Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers
Several stable O -alkyl and aryl sulfonyl conjugated p -nitro-Ph and o -, m -, p -pyridine N ′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage....
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| Veröffentlicht in: | Photochemical & photobiological sciences 2016-03, Vol.15 (3), p.351-360 |
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| creator | Papastergiou, A. Perontsis, S. Gritzapis, P. Koumbis, A. E. Koffa, M. Psomas, G. Fylaktakidou, K. C. |
| description | Several stable
O
-alkyl and aryl sulfonyl conjugated
p
-nitro-Ph and
o
-,
m
-,
p
-pyridine
N
′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage. Both alkyl and aryl sulfonyl derivatives were active and the order
p
-pyridine >
p
-nitro-Ph >
o
-pyridine >
m
-pyridine was schematized for the
N
′-hydroxy imidamides moiety. Calf thymus-DNA affinity studies which comprised UV interactions, viscosity experiments and competitive studies with ethidium bromide showed good to excellent affinity of the compounds. These properties revealed sulfonyl amidoximes as novel effective DNA-photo-cleavers and may serve in the discovery of new leads for “on demand” biotechnological and medical applications. |
| doi_str_mv | 10.1039/c5pp00439j |
| format | Article |
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O
-alkyl and aryl sulfonyl conjugated
p
-nitro-Ph and
o
-,
m
-,
p
-pyridine
N
′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage. Both alkyl and aryl sulfonyl derivatives were active and the order
p
-pyridine >
p
-nitro-Ph >
o
-pyridine >
m
-pyridine was schematized for the
N
′-hydroxy imidamides moiety. Calf thymus-DNA affinity studies which comprised UV interactions, viscosity experiments and competitive studies with ethidium bromide showed good to excellent affinity of the compounds. These properties revealed sulfonyl amidoximes as novel effective DNA-photo-cleavers and may serve in the discovery of new leads for “on demand” biotechnological and medical applications.</description><identifier>ISSN: 1474-905X</identifier><identifier>EISSN: 1474-9092</identifier><identifier>DOI: 10.1039/c5pp00439j</identifier><identifier>PMID: 26959855</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Animals ; Biochemistry ; Biomaterials ; Cattle ; Chemistry ; DNA - chemistry ; DNA - drug effects ; DNA - radiation effects ; DNA Cleavage - drug effects ; DNA Cleavage - radiation effects ; Molecular Structure ; Oximes - chemistry ; Oximes - pharmacology ; Oximes - radiation effects ; Photolysis - drug effects ; Photolysis - radiation effects ; Physical Chemistry ; Plant Sciences</subject><ispartof>Photochemical & photobiological sciences, 2016-03, Vol.15 (3), p.351-360</ispartof><rights>The Royal Society of Chemistry and Owner Societies 2016</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-8fc4a1ab748a26bae3a4881c9a58f57956a7503f828612f3f81cb8251b60972d3</citedby><cites>FETCH-LOGICAL-c434t-8fc4a1ab748a26bae3a4881c9a58f57956a7503f828612f3f81cb8251b60972d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1039/c5pp00439j$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1039/c5pp00439j$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26959855$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Papastergiou, A.</creatorcontrib><creatorcontrib>Perontsis, S.</creatorcontrib><creatorcontrib>Gritzapis, P.</creatorcontrib><creatorcontrib>Koumbis, A. E.</creatorcontrib><creatorcontrib>Koffa, M.</creatorcontrib><creatorcontrib>Psomas, G.</creatorcontrib><creatorcontrib>Fylaktakidou, K. C.</creatorcontrib><title>Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers</title><title>Photochemical & photobiological sciences</title><addtitle>Photochem Photobiol Sci</addtitle><addtitle>Photochem Photobiol Sci</addtitle><description>Several stable
O
-alkyl and aryl sulfonyl conjugated
p
-nitro-Ph and
o
-,
m
-,
p
-pyridine
N
′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage. Both alkyl and aryl sulfonyl derivatives were active and the order
p
-pyridine >
p
-nitro-Ph >
o
-pyridine >
m
-pyridine was schematized for the
N
′-hydroxy imidamides moiety. Calf thymus-DNA affinity studies which comprised UV interactions, viscosity experiments and competitive studies with ethidium bromide showed good to excellent affinity of the compounds. These properties revealed sulfonyl amidoximes as novel effective DNA-photo-cleavers and may serve in the discovery of new leads for “on demand” biotechnological and medical applications.</description><subject>Animals</subject><subject>Biochemistry</subject><subject>Biomaterials</subject><subject>Cattle</subject><subject>Chemistry</subject><subject>DNA - chemistry</subject><subject>DNA - drug effects</subject><subject>DNA - radiation effects</subject><subject>DNA Cleavage - drug effects</subject><subject>DNA Cleavage - radiation effects</subject><subject>Molecular Structure</subject><subject>Oximes - chemistry</subject><subject>Oximes - pharmacology</subject><subject>Oximes - radiation effects</subject><subject>Photolysis - drug effects</subject><subject>Photolysis - radiation effects</subject><subject>Physical Chemistry</subject><subject>Plant Sciences</subject><issn>1474-905X</issn><issn>1474-9092</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkT1PwzAYhC0EglJY-AHIIwIFbMd27LHiW0J0AYktclyHpjhxaicV_HtcWtqFgek9vffohjsATjC6xCiVV5q1LUI0lbMdMMA0o4lEkuxuNHs7AIchzBDCjPJsHxwQLpkUjA3A_HahbK-6yjXQlXCcKPvxZaFqJlD5KEJvS9csP97VEdM_1tR0xrvtq64m7rOqTYAqwMYtjIWt60zTwZvnEWynrnOJtkYtjA9HYK9UNpjj9R2C17vbl-uH5Gl8_3g9eko0TWmXiFJThVWRUaEIL5RJFRUCa6mYKFkmGVcZQ2kpiOCYlFFgXQjCcMGRzMgkHYKzVW7r3bw3ocvrKmhjrWqM60OOs4xzRphE_0GJIDLlNKLnK1R7F4I3Zd76qo5V5RjlyzXy7RoRPl3n9kVtJhv0t_4IXKyAEK3m3fh85nrfxFr-ivsGslmUlg</recordid><startdate>201603</startdate><enddate>201603</enddate><creator>Papastergiou, A.</creator><creator>Perontsis, S.</creator><creator>Gritzapis, P.</creator><creator>Koumbis, A. E.</creator><creator>Koffa, M.</creator><creator>Psomas, G.</creator><creator>Fylaktakidou, K. C.</creator><general>Springer International Publishing</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>7X8</scope><scope>7TM</scope></search><sort><creationdate>201603</creationdate><title>Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers</title><author>Papastergiou, A. ; Perontsis, S. ; Gritzapis, P. ; Koumbis, A. E. ; Koffa, M. ; Psomas, G. ; Fylaktakidou, K. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c434t-8fc4a1ab748a26bae3a4881c9a58f57956a7503f828612f3f81cb8251b60972d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Biochemistry</topic><topic>Biomaterials</topic><topic>Cattle</topic><topic>Chemistry</topic><topic>DNA - chemistry</topic><topic>DNA - drug effects</topic><topic>DNA - radiation effects</topic><topic>DNA Cleavage - drug effects</topic><topic>DNA Cleavage - radiation effects</topic><topic>Molecular Structure</topic><topic>Oximes - chemistry</topic><topic>Oximes - pharmacology</topic><topic>Oximes - radiation effects</topic><topic>Photolysis - drug effects</topic><topic>Photolysis - radiation effects</topic><topic>Physical Chemistry</topic><topic>Plant Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Papastergiou, A.</creatorcontrib><creatorcontrib>Perontsis, S.</creatorcontrib><creatorcontrib>Gritzapis, P.</creatorcontrib><creatorcontrib>Koumbis, A. E.</creatorcontrib><creatorcontrib>Koffa, M.</creatorcontrib><creatorcontrib>Psomas, G.</creatorcontrib><creatorcontrib>Fylaktakidou, K. C.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Photochemical & photobiological sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Papastergiou, A.</au><au>Perontsis, S.</au><au>Gritzapis, P.</au><au>Koumbis, A. E.</au><au>Koffa, M.</au><au>Psomas, G.</au><au>Fylaktakidou, K. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers</atitle><jtitle>Photochemical & photobiological sciences</jtitle><stitle>Photochem Photobiol Sci</stitle><addtitle>Photochem Photobiol Sci</addtitle><date>2016-03</date><risdate>2016</risdate><volume>15</volume><issue>3</issue><spage>351</spage><epage>360</epage><pages>351-360</pages><issn>1474-905X</issn><eissn>1474-9092</eissn><abstract>Several stable
O
-alkyl and aryl sulfonyl conjugated
p
-nitro-Ph and
o
-,
m
-,
p
-pyridine
N
′-hydroxy imidamides, were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA pBluescript KS II. The generated amidinyl and sulfonyloxyl radicals led to effective DNA photo-cleavage. Both alkyl and aryl sulfonyl derivatives were active and the order
p
-pyridine >
p
-nitro-Ph >
o
-pyridine >
m
-pyridine was schematized for the
N
′-hydroxy imidamides moiety. Calf thymus-DNA affinity studies which comprised UV interactions, viscosity experiments and competitive studies with ethidium bromide showed good to excellent affinity of the compounds. These properties revealed sulfonyl amidoximes as novel effective DNA-photo-cleavers and may serve in the discovery of new leads for “on demand” biotechnological and medical applications.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>26959855</pmid><doi>10.1039/c5pp00439j</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Photochemical & photobiological sciences, 2016-03, Vol.15 (3), p.351-360 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Springer Nature - Complete Springer Journals |
| subjects | Animals Biochemistry Biomaterials Cattle Chemistry DNA - chemistry DNA - drug effects DNA - radiation effects DNA Cleavage - drug effects DNA Cleavage - radiation effects Molecular Structure Oximes - chemistry Oximes - pharmacology Oximes - radiation effects Photolysis - drug effects Photolysis - radiation effects Physical Chemistry Plant Sciences |
| title | Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers |
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