New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies
Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η -C H CH[double bond, length as m-dash]N-(CH ) -Pz-R)Re(CO) ] (Pz-R: -alkyl or aryl piperazine). The piperazine-bas...
Gespeichert in:
| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2018, Vol.47 (4), p.1233-1242 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1242 |
|---|---|
| container_issue | 4 |
| container_start_page | 1233 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 47 |
| creator | Muñoz-Osses, Michelle Godoy, Fernando Fierro, Angélica Gómez, Alejandra Metzler-Nolte, Nils |
| description | Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η
-C
H
CH[double bond, length as m-dash]N-(CH
)
-Pz-R)Re(CO)
] (Pz-R: -alkyl or aryl piperazine). The piperazine-based ligands were designed to be potential inhibitors of GSK-3β kinase. All the ligands and complexes were fully characterized and evaluated against the HT-29 and PT-45 cancer cell lines, in which GSK-3β plays a crucial role. In this context, we carried out biological evaluation using the MTT colorimetric assay. In terms of structure activity relationship, our findings indicated improved biological activity when aromaticity increased in the organic ligands (3d). In addition, the presence of the rhenium fragment in the imines (5a-d) leads to better activity with IC
values in the range of 25-100 μM. In addition, our experimental studies were complemented by computational studies, where the volume and electrostatic surface of the organic ligands and organometallic compounds as well as their binding to the kinase protein are calculated. |
| doi_str_mv | 10.1039/c7dt04344a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1984750802</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2010866300</sourcerecordid><originalsourceid>FETCH-LOGICAL-c315t-ba2ef58033934e742053cf7cdbf69b04acf41ae4432332cd4f9a537cbe0b7d3e3</originalsourceid><addsrcrecordid>eNpd0UtOxDAMBuAIgXgMbDgAisRmQBTSOJ1M2KEBBgSCBbCu0tRlgtpmSFIh4FYchDNRngtW9uKzZesnZDNl-ykDdWBkGZkAIfQCWU2FlIniIBb_ej5aIWshPDDGOcv4MlnhiiuVyWyVvF7hE3X-Xreuwajr2hpqG9tioK6ifoat7Zqh3aE60LmL2Eara1rbfqD8ItObiwTe3w5peG7jDIMNe9TMtNcmorcvOlrX0h7Twrra3VvTj4fYlRbDOlmqdB1w46cOyN3pye3kLLm8np5Pji4TA2kWk0JzrLIxA1AgUIr-BzCVNGVRjVTBhDaVSDUKARyAm1JUSmcgTYGskCUgDMjwe-_cu8cOQ8wbGwzWtW7RdSFP1VjIjI0Z7-n2P_rgOt_21-WcpWw8GgFjvdr9Vsa7EDxW-dzbRvvnPGX5ZyT5RB7ffkVy1OOtn5Vd0WD5R38zgA_YZ4gr</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2010866300</pqid></control><display><type>article</type><title>New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Muñoz-Osses, Michelle ; Godoy, Fernando ; Fierro, Angélica ; Gómez, Alejandra ; Metzler-Nolte, Nils</creator><creatorcontrib>Muñoz-Osses, Michelle ; Godoy, Fernando ; Fierro, Angélica ; Gómez, Alejandra ; Metzler-Nolte, Nils</creatorcontrib><description>Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η
-C
H
CH[double bond, length as m-dash]N-(CH
)
-Pz-R)Re(CO)
] (Pz-R: -alkyl or aryl piperazine). The piperazine-based ligands were designed to be potential inhibitors of GSK-3β kinase. All the ligands and complexes were fully characterized and evaluated against the HT-29 and PT-45 cancer cell lines, in which GSK-3β plays a crucial role. In this context, we carried out biological evaluation using the MTT colorimetric assay. In terms of structure activity relationship, our findings indicated improved biological activity when aromaticity increased in the organic ligands (3d). In addition, the presence of the rhenium fragment in the imines (5a-d) leads to better activity with IC
values in the range of 25-100 μM. In addition, our experimental studies were complemented by computational studies, where the volume and electrostatic surface of the organic ligands and organometallic compounds as well as their binding to the kinase protein are calculated.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c7dt04344a</identifier><identifier>PMID: 29299575</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Aromaticity ; Biological activity ; Chemistry Techniques, Synthetic ; Colorimetry ; Coordination compounds ; Glycogen Synthase Kinase 3 beta - chemistry ; Glycogen Synthase Kinase 3 beta - metabolism ; HT29 Cells ; Humans ; Imines ; Imines - chemistry ; Ligands ; Models, Molecular ; Organometallic compounds ; Organometallic Compounds - chemical synthesis ; Organometallic Compounds - chemistry ; Organometallic Compounds - metabolism ; Protein Conformation ; Rhenium ; Rhenium - chemistry</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2018, Vol.47 (4), p.1233-1242</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-ba2ef58033934e742053cf7cdbf69b04acf41ae4432332cd4f9a537cbe0b7d3e3</citedby><cites>FETCH-LOGICAL-c315t-ba2ef58033934e742053cf7cdbf69b04acf41ae4432332cd4f9a537cbe0b7d3e3</cites><orcidid>0000-0002-3916-4753 ; 0000-0001-8111-9959</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29299575$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Muñoz-Osses, Michelle</creatorcontrib><creatorcontrib>Godoy, Fernando</creatorcontrib><creatorcontrib>Fierro, Angélica</creatorcontrib><creatorcontrib>Gómez, Alejandra</creatorcontrib><creatorcontrib>Metzler-Nolte, Nils</creatorcontrib><title>New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η
-C
H
CH[double bond, length as m-dash]N-(CH
)
-Pz-R)Re(CO)
] (Pz-R: -alkyl or aryl piperazine). The piperazine-based ligands were designed to be potential inhibitors of GSK-3β kinase. All the ligands and complexes were fully characterized and evaluated against the HT-29 and PT-45 cancer cell lines, in which GSK-3β plays a crucial role. In this context, we carried out biological evaluation using the MTT colorimetric assay. In terms of structure activity relationship, our findings indicated improved biological activity when aromaticity increased in the organic ligands (3d). In addition, the presence of the rhenium fragment in the imines (5a-d) leads to better activity with IC
values in the range of 25-100 μM. In addition, our experimental studies were complemented by computational studies, where the volume and electrostatic surface of the organic ligands and organometallic compounds as well as their binding to the kinase protein are calculated.</description><subject>Aromatic compounds</subject><subject>Aromaticity</subject><subject>Biological activity</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Colorimetry</subject><subject>Coordination compounds</subject><subject>Glycogen Synthase Kinase 3 beta - chemistry</subject><subject>Glycogen Synthase Kinase 3 beta - metabolism</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Imines</subject><subject>Imines - chemistry</subject><subject>Ligands</subject><subject>Models, Molecular</subject><subject>Organometallic compounds</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organometallic Compounds - metabolism</subject><subject>Protein Conformation</subject><subject>Rhenium</subject><subject>Rhenium - chemistry</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0UtOxDAMBuAIgXgMbDgAisRmQBTSOJ1M2KEBBgSCBbCu0tRlgtpmSFIh4FYchDNRngtW9uKzZesnZDNl-ykDdWBkGZkAIfQCWU2FlIniIBb_ej5aIWshPDDGOcv4MlnhiiuVyWyVvF7hE3X-Xreuwajr2hpqG9tioK6ifoat7Zqh3aE60LmL2Eara1rbfqD8ItObiwTe3w5peG7jDIMNe9TMtNcmorcvOlrX0h7Twrra3VvTj4fYlRbDOlmqdB1w46cOyN3pye3kLLm8np5Pji4TA2kWk0JzrLIxA1AgUIr-BzCVNGVRjVTBhDaVSDUKARyAm1JUSmcgTYGskCUgDMjwe-_cu8cOQ8wbGwzWtW7RdSFP1VjIjI0Z7-n2P_rgOt_21-WcpWw8GgFjvdr9Vsa7EDxW-dzbRvvnPGX5ZyT5RB7ffkVy1OOtn5Vd0WD5R38zgA_YZ4gr</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Muñoz-Osses, Michelle</creator><creator>Godoy, Fernando</creator><creator>Fierro, Angélica</creator><creator>Gómez, Alejandra</creator><creator>Metzler-Nolte, Nils</creator><general>Royal Society of Chemistry</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3916-4753</orcidid><orcidid>https://orcid.org/0000-0001-8111-9959</orcidid></search><sort><creationdate>2018</creationdate><title>New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies</title><author>Muñoz-Osses, Michelle ; Godoy, Fernando ; Fierro, Angélica ; Gómez, Alejandra ; Metzler-Nolte, Nils</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-ba2ef58033934e742053cf7cdbf69b04acf41ae4432332cd4f9a537cbe0b7d3e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Aromaticity</topic><topic>Biological activity</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Colorimetry</topic><topic>Coordination compounds</topic><topic>Glycogen Synthase Kinase 3 beta - chemistry</topic><topic>Glycogen Synthase Kinase 3 beta - metabolism</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>Imines</topic><topic>Imines - chemistry</topic><topic>Ligands</topic><topic>Models, Molecular</topic><topic>Organometallic compounds</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organometallic Compounds - metabolism</topic><topic>Protein Conformation</topic><topic>Rhenium</topic><topic>Rhenium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muñoz-Osses, Michelle</creatorcontrib><creatorcontrib>Godoy, Fernando</creatorcontrib><creatorcontrib>Fierro, Angélica</creatorcontrib><creatorcontrib>Gómez, Alejandra</creatorcontrib><creatorcontrib>Metzler-Nolte, Nils</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muñoz-Osses, Michelle</au><au>Godoy, Fernando</au><au>Fierro, Angélica</au><au>Gómez, Alejandra</au><au>Metzler-Nolte, Nils</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2018</date><risdate>2018</risdate><volume>47</volume><issue>4</issue><spage>1233</spage><epage>1242</epage><pages>1233-1242</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η
-C
H
CH[double bond, length as m-dash]N-(CH
)
-Pz-R)Re(CO)
] (Pz-R: -alkyl or aryl piperazine). The piperazine-based ligands were designed to be potential inhibitors of GSK-3β kinase. All the ligands and complexes were fully characterized and evaluated against the HT-29 and PT-45 cancer cell lines, in which GSK-3β plays a crucial role. In this context, we carried out biological evaluation using the MTT colorimetric assay. In terms of structure activity relationship, our findings indicated improved biological activity when aromaticity increased in the organic ligands (3d). In addition, the presence of the rhenium fragment in the imines (5a-d) leads to better activity with IC
values in the range of 25-100 μM. In addition, our experimental studies were complemented by computational studies, where the volume and electrostatic surface of the organic ligands and organometallic compounds as well as their binding to the kinase protein are calculated.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29299575</pmid><doi>10.1039/c7dt04344a</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-3916-4753</orcidid><orcidid>https://orcid.org/0000-0001-8111-9959</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2018, Vol.47 (4), p.1233-1242 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1984750802 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aromatic compounds Aromaticity Biological activity Chemistry Techniques, Synthetic Colorimetry Coordination compounds Glycogen Synthase Kinase 3 beta - chemistry Glycogen Synthase Kinase 3 beta - metabolism HT29 Cells Humans Imines Imines - chemistry Ligands Models, Molecular Organometallic compounds Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Organometallic Compounds - metabolism Protein Conformation Rhenium Rhenium - chemistry |
| title | New organometallic imines of rhenium(i) as potential ligands of GSK-3β: synthesis, characterization and biological studies |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T20%3A34%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20organometallic%20imines%20of%20rhenium(i)%20as%20potential%20ligands%20of%20GSK-3%CE%B2:%20synthesis,%20characterization%20and%20biological%20studies&rft.jtitle=Dalton%20transactions%20:%20an%20international%20journal%20of%20inorganic%20chemistry&rft.au=Mu%C3%B1oz-Osses,%20Michelle&rft.date=2018&rft.volume=47&rft.issue=4&rft.spage=1233&rft.epage=1242&rft.pages=1233-1242&rft.issn=1477-9226&rft.eissn=1477-9234&rft_id=info:doi/10.1039/c7dt04344a&rft_dat=%3Cproquest_cross%3E2010866300%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2010866300&rft_id=info:pmid/29299575&rfr_iscdi=true |