Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential
To our previously reported first crystal structure of a homoleptic zinc curcuminoid complex with square pyramidal geometry, we add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseud...
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creator | Meza-Morales, William Alvarez-Ricardo, Yair Obregón-Mendoza, Marco A Arenaza-Corona, Antonino Ramírez-Apan, María Teresa Toscano, Rubén A Poveda-Jaramillo, Juan Carlos Enríquez, Raúl G |
description | To our previously reported first crystal structure of a homoleptic zinc curcuminoid complex with square pyramidal geometry, we add herein three new geometries of homoleptic type complexes
i.e.
octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseudo-polymorph of the DAC-Zn complex resulting from crystallization in DMF, while square-pyramidal geometry was obtained in DMSO. Improving crystallinity involved suppressing the phenolic interactions by etherification and esterification. The complete characterization of these complexes was carried out using SCXRD, IR, MS, EA, liquid, and solid-state NMR. Moreover, the cytotoxic activity of all complexes was evaluated. The IC
50
values for the DiMeOC-Zn (
7
) complex were 8 or 22 times higher than for cisplatin in the U251 and HCT-15 cell lines, indicating a high antiproliferative and therapeutic potential.
We add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Moreover, the IC
50
values for the DiMeOC-Zn complex were 8 or 22 times higher than cisplatin in the U251 and HCT15 cell lines. |
doi_str_mv | 10.1039/d3ra00167a |
format | Article |
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i.e.
octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseudo-polymorph of the DAC-Zn complex resulting from crystallization in DMF, while square-pyramidal geometry was obtained in DMSO. Improving crystallinity involved suppressing the phenolic interactions by etherification and esterification. The complete characterization of these complexes was carried out using SCXRD, IR, MS, EA, liquid, and solid-state NMR. Moreover, the cytotoxic activity of all complexes was evaluated. The IC
50
values for the DiMeOC-Zn (
7
) complex were 8 or 22 times higher than for cisplatin in the U251 and HCT-15 cell lines, indicating a high antiproliferative and therapeutic potential.
We add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Moreover, the IC
50
values for the DiMeOC-Zn complex were 8 or 22 times higher than cisplatin in the U251 and HCT15 cell lines.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d3ra00167a</identifier><identifier>PMID: 36936838</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Antiproliferatives ; Chemistry ; Crystal structure ; Crystallization ; Esterification ; NMR ; Nuclear magnetic resonance ; Zinc</subject><ispartof>RSC advances, 2023-03, Vol.13 (13), p.8577-8585</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-6e50ce6c3b3f273559a854491ea60310a9b0da478d1544d2248df59ef9fef2543</citedby><cites>FETCH-LOGICAL-c429t-6e50ce6c3b3f273559a854491ea60310a9b0da478d1544d2248df59ef9fef2543</cites><orcidid>0000-0002-2671-615X ; 0000-0002-8197-9032</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10016078/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10016078/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36936838$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meza-Morales, William</creatorcontrib><creatorcontrib>Alvarez-Ricardo, Yair</creatorcontrib><creatorcontrib>Obregón-Mendoza, Marco A</creatorcontrib><creatorcontrib>Arenaza-Corona, Antonino</creatorcontrib><creatorcontrib>Ramírez-Apan, María Teresa</creatorcontrib><creatorcontrib>Toscano, Rubén A</creatorcontrib><creatorcontrib>Poveda-Jaramillo, Juan Carlos</creatorcontrib><creatorcontrib>Enríquez, Raúl G</creatorcontrib><title>Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>To our previously reported first crystal structure of a homoleptic zinc curcuminoid complex with square pyramidal geometry, we add herein three new geometries of homoleptic type complexes
i.e.
octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseudo-polymorph of the DAC-Zn complex resulting from crystallization in DMF, while square-pyramidal geometry was obtained in DMSO. Improving crystallinity involved suppressing the phenolic interactions by etherification and esterification. The complete characterization of these complexes was carried out using SCXRD, IR, MS, EA, liquid, and solid-state NMR. Moreover, the cytotoxic activity of all complexes was evaluated. The IC
50
values for the DiMeOC-Zn (
7
) complex were 8 or 22 times higher than for cisplatin in the U251 and HCT-15 cell lines, indicating a high antiproliferative and therapeutic potential.
We add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Moreover, the IC
50
values for the DiMeOC-Zn complex were 8 or 22 times higher than cisplatin in the U251 and HCT15 cell lines.</description><subject>Antiproliferatives</subject><subject>Chemistry</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Esterification</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Zinc</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdks1vFCEYxonR2Kb24l1D4sU0WeVjhoGT2VSrJk1MTL14ISy87NDMwAgzrf730t26VrkA7_PLwwsPCD2n5A0lXL11PBtCqOjMI3TMSCNWjAj1-MH6CJ2Wck3qEC1lgj5FR1woLiSXx-j2qs8AOMIttillF6KZQ4p4C2mEOQcoOHncpzENMM3B4u-xguM0wM-9ZJdslzHEFFzBJjo89xAy7sO2r9s5TDkNwUOutjeApzRDLZrhGXrizVDg9H4-Qd8uPlydf1pdfvn4-Xx9ubINU_NKQEssCMs33LOOt60ysm0aRcEIwikxakOcaTrpaC07xhrpfKvAKw-etQ0_Qe_2vtOyGcHZeno2g55yGE3-pZMJ-l8lhl5v042md49KOlkdXt875PRjgTLrMRQLw2AipKVo1kkpCZM79NV_6HVacqz321FN9eSqUmd7yuZUSgZ_6IYSfZepfs-_rneZriv88mH_B_RPghV4sQdysQf176fgvwGC76ix</recordid><startdate>20230314</startdate><enddate>20230314</enddate><creator>Meza-Morales, William</creator><creator>Alvarez-Ricardo, Yair</creator><creator>Obregón-Mendoza, Marco A</creator><creator>Arenaza-Corona, Antonino</creator><creator>Ramírez-Apan, María Teresa</creator><creator>Toscano, Rubén A</creator><creator>Poveda-Jaramillo, Juan Carlos</creator><creator>Enríquez, Raúl G</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-2671-615X</orcidid><orcidid>https://orcid.org/0000-0002-8197-9032</orcidid></search><sort><creationdate>20230314</creationdate><title>Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential</title><author>Meza-Morales, William ; Alvarez-Ricardo, Yair ; Obregón-Mendoza, Marco A ; Arenaza-Corona, Antonino ; Ramírez-Apan, María Teresa ; Toscano, Rubén A ; Poveda-Jaramillo, Juan Carlos ; Enríquez, Raúl G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-6e50ce6c3b3f273559a854491ea60310a9b0da478d1544d2248df59ef9fef2543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antiproliferatives</topic><topic>Chemistry</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Esterification</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meza-Morales, William</creatorcontrib><creatorcontrib>Alvarez-Ricardo, Yair</creatorcontrib><creatorcontrib>Obregón-Mendoza, Marco A</creatorcontrib><creatorcontrib>Arenaza-Corona, Antonino</creatorcontrib><creatorcontrib>Ramírez-Apan, María Teresa</creatorcontrib><creatorcontrib>Toscano, Rubén A</creatorcontrib><creatorcontrib>Poveda-Jaramillo, Juan Carlos</creatorcontrib><creatorcontrib>Enríquez, Raúl G</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Meza-Morales, William</au><au>Alvarez-Ricardo, Yair</au><au>Obregón-Mendoza, Marco A</au><au>Arenaza-Corona, Antonino</au><au>Ramírez-Apan, María Teresa</au><au>Toscano, Rubén A</au><au>Poveda-Jaramillo, Juan Carlos</au><au>Enríquez, Raúl G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2023-03-14</date><risdate>2023</risdate><volume>13</volume><issue>13</issue><spage>8577</spage><epage>8585</epage><pages>8577-8585</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>To our previously reported first crystal structure of a homoleptic zinc curcuminoid complex with square pyramidal geometry, we add herein three new geometries of homoleptic type complexes
i.e.
octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Octahedral geometry was observed in the new pseudo-polymorph of the DAC-Zn complex resulting from crystallization in DMF, while square-pyramidal geometry was obtained in DMSO. Improving crystallinity involved suppressing the phenolic interactions by etherification and esterification. The complete characterization of these complexes was carried out using SCXRD, IR, MS, EA, liquid, and solid-state NMR. Moreover, the cytotoxic activity of all complexes was evaluated. The IC
50
values for the DiMeOC-Zn (
7
) complex were 8 or 22 times higher than for cisplatin in the U251 and HCT-15 cell lines, indicating a high antiproliferative and therapeutic potential.
We add herein three new geometries of homoleptic type complexes i.e. octahedral, trigonal-pyramidal, and trigonal-bipyramidal. Moreover, the IC
50
values for the DiMeOC-Zn complex were 8 or 22 times higher than cisplatin in the U251 and HCT15 cell lines.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36936838</pmid><doi>10.1039/d3ra00167a</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-2671-615X</orcidid><orcidid>https://orcid.org/0000-0002-8197-9032</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Antiproliferatives Chemistry Crystal structure Crystallization Esterification NMR Nuclear magnetic resonance Zinc |
title | Three new coordination geometries of homoleptic Zn complexes of curcuminoids and their high antiproliferative potential |
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