkanones",
abstract = "A series of Mannich ketones of cycloalkanones were synthesized to study the relative importance of structure and specific substitutions in relation to their hydrophobicity and anti-tumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl, and tetrahydro-isoquinolyl groups in various position on four different base structures. Hydrophobicity of Mannich ketones was characterized by chromatography data fhollosy@puskin.sote.hu (log k′) and by software calculated parameters (c log P). Cell proliferation inhibitory activity of cycloalkanones was evaluated by MTT and apoptosis assays on A431 human adenocarcinoma cells. Our results suggest that the higher the hydrophobicity values (log k′ and c log P) the higher the antitumor- and apoptotic activity of Mannich ketones. Determination of hydrophobicity by measuring the log k′ or by calculating the c log P values of the compounds may help to predict their biological activities.",
author = "F. Holl{\'o}sy and T. L{\'o}r{\'a}nd and L. Őrfi and D{\'a}niel Ers and G. K{\'e}ri and M. Idei",
year = "2002",
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TY - JOUR

T1 - Evaluation of hydrophobicity and antitumor activity of a molecule library of Mannich ketones of cycloalkanones

AU - Hollósy, F.

AU - Lóránd, T.

AU - Őrfi, L.

AU - Ers, Dániel

AU - Kéri, G.

AU - Idei, M.

PY - 2002

Y1 - 2002

N2 - A series of Mannich ketones of cycloalkanones were synthesized to study the relative importance of structure and specific substitutions in relation to their hydrophobicity and anti-tumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl, and tetrahydro-isoquinolyl groups in various position on four different base structures. Hydrophobicity of Mannich ketones was characterized by chromatography data fhollosy@puskin.sote.hu (log k′) and by software calculated parameters (c log P). Cell proliferation inhibitory activity of cycloalkanones was evaluated by MTT and apoptosis assays on A431 human adenocarcinoma cells. Our results suggest that the higher the hydrophobicity values (log k′ and c log P) the higher the antitumor- and apoptotic activity of Mannich ketones. Determination of hydrophobicity by measuring the log k′ or by calculating the c log P values of the compounds may help to predict their biological activities.

AB - A series of Mannich ketones of cycloalkanones were synthesized to study the relative importance of structure and specific substitutions in relation to their hydrophobicity and anti-tumor activity. Substitutions were carried out with morpholinyl, pirrolidinyl, piperidyl, and tetrahydro-isoquinolyl groups in various position on four different base structures. Hydrophobicity of Mannich ketones was characterized by chromatography data fhollosy@puskin.sote.hu (log k′) and by software calculated parameters (c log P). Cell proliferation inhibitory activity of cycloalkanones was evaluated by MTT and apoptosis assays on A431 human adenocarcinoma cells. Our results suggest that the higher the hydrophobicity values (log k′ and c log P) the higher the antitumor- and apoptotic activity of Mannich ketones. Determination of hydrophobicity by measuring the log k′ or by calculating the c log P values of the compounds may help to predict their biological activities.

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U2 - 10.1081/JLC-120003430

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