Structure-mutagenicity relationships of four amino-imidazonaphthyridines and imidazoquinolines
We tested four isomeric imidazonaphthyridines and one imidazoquinoline compound for mutagenic activity in the Ames/Salmonella mutagenicity assay, using strain TA98 and strain YG1024, an analogue of strain TA98 with elevated O‐acetyl‐transferase levels. Their potency was related to calculated electro...
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| Veröffentlicht in: | Environmental and molecular mutagenesis 1995, Vol.26 (1), p.79-85 |
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| container_title | Environmental and molecular mutagenesis |
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| creator | Vikse, R. Hatch, F. T. Winter, N. W. Knize, M. G. Grivas, S. Felton, J. S. |
| description | We tested four isomeric imidazonaphthyridines and one imidazoquinoline compound for mutagenic activity in the Ames/Salmonella mutagenicity assay, using strain TA98 and strain YG1024, an analogue of strain TA98 with elevated O‐acetyl‐transferase levels. Their potency was related to calculated electronic parameters. Five compounds with a linear arrangement of 3 rings showed a positive response in strain YG1024. Compound 2 (1‐methyl‐imidazo[4,5‐b][1,7]naphthyridin‐2‐amine) is the most mutagenic in both strains, giving specific activities of about 200 and 30 revertants per microgram in strains YG1024 and TA98, respectively. Three of the compounds were weak mutagens, giving a positive dose‐response only in strain YG1024, with 3–5 revertants per microgram. A higher response of all five compounds in strain YG1024 as opposed to TA98 indicates that they require O‐acetyltransferase activity for their metabolism. Mutagenic potencies in strain YG1024 were positively correlated to the energy of the LUMO (lowest unoccupied molecular orbital) of the nitrenium ion. © 1995 Wiley‐Liss, Inc. |
| doi_str_mv | 10.1002/em.2850260112 |
| format | Article |
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T. ; Winter, N. W. ; Knize, M. G. ; Grivas, S. ; Felton, J. S.</creator><creatorcontrib>Vikse, R. ; Hatch, F. T. ; Winter, N. W. ; Knize, M. G. ; Grivas, S. ; Felton, J. S.</creatorcontrib><description>We tested four isomeric imidazonaphthyridines and one imidazoquinoline compound for mutagenic activity in the Ames/Salmonella mutagenicity assay, using strain TA98 and strain YG1024, an analogue of strain TA98 with elevated O‐acetyl‐transferase levels. Their potency was related to calculated electronic parameters. Five compounds with a linear arrangement of 3 rings showed a positive response in strain YG1024. Compound 2 (1‐methyl‐imidazo[4,5‐b][1,7]naphthyridin‐2‐amine) is the most mutagenic in both strains, giving specific activities of about 200 and 30 revertants per microgram in strains YG1024 and TA98, respectively. Three of the compounds were weak mutagens, giving a positive dose‐response only in strain YG1024, with 3–5 revertants per microgram. A higher response of all five compounds in strain YG1024 as opposed to TA98 indicates that they require O‐acetyltransferase activity for their metabolism. Mutagenic potencies in strain YG1024 were positively correlated to the energy of the LUMO (lowest unoccupied molecular orbital) of the nitrenium ion. © 1995 Wiley‐Liss, Inc.</description><identifier>ISSN: 0893-6692</identifier><identifier>EISSN: 1098-2280</identifier><identifier>DOI: 10.1002/em.2850260112</identifier><identifier>PMID: 7641711</identifier><identifier>CODEN: EMMUEG</identifier><language>eng</language><publisher>New York: Wiley Subscription Services, Inc., A Wiley Company</publisher><subject>Ames test ; aminoimidazo-azaarenes ; aromatic amines ; Biological and medical sciences ; Chemical mutagenesis ; Dose-Response Relationship, Drug ; Imidazoles - chemistry ; Imidazoles - pharmacology ; Medical sciences ; Molecular Structure ; Mutagenicity Tests ; Mutagens - chemistry ; Mutagens - pharmacology ; Naphthyridines - chemistry ; Naphthyridines - pharmacology ; Quinolines - chemistry ; Quinolines - pharmacology ; Salmonella mutagenicity ; Salmonella typhimurium ; Salmonella typhimurium - drug effects ; Structure-Activity Relationship ; structure/activity ; Toxicology ; YG1024</subject><ispartof>Environmental and molecular mutagenesis, 1995, Vol.26 (1), p.79-85</ispartof><rights>Copyright © 1995 Wiley‐Liss, Inc., A Wiley Company</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3492-239b717d1ba31dc60ac5809520b5a53ad1da0312dfdca3f68d9d3e84d0981dd83</citedby><cites>FETCH-LOGICAL-c3492-239b717d1ba31dc60ac5809520b5a53ad1da0312dfdca3f68d9d3e84d0981dd83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fem.2850260112$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fem.2850260112$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,4010,27900,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3608717$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7641711$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vikse, R.</creatorcontrib><creatorcontrib>Hatch, F. T.</creatorcontrib><creatorcontrib>Winter, N. W.</creatorcontrib><creatorcontrib>Knize, M. G.</creatorcontrib><creatorcontrib>Grivas, S.</creatorcontrib><creatorcontrib>Felton, J. S.</creatorcontrib><title>Structure-mutagenicity relationships of four amino-imidazonaphthyridines and imidazoquinolines</title><title>Environmental and molecular mutagenesis</title><addtitle>Environ. Mol. Mutagen</addtitle><description>We tested four isomeric imidazonaphthyridines and one imidazoquinoline compound for mutagenic activity in the Ames/Salmonella mutagenicity assay, using strain TA98 and strain YG1024, an analogue of strain TA98 with elevated O‐acetyl‐transferase levels. Their potency was related to calculated electronic parameters. Five compounds with a linear arrangement of 3 rings showed a positive response in strain YG1024. Compound 2 (1‐methyl‐imidazo[4,5‐b][1,7]naphthyridin‐2‐amine) is the most mutagenic in both strains, giving specific activities of about 200 and 30 revertants per microgram in strains YG1024 and TA98, respectively. Three of the compounds were weak mutagens, giving a positive dose‐response only in strain YG1024, with 3–5 revertants per microgram. A higher response of all five compounds in strain YG1024 as opposed to TA98 indicates that they require O‐acetyltransferase activity for their metabolism. Mutagenic potencies in strain YG1024 were positively correlated to the energy of the LUMO (lowest unoccupied molecular orbital) of the nitrenium ion. © 1995 Wiley‐Liss, Inc.</description><subject>Ames test</subject><subject>aminoimidazo-azaarenes</subject><subject>aromatic amines</subject><subject>Biological and medical sciences</subject><subject>Chemical mutagenesis</subject><subject>Dose-Response Relationship, Drug</subject><subject>Imidazoles - chemistry</subject><subject>Imidazoles - pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Mutagenicity Tests</subject><subject>Mutagens - chemistry</subject><subject>Mutagens - pharmacology</subject><subject>Naphthyridines - chemistry</subject><subject>Naphthyridines - pharmacology</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>Salmonella mutagenicity</subject><subject>Salmonella typhimurium</subject><subject>Salmonella typhimurium - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>structure/activity</subject><subject>Toxicology</subject><subject>YG1024</subject><issn>0893-6692</issn><issn>1098-2280</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kDtPwzAUhS0EKuUxMiJlQGwBPxrHGRFqAxKPoaBuWLe2Qw15FDsRlF-Pq0ZFLEyWfL577zkHoROCLwjG9NJUF1QkmHJMCN1BQ4IzEVMq8C4aYpGxmPOM7qMD799wQEYZHaBBykckJWSIXqat61TbORNXXQuvprbKtqvImRJa29R-YZc-aoqoaDoXQWXrJraV1fDd1LBctIuVs9rWxkdQ66hXPrqAlevfI7RXQOnNcf8eoufJ-On6Jr57zG-vr-5ixYKhmLJsnpJUkzkwohXHoBKBs4TieQIJA000YEaoLrQCVnChM82MGOmQlWgt2CE63-xdunDd-FZW1itTllCbpvOScDHimKcBjDegco33zhRy6WwFbiUJlus-pankb5-BP-0Xd_PK6C3dFxj0s14Hr6AsHNTK-i3GOBYhWMDSDfZpS7P6_6Yc3_8x0Bu2vjVf20lw7zLESRM5e8jlbMbyyfR-KnP2A1Srnv4</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>Vikse, R.</creator><creator>Hatch, F. T.</creator><creator>Winter, N. W.</creator><creator>Knize, M. G.</creator><creator>Grivas, S.</creator><creator>Felton, J. S.</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><general>Wiley-Liss</general><scope>BSCLL</scope><scope>IQODW</scope><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>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>1995</creationdate><title>Structure-mutagenicity relationships of four amino-imidazonaphthyridines and imidazoquinolines</title><author>Vikse, R. ; Hatch, F. T. ; Winter, N. W. ; Knize, M. G. ; Grivas, S. ; Felton, J. S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3492-239b717d1ba31dc60ac5809520b5a53ad1da0312dfdca3f68d9d3e84d0981dd83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Ames test</topic><topic>aminoimidazo-azaarenes</topic><topic>aromatic amines</topic><topic>Biological and medical sciences</topic><topic>Chemical mutagenesis</topic><topic>Dose-Response Relationship, Drug</topic><topic>Imidazoles - chemistry</topic><topic>Imidazoles - pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Mutagenicity Tests</topic><topic>Mutagens - chemistry</topic><topic>Mutagens - pharmacology</topic><topic>Naphthyridines - chemistry</topic><topic>Naphthyridines - pharmacology</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>Salmonella mutagenicity</topic><topic>Salmonella typhimurium</topic><topic>Salmonella typhimurium - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>structure/activity</topic><topic>Toxicology</topic><topic>YG1024</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vikse, R.</creatorcontrib><creatorcontrib>Hatch, F. T.</creatorcontrib><creatorcontrib>Winter, N. W.</creatorcontrib><creatorcontrib>Knize, M. G.</creatorcontrib><creatorcontrib>Grivas, S.</creatorcontrib><creatorcontrib>Felton, J. 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S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure-mutagenicity relationships of four amino-imidazonaphthyridines and imidazoquinolines</atitle><jtitle>Environmental and molecular mutagenesis</jtitle><addtitle>Environ. Mol. Mutagen</addtitle><date>1995</date><risdate>1995</risdate><volume>26</volume><issue>1</issue><spage>79</spage><epage>85</epage><pages>79-85</pages><issn>0893-6692</issn><eissn>1098-2280</eissn><coden>EMMUEG</coden><abstract>We tested four isomeric imidazonaphthyridines and one imidazoquinoline compound for mutagenic activity in the Ames/Salmonella mutagenicity assay, using strain TA98 and strain YG1024, an analogue of strain TA98 with elevated O‐acetyl‐transferase levels. Their potency was related to calculated electronic parameters. Five compounds with a linear arrangement of 3 rings showed a positive response in strain YG1024. Compound 2 (1‐methyl‐imidazo[4,5‐b][1,7]naphthyridin‐2‐amine) is the most mutagenic in both strains, giving specific activities of about 200 and 30 revertants per microgram in strains YG1024 and TA98, respectively. Three of the compounds were weak mutagens, giving a positive dose‐response only in strain YG1024, with 3–5 revertants per microgram. A higher response of all five compounds in strain YG1024 as opposed to TA98 indicates that they require O‐acetyltransferase activity for their metabolism. Mutagenic potencies in strain YG1024 were positively correlated to the energy of the LUMO (lowest unoccupied molecular orbital) of the nitrenium ion. © 1995 Wiley‐Liss, Inc.</abstract><cop>New York</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>7641711</pmid><doi>10.1002/em.2850260112</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0893-6692 |
| ispartof | Environmental and molecular mutagenesis, 1995, Vol.26 (1), p.79-85 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Ames test aminoimidazo-azaarenes aromatic amines Biological and medical sciences Chemical mutagenesis Dose-Response Relationship, Drug Imidazoles - chemistry Imidazoles - pharmacology Medical sciences Molecular Structure Mutagenicity Tests Mutagens - chemistry Mutagens - pharmacology Naphthyridines - chemistry Naphthyridines - pharmacology Quinolines - chemistry Quinolines - pharmacology Salmonella mutagenicity Salmonella typhimurium Salmonella typhimurium - drug effects Structure-Activity Relationship structure/activity Toxicology YG1024 |
| title | Structure-mutagenicity relationships of four amino-imidazonaphthyridines and imidazoquinolines |
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