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Antiproliferative activity of β-hydroxy- β-arylalkanoic acids

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2007
ijms-08-00214.pdf (407.8Kb)
Authors
Dilber, Sanda P.
Žižak, Željko
Stanojković, Tatjana
Juranić, Zorica
Drakulić, Branko
Article (Published version)
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Abstract
Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal ...importance as lipophilicity.

Keywords:
β-hydroxy-β-arylalkanoic acids / Antiproliferative activity / Human dedifferentiate cells / QSAR / Reformatsky reaction / Antiproliferativna aktivnost
Source:
International Journal of Molecular Sciences, 2007, 8, 3, 214-228
Publisher:
  • MDPI
Funding / projects:
  • Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-142010)

DOI: 10.3390/i8030214

ISSN: 1661-6596; 1422-0067

WoS: 000245396500004

Scopus: 2-s2.0-34047235830
[ Google Scholar ]
8
7
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4305
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Dilber, Sanda P.
AU  - Žižak, Željko
AU  - Stanojković, Tatjana
AU  - Juranić, Zorica
AU  - Drakulić, Branko
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4305
AB  - Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal importance as lipophilicity.
PB  - MDPI
T2  - International Journal of Molecular Sciences
T1  - Antiproliferative activity of β-hydroxy- β-arylalkanoic acids
VL  - 8
IS  - 3
SP  - 214
EP  - 228
DO  - 10.3390/i8030214
ER  - 
@article{
author = "Dilber, Sanda P. and Žižak, Željko and Stanojković, Tatjana and Juranić, Zorica and Drakulić, Branko",
year = "2007",
abstract = "Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal importance as lipophilicity.",
publisher = "MDPI",
journal = "International Journal of Molecular Sciences",
title = "Antiproliferative activity of β-hydroxy- β-arylalkanoic acids",
volume = "8",
number = "3",
pages = "214-228",
doi = "10.3390/i8030214"
}
Dilber, S. P., Žižak, Ž., Stanojković, T., Juranić, Z.,& Drakulić, B.. (2007). Antiproliferative activity of β-hydroxy- β-arylalkanoic acids. in International Journal of Molecular Sciences
MDPI., 8(3), 214-228.
https://doi.org/10.3390/i8030214
Dilber SP, Žižak Ž, Stanojković T, Juranić Z, Drakulić B. Antiproliferative activity of β-hydroxy- β-arylalkanoic acids. in International Journal of Molecular Sciences. 2007;8(3):214-228.
doi:10.3390/i8030214 .
Dilber, Sanda P., Žižak, Željko, Stanojković, Tatjana, Juranić, Zorica, Drakulić, Branko, "Antiproliferative activity of β-hydroxy- β-arylalkanoic acids" in International Journal of Molecular Sciences, 8, no. 3 (2007):214-228,
https://doi.org/10.3390/i8030214 . .

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