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Cytotoxic activity of new cerium (III) complexes of bis-coumarins
Complexes of cerium (III) with bis-coumarins: 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) and bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)-methane were synthesized by reaction of cerium (III) salt and the ligands, in amounts equal to metal/ligand molar ratio of 1:2. The complexes...
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| Published in: | European journal of medicinal chemistry 2005-12, Vol.40 (12), p.1246-1254 |
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| cited_by | cdi_FETCH-LOGICAL-c390t-2304651080fa40811897e20c062ef28766bb998fec68b58d96df884c357a4a73 |
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| container_end_page | 1254 |
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| container_title | European journal of medicinal chemistry |
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| creator | Kostova, Irena Manolov, Ilia Momekov, Georgi Tzanova, Tzvetomira Konstantinov, Spiro Karaivanova, Margarita |
| description | Complexes of cerium (III) with bis-coumarins: 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) and bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)-methane were synthesized by reaction of cerium (III) salt and the ligands, in amounts equal to metal/ligand molar ratio of 1:2. The complexes were prepared by adding an aqueous solution of cerium (III) salt to an aqueous solution of the ligand subsequently raising the pH of the mixture gradually to ca. 5.0 by adding dilute solution of sodium hydroxide. The cerium (III) complexes with bis-coumarins were characterized by different physicochemical methods—elemental analysis, IR-,
1H- and
13C-NMR-spectroscopies and mass-spectral data. The spectral data of cerium (III) complexes were interpreted on the basis of comparison with the spectra of the free ligands. This analysis showed that in the Ce (III) complexes the ligands coordinated to the metal ion through both deprotonated hydroxyl groups. On the basis of the ν(C=O) red shift observed, participation of the carbonyl groups in the coordination to the metal ion was also suggested. Cytotoxic screening by MTT assay was carried out. In the present study we performed comparative evaluation of the cytotoxic effects of the two newly synthesized cerium complexes against the acute myeloid leukemia derived HL-60 and the chronic myeloid leukemia (CML)-derived BV-173. In addition the cytotoxic effects of Ce (III) complex with 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) were evaluated on the CML-derived K-562 and LAMA-84 cells, characterized by relative low responsiveness to chemotherapy. The DNA isolated from the cytosolic fraction of BV-173 cells after 24 h treatment with the same complex (at 100 and 200 μM) demonstrated a laddering phenomenon that is indicative for apoptotic cell death. |
| doi_str_mv | 10.1016/j.ejmech.2005.07.010 |
| format | article |
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1H- and
13C-NMR-spectroscopies and mass-spectral data. The spectral data of cerium (III) complexes were interpreted on the basis of comparison with the spectra of the free ligands. This analysis showed that in the Ce (III) complexes the ligands coordinated to the metal ion through both deprotonated hydroxyl groups. On the basis of the ν(C=O) red shift observed, participation of the carbonyl groups in the coordination to the metal ion was also suggested. Cytotoxic screening by MTT assay was carried out. In the present study we performed comparative evaluation of the cytotoxic effects of the two newly synthesized cerium complexes against the acute myeloid leukemia derived HL-60 and the chronic myeloid leukemia (CML)-derived BV-173. In addition the cytotoxic effects of Ce (III) complex with 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) were evaluated on the CML-derived K-562 and LAMA-84 cells, characterized by relative low responsiveness to chemotherapy. The DNA isolated from the cytosolic fraction of BV-173 cells after 24 h treatment with the same complex (at 100 and 200 μM) demonstrated a laddering phenomenon that is indicative for apoptotic cell death.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2005.07.010</identifier><identifier>PMID: 16143428</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Antineoplastic agents ; Biological and medical sciences ; Bis-coumarins ; Carbon Isotopes ; Cell Line, Tumor ; Cell Survival - drug effects ; Cerium (III) complexes ; Cerium - chemistry ; Coumarins - chemistry ; Cytotoxic activity ; DNA ; DNA - drug effects ; Drug Design ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; IR- and NMR-spectra ; Ligands ; Magnetic Resonance Spectroscopy - methods ; Magnetic Resonance Spectroscopy - standards ; Medical sciences ; Molecular Structure ; Organometallic Compounds - chemical synthesis ; Organometallic Compounds - chemistry ; Organometallic Compounds - pharmacology ; Pharmacology. Drug treatments ; Protons ; Reference Standards</subject><ispartof>European journal of medicinal chemistry, 2005-12, Vol.40 (12), p.1246-1254</ispartof><rights>2005 Elsevier SAS</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-2304651080fa40811897e20c062ef28766bb998fec68b58d96df884c357a4a73</citedby><cites>FETCH-LOGICAL-c390t-2304651080fa40811897e20c062ef28766bb998fec68b58d96df884c357a4a73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,783,787,27936,27937</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17376398$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16143428$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kostova, Irena</creatorcontrib><creatorcontrib>Manolov, Ilia</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Tzanova, Tzvetomira</creatorcontrib><creatorcontrib>Konstantinov, Spiro</creatorcontrib><creatorcontrib>Karaivanova, Margarita</creatorcontrib><title>Cytotoxic activity of new cerium (III) complexes of bis-coumarins</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Complexes of cerium (III) with bis-coumarins: 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) and bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)-methane were synthesized by reaction of cerium (III) salt and the ligands, in amounts equal to metal/ligand molar ratio of 1:2. The complexes were prepared by adding an aqueous solution of cerium (III) salt to an aqueous solution of the ligand subsequently raising the pH of the mixture gradually to ca. 5.0 by adding dilute solution of sodium hydroxide. The cerium (III) complexes with bis-coumarins were characterized by different physicochemical methods—elemental analysis, IR-,
1H- and
13C-NMR-spectroscopies and mass-spectral data. The spectral data of cerium (III) complexes were interpreted on the basis of comparison with the spectra of the free ligands. This analysis showed that in the Ce (III) complexes the ligands coordinated to the metal ion through both deprotonated hydroxyl groups. On the basis of the ν(C=O) red shift observed, participation of the carbonyl groups in the coordination to the metal ion was also suggested. Cytotoxic screening by MTT assay was carried out. In the present study we performed comparative evaluation of the cytotoxic effects of the two newly synthesized cerium complexes against the acute myeloid leukemia derived HL-60 and the chronic myeloid leukemia (CML)-derived BV-173. In addition the cytotoxic effects of Ce (III) complex with 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) were evaluated on the CML-derived K-562 and LAMA-84 cells, characterized by relative low responsiveness to chemotherapy. The DNA isolated from the cytosolic fraction of BV-173 cells after 24 h treatment with the same complex (at 100 and 200 μM) demonstrated a laddering phenomenon that is indicative for apoptotic cell death.</description><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Bis-coumarins</subject><subject>Carbon Isotopes</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Cerium (III) complexes</subject><subject>Cerium - chemistry</subject><subject>Coumarins - chemistry</subject><subject>Cytotoxic activity</subject><subject>DNA</subject><subject>DNA - drug effects</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>IR- and NMR-spectra</subject><subject>Ligands</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>Magnetic Resonance Spectroscopy - standards</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organometallic Compounds - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Protons</subject><subject>Reference Standards</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9kEtr3DAUhUVpaSZp_0Ep3rS0C7tXD0vyJhCGPgYC3WQv5OtrqsG2ppKdZP59PcxAdl3dxf3O4fAx9oFDxYHrb_uK9iPhn0oA1BWYCji8YhtutC2lqNVrtgEhZFkLqa7Ydc57WEEN8JZdcc2VVMJu2N32OMc5PgcsPM7hMczHIvbFRE8FUgrLWHzZ7XZfC4zjYaBnyqdvG3KJcRl9ClN-x970fsj0_nJv2MOP7w_bX-X975-77d19ibKBuRQSlK45WOi9Asu5bQwJQNCCemGN1m3bNLYn1LatbdforrdWoayNV97IG_b5XHtI8e9CeXZjyEjD4CeKS3ba2rWbNyuoziCmmHOi3h1SWKceHQd3Muf27mzOncw5MG41t8Y-XvqXdqTuJXRRtQKfLoDP6Ic--QlDfuGMNFo2J-72zNEq4zFQchkDTUhdSISz62L4_5J_rN2L1A</recordid><startdate>20051201</startdate><enddate>20051201</enddate><creator>Kostova, Irena</creator><creator>Manolov, Ilia</creator><creator>Momekov, Georgi</creator><creator>Tzanova, Tzvetomira</creator><creator>Konstantinov, Spiro</creator><creator>Karaivanova, Margarita</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051201</creationdate><title>Cytotoxic activity of new cerium (III) complexes of bis-coumarins</title><author>Kostova, Irena ; Manolov, Ilia ; Momekov, Georgi ; Tzanova, Tzvetomira ; Konstantinov, Spiro ; Karaivanova, Margarita</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-2304651080fa40811897e20c062ef28766bb998fec68b58d96df884c357a4a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Bis-coumarins</topic><topic>Carbon Isotopes</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Cerium (III) complexes</topic><topic>Cerium - chemistry</topic><topic>Coumarins - chemistry</topic><topic>Cytotoxic activity</topic><topic>DNA</topic><topic>DNA - drug effects</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>IR- and NMR-spectra</topic><topic>Ligands</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>Magnetic Resonance Spectroscopy - standards</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organometallic Compounds - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Protons</topic><topic>Reference Standards</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kostova, Irena</creatorcontrib><creatorcontrib>Manolov, Ilia</creatorcontrib><creatorcontrib>Momekov, Georgi</creatorcontrib><creatorcontrib>Tzanova, Tzvetomira</creatorcontrib><creatorcontrib>Konstantinov, Spiro</creatorcontrib><creatorcontrib>Karaivanova, Margarita</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kostova, Irena</au><au>Manolov, Ilia</au><au>Momekov, Georgi</au><au>Tzanova, Tzvetomira</au><au>Konstantinov, Spiro</au><au>Karaivanova, Margarita</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic activity of new cerium (III) complexes of bis-coumarins</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2005-12-01</date><risdate>2005</risdate><volume>40</volume><issue>12</issue><spage>1246</spage><epage>1254</epage><pages>1246-1254</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Complexes of cerium (III) with bis-coumarins: 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) and bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)-methane were synthesized by reaction of cerium (III) salt and the ligands, in amounts equal to metal/ligand molar ratio of 1:2. The complexes were prepared by adding an aqueous solution of cerium (III) salt to an aqueous solution of the ligand subsequently raising the pH of the mixture gradually to ca. 5.0 by adding dilute solution of sodium hydroxide. The cerium (III) complexes with bis-coumarins were characterized by different physicochemical methods—elemental analysis, IR-,
1H- and
13C-NMR-spectroscopies and mass-spectral data. The spectral data of cerium (III) complexes were interpreted on the basis of comparison with the spectra of the free ligands. This analysis showed that in the Ce (III) complexes the ligands coordinated to the metal ion through both deprotonated hydroxyl groups. On the basis of the ν(C=O) red shift observed, participation of the carbonyl groups in the coordination to the metal ion was also suggested. Cytotoxic screening by MTT assay was carried out. In the present study we performed comparative evaluation of the cytotoxic effects of the two newly synthesized cerium complexes against the acute myeloid leukemia derived HL-60 and the chronic myeloid leukemia (CML)-derived BV-173. In addition the cytotoxic effects of Ce (III) complex with 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) were evaluated on the CML-derived K-562 and LAMA-84 cells, characterized by relative low responsiveness to chemotherapy. The DNA isolated from the cytosolic fraction of BV-173 cells after 24 h treatment with the same complex (at 100 and 200 μM) demonstrated a laddering phenomenon that is indicative for apoptotic cell death.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>16143428</pmid><doi>10.1016/j.ejmech.2005.07.010</doi><tpages>9</tpages></addata></record> |
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| subjects | Antineoplastic agents Biological and medical sciences Bis-coumarins Carbon Isotopes Cell Line, Tumor Cell Survival - drug effects Cerium (III) complexes Cerium - chemistry Coumarins - chemistry Cytotoxic activity DNA DNA - drug effects Drug Design Drug Screening Assays, Antitumor General aspects Humans IR- and NMR-spectra Ligands Magnetic Resonance Spectroscopy - methods Magnetic Resonance Spectroscopy - standards Medical sciences Molecular Structure Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Organometallic Compounds - pharmacology Pharmacology. Drug treatments Protons Reference Standards |
| title | Cytotoxic activity of new cerium (III) complexes of bis-coumarins |
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