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Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity
Three copper(ii) complexes, [Cu(L1)(NO ) ] ( ), [Cu(L2)Cl ] ( ) and [Cu(L2)SO ] ·H O ( ), were designed and synthesized by the reaction of Cu(NO ) ·3H O, CuCl ·2H O and CuSO ·5H O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-a...
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| Published in: | MedChemComm 2018-10, Vol.9 (10), p.1663-1672 |
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| creator | Hu, Kun Liu, Chensi Li, Jingui Liang, Fupei |
| description | Three copper(ii) complexes, [Cu(L1)(NO
)
] (
), [Cu(L2)Cl
] (
) and [Cu(L2)SO
]
·H
O (
), were designed and synthesized by the reaction of Cu(NO
)
·3H
O, CuCl
·2H
O and CuSO
·5H
O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-aminobenzoic acid methyl ester or 4-aminobenzoic acid ethyl ester (benzocaine). The efficient bindings of the
-
complexes with human serum albumin (HSA) and calf thymus DNA (CT-DNA) were analyzed by spectroscopy and molecular docking. These complexes could significantly quench the fluorescence of HSA through the static quenching process, and hydrophobic interactions with HSA through the sub-domain IIA and IIIA cavities. The complexes bind to DNA
the intercalative mode and they fit well into the curved contour of the DNA target in the minor groove region. Furthermore, the interaction abilities of the Cu(ii) complexes with HSA/DNA were greater as compared to their corresponding ligands. Interestingly,
-
, particularly
, exhibited more cytotoxicity toward HeLa cells compared to normal HL-7702 cells and three other tumor cell lines (Hep-G2, NCI-H460, and MGC80-3). Their cytotoxicity toward the HeLa cell lines was 1.9-3.5-fold more potent than cisplatin. Further studies indicated that these complexes arrested the cell cycle in the G0/G1 phase and promoted tumor cell apoptosis
a reactive oxygen species (ROS)-mediated mitochondrial pathway. |
| doi_str_mv | 10.1039/c8md00223a |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2133825166</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2133825166</sourcerecordid><originalsourceid>FETCH-LOGICAL-c351t-97cb51ec3378e7722663adf06b0d9f6e4d4a6bd32262805b87efa1d083ce30dd3</originalsourceid><addsrcrecordid>eNpdkc9O3DAQxi1EVdCWSx8AWeJC0QbGdv44va2WtlSi7YH2HDn2hDVK7GAniOUxeOKaQjkwkjUjz-_7ZPkj5CODUwaiPtNyMACcC7VD9jnkkPGCsd3XGcQeOYjxBlIJLmWdvyd7AnJe1xXbJ49rP44Yjq39RLUfxh7vMdJWRTTUO3o7W-d76zAzGOxdurzSG9t12RNBe3utnImfady6aYPRxiXVGxWUnhL9oCbr3ZJeXK3Ozn-uaGudse6aqtb2dtouadKmM1mtnMZAk8repcUH8q5TfcSDl74gf75--b2-yC5_ffu-Xl1mWhRsyupKtwVDLUQlsao4L0uhTAdlC6buSsxNrsrWiLTgEopWVtgpZkAKjQKMEQty_Ow7Bn87Y5yawUaNfa8c-jk2nAkh02cm3wU5eoPe-Dm49LpEcZAyL2pI1MkzpYOPMWDXjMEOKmwbBs1TWM1a_jj_F9YqwYcvlnM7oHlF_0cj_gKNMo-g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2120884590</pqid></control><display><type>article</type><title>Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity</title><source>PubMed Central (Open access)</source><source>Royal Society of Chemistry</source><creator>Hu, Kun ; Liu, Chensi ; Li, Jingui ; Liang, Fupei</creator><creatorcontrib>Hu, Kun ; Liu, Chensi ; Li, Jingui ; Liang, Fupei</creatorcontrib><description>Three copper(ii) complexes, [Cu(L1)(NO
)
] (
), [Cu(L2)Cl
] (
) and [Cu(L2)SO
]
·H
O (
), were designed and synthesized by the reaction of Cu(NO
)
·3H
O, CuCl
·2H
O and CuSO
·5H
O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-aminobenzoic acid methyl ester or 4-aminobenzoic acid ethyl ester (benzocaine). The efficient bindings of the
-
complexes with human serum albumin (HSA) and calf thymus DNA (CT-DNA) were analyzed by spectroscopy and molecular docking. These complexes could significantly quench the fluorescence of HSA through the static quenching process, and hydrophobic interactions with HSA through the sub-domain IIA and IIIA cavities. The complexes bind to DNA
the intercalative mode and they fit well into the curved contour of the DNA target in the minor groove region. Furthermore, the interaction abilities of the Cu(ii) complexes with HSA/DNA were greater as compared to their corresponding ligands. Interestingly,
-
, particularly
, exhibited more cytotoxicity toward HeLa cells compared to normal HL-7702 cells and three other tumor cell lines (Hep-G2, NCI-H460, and MGC80-3). Their cytotoxicity toward the HeLa cell lines was 1.9-3.5-fold more potent than cisplatin. Further studies indicated that these complexes arrested the cell cycle in the G0/G1 phase and promoted tumor cell apoptosis
a reactive oxygen species (ROS)-mediated mitochondrial pathway.</description><identifier>ISSN: 2040-2503</identifier><identifier>EISSN: 2040-2511</identifier><identifier>DOI: 10.1039/c8md00223a</identifier><identifier>PMID: 30429971</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Anticancer properties ; Antitumor activity ; Apoptosis ; Biotechnology ; Calf thymus ; Cell cycle ; Chemical synthesis ; Cisplatin ; Coordination compounds ; Copper ; Copper chloride ; Copper compounds ; Crystallography ; Cytotoxicity ; Deoxyribonucleic acid ; DNA ; DNA biosynthesis ; Fluorescence ; G1 phase ; Human serum albumin ; Hydrophobicity ; Imines ; Ligands ; Mitochondria ; Molecular docking ; Quinoline ; Reactive oxygen species ; Serum albumin ; Spectroscopy ; Toxicity ; Tumor cell lines ; Tumors</subject><ispartof>MedChemComm, 2018-10, Vol.9 (10), p.1663-1672</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-97cb51ec3378e7722663adf06b0d9f6e4d4a6bd32262805b87efa1d083ce30dd3</citedby><cites>FETCH-LOGICAL-c351t-97cb51ec3378e7722663adf06b0d9f6e4d4a6bd32262805b87efa1d083ce30dd3</cites><orcidid>0000-0003-4420-2467 ; 0000-0001-7435-0140</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30429971$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, Kun</creatorcontrib><creatorcontrib>Liu, Chensi</creatorcontrib><creatorcontrib>Li, Jingui</creatorcontrib><creatorcontrib>Liang, Fupei</creatorcontrib><title>Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity</title><title>MedChemComm</title><addtitle>Medchemcomm</addtitle><description>Three copper(ii) complexes, [Cu(L1)(NO
)
] (
), [Cu(L2)Cl
] (
) and [Cu(L2)SO
]
·H
O (
), were designed and synthesized by the reaction of Cu(NO
)
·3H
O, CuCl
·2H
O and CuSO
·5H
O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-aminobenzoic acid methyl ester or 4-aminobenzoic acid ethyl ester (benzocaine). The efficient bindings of the
-
complexes with human serum albumin (HSA) and calf thymus DNA (CT-DNA) were analyzed by spectroscopy and molecular docking. These complexes could significantly quench the fluorescence of HSA through the static quenching process, and hydrophobic interactions with HSA through the sub-domain IIA and IIIA cavities. The complexes bind to DNA
the intercalative mode and they fit well into the curved contour of the DNA target in the minor groove region. Furthermore, the interaction abilities of the Cu(ii) complexes with HSA/DNA were greater as compared to their corresponding ligands. Interestingly,
-
, particularly
, exhibited more cytotoxicity toward HeLa cells compared to normal HL-7702 cells and three other tumor cell lines (Hep-G2, NCI-H460, and MGC80-3). Their cytotoxicity toward the HeLa cell lines was 1.9-3.5-fold more potent than cisplatin. Further studies indicated that these complexes arrested the cell cycle in the G0/G1 phase and promoted tumor cell apoptosis
a reactive oxygen species (ROS)-mediated mitochondrial pathway.</description><subject>Anticancer properties</subject><subject>Antitumor activity</subject><subject>Apoptosis</subject><subject>Biotechnology</subject><subject>Calf thymus</subject><subject>Cell cycle</subject><subject>Chemical synthesis</subject><subject>Cisplatin</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Copper chloride</subject><subject>Copper compounds</subject><subject>Crystallography</subject><subject>Cytotoxicity</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA biosynthesis</subject><subject>Fluorescence</subject><subject>G1 phase</subject><subject>Human serum albumin</subject><subject>Hydrophobicity</subject><subject>Imines</subject><subject>Ligands</subject><subject>Mitochondria</subject><subject>Molecular docking</subject><subject>Quinoline</subject><subject>Reactive oxygen species</subject><subject>Serum albumin</subject><subject>Spectroscopy</subject><subject>Toxicity</subject><subject>Tumor cell lines</subject><subject>Tumors</subject><issn>2040-2503</issn><issn>2040-2511</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkc9O3DAQxi1EVdCWSx8AWeJC0QbGdv44va2WtlSi7YH2HDn2hDVK7GAniOUxeOKaQjkwkjUjz-_7ZPkj5CODUwaiPtNyMACcC7VD9jnkkPGCsd3XGcQeOYjxBlIJLmWdvyd7AnJe1xXbJ49rP44Yjq39RLUfxh7vMdJWRTTUO3o7W-d76zAzGOxdurzSG9t12RNBe3utnImfady6aYPRxiXVGxWUnhL9oCbr3ZJeXK3Ozn-uaGudse6aqtb2dtouadKmM1mtnMZAk8repcUH8q5TfcSDl74gf75--b2-yC5_ffu-Xl1mWhRsyupKtwVDLUQlsao4L0uhTAdlC6buSsxNrsrWiLTgEopWVtgpZkAKjQKMEQty_Ow7Bn87Y5yawUaNfa8c-jk2nAkh02cm3wU5eoPe-Dm49LpEcZAyL2pI1MkzpYOPMWDXjMEOKmwbBs1TWM1a_jj_F9YqwYcvlnM7oHlF_0cj_gKNMo-g</recordid><startdate>20181001</startdate><enddate>20181001</enddate><creator>Hu, Kun</creator><creator>Liu, Chensi</creator><creator>Li, Jingui</creator><creator>Liang, Fupei</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T5</scope><scope>7T7</scope><scope>7TO</scope><scope>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4420-2467</orcidid><orcidid>https://orcid.org/0000-0001-7435-0140</orcidid></search><sort><creationdate>20181001</creationdate><title>Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity</title><author>Hu, Kun ; Liu, Chensi ; Li, Jingui ; Liang, Fupei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-97cb51ec3378e7722663adf06b0d9f6e4d4a6bd32262805b87efa1d083ce30dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anticancer properties</topic><topic>Antitumor activity</topic><topic>Apoptosis</topic><topic>Biotechnology</topic><topic>Calf thymus</topic><topic>Cell cycle</topic><topic>Chemical synthesis</topic><topic>Cisplatin</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Copper chloride</topic><topic>Copper compounds</topic><topic>Crystallography</topic><topic>Cytotoxicity</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA biosynthesis</topic><topic>Fluorescence</topic><topic>G1 phase</topic><topic>Human serum albumin</topic><topic>Hydrophobicity</topic><topic>Imines</topic><topic>Ligands</topic><topic>Mitochondria</topic><topic>Molecular docking</topic><topic>Quinoline</topic><topic>Reactive oxygen species</topic><topic>Serum albumin</topic><topic>Spectroscopy</topic><topic>Toxicity</topic><topic>Tumor cell lines</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Kun</creatorcontrib><creatorcontrib>Liu, Chensi</creatorcontrib><creatorcontrib>Li, Jingui</creatorcontrib><creatorcontrib>Liang, Fupei</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Immunology Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>MedChemComm</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Kun</au><au>Liu, Chensi</au><au>Li, Jingui</au><au>Liang, Fupei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity</atitle><jtitle>MedChemComm</jtitle><addtitle>Medchemcomm</addtitle><date>2018-10-01</date><risdate>2018</risdate><volume>9</volume><issue>10</issue><spage>1663</spage><epage>1672</epage><pages>1663-1672</pages><issn>2040-2503</issn><eissn>2040-2511</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Three copper(ii) complexes, [Cu(L1)(NO
)
] (
), [Cu(L2)Cl
] (
) and [Cu(L2)SO
]
·H
O (
), were designed and synthesized by the reaction of Cu(NO
)
·3H
O, CuCl
·2H
O and CuSO
·5H
O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-aminobenzoic acid methyl ester or 4-aminobenzoic acid ethyl ester (benzocaine). The efficient bindings of the
-
complexes with human serum albumin (HSA) and calf thymus DNA (CT-DNA) were analyzed by spectroscopy and molecular docking. These complexes could significantly quench the fluorescence of HSA through the static quenching process, and hydrophobic interactions with HSA through the sub-domain IIA and IIIA cavities. The complexes bind to DNA
the intercalative mode and they fit well into the curved contour of the DNA target in the minor groove region. Furthermore, the interaction abilities of the Cu(ii) complexes with HSA/DNA were greater as compared to their corresponding ligands. Interestingly,
-
, particularly
, exhibited more cytotoxicity toward HeLa cells compared to normal HL-7702 cells and three other tumor cell lines (Hep-G2, NCI-H460, and MGC80-3). Their cytotoxicity toward the HeLa cell lines was 1.9-3.5-fold more potent than cisplatin. Further studies indicated that these complexes arrested the cell cycle in the G0/G1 phase and promoted tumor cell apoptosis
a reactive oxygen species (ROS)-mediated mitochondrial pathway.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30429971</pmid><doi>10.1039/c8md00223a</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-4420-2467</orcidid><orcidid>https://orcid.org/0000-0001-7435-0140</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2040-2503 |
| ispartof | MedChemComm, 2018-10, Vol.9 (10), p.1663-1672 |
| issn | 2040-2503 2040-2511 |
| language | eng |
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| source | PubMed Central (Open access); Royal Society of Chemistry |
| subjects | Anticancer properties Antitumor activity Apoptosis Biotechnology Calf thymus Cell cycle Chemical synthesis Cisplatin Coordination compounds Copper Copper chloride Copper compounds Crystallography Cytotoxicity Deoxyribonucleic acid DNA DNA biosynthesis Fluorescence G1 phase Human serum albumin Hydrophobicity Imines Ligands Mitochondria Molecular docking Quinoline Reactive oxygen species Serum albumin Spectroscopy Toxicity Tumor cell lines Tumors |
| title | Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity |
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