N,O‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery
Herein a new class of iminoboronates obtained from 2‐acetylbenzene boronic acids and aminophenols is presented. The N,O‐ligand topology enabled the formation of an additional B−O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve...
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| Veröffentlicht in: | Chemistry : a European journal 2018-08, Vol.24 (48), p.12495-12499 |
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| creator | Lopes, Ricardo M. R. M. Ventura, Ana E. Silva, Liana C. Faustino, Hélio Gois, Pedro M. P. |
| description | Herein a new class of iminoboronates obtained from 2‐acetylbenzene boronic acids and aminophenols is presented. The N,O‐ligand topology enabled the formation of an additional B−O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct′s stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2‐Acetylbenzene boronic acid was reacted with a fluorescent amino‐coumarin to yield a stable and non‐fluorescent N,O‐iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.
Improving iminoboronate stability: A new class of iminoboronates featuring an additional B−O bond demonstrated improved stability in biocompatible conditions, while retaining the iminoboronate′s reversibility in acidic environments. This core enabled the development of a fluorescence “off–on” mechanism using a fluorescent amino‐coumarin to prepare a stable and non‐fluorescent N,O‐iminoboronate. This methodology was further used to assemble a folate receptor‐targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells. |
| doi_str_mv | 10.1002/chem.201802515 |
| format | Article |
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Improving iminoboronate stability: A new class of iminoboronates featuring an additional B−O bond demonstrated improved stability in biocompatible conditions, while retaining the iminoboronate′s reversibility in acidic environments. This core enabled the development of a fluorescence “off–on” mechanism using a fluorescent amino‐coumarin to prepare a stable and non‐fluorescent N,O‐iminoboronate. This methodology was further used to assemble a folate receptor‐targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201802515</identifier><identifier>PMID: 29889332</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Biocompatibility ; Boron ; boronic acids ; Boronic Acids - chemistry ; Breast cancer ; Cancer ; Cell Line, Tumor ; Chemistry ; Coumarin ; Coumarins - administration & dosage ; Coumarins - chemistry ; Drug Carriers - chemistry ; drug delivery ; Drug Liberation ; Drug Stability ; Fluorescence ; Fluorescent Dyes - administration & dosage ; Fluorescent Dyes - chemistry ; Folic acid ; Folic Acid Transporters - metabolism ; Humans ; Hydrogen-Ion Concentration ; Imines - chemistry ; iminoboronate ; Locks ; reversibility ; small-molecule-drug conjugates ; Stability ; Topology ; Tumor Microenvironment</subject><ispartof>Chemistry : a European journal, 2018-08, Vol.24 (48), p.12495-12499</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4105-a6198d707cfda0759ca5c519471ba4f98af654919aab7cfe7e8fd2cc1477ff7b3</citedby><cites>FETCH-LOGICAL-c4105-a6198d707cfda0759ca5c519471ba4f98af654919aab7cfe7e8fd2cc1477ff7b3</cites><orcidid>0000-0002-7698-630X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201802515$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201802515$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29889332$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lopes, Ricardo M. R. M.</creatorcontrib><creatorcontrib>Ventura, Ana E.</creatorcontrib><creatorcontrib>Silva, Liana C.</creatorcontrib><creatorcontrib>Faustino, Hélio</creatorcontrib><creatorcontrib>Gois, Pedro M. P.</creatorcontrib><title>N,O‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Herein a new class of iminoboronates obtained from 2‐acetylbenzene boronic acids and aminophenols is presented. The N,O‐ligand topology enabled the formation of an additional B−O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct′s stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2‐Acetylbenzene boronic acid was reacted with a fluorescent amino‐coumarin to yield a stable and non‐fluorescent N,O‐iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.
Improving iminoboronate stability: A new class of iminoboronates featuring an additional B−O bond demonstrated improved stability in biocompatible conditions, while retaining the iminoboronate′s reversibility in acidic environments. This core enabled the development of a fluorescence “off–on” mechanism using a fluorescent amino‐coumarin to prepare a stable and non‐fluorescent N,O‐iminoboronate. This methodology was further used to assemble a folate receptor‐targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.</description><subject>Biocompatibility</subject><subject>Boron</subject><subject>boronic acids</subject><subject>Boronic Acids - chemistry</subject><subject>Breast cancer</subject><subject>Cancer</subject><subject>Cell Line, Tumor</subject><subject>Chemistry</subject><subject>Coumarin</subject><subject>Coumarins - administration & dosage</subject><subject>Coumarins - chemistry</subject><subject>Drug Carriers - chemistry</subject><subject>drug delivery</subject><subject>Drug Liberation</subject><subject>Drug Stability</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - administration & dosage</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Folic acid</subject><subject>Folic Acid Transporters - metabolism</subject><subject>Humans</subject><subject>Hydrogen-Ion Concentration</subject><subject>Imines - chemistry</subject><subject>iminoboronate</subject><subject>Locks</subject><subject>reversibility</subject><subject>small-molecule-drug conjugates</subject><subject>Stability</subject><subject>Topology</subject><subject>Tumor Microenvironment</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkclOwzAURS0EgjJsWaJIbFiQ4iGOY3aolEEqIEFZR47zDK4ygJ226o5P4Bv5EozKINiwepLf8dG1L0K7BPcJxvRIP0Ldp5hkmHLCV1CPcEpiJlK-inpYJiJOOZMbaNP7CcZYpoytow0qs0wyRntocn148_byelnbpi1a1zaqA38c3cIMnLdFBdHvVTS33WM4e3LtDMrorlOFrWy3iEzrooFqNIQBVeWjsXIP0AXmFCobbItttGZU5WHnc26h-7PheHARj27OLwcno1gnBPNYpURmpcBCm1JhwaVWXHMSnkIKlRiZKZPyRBKpVBEYEJCZkmpNEiGMEQXbQgdLb8j4PAXf5bX1OmRSDbRTn1PMGRUkGAO6_wedtFPXhHSBCnsu04QFqr-ktGu9d2DyJ2dr5RY5wflHC_lHC_l3C-HC3qd2WtRQfuNf3x4AuQTmtoLFP7p8cDG8-pG_A2DHlao</recordid><startdate>20180827</startdate><enddate>20180827</enddate><creator>Lopes, Ricardo M. R. M.</creator><creator>Ventura, Ana E.</creator><creator>Silva, Liana C.</creator><creator>Faustino, Hélio</creator><creator>Gois, Pedro M. P.</creator><general>Wiley Subscription Services, Inc</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>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7698-630X</orcidid></search><sort><creationdate>20180827</creationdate><title>N,O‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery</title><author>Lopes, Ricardo M. R. M. ; Ventura, Ana E. ; Silva, Liana C. ; Faustino, Hélio ; Gois, Pedro M. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4105-a6198d707cfda0759ca5c519471ba4f98af654919aab7cfe7e8fd2cc1477ff7b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Biocompatibility</topic><topic>Boron</topic><topic>boronic acids</topic><topic>Boronic Acids - chemistry</topic><topic>Breast cancer</topic><topic>Cancer</topic><topic>Cell Line, Tumor</topic><topic>Chemistry</topic><topic>Coumarin</topic><topic>Coumarins - administration & dosage</topic><topic>Coumarins - chemistry</topic><topic>Drug Carriers - chemistry</topic><topic>drug delivery</topic><topic>Drug Liberation</topic><topic>Drug Stability</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - administration & dosage</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Folic acid</topic><topic>Folic Acid Transporters - metabolism</topic><topic>Humans</topic><topic>Hydrogen-Ion Concentration</topic><topic>Imines - chemistry</topic><topic>iminoboronate</topic><topic>Locks</topic><topic>reversibility</topic><topic>small-molecule-drug conjugates</topic><topic>Stability</topic><topic>Topology</topic><topic>Tumor Microenvironment</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lopes, Ricardo M. R. M.</creatorcontrib><creatorcontrib>Ventura, Ana E.</creatorcontrib><creatorcontrib>Silva, Liana C.</creatorcontrib><creatorcontrib>Faustino, Hélio</creatorcontrib><creatorcontrib>Gois, Pedro M. P.</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>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lopes, Ricardo M. R. M.</au><au>Ventura, Ana E.</au><au>Silva, Liana C.</au><au>Faustino, Hélio</au><au>Gois, Pedro M. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N,O‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2018-08-27</date><risdate>2018</risdate><volume>24</volume><issue>48</issue><spage>12495</spage><epage>12499</epage><pages>12495-12499</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Herein a new class of iminoboronates obtained from 2‐acetylbenzene boronic acids and aminophenols is presented. The N,O‐ligand topology enabled the formation of an additional B−O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct′s stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2‐Acetylbenzene boronic acid was reacted with a fluorescent amino‐coumarin to yield a stable and non‐fluorescent N,O‐iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.
Improving iminoboronate stability: A new class of iminoboronates featuring an additional B−O bond demonstrated improved stability in biocompatible conditions, while retaining the iminoboronate′s reversibility in acidic environments. This core enabled the development of a fluorescence “off–on” mechanism using a fluorescent amino‐coumarin to prepare a stable and non‐fluorescent N,O‐iminoboronate. This methodology was further used to assemble a folate receptor‐targeting conjugate that selectively delivered the fluorescent amino‐coumarin to MDA‐MB‐231 human breast cancer cells.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29889332</pmid><doi>10.1002/chem.201802515</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-7698-630X</orcidid></addata></record> |
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| subjects | Biocompatibility Boron boronic acids Boronic Acids - chemistry Breast cancer Cancer Cell Line, Tumor Chemistry Coumarin Coumarins - administration & dosage Coumarins - chemistry Drug Carriers - chemistry drug delivery Drug Liberation Drug Stability Fluorescence Fluorescent Dyes - administration & dosage Fluorescent Dyes - chemistry Folic acid Folic Acid Transporters - metabolism Humans Hydrogen-Ion Concentration Imines - chemistry iminoboronate Locks reversibility small-molecule-drug conjugates Stability Topology Tumor Microenvironment |
| title | N,O‐Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery |
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