Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders
A series of disubstituted bis(vinylquinolinium)benzene derivatives were designed, which were prepared through a facile three-component one-pot reaction in good yield. FRET results showed that 1,3-disubstituted benzene derivatives had much stronger stabilization effect on G-quadruplex DNA than that o...
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| Veröffentlicht in: | Tetrahedron 2013-06, Vol.69 (24), p.4922-4932 |
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| container_issue | 24 |
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| container_title | Tetrahedron |
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| creator | Liu, Zhen-Quan Zhuo, Shi-Tian Tan, Jia-Heng Ou, Tian-Miao Li, Ding Gu, Lian-Quan Huang, Zhi-Shu |
| description | A series of disubstituted bis(vinylquinolinium)benzene derivatives were designed, which were prepared through a facile three-component one-pot reaction in good yield. FRET results showed that 1,3-disubstituted benzene derivatives had much stronger stabilization effect on G-quadruplex DNA than that of 1,4-disubstituted benzene derivatives. The introduction of substituted amine side chain at quinolinium obviously increased the binding affinity of compounds to G-quadruplex DNA. It was also found that 1,3-disubstituted benzene derivatives and 1,4-disubstituted benzene derivatives had different effects on the conformation of G-quadruplex DNA by CD spectroscopy analysis. The differences for the interactions of these two classes of compounds with G-quadruplex were further studied and elaborated through molecular modeling experiments.
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| doi_str_mv | 10.1016/j.tet.2013.04.045 |
| format | Article |
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[Display omitted]</description><subject>Affinity</subject><subject>Benzene</subject><subject>Binding</subject><subject>Binding agents</subject><subject>Bisquinolinium derivatives</subject><subject>Deoxyribonucleic acid</subject><subject>Derivatives</subject><subject>Dichroism</subject><subject>Fretting</subject><subject>G-quadruplex</subject><subject>One-pot reaction</subject><subject>SNAr reaction</subject><subject>Stabilization</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkE1rGzEQhkVpoW6aH9DbHtPDuqOP1Vb0FNIkDYT2kpyFVpqlMmutrdGaOr--Mu65gYGBmecZmJexTxzWHLj-slkXLGsBXK5B1eresBVXWrWd4votWwEoaBUIeM8-EG0AgHMhV2y8cz5O2NAxld9ISM08NiHSMlCJZSkYmiHS1SGm47RfYpqnmOKy_TxgesGETcAcD67EQzUdNfftfnEhL7sJ_zTff15XOVWEPrJ3o5sIL__1C_Z8d_t086N9_HX_cHP92HolTGlRG-ON7oPQ2gnBYRBGOyO-QuCGh17hKDvj63jwY49Oeux6b7yA0zZwecGuznd3ed4vSMVuI3mcJpdwXsjyXiltlJLwOtpBJyWXWlaUn1GfZ6KMo93luHX5aDnYU_x2Y2v89hS_BVWrq863s4P13UPEbMlHTB5DzOiLDXP8j_0X_y-Olg</recordid><startdate>20130601</startdate><enddate>20130601</enddate><creator>Liu, Zhen-Quan</creator><creator>Zhuo, Shi-Tian</creator><creator>Tan, Jia-Heng</creator><creator>Ou, Tian-Miao</creator><creator>Li, Ding</creator><creator>Gu, Lian-Quan</creator><creator>Huang, Zhi-Shu</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20130601</creationdate><title>Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders</title><author>Liu, Zhen-Quan ; Zhuo, Shi-Tian ; Tan, Jia-Heng ; Ou, Tian-Miao ; Li, Ding ; Gu, Lian-Quan ; Huang, Zhi-Shu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-e699c967d266a2210b296a9280d191d74ef359c0b2bcf7ea3ce57c9c2091d7d13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Affinity</topic><topic>Benzene</topic><topic>Binding</topic><topic>Binding agents</topic><topic>Bisquinolinium derivatives</topic><topic>Deoxyribonucleic acid</topic><topic>Derivatives</topic><topic>Dichroism</topic><topic>Fretting</topic><topic>G-quadruplex</topic><topic>One-pot reaction</topic><topic>SNAr reaction</topic><topic>Stabilization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Zhen-Quan</creatorcontrib><creatorcontrib>Zhuo, Shi-Tian</creatorcontrib><creatorcontrib>Tan, Jia-Heng</creatorcontrib><creatorcontrib>Ou, Tian-Miao</creatorcontrib><creatorcontrib>Li, Ding</creatorcontrib><creatorcontrib>Gu, Lian-Quan</creatorcontrib><creatorcontrib>Huang, Zhi-Shu</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Zhen-Quan</au><au>Zhuo, Shi-Tian</au><au>Tan, Jia-Heng</au><au>Ou, Tian-Miao</au><au>Li, Ding</au><au>Gu, Lian-Quan</au><au>Huang, Zhi-Shu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders</atitle><jtitle>Tetrahedron</jtitle><date>2013-06-01</date><risdate>2013</risdate><volume>69</volume><issue>24</issue><spage>4922</spage><epage>4932</epage><pages>4922-4932</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A series of disubstituted bis(vinylquinolinium)benzene derivatives were designed, which were prepared through a facile three-component one-pot reaction in good yield. FRET results showed that 1,3-disubstituted benzene derivatives had much stronger stabilization effect on G-quadruplex DNA than that of 1,4-disubstituted benzene derivatives. The introduction of substituted amine side chain at quinolinium obviously increased the binding affinity of compounds to G-quadruplex DNA. It was also found that 1,3-disubstituted benzene derivatives and 1,4-disubstituted benzene derivatives had different effects on the conformation of G-quadruplex DNA by CD spectroscopy analysis. The differences for the interactions of these two classes of compounds with G-quadruplex were further studied and elaborated through molecular modeling experiments.
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| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2013-06, Vol.69 (24), p.4922-4932 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744694430 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Affinity Benzene Binding Binding agents Bisquinolinium derivatives Deoxyribonucleic acid Derivatives Dichroism Fretting G-quadruplex One-pot reaction SNAr reaction Stabilization |
| title | Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders |
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