Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates
Novel gold(I) and gold(III) complexes containing derivatives of d -galactose, d -ribose and d -glucono-1,5-lactone as ligands were synthesized and characterized by IR, 1 H, and 13 C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity...
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| Veröffentlicht in: | Biometals 2015-10, Vol.28 (5), p.845-860 |
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| creator | Chaves, Joana Darc Souza Damasceno, Jaqueline Lopes Paula, Marcela Cristina Ferreira de Oliveira, Pollyanna Francielli Azevedo, Gustavo Chevitarese Matos, Renato Camargo Lourenço, Maria Cristina S. Tavares, Denise Crispim Silva, Heveline Fontes, Ana Paula Soares de Almeida, Mauro Vieira |
| description | Novel gold(I) and gold(III) complexes containing derivatives of
d
-galactose,
d
-ribose and
d
-glucono-1,5-lactone as ligands were synthesized and characterized by IR,
1
H, and
13
C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity against three types of tumor cells: cervical carcinoma (HeLa) breast adenocarcinoma (MCF-7) and glioblastoma (MO59J) and one non-tumor cell line: human lung fibroblasts (GM07492A). Their antitubercular activity was evaluated as well expressed as the minimum inhibitory concentration (MIC
90
) in μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (
1
) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (
8
) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity. The study of the cytotoxic activity revealed effective antitumor activities for the gold(I) complexes, being more active than cisplatin in all the tested tumor cell lines. Gold(I) compounds (
1
), (
2
), (
3
), (
4
) and (
6
) exhibited relevant antitubercular activity even when compared with first line drugs such as rifampicin. |
| doi_str_mv | 10.1007/s10534-015-9870-8 |
| format | Article |
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d
-galactose,
d
-ribose and
d
-glucono-1,5-lactone as ligands were synthesized and characterized by IR,
1
H, and
13
C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity against three types of tumor cells: cervical carcinoma (HeLa) breast adenocarcinoma (MCF-7) and glioblastoma (MO59J) and one non-tumor cell line: human lung fibroblasts (GM07492A). Their antitubercular activity was evaluated as well expressed as the minimum inhibitory concentration (MIC
90
) in μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (
1
) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (
8
) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity. The study of the cytotoxic activity revealed effective antitumor activities for the gold(I) complexes, being more active than cisplatin in all the tested tumor cell lines. Gold(I) compounds (
1
), (
2
), (
3
), (
4
) and (
6
) exhibited relevant antitubercular activity even when compared with first line drugs such as rifampicin.</description><identifier>ISSN: 0966-0844</identifier><identifier>EISSN: 1572-8773</identifier><identifier>DOI: 10.1007/s10534-015-9870-8</identifier><identifier>PMID: 26091950</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Biochemistry ; Biomedical and Life Sciences ; Biosynthesis ; Biotechnology ; Breast ; Carbohydrates ; Carbohydrates - administration & dosage ; Carbohydrates - chemical synthesis ; Carbohydrates - chemistry ; Cell Biology ; Cell Proliferation - drug effects ; Cisplatin - administration & dosage ; Coordination Complexes - chemical synthesis ; Coordination Complexes - chemistry ; Coordination Complexes - pharmacology ; Coordination compounds ; Cytotoxicity ; Derivatives ; Fibroblasts - drug effects ; Fibroblasts - pathology ; Gold ; Gold - administration & dosage ; Gold - chemistry ; HeLa Cells ; Humans ; Life Sciences ; Ligands ; Lung - drug effects ; Lung - pathology ; Magnetic Resonance Spectroscopy ; Mass spectra ; MCF-7 Cells ; Medicine/Public Health ; Microbiology ; Pharmacology/Toxicology ; Phosphines ; Plant Physiology ; Rifampin - administration & dosage ; Structure-Activity Relationship ; Tumors</subject><ispartof>Biometals, 2015-10, Vol.28 (5), p.845-860</ispartof><rights>Springer Science+Business Media New York 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c574t-6513a6774a6362af81bd2a4e83504c02eaf1866bc18e90cd67143c9614e6e7053</citedby><cites>FETCH-LOGICAL-c574t-6513a6774a6362af81bd2a4e83504c02eaf1866bc18e90cd67143c9614e6e7053</cites><orcidid>0000-0003-1112-0801</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10534-015-9870-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10534-015-9870-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26091950$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chaves, Joana Darc Souza</creatorcontrib><creatorcontrib>Damasceno, Jaqueline Lopes</creatorcontrib><creatorcontrib>Paula, Marcela Cristina Ferreira</creatorcontrib><creatorcontrib>de Oliveira, Pollyanna Francielli</creatorcontrib><creatorcontrib>Azevedo, Gustavo Chevitarese</creatorcontrib><creatorcontrib>Matos, Renato Camargo</creatorcontrib><creatorcontrib>Lourenço, Maria Cristina S.</creatorcontrib><creatorcontrib>Tavares, Denise Crispim</creatorcontrib><creatorcontrib>Silva, Heveline</creatorcontrib><creatorcontrib>Fontes, Ana Paula Soares</creatorcontrib><creatorcontrib>de Almeida, Mauro Vieira</creatorcontrib><title>Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates</title><title>Biometals</title><addtitle>Biometals</addtitle><addtitle>Biometals</addtitle><description>Novel gold(I) and gold(III) complexes containing derivatives of
d
-galactose,
d
-ribose and
d
-glucono-1,5-lactone as ligands were synthesized and characterized by IR,
1
H, and
13
C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity against three types of tumor cells: cervical carcinoma (HeLa) breast adenocarcinoma (MCF-7) and glioblastoma (MO59J) and one non-tumor cell line: human lung fibroblasts (GM07492A). Their antitubercular activity was evaluated as well expressed as the minimum inhibitory concentration (MIC
90
) in μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (
1
) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (
8
) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity. The study of the cytotoxic activity revealed effective antitumor activities for the gold(I) complexes, being more active than cisplatin in all the tested tumor cell lines. Gold(I) compounds (
1
), (
2
), (
3
), (
4
) and (
6
) exhibited relevant antitubercular activity even when compared with first line drugs such as rifampicin.</description><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biosynthesis</subject><subject>Biotechnology</subject><subject>Breast</subject><subject>Carbohydrates</subject><subject>Carbohydrates - administration & dosage</subject><subject>Carbohydrates - chemical synthesis</subject><subject>Carbohydrates - chemistry</subject><subject>Cell Biology</subject><subject>Cell Proliferation - drug effects</subject><subject>Cisplatin - administration & dosage</subject><subject>Coordination Complexes - chemical synthesis</subject><subject>Coordination Complexes - chemistry</subject><subject>Coordination Complexes - pharmacology</subject><subject>Coordination compounds</subject><subject>Cytotoxicity</subject><subject>Derivatives</subject><subject>Fibroblasts - drug effects</subject><subject>Fibroblasts - pathology</subject><subject>Gold</subject><subject>Gold - administration & dosage</subject><subject>Gold - chemistry</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Life Sciences</subject><subject>Ligands</subject><subject>Lung - drug effects</subject><subject>Lung - pathology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass spectra</subject><subject>MCF-7 Cells</subject><subject>Medicine/Public Health</subject><subject>Microbiology</subject><subject>Pharmacology/Toxicology</subject><subject>Phosphines</subject><subject>Plant Physiology</subject><subject>Rifampin - administration & dosage</subject><subject>Structure-Activity Relationship</subject><subject>Tumors</subject><issn>0966-0844</issn><issn>1572-8773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNqNkk2LFDEQhoMo7rj6A7xIwMsKtlbS6SR9XBY_BhY8qOcmna6eydKTjEl63fGf-G_NbK8igrCHUPl46i2q8hLynMEbBqDeJgZNLSpgTdVqBZV-QFasUbzSStUPyQpaKSvQQpyQJyldAUCrQD4mJ1xCy9oGVuTn54PPW0wuvaZ2a6KxGaP7YbILvtwccsjhxllq_FBWdnnuMdp5MpEW1F277DDRMFKP3-kmTMPZ-tUtvOzX5WTDbj_hTcFs8Nk47_yGTm5TqESHUu0aBzrGsKPWxD5sD0M0GdNT8mg0U8Jnd_GUfH3_7svFx-ry04f1xfllZRslciUbVhuplDCyltyMmvUDNwJ13YCwwNGMTEvZW6axBTtIxURtW8kESlRlfqfkbNHdx_BtxpS7nUsWp8l4DHPqmGrqRgjF2f1QqEHeR5VxpXRpoaAv_0Gvwhx96fmW4krwWheKLZSNIaWIY7ePbmfioWPQHd3QLW7oihu6oxu6Y86LO-W53-HwJ-P39xeAL0AqT36D8a_S_1X9BaW7v_Y</recordid><startdate>20151001</startdate><enddate>20151001</enddate><creator>Chaves, Joana Darc Souza</creator><creator>Damasceno, Jaqueline Lopes</creator><creator>Paula, Marcela Cristina Ferreira</creator><creator>de Oliveira, Pollyanna Francielli</creator><creator>Azevedo, Gustavo Chevitarese</creator><creator>Matos, Renato Camargo</creator><creator>Lourenço, Maria Cristina S.</creator><creator>Tavares, Denise Crispim</creator><creator>Silva, Heveline</creator><creator>Fontes, Ana Paula Soares</creator><creator>de Almeida, Mauro Vieira</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><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>3V.</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7U5</scope><scope>7U7</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>L6V</scope><scope>L7M</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>P64</scope><scope>PATMY</scope><scope>PCBAR</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1112-0801</orcidid></search><sort><creationdate>20151001</creationdate><title>Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates</title><author>Chaves, Joana Darc Souza ; Damasceno, Jaqueline Lopes ; Paula, Marcela Cristina Ferreira ; de Oliveira, Pollyanna Francielli ; Azevedo, Gustavo Chevitarese ; Matos, Renato Camargo ; Lourenço, Maria Cristina S. ; Tavares, Denise Crispim ; Silva, Heveline ; Fontes, Ana Paula Soares ; de Almeida, Mauro Vieira</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c574t-6513a6774a6362af81bd2a4e83504c02eaf1866bc18e90cd67143c9614e6e7053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biosynthesis</topic><topic>Biotechnology</topic><topic>Breast</topic><topic>Carbohydrates</topic><topic>Carbohydrates - administration & dosage</topic><topic>Carbohydrates - chemical synthesis</topic><topic>Carbohydrates - chemistry</topic><topic>Cell Biology</topic><topic>Cell Proliferation - drug effects</topic><topic>Cisplatin - administration & dosage</topic><topic>Coordination Complexes - chemical synthesis</topic><topic>Coordination Complexes - chemistry</topic><topic>Coordination Complexes - pharmacology</topic><topic>Coordination compounds</topic><topic>Cytotoxicity</topic><topic>Derivatives</topic><topic>Fibroblasts - drug effects</topic><topic>Fibroblasts - pathology</topic><topic>Gold</topic><topic>Gold - administration & dosage</topic><topic>Gold - chemistry</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Life Sciences</topic><topic>Ligands</topic><topic>Lung - drug effects</topic><topic>Lung - pathology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass spectra</topic><topic>MCF-7 Cells</topic><topic>Medicine/Public Health</topic><topic>Microbiology</topic><topic>Pharmacology/Toxicology</topic><topic>Phosphines</topic><topic>Plant Physiology</topic><topic>Rifampin - 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Academic</collection><jtitle>Biometals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chaves, Joana Darc Souza</au><au>Damasceno, Jaqueline Lopes</au><au>Paula, Marcela Cristina Ferreira</au><au>de Oliveira, Pollyanna Francielli</au><au>Azevedo, Gustavo Chevitarese</au><au>Matos, Renato Camargo</au><au>Lourenço, Maria Cristina S.</au><au>Tavares, Denise Crispim</au><au>Silva, Heveline</au><au>Fontes, Ana Paula Soares</au><au>de Almeida, Mauro Vieira</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates</atitle><jtitle>Biometals</jtitle><stitle>Biometals</stitle><addtitle>Biometals</addtitle><date>2015-10-01</date><risdate>2015</risdate><volume>28</volume><issue>5</issue><spage>845</spage><epage>860</epage><pages>845-860</pages><issn>0966-0844</issn><eissn>1572-8773</eissn><abstract>Novel gold(I) and gold(III) complexes containing derivatives of
d
-galactose,
d
-ribose and
d
-glucono-1,5-lactone as ligands were synthesized and characterized by IR,
1
H, and
13
C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity against three types of tumor cells: cervical carcinoma (HeLa) breast adenocarcinoma (MCF-7) and glioblastoma (MO59J) and one non-tumor cell line: human lung fibroblasts (GM07492A). Their antitubercular activity was evaluated as well expressed as the minimum inhibitory concentration (MIC
90
) in μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (
1
) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (
8
) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity. The study of the cytotoxic activity revealed effective antitumor activities for the gold(I) complexes, being more active than cisplatin in all the tested tumor cell lines. Gold(I) compounds (
1
), (
2
), (
3
), (
4
) and (
6
) exhibited relevant antitubercular activity even when compared with first line drugs such as rifampicin.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><pmid>26091950</pmid><doi>10.1007/s10534-015-9870-8</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0003-1112-0801</orcidid></addata></record> |
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| ispartof | Biometals, 2015-10, Vol.28 (5), p.845-860 |
| issn | 0966-0844 1572-8773 |
| language | eng |
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| source | MEDLINE; SpringerLink Journals |
| subjects | Biochemistry Biomedical and Life Sciences Biosynthesis Biotechnology Breast Carbohydrates Carbohydrates - administration & dosage Carbohydrates - chemical synthesis Carbohydrates - chemistry Cell Biology Cell Proliferation - drug effects Cisplatin - administration & dosage Coordination Complexes - chemical synthesis Coordination Complexes - chemistry Coordination Complexes - pharmacology Coordination compounds Cytotoxicity Derivatives Fibroblasts - drug effects Fibroblasts - pathology Gold Gold - administration & dosage Gold - chemistry HeLa Cells Humans Life Sciences Ligands Lung - drug effects Lung - pathology Magnetic Resonance Spectroscopy Mass spectra MCF-7 Cells Medicine/Public Health Microbiology Pharmacology/Toxicology Phosphines Plant Physiology Rifampin - administration & dosage Structure-Activity Relationship Tumors |
| title | Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates |
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