Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide
Environment-sensitive fluorophores have different quantum yields in different solvents. 6-Dimethylaminonaphthalimide (6-DMN), for example, has a low quantum yield in aqueous solutions, but is highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. 6-DMN h...
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| Veröffentlicht in: | Nature protocols 2011-12, Vol.6 (12), p.1990-1997 |
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| creator | Baathulaa, Kishore Xu, Yufang Qian, Xuhong |
| description | Environment-sensitive fluorophores have different quantum yields in different solvents. 6-Dimethylaminonaphthalimide (6-DMN), for example, has a low quantum yield in aqueous solutions, but is highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. 6-DMN has been used to investigate protein-protein interactions, as well as the in-tissue distribution and internalization of δ-receptors. This protocol describes a highly efficient three-stage synthesis of 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride (compound 1), which is a stable precursor that can be converted to 6-DMN. The three stages are (i) photo-bromination of 4-nitro-
o
-xylene (yield 82%), (ii) Diels-Alder reaction followed by base hydrolysis, resulting in 6-nitro-2,3-naphthalenedicarboxylic acid (yield 87%) and (iii) reductive amination followed by dehydration (yield 76.5%) to form compound 1. The synthesis can be performed on a gram scale (in 55 h over 3 d) with an overall yield of about 55%. It can easily be modified to prepare related compounds by, for example, performing different reactions using 6-nitro-2,3-naphthalenedicarboxylic acid. |
| doi_str_mv | 10.1038/nprot.2011.415 |
| format | Article |
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o
-xylene (yield 82%), (ii) Diels-Alder reaction followed by base hydrolysis, resulting in 6-nitro-2,3-naphthalenedicarboxylic acid (yield 87%) and (iii) reductive amination followed by dehydration (yield 76.5%) to form compound 1. The synthesis can be performed on a gram scale (in 55 h over 3 d) with an overall yield of about 55%. It can easily be modified to prepare related compounds by, for example, performing different reactions using 6-nitro-2,3-naphthalenedicarboxylic acid.</description><identifier>ISSN: 1754-2189</identifier><identifier>EISSN: 1750-2799</identifier><identifier>DOI: 10.1038/nprot.2011.415</identifier><identifier>PMID: 22134124</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>631/1647/666 ; Amination ; Amino acids ; Analytical Chemistry ; Anhydrides ; Binding sites ; Biological activity ; Biological Techniques ; Biomedical and Life Sciences ; Chemical synthesis ; Computational Biology/Bioinformatics ; Dehydration ; Fluorescent chemicals ; Fluorescent Dyes ; Hydrolysis ; Life Sciences ; Methods ; Microarrays ; Naphthalenes - chemical synthesis ; Naphthalenes - chemistry ; Naphthalimides - chemistry ; Narcotics ; Organic Chemistry ; Peptides ; Production processes ; Proteins ; protocol ; Solvents ; Xylene</subject><ispartof>Nature protocols, 2011-12, Vol.6 (12), p.1990-1997</ispartof><rights>Springer Nature Limited 2011</rights><rights>COPYRIGHT 2011 Nature Publishing Group</rights><rights>Copyright Nature Publishing Group Dec 2011</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431t-7622ff7b06f74cd7d368ca3170e7639f5823839aca8bd090652386a34ee04d0a3</citedby><cites>FETCH-LOGICAL-c431t-7622ff7b06f74cd7d368ca3170e7639f5823839aca8bd090652386a34ee04d0a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1038/nprot.2011.415$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1038/nprot.2011.415$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22134124$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Baathulaa, Kishore</creatorcontrib><creatorcontrib>Xu, Yufang</creatorcontrib><creatorcontrib>Qian, Xuhong</creatorcontrib><title>Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide</title><title>Nature protocols</title><addtitle>Nat Protoc</addtitle><addtitle>Nat Protoc</addtitle><description>Environment-sensitive fluorophores have different quantum yields in different solvents. 6-Dimethylaminonaphthalimide (6-DMN), for example, has a low quantum yield in aqueous solutions, but is highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. 6-DMN has been used to investigate protein-protein interactions, as well as the in-tissue distribution and internalization of δ-receptors. This protocol describes a highly efficient three-stage synthesis of 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride (compound 1), which is a stable precursor that can be converted to 6-DMN. The three stages are (i) photo-bromination of 4-nitro-
o
-xylene (yield 82%), (ii) Diels-Alder reaction followed by base hydrolysis, resulting in 6-nitro-2,3-naphthalenedicarboxylic acid (yield 87%) and (iii) reductive amination followed by dehydration (yield 76.5%) to form compound 1. The synthesis can be performed on a gram scale (in 55 h over 3 d) with an overall yield of about 55%. It can easily be modified to prepare related compounds by, for example, performing different reactions using 6-nitro-2,3-naphthalenedicarboxylic acid.</description><subject>631/1647/666</subject><subject>Amination</subject><subject>Amino acids</subject><subject>Analytical Chemistry</subject><subject>Anhydrides</subject><subject>Binding sites</subject><subject>Biological activity</subject><subject>Biological Techniques</subject><subject>Biomedical and Life Sciences</subject><subject>Chemical synthesis</subject><subject>Computational Biology/Bioinformatics</subject><subject>Dehydration</subject><subject>Fluorescent chemicals</subject><subject>Fluorescent Dyes</subject><subject>Hydrolysis</subject><subject>Life Sciences</subject><subject>Methods</subject><subject>Microarrays</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - chemistry</subject><subject>Naphthalimides - chemistry</subject><subject>Narcotics</subject><subject>Organic Chemistry</subject><subject>Peptides</subject><subject>Production processes</subject><subject>Proteins</subject><subject>protocol</subject><subject>Solvents</subject><subject>Xylene</subject><issn>1754-2189</issn><issn>1750-2799</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp1kd1rFDEUxYNYbF199VEGX4rIbPM1yczjslgtlAq24mPIztzZSckkY5IpLvSPN9utikIhkFzOL4d770HoDcFLgll95qbg05JiQpacVM_QCZEVLqlsmucPb15SUjfH6GWMtxhzyYR8gY4pJYwTyk_Q_fXgQyq064rYaqs3Foq4c2mAaGLh-6zkM-y6YDoopgDtHKIPeyUzBbg7E7wbwaUygosmmTsoejv74KfsDIUoOzNCGnZWj8Z5p6chDdqaMfu9Qke9thFeP94L9O384836c3n55dPFenVZtpyRVEpBad_LDRa95G0nOybqVjMiMUjBmr6qKatZo1tdbzrcYFHlWmjGATDvsGYLdHrwzcv6MUNMajSxBWu1Az9H1eBasrrKJgv07j_y1s_B5eZUQzHlXEiWofcHaKstKONa7xL8TFs9x6gurr-qlWC0JhWXOLMfnmZXN9_XV__SywPdBh9jgF5NwYw67BTBap-3eshb7fNWOe_84e1jv_NmhO4P_jvgDJwdgJglt4Xwd6AnLH8BG2K3TA</recordid><startdate>20111201</startdate><enddate>20111201</enddate><creator>Baathulaa, Kishore</creator><creator>Xu, Yufang</creator><creator>Qian, Xuhong</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</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>ATWCN</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7T5</scope><scope>7T7</scope><scope>7TM</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PATMY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PYCSY</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20111201</creationdate><title>Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide</title><author>Baathulaa, Kishore ; Xu, Yufang ; Qian, Xuhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c431t-7622ff7b06f74cd7d368ca3170e7639f5823839aca8bd090652386a34ee04d0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>631/1647/666</topic><topic>Amination</topic><topic>Amino acids</topic><topic>Analytical Chemistry</topic><topic>Anhydrides</topic><topic>Binding sites</topic><topic>Biological activity</topic><topic>Biological Techniques</topic><topic>Biomedical and Life Sciences</topic><topic>Chemical synthesis</topic><topic>Computational Biology/Bioinformatics</topic><topic>Dehydration</topic><topic>Fluorescent chemicals</topic><topic>Fluorescent Dyes</topic><topic>Hydrolysis</topic><topic>Life Sciences</topic><topic>Methods</topic><topic>Microarrays</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - chemistry</topic><topic>Naphthalimides - chemistry</topic><topic>Narcotics</topic><topic>Organic Chemistry</topic><topic>Peptides</topic><topic>Production processes</topic><topic>Proteins</topic><topic>protocol</topic><topic>Solvents</topic><topic>Xylene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baathulaa, Kishore</creatorcontrib><creatorcontrib>Xu, Yufang</creatorcontrib><creatorcontrib>Qian, Xuhong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Gale In Context: Middle School</collection><collection>Gale In Context: Science</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Immunology Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environmental Science Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>Environmental Science Collection</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Nature protocols</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Baathulaa, Kishore</au><au>Xu, Yufang</au><au>Qian, Xuhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide</atitle><jtitle>Nature protocols</jtitle><stitle>Nat Protoc</stitle><addtitle>Nat Protoc</addtitle><date>2011-12-01</date><risdate>2011</risdate><volume>6</volume><issue>12</issue><spage>1990</spage><epage>1997</epage><pages>1990-1997</pages><issn>1754-2189</issn><eissn>1750-2799</eissn><abstract>Environment-sensitive fluorophores have different quantum yields in different solvents. 6-Dimethylaminonaphthalimide (6-DMN), for example, has a low quantum yield in aqueous solutions, but is highly fluorescent in nonpolar solvents or when bound to hydrophobic sites in proteins or membranes. 6-DMN has been used to investigate protein-protein interactions, as well as the in-tissue distribution and internalization of δ-receptors. This protocol describes a highly efficient three-stage synthesis of 6-dimethylamino-2,3-naphthalenedicarboxylic anhydride (compound 1), which is a stable precursor that can be converted to 6-DMN. The three stages are (i) photo-bromination of 4-nitro-
o
-xylene (yield 82%), (ii) Diels-Alder reaction followed by base hydrolysis, resulting in 6-nitro-2,3-naphthalenedicarboxylic acid (yield 87%) and (iii) reductive amination followed by dehydration (yield 76.5%) to form compound 1. The synthesis can be performed on a gram scale (in 55 h over 3 d) with an overall yield of about 55%. It can easily be modified to prepare related compounds by, for example, performing different reactions using 6-nitro-2,3-naphthalenedicarboxylic acid.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>22134124</pmid><doi>10.1038/nprot.2011.415</doi><tpages>8</tpages></addata></record> |
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| subjects | 631/1647/666 Amination Amino acids Analytical Chemistry Anhydrides Binding sites Biological activity Biological Techniques Biomedical and Life Sciences Chemical synthesis Computational Biology/Bioinformatics Dehydration Fluorescent chemicals Fluorescent Dyes Hydrolysis Life Sciences Methods Microarrays Naphthalenes - chemical synthesis Naphthalenes - chemistry Naphthalimides - chemistry Narcotics Organic Chemistry Peptides Production processes Proteins protocol Solvents Xylene |
| title | Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide |
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