Catherine Koukoulitsa - Academia.edu (original) (raw)

Papers by Catherine Koukoulitsa

Research paper thumbnail of Comparison of thermal effects of stilbenoid analogs in lipid bilayers using differential scanning calorimetry and molecular dynamics: correlation of thermal effects and topographical position with antioxidant activity

Biophysics of Structure and Mechanism, May 8, 2011

Research paper thumbnail of Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, Feb 26, 2010

Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2... more Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2), anthemin C (3), tatridin A (4), 1-epi-tatridin B (5), anthemin B (6), 6-deacetyl-beta-cyclopyrethrosin (7), elegalactone A (8), and 1beta,4alpha,6alpha-trihydroxyeudesm-11-en-8alpha-12-olide (9), were isolated from the aerial parts of A. melanolepis in addition to eight known flavonoids and three phenolic acids. Compounds 1, 3, and 6 are new natural products. The structures of the compounds were deduced by spectroscopic methods. The in vitro antimicrobial potential of the isolated sesquiterpene lactones against four Gram-positive and five Gram-negative bacteria and one fungus was evaluated using the microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines. Furthermore, the pharmacokinetic profile of the sesquiterpene lactones was investigated using computational methods.

Research paper thumbnail of Testing the 3D QSAR/ComFA-CoMSIA results of flexible bioactive compounds with molecular docking studies

Drugs of the Future, 2007

Research paper thumbnail of Evaluation of aldose reductase inhibition and docking studies of 6′-nitro and 6′,6″-dinitrorosmarinic acids

European Journal of Medicinal Chemistry, Apr 1, 2010

Research paper thumbnail of A computational study on cannabinoid receptors and potent bioactive cannabinoid ligands: homology modeling, docking, de novo drug design and molecular dynamics analysis

Molecular Diversity, 2010

Research paper thumbnail of Partial interdigitation of lipid bilayers

Research paper thumbnail of A novel sesquiterpene lactone from Centaurea pullata : Structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties

Bioorganic Medicinal Chemistry, Apr 1, 2008

Research paper thumbnail of Inhibitory effect on soybean lipoxygenase and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum

In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12... more In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12-hydroxyjasmonic acid 12-O-beta-glucoside and p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside) isolated from the polar extracts of the plant Origanum vulgare L. ssp. hirtum, were tested in vitro for their ability to inhibit soybean lipoxygenase. Among the examined compounds, lithospermic acid B demonstrated the best inhibitory activity on soybean lipoxygenase with IC50 = 0.1 mM. Docking studies have been undertaken as an attempt for better understanding the interactions of these compounds within the active site of soybean lipoxygenase. The predicted binding energy values correlated well with the observed biological data.

Research paper thumbnail of The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand binding domain of estrogen receptor-α

Oncology Research Featuring Preclinical and Clinical Cancer Therapeutics

In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL),... more In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL), we have synthesized a new estrone D-lactam steroidal ester of CBL (ESBL). The aim of this study was to investigate the in vitro activity of ESBL against primary breast carcinoma (BC) cells of operable tumors in comparison with CBL. Cells derived from fresh tumor sections that were obtained from 28 postmenopausal women with ductal BC were treated with CBL and ESBL. Apoptotic cells were distinguished from viable ones with flow cytometric methods. ESBL generated a significantly higher rate of cell apoptosis and cytotoxicity than CBL. ESBL cytotoxic effect demonstrated a significant positive weak to moderate dose-dependent correlation with the ER expression. ESBL produced antineoplastic activity superior to CBL on primary BC tumors in vitro. Moreover, a docking study on the binding interactions of ESBL with the ligand binding domain (LBD) of estrogen receptor-alpha (ERalpha) was investigated. ESBL was found to be positioned inside the binding cavity with its steroidal moiety, whereas the alkylating moiety protruded out of receptor's pocket.

Research paper thumbnail of Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE–ligand interactions by docking calculations and molecular dynamics simulations

Research paper thumbnail of The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand binding domain of estrogen receptor-alpha

Oncology research, 2005

In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL),... more In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL), we have synthesized a new estrone D-lactam steroidal ester of CBL (ESBL). The aim of this study was to investigate the in vitro activity of ESBL against primary breast carcinoma (BC) cells of operable tumors in comparison with CBL. Cells derived from fresh tumor sections that were obtained from 28 postmenopausal women with ductal BC were treated with CBL and ESBL. Apoptotic cells were distinguished from viable ones with flow cytometric methods. ESBL generated a significantly higher rate of cell apoptosis and cytotoxicity than CBL. ESBL cytotoxic effect demonstrated a significant positive weak to moderate dose-dependent correlation with the ER expression. ESBL produced antineoplastic activity superior to CBL on primary BC tumors in vitro. Moreover, a docking study on the binding interactions of ESBL with the ligand binding domain (LBD) of estrogen receptor-alpha (ERalpha) was investigate...

Research paper thumbnail of A computational study on cannabinoid receptors and potent bioactive cannabinoid ligands: Homology modeling, docking, de novo drug design and molecular dynamics analysis

Molecular Diversity, 2010

Research paper thumbnail of A simulation study of the interaction of sulfhydryl nucleophiles with several antifungal sesquiterpene lactones isolated from Greek Centaurea sp

Journal of Molecular Structure: THEOCHEM, 2006

Research paper thumbnail of Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE–ligand interactions by docking calculations and molecular dynamics simulations

European Journal of Medicinal Chemistry, 2014

Research paper thumbnail of Inhibitory effect of polar oregano extracts on aldose reductase and soybean lipoxygenasein vitro

Phytotherapy Research, 2006

The effect of methanol and aqueous methanol extract of Origanum vulgare L. ssp. hirtum on aldose ... more The effect of methanol and aqueous methanol extract of Origanum vulgare L. ssp. hirtum on aldose reductase and soybean lipoxygenase was investigated. The results revealed a promising potential of oregano for preventing diabetes complications in the long term and an antiinflammatory efficacy by inhibiting soybean lipoxygenase.

Research paper thumbnail of Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

Research paper thumbnail of PLS Analysis for Antibacterial Activity of Natural Coumarins Using VolSurf Descriptors

QSAR & Combinatorial Science, 2009

Research paper thumbnail of Correction to Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, 2012

Research paper thumbnail of Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, 2010

Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2... more Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2), anthemin C (3), tatridin A (4), 1-epi-tatridin B (5), anthemin B (6), 6-deacetyl-beta-cyclopyrethrosin (7), elegalactone A (8), and 1beta,4alpha,6alpha-trihydroxyeudesm-11-en-8alpha-12-olide (9), were isolated from the aerial parts of A. melanolepis in addition to eight known flavonoids and three phenolic acids. Compounds 1, 3, and 6 are new natural products. The structures of the compounds were deduced by spectroscopic methods. The in vitro antimicrobial potential of the isolated sesquiterpene lactones against four Gram-positive and five Gram-negative bacteria and one fungus was evaluated using the microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines. Furthermore, the pharmacokinetic profile of the sesquiterpene lactones was investigated using computational methods.

Research paper thumbnail of Inhibitory effect on soybean lipoxygenase and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum

Journal of Enzyme Inhibition and Medicinal Chemistry, 2007

In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12... more In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12-hydroxyjasmonic acid 12-O-beta-glucoside and p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside) isolated from the polar extracts of the plant Origanum vulgare L. ssp. hirtum, were tested in vitro for their ability to inhibit soybean lipoxygenase. Among the examined compounds, lithospermic acid B demonstrated the best inhibitory activity on soybean lipoxygenase with IC50 = 0.1 mM. Docking studies have been undertaken as an attempt for better understanding the interactions of these compounds within the active site of soybean lipoxygenase. The predicted binding energy values correlated well with the observed biological data.

Research paper thumbnail of Comparison of thermal effects of stilbenoid analogs in lipid bilayers using differential scanning calorimetry and molecular dynamics: correlation of thermal effects and topographical position with antioxidant activity

Biophysics of Structure and Mechanism, May 8, 2011

Research paper thumbnail of Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, Feb 26, 2010

Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2... more Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2), anthemin C (3), tatridin A (4), 1-epi-tatridin B (5), anthemin B (6), 6-deacetyl-beta-cyclopyrethrosin (7), elegalactone A (8), and 1beta,4alpha,6alpha-trihydroxyeudesm-11-en-8alpha-12-olide (9), were isolated from the aerial parts of A. melanolepis in addition to eight known flavonoids and three phenolic acids. Compounds 1, 3, and 6 are new natural products. The structures of the compounds were deduced by spectroscopic methods. The in vitro antimicrobial potential of the isolated sesquiterpene lactones against four Gram-positive and five Gram-negative bacteria and one fungus was evaluated using the microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines. Furthermore, the pharmacokinetic profile of the sesquiterpene lactones was investigated using computational methods.

Research paper thumbnail of Testing the 3D QSAR/ComFA-CoMSIA results of flexible bioactive compounds with molecular docking studies

Drugs of the Future, 2007

Research paper thumbnail of Evaluation of aldose reductase inhibition and docking studies of 6′-nitro and 6′,6″-dinitrorosmarinic acids

European Journal of Medicinal Chemistry, Apr 1, 2010

Research paper thumbnail of A computational study on cannabinoid receptors and potent bioactive cannabinoid ligands: homology modeling, docking, de novo drug design and molecular dynamics analysis

Molecular Diversity, 2010

Research paper thumbnail of Partial interdigitation of lipid bilayers

Research paper thumbnail of A novel sesquiterpene lactone from Centaurea pullata : Structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties

Bioorganic Medicinal Chemistry, Apr 1, 2008

Research paper thumbnail of Inhibitory effect on soybean lipoxygenase and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum

In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12... more In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12-hydroxyjasmonic acid 12-O-beta-glucoside and p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside) isolated from the polar extracts of the plant Origanum vulgare L. ssp. hirtum, were tested in vitro for their ability to inhibit soybean lipoxygenase. Among the examined compounds, lithospermic acid B demonstrated the best inhibitory activity on soybean lipoxygenase with IC50 = 0.1 mM. Docking studies have been undertaken as an attempt for better understanding the interactions of these compounds within the active site of soybean lipoxygenase. The predicted binding energy values correlated well with the observed biological data.

Research paper thumbnail of The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand binding domain of estrogen receptor-α

Oncology Research Featuring Preclinical and Clinical Cancer Therapeutics

In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL),... more In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL), we have synthesized a new estrone D-lactam steroidal ester of CBL (ESBL). The aim of this study was to investigate the in vitro activity of ESBL against primary breast carcinoma (BC) cells of operable tumors in comparison with CBL. Cells derived from fresh tumor sections that were obtained from 28 postmenopausal women with ductal BC were treated with CBL and ESBL. Apoptotic cells were distinguished from viable ones with flow cytometric methods. ESBL generated a significantly higher rate of cell apoptosis and cytotoxicity than CBL. ESBL cytotoxic effect demonstrated a significant positive weak to moderate dose-dependent correlation with the ER expression. ESBL produced antineoplastic activity superior to CBL on primary BC tumors in vitro. Moreover, a docking study on the binding interactions of ESBL with the ligand binding domain (LBD) of estrogen receptor-alpha (ERalpha) was investigated. ESBL was found to be positioned inside the binding cavity with its steroidal moiety, whereas the alkylating moiety protruded out of receptor's pocket.

Research paper thumbnail of Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE–ligand interactions by docking calculations and molecular dynamics simulations

Research paper thumbnail of The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand binding domain of estrogen receptor-alpha

Oncology research, 2005

In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL),... more In order to further improve the toxicity profile and the anticancer effect of chlorambucil (CBL), we have synthesized a new estrone D-lactam steroidal ester of CBL (ESBL). The aim of this study was to investigate the in vitro activity of ESBL against primary breast carcinoma (BC) cells of operable tumors in comparison with CBL. Cells derived from fresh tumor sections that were obtained from 28 postmenopausal women with ductal BC were treated with CBL and ESBL. Apoptotic cells were distinguished from viable ones with flow cytometric methods. ESBL generated a significantly higher rate of cell apoptosis and cytotoxicity than CBL. ESBL cytotoxic effect demonstrated a significant positive weak to moderate dose-dependent correlation with the ER expression. ESBL produced antineoplastic activity superior to CBL on primary BC tumors in vitro. Moreover, a docking study on the binding interactions of ESBL with the ligand binding domain (LBD) of estrogen receptor-alpha (ERalpha) was investigate...

Research paper thumbnail of A computational study on cannabinoid receptors and potent bioactive cannabinoid ligands: Homology modeling, docking, de novo drug design and molecular dynamics analysis

Molecular Diversity, 2010

Research paper thumbnail of A simulation study of the interaction of sulfhydryl nucleophiles with several antifungal sesquiterpene lactones isolated from Greek Centaurea sp

Journal of Molecular Structure: THEOCHEM, 2006

Research paper thumbnail of Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE–ligand interactions by docking calculations and molecular dynamics simulations

European Journal of Medicinal Chemistry, 2014

Research paper thumbnail of Inhibitory effect of polar oregano extracts on aldose reductase and soybean lipoxygenasein vitro

Phytotherapy Research, 2006

The effect of methanol and aqueous methanol extract of Origanum vulgare L. ssp. hirtum on aldose ... more The effect of methanol and aqueous methanol extract of Origanum vulgare L. ssp. hirtum on aldose reductase and soybean lipoxygenase was investigated. The results revealed a promising potential of oregano for preventing diabetes complications in the long term and an antiinflammatory efficacy by inhibiting soybean lipoxygenase.

Research paper thumbnail of Facile and Efficient Syntheses of a Series of N-Benzyl and N-Biphenylmethyl Substituted Imidazole Derivatives Based on (E)-Urocanic acid, as Angiotensin II AT1 Receptor Blockers

Research paper thumbnail of PLS Analysis for Antibacterial Activity of Natural Coumarins Using VolSurf Descriptors

QSAR & Combinatorial Science, 2009

Research paper thumbnail of Correction to Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, 2012

Research paper thumbnail of Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Journal of Natural Products, 2010

Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2... more Nine sesquiterpene lactones, anthemin A (1), 1alpha-hydroxydeacetylirinol-4alpha,5beta-epoxide (2), anthemin C (3), tatridin A (4), 1-epi-tatridin B (5), anthemin B (6), 6-deacetyl-beta-cyclopyrethrosin (7), elegalactone A (8), and 1beta,4alpha,6alpha-trihydroxyeudesm-11-en-8alpha-12-olide (9), were isolated from the aerial parts of A. melanolepis in addition to eight known flavonoids and three phenolic acids. Compounds 1, 3, and 6 are new natural products. The structures of the compounds were deduced by spectroscopic methods. The in vitro antimicrobial potential of the isolated sesquiterpene lactones against four Gram-positive and five Gram-negative bacteria and one fungus was evaluated using the microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines. Furthermore, the pharmacokinetic profile of the sesquiterpene lactones was investigated using computational methods.

Research paper thumbnail of Inhibitory effect on soybean lipoxygenase and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum

Journal of Enzyme Inhibition and Medicinal Chemistry, 2007

In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12... more In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12-hydroxyjasmonic acid 12-O-beta-glucoside and p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside) isolated from the polar extracts of the plant Origanum vulgare L. ssp. hirtum, were tested in vitro for their ability to inhibit soybean lipoxygenase. Among the examined compounds, lithospermic acid B demonstrated the best inhibitory activity on soybean lipoxygenase with IC50 = 0.1 mM. Docking studies have been undertaken as an attempt for better understanding the interactions of these compounds within the active site of soybean lipoxygenase. The predicted binding energy values correlated well with the observed biological data.