Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing
A series of simple copper N 2 S 2 macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous bu...
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creator | Sowden, Rebecca J. Trotter, Katherine D. Dunbar, Lynsey Craig, Gemma Erdemli, Omer Spickett, Corinne M. Reglinski, John |
description | A series of simple copper N
2
S
2
macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous buffer. A less efficient reduction was also achieved by vitamin E in DMSO. Oxidation of the corresponding univalent copper species by sodium hypochlorite resulted in only partial (~65 %) recovery of the divalent form. This was concluded to be due to competition between metal oxidation and ligand oxidation, which is believed to contribute to macrocycle demetallation. Electrospray mass spectrometry confirmed that ligand oxidation had occurred. Moreover, the macrocyclic complexes could be demetallated by incubation with EDTA and bovine serum albumin, demonstrating that they would be inappropriate for use in biological systems. The susceptibility to oxidation and demetallation was hypothesized to be due to oxidation of the secondary amines. Consequently these were modified to incorporate additional oxygen donor atoms. This modification led to greater resistance to demetallation and ligand oxidation, providing a better platform for further development of copper macrocycles as redox sensors for use in biological systems. |
doi_str_mv | 10.1007/s10534-012-9596-9 |
format | Article |
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2
S
2
macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous buffer. A less efficient reduction was also achieved by vitamin E in DMSO. Oxidation of the corresponding univalent copper species by sodium hypochlorite resulted in only partial (~65 %) recovery of the divalent form. This was concluded to be due to competition between metal oxidation and ligand oxidation, which is believed to contribute to macrocycle demetallation. Electrospray mass spectrometry confirmed that ligand oxidation had occurred. Moreover, the macrocyclic complexes could be demetallated by incubation with EDTA and bovine serum albumin, demonstrating that they would be inappropriate for use in biological systems. The susceptibility to oxidation and demetallation was hypothesized to be due to oxidation of the secondary amines. Consequently these were modified to incorporate additional oxygen donor atoms. This modification led to greater resistance to demetallation and ligand oxidation, providing a better platform for further development of copper macrocycles as redox sensors for use in biological systems.</description><identifier>ISSN: 0966-0844</identifier><identifier>EISSN: 1572-8773</identifier><identifier>DOI: 10.1007/s10534-012-9596-9</identifier><identifier>PMID: 23160798</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Amines ; Animals ; Antioxidants ; Antioxidants - chemistry ; Ascorbic Acid - chemistry ; Biochemistry ; Biological ; Biomedical and Life Sciences ; Cattle ; Cell Biology ; Chelating Agents - chemistry ; Coordination Complexes - chemistry ; Copper ; Copper - chemistry ; Edetic Acid - chemistry ; EDTA ; Electrode potentials ; Ethers, Cyclic - chemistry ; Glutathione - chemistry ; Hypochlorous Acid - chemistry ; Life Sciences ; Ligands ; Macrocyclic compounds ; Mass spectrometry ; Medicine/Public Health ; Microbiology ; Molecular Weight ; Oxidants - chemistry ; Oxidation ; Oxidation-Reduction ; Oxidative stress ; Pharmacology/Toxicology ; Plant Physiology ; Reducing Agents - chemistry ; Reduction ; Sensors ; Serum Albumin, Bovine - chemistry ; Sodium Hypochlorite - chemistry ; Solutions ; Sulfides - chemistry ; Vitamin E ; Vitamin E - chemistry</subject><ispartof>Biometals, 2013-02, Vol.26 (1), p.85-96</ispartof><rights>Springer Science+Business Media New York 2012</rights><rights>Springer Science+Business Media New York 2013</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-d2423f62497e971a9fb9f474d4bec142220db6a8db562d51868f6d340cd6c8cf3</citedby><cites>FETCH-LOGICAL-c405t-d2423f62497e971a9fb9f474d4bec142220db6a8db562d51868f6d340cd6c8cf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10534-012-9596-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10534-012-9596-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27926,27927,41490,42559,51321</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23160798$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sowden, Rebecca J.</creatorcontrib><creatorcontrib>Trotter, Katherine D.</creatorcontrib><creatorcontrib>Dunbar, Lynsey</creatorcontrib><creatorcontrib>Craig, Gemma</creatorcontrib><creatorcontrib>Erdemli, Omer</creatorcontrib><creatorcontrib>Spickett, Corinne M.</creatorcontrib><creatorcontrib>Reglinski, John</creatorcontrib><title>Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing</title><title>Biometals</title><addtitle>Biometals</addtitle><addtitle>Biometals</addtitle><description>A series of simple copper N
2
S
2
macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous buffer. A less efficient reduction was also achieved by vitamin E in DMSO. Oxidation of the corresponding univalent copper species by sodium hypochlorite resulted in only partial (~65 %) recovery of the divalent form. This was concluded to be due to competition between metal oxidation and ligand oxidation, which is believed to contribute to macrocycle demetallation. Electrospray mass spectrometry confirmed that ligand oxidation had occurred. Moreover, the macrocyclic complexes could be demetallated by incubation with EDTA and bovine serum albumin, demonstrating that they would be inappropriate for use in biological systems. The susceptibility to oxidation and demetallation was hypothesized to be due to oxidation of the secondary amines. Consequently these were modified to incorporate additional oxygen donor atoms. This modification led to greater resistance to demetallation and ligand oxidation, providing a better platform for further development of copper macrocycles as redox sensors for use in biological systems.</description><subject>Amines</subject><subject>Animals</subject><subject>Antioxidants</subject><subject>Antioxidants - chemistry</subject><subject>Ascorbic Acid - chemistry</subject><subject>Biochemistry</subject><subject>Biological</subject><subject>Biomedical and Life Sciences</subject><subject>Cattle</subject><subject>Cell Biology</subject><subject>Chelating Agents - chemistry</subject><subject>Coordination Complexes - chemistry</subject><subject>Copper</subject><subject>Copper - chemistry</subject><subject>Edetic Acid - chemistry</subject><subject>EDTA</subject><subject>Electrode potentials</subject><subject>Ethers, Cyclic - chemistry</subject><subject>Glutathione - chemistry</subject><subject>Hypochlorous Acid - chemistry</subject><subject>Life Sciences</subject><subject>Ligands</subject><subject>Macrocyclic compounds</subject><subject>Mass spectrometry</subject><subject>Medicine/Public Health</subject><subject>Microbiology</subject><subject>Molecular Weight</subject><subject>Oxidants - chemistry</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Oxidative stress</subject><subject>Pharmacology/Toxicology</subject><subject>Plant Physiology</subject><subject>Reducing Agents - chemistry</subject><subject>Reduction</subject><subject>Sensors</subject><subject>Serum Albumin, Bovine - chemistry</subject><subject>Sodium Hypochlorite - chemistry</subject><subject>Solutions</subject><subject>Sulfides - chemistry</subject><subject>Vitamin E</subject><subject>Vitamin E - chemistry</subject><issn>0966-0844</issn><issn>1572-8773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</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>eNqFkV1rFDEUhoModm39Ab2RgDfejJ6cZJJJ78qitlAoiL0OmXxsp8xOpskstv_eLFuLFMSrw-E8eXOSh5BTBp8ZgPpSGLRcNMCw0a2WjX5FVqxV2HRK8ddkBVrKBjohjsi7Uu4AQCuQb8kRciZB6W5F-h_BumVIU6EpUpfmOWS6tS4n9-jGUOivYbmldqrIw-BrLbXx9OJ6PZ7ROS2hTuxIY8q0H9KYNoOrbQ4-PdASpjJMmxPyJtqxhPdP9ZjcfPv6c33RXF1_v1yfXzVOQLs0HgXyKFFoFbRiVsdeR6GEF31wTCAi-F7azvetRN-yTnZRei7Aeek6F_kx-XTInXO634WymO1QXBhHO4W0K4Zx5IhcCP1_FDuOCrSGin58gd6lXZ7qQ_YUtozpVlSKHaj6caXkEM2ch63Nj4aB2bsyB1emujJ7V2a_xIen5F2_Df75xB85FcADUOpo2oT819X_TP0NGRyefQ</recordid><startdate>20130201</startdate><enddate>20130201</enddate><creator>Sowden, Rebecca J.</creator><creator>Trotter, Katherine D.</creator><creator>Dunbar, Lynsey</creator><creator>Craig, Gemma</creator><creator>Erdemli, Omer</creator><creator>Spickett, Corinne M.</creator><creator>Reglinski, John</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>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></search><sort><creationdate>20130201</creationdate><title>Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing</title><author>Sowden, Rebecca J. ; Trotter, Katherine D. ; Dunbar, Lynsey ; Craig, Gemma ; Erdemli, Omer ; Spickett, Corinne M. ; Reglinski, John</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-d2423f62497e971a9fb9f474d4bec142220db6a8db562d51868f6d340cd6c8cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Amines</topic><topic>Animals</topic><topic>Antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>Ascorbic Acid - chemistry</topic><topic>Biochemistry</topic><topic>Biological</topic><topic>Biomedical and Life Sciences</topic><topic>Cattle</topic><topic>Cell Biology</topic><topic>Chelating Agents - chemistry</topic><topic>Coordination Complexes - chemistry</topic><topic>Copper</topic><topic>Copper - chemistry</topic><topic>Edetic Acid - chemistry</topic><topic>EDTA</topic><topic>Electrode potentials</topic><topic>Ethers, Cyclic - chemistry</topic><topic>Glutathione - chemistry</topic><topic>Hypochlorous Acid - chemistry</topic><topic>Life Sciences</topic><topic>Ligands</topic><topic>Macrocyclic compounds</topic><topic>Mass spectrometry</topic><topic>Medicine/Public Health</topic><topic>Microbiology</topic><topic>Molecular Weight</topic><topic>Oxidants - chemistry</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Oxidative stress</topic><topic>Pharmacology/Toxicology</topic><topic>Plant Physiology</topic><topic>Reducing Agents - chemistry</topic><topic>Reduction</topic><topic>Sensors</topic><topic>Serum Albumin, Bovine - chemistry</topic><topic>Sodium Hypochlorite - chemistry</topic><topic>Solutions</topic><topic>Sulfides - chemistry</topic><topic>Vitamin E</topic><topic>Vitamin E - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sowden, Rebecca J.</creatorcontrib><creatorcontrib>Trotter, Katherine D.</creatorcontrib><creatorcontrib>Dunbar, Lynsey</creatorcontrib><creatorcontrib>Craig, Gemma</creatorcontrib><creatorcontrib>Erdemli, Omer</creatorcontrib><creatorcontrib>Spickett, Corinne M.</creatorcontrib><creatorcontrib>Reglinski, John</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology 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>Materials Science & Engineering Collection</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>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic 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>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Engineering Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environmental Science Database</collection><collection>Earth, Atmospheric & Aquatic 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>Engineering Collection</collection><collection>Environmental Science Collection</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Biometals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sowden, Rebecca J.</au><au>Trotter, Katherine D.</au><au>Dunbar, Lynsey</au><au>Craig, Gemma</au><au>Erdemli, Omer</au><au>Spickett, Corinne M.</au><au>Reglinski, John</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing</atitle><jtitle>Biometals</jtitle><stitle>Biometals</stitle><addtitle>Biometals</addtitle><date>2013-02-01</date><risdate>2013</risdate><volume>26</volume><issue>1</issue><spage>85</spage><epage>96</epage><pages>85-96</pages><issn>0966-0844</issn><eissn>1572-8773</eissn><abstract>A series of simple copper N
2
S
2
macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous buffer. A less efficient reduction was also achieved by vitamin E in DMSO. Oxidation of the corresponding univalent copper species by sodium hypochlorite resulted in only partial (~65 %) recovery of the divalent form. This was concluded to be due to competition between metal oxidation and ligand oxidation, which is believed to contribute to macrocycle demetallation. Electrospray mass spectrometry confirmed that ligand oxidation had occurred. Moreover, the macrocyclic complexes could be demetallated by incubation with EDTA and bovine serum albumin, demonstrating that they would be inappropriate for use in biological systems. The susceptibility to oxidation and demetallation was hypothesized to be due to oxidation of the secondary amines. Consequently these were modified to incorporate additional oxygen donor atoms. This modification led to greater resistance to demetallation and ligand oxidation, providing a better platform for further development of copper macrocycles as redox sensors for use in biological systems.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><pmid>23160798</pmid><doi>10.1007/s10534-012-9596-9</doi><tpages>12</tpages></addata></record> |
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subjects | Amines Animals Antioxidants Antioxidants - chemistry Ascorbic Acid - chemistry Biochemistry Biological Biomedical and Life Sciences Cattle Cell Biology Chelating Agents - chemistry Coordination Complexes - chemistry Copper Copper - chemistry Edetic Acid - chemistry EDTA Electrode potentials Ethers, Cyclic - chemistry Glutathione - chemistry Hypochlorous Acid - chemistry Life Sciences Ligands Macrocyclic compounds Mass spectrometry Medicine/Public Health Microbiology Molecular Weight Oxidants - chemistry Oxidation Oxidation-Reduction Oxidative stress Pharmacology/Toxicology Plant Physiology Reducing Agents - chemistry Reduction Sensors Serum Albumin, Bovine - chemistry Sodium Hypochlorite - chemistry Solutions Sulfides - chemistry Vitamin E Vitamin E - chemistry |
title | Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing |
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