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Furanochromone radical cations: generation, characterization and interaction with DNA
The radical cations of naturally occurring furanochromones visnagin (VI) and khellin (KH) have been generated and identified for the first time by use of laser flash photolysis and pulse radiolysis techniques. The lifetimes of VI ·+ and KH ·+ are determined as ∼6 and ∼35 μs under these conditions, r...
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| Published in: | Biophysical chemistry 2001-07, Vol.91 (2), p.105-113 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c361t-1223690e0edccad700707ada9b14b64b5acfa4bb6235b03c42cea63d337095023 |
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| cites | cdi_FETCH-LOGICAL-c361t-1223690e0edccad700707ada9b14b64b5acfa4bb6235b03c42cea63d337095023 |
| container_end_page | 113 |
| container_issue | 2 |
| container_start_page | 105 |
| container_title | Biophysical chemistry |
| container_volume | 91 |
| creator | Pan, Jing-Xi Han, Zhen-Hui Miao, Jin-Ling Yao, Si-De Lin, Nian-Yun Zhu, Da-Yuan |
| description | The radical cations of naturally occurring furanochromones visnagin (VI) and khellin (KH) have been generated and identified for the first time by use of laser flash photolysis and pulse radiolysis techniques. The lifetimes of VI
·+ and KH
·+ are determined as ∼6 and ∼35 μs under these conditions, respectively. Direct 308-nm excitation of VI in aqueous buffer at physiological pH results in monophotonic photoionization to generate VI
·+, with a quantum yield of 0.075, which is much higher than that of 8-methoxypsoralen and KH under identical conditions. Though VI
·+ is a more powerful oxidant than KH
·+, both of them react with guanosine mononucleotide (
k=1.2×10
9 and 3.8×10
7 dm
3 mol
−1 s
−1, respectively) via electron transfer to give the guanine radical cation. Furthermore, selective oxidation of guanine in single and double strand DNA by VI
·+ was also observed. These novel findings suggest that electron transfer reactions involving furanochromone radical cations may be of considerable importance in furanochromone photochemotherapy. |
| doi_str_mv | 10.1016/S0301-4622(01)00158-2 |
| format | article |
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·+ and KH
·+ are determined as ∼6 and ∼35 μs under these conditions, respectively. Direct 308-nm excitation of VI in aqueous buffer at physiological pH results in monophotonic photoionization to generate VI
·+, with a quantum yield of 0.075, which is much higher than that of 8-methoxypsoralen and KH under identical conditions. Though VI
·+ is a more powerful oxidant than KH
·+, both of them react with guanosine mononucleotide (
k=1.2×10
9 and 3.8×10
7 dm
3 mol
−1 s
−1, respectively) via electron transfer to give the guanine radical cation. Furthermore, selective oxidation of guanine in single and double strand DNA by VI
·+ was also observed. These novel findings suggest that electron transfer reactions involving furanochromone radical cations may be of considerable importance in furanochromone photochemotherapy.</description><identifier>ISSN: 0301-4622</identifier><identifier>EISSN: 1873-4200</identifier><identifier>DOI: 10.1016/S0301-4622(01)00158-2</identifier><identifier>PMID: 11429200</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Cations ; DNA ; DNA - chemistry ; Electron transfer ; Free Radicals ; Furanochromones ; Khellin - analogs & derivatives ; Khellin - chemistry ; Laser flash photolysis ; Photoionization ; Radical cation</subject><ispartof>Biophysical chemistry, 2001-07, Vol.91 (2), p.105-113</ispartof><rights>2001 Elsevier Science B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-1223690e0edccad700707ada9b14b64b5acfa4bb6235b03c42cea63d337095023</citedby><cites>FETCH-LOGICAL-c361t-1223690e0edccad700707ada9b14b64b5acfa4bb6235b03c42cea63d337095023</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11429200$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pan, Jing-Xi</creatorcontrib><creatorcontrib>Han, Zhen-Hui</creatorcontrib><creatorcontrib>Miao, Jin-Ling</creatorcontrib><creatorcontrib>Yao, Si-De</creatorcontrib><creatorcontrib>Lin, Nian-Yun</creatorcontrib><creatorcontrib>Zhu, Da-Yuan</creatorcontrib><title>Furanochromone radical cations: generation, characterization and interaction with DNA</title><title>Biophysical chemistry</title><addtitle>Biophys Chem</addtitle><description>The radical cations of naturally occurring furanochromones visnagin (VI) and khellin (KH) have been generated and identified for the first time by use of laser flash photolysis and pulse radiolysis techniques. The lifetimes of VI
·+ and KH
·+ are determined as ∼6 and ∼35 μs under these conditions, respectively. Direct 308-nm excitation of VI in aqueous buffer at physiological pH results in monophotonic photoionization to generate VI
·+, with a quantum yield of 0.075, which is much higher than that of 8-methoxypsoralen and KH under identical conditions. Though VI
·+ is a more powerful oxidant than KH
·+, both of them react with guanosine mononucleotide (
k=1.2×10
9 and 3.8×10
7 dm
3 mol
−1 s
−1, respectively) via electron transfer to give the guanine radical cation. Furthermore, selective oxidation of guanine in single and double strand DNA by VI
·+ was also observed. These novel findings suggest that electron transfer reactions involving furanochromone radical cations may be of considerable importance in furanochromone photochemotherapy.</description><subject>Cations</subject><subject>DNA</subject><subject>DNA - chemistry</subject><subject>Electron transfer</subject><subject>Free Radicals</subject><subject>Furanochromones</subject><subject>Khellin - analogs & derivatives</subject><subject>Khellin - chemistry</subject><subject>Laser flash photolysis</subject><subject>Photoionization</subject><subject>Radical cation</subject><issn>0301-4622</issn><issn>1873-4200</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><recordid>eNqFkF1LwzAUhoMobk5_gtIrUbB6krRp642M-QlDL9TrkCZnLtI1mnSK_nqzD_TS3BzOy5O85CFkn8IpBSrOHoEDTTPB2BHQYwCalynbIH1aFjzNGMAm6f8iPbITwivEUwJskx6lGasi0yfP13OvWqen3s1ci4lXxmrVJFp11rXhPHnBFv1yOUn0VHmlO_T2e5kkqjWJbWMQ08X-abtpcnk_3CVbE9UE3FvPQey5ehrdpuOHm7vRcJxqLmiXUsa4qAABjdbKFAAFFMqoqqZZLbI6V3qisroWjOc1cJ0xjUpww3kBVQ6MD8jh6t03797nGDo5s0Fj06gW3TzIiIlS5CKC-QrU3oXgcSLfvJ0p_yUpyIVPufQpF7JknEufclFwsC6Y1zM0f7fWAiNwsQIwfvPDopdBW2w1GutRd9I4-0_FD7g4hRc</recordid><startdate>20010702</startdate><enddate>20010702</enddate><creator>Pan, Jing-Xi</creator><creator>Han, Zhen-Hui</creator><creator>Miao, Jin-Ling</creator><creator>Yao, Si-De</creator><creator>Lin, Nian-Yun</creator><creator>Zhu, Da-Yuan</creator><general>Elsevier 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>7X8</scope></search><sort><creationdate>20010702</creationdate><title>Furanochromone radical cations: generation, characterization and interaction with DNA</title><author>Pan, Jing-Xi ; Han, Zhen-Hui ; Miao, Jin-Ling ; Yao, Si-De ; Lin, Nian-Yun ; Zhu, Da-Yuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-1223690e0edccad700707ada9b14b64b5acfa4bb6235b03c42cea63d337095023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Cations</topic><topic>DNA</topic><topic>DNA - chemistry</topic><topic>Electron transfer</topic><topic>Free Radicals</topic><topic>Furanochromones</topic><topic>Khellin - analogs & derivatives</topic><topic>Khellin - chemistry</topic><topic>Laser flash photolysis</topic><topic>Photoionization</topic><topic>Radical cation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pan, Jing-Xi</creatorcontrib><creatorcontrib>Han, Zhen-Hui</creatorcontrib><creatorcontrib>Miao, Jin-Ling</creatorcontrib><creatorcontrib>Yao, Si-De</creatorcontrib><creatorcontrib>Lin, Nian-Yun</creatorcontrib><creatorcontrib>Zhu, Da-Yuan</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><jtitle>Biophysical chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pan, Jing-Xi</au><au>Han, Zhen-Hui</au><au>Miao, Jin-Ling</au><au>Yao, Si-De</au><au>Lin, Nian-Yun</au><au>Zhu, Da-Yuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Furanochromone radical cations: generation, characterization and interaction with DNA</atitle><jtitle>Biophysical chemistry</jtitle><addtitle>Biophys Chem</addtitle><date>2001-07-02</date><risdate>2001</risdate><volume>91</volume><issue>2</issue><spage>105</spage><epage>113</epage><pages>105-113</pages><issn>0301-4622</issn><eissn>1873-4200</eissn><abstract>The radical cations of naturally occurring furanochromones visnagin (VI) and khellin (KH) have been generated and identified for the first time by use of laser flash photolysis and pulse radiolysis techniques. The lifetimes of VI
·+ and KH
·+ are determined as ∼6 and ∼35 μs under these conditions, respectively. Direct 308-nm excitation of VI in aqueous buffer at physiological pH results in monophotonic photoionization to generate VI
·+, with a quantum yield of 0.075, which is much higher than that of 8-methoxypsoralen and KH under identical conditions. Though VI
·+ is a more powerful oxidant than KH
·+, both of them react with guanosine mononucleotide (
k=1.2×10
9 and 3.8×10
7 dm
3 mol
−1 s
−1, respectively) via electron transfer to give the guanine radical cation. Furthermore, selective oxidation of guanine in single and double strand DNA by VI
·+ was also observed. These novel findings suggest that electron transfer reactions involving furanochromone radical cations may be of considerable importance in furanochromone photochemotherapy.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>11429200</pmid><doi>10.1016/S0301-4622(01)00158-2</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0301-4622 |
| ispartof | Biophysical chemistry, 2001-07, Vol.91 (2), p.105-113 |
| issn | 0301-4622 1873-4200 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70968656 |
| source | Elsevier |
| subjects | Cations DNA DNA - chemistry Electron transfer Free Radicals Furanochromones Khellin - analogs & derivatives Khellin - chemistry Laser flash photolysis Photoionization Radical cation |
| title | Furanochromone radical cations: generation, characterization and interaction with DNA |
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