ParkinsonFranceV1, Istex, Corpus, bibRecord, 002132

Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

Identifieur interne : 002132 ( Istex/Corpus ); précédent : 002131; suivant : 002133

Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

Auteurs : Julien Debray ; Walid Zeghida ; Muriel Jourdan ; David Monchaud ; Marie-Louise Dheu-Andries ; Pascal Dumy ; Marie-Paule Teulade-Fichou ; Martine Demeunynck

Source :

Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2009.

RBID : ISTEX:38CA4F05590C6A15B3B5068479E51610520039C5

Abstract

The present article reports on the design and the synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders. It is shown that bispyrimidinoacridines represent an interesting compromise between easy synthetic access and efficiency in terms of quadruplex interaction (both affinic and selective), as judged by G4-FID assay and molecular modelling. The present study also highlights that control of the -stacking interactions taking place between the ligand and the accessible G-tetrad of a quadruplex-DNA is indeed essential for good recognition but not exclusively (key role of direct and water-mediated H-bonds). The introduction of additional amino side chains, valuable in the acridine series, results here in steric perturbations of the ligand/quadruplex recognition and lowers the quadruplex/duplex selectivity.

Url:

https://api.istex.fr/document/38CA4F05590C6A15B3B5068479E51610520039C5/fulltext/pdf

DOI: 10.1039/b912716j

Links to Exploration step

ISTEX:38CA4F05590C6A15B3B5068479E51610520039C5

Le document en format XML

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 <title>Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19<fnoteref></fnoteref>
<footnote id="fn1">Electronic supplementary information (ESI) available: Tables collecting the data obtained for energy calculations for the three major tautomers of compound <compoundref>12</compoundref>
 and the calculated pKa values of compounds <compoundref>12</compoundref>
 and <compoundref>18</compoundref>
; HPLC analysis. See DOI: <url>10.1039/b912716j</url>
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 <addrelt>CNRS/Université Joseph Fourier</addrelt>
 <addrelt>BP 53</addrelt>
 <postcode>38041 Grenoble cedex 9</postcode>
 <country>France</country>
 </address>
 <email>martine.demeunynck@ujf-grenoble.fr</email>
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 <phone>+33 476 514429</phone>
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 <p>The present article reports on the design and the synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders. It is shown that bispyrimidinoacridines represent an interesting compromise between easy synthetic access and efficiency in terms of quadruplex interaction (both affinic and selective), as judged by G4-FID assay and molecular modelling. The present study also highlights that control of the π-stacking interactions taking place between the ligand and the accessible G-tetrad of a quadruplex-DNA is indeed essential for good recognition but not exclusively (key role of direct and water-mediated H-bonds). The introduction of additional amino side chains, valuable in the acridine series, results here in steric perturbations of the ligand/quadruplex recognition and lowers the quadruplex/duplex selectivity.</p>
 </abstract>
 </art-front>
 <art-back>
 <ack>
 <p>We thank Dr Helène Jamet for the RESP calculation, and Dr Jose Granadino is also warmly thanked for his help and support with the Docking protocol.</p>
 </ack>
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<mods version="3.6"><titleInfo><title>Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19</title>
</titleInfo>
<titleInfo type="alternative" contentType="CDATA"><title>Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19</title>
</titleInfo>
<name type="personal"><namePart type="given">Julien</namePart>
<namePart type="family">Debray</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
</name>
<name type="personal"><namePart type="given">Walid</namePart>
<namePart type="family">Zeghida</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
</name>
<name type="personal"><namePart type="given">Muriel</namePart>
<namePart type="family">Jourdan</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
</name>
<name type="personal"><namePart type="given">David</namePart>
<namePart type="family">Monchaud</namePart>
<affiliation>Institut Curie, Section Recherche, CNRS UMR176, Centre Universitaire Paris XI, 91405 Orsay, Bat. 110, France</affiliation>
</name>
<name type="personal"><namePart type="given">Marie-Louise</namePart>
<namePart type="family">Dheu-Andries</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
</name>
<name type="personal"><namePart type="given">Pascal</namePart>
<namePart type="family">Dumy</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
</name>
<name type="personal"><namePart type="given">Marie-Paule</namePart>
<namePart type="family">Teulade-Fichou</namePart>
<affiliation>Institut Curie, Section Recherche, CNRS UMR176, Centre Universitaire Paris XI, 91405 Orsay, Bat. 110, France</affiliation>
</name>
<name type="personal"><namePart type="given">Martine</namePart>
<namePart type="family">Demeunynck</namePart>
<affiliation>Dpartement Chimie Molculaire, 38041 Grenoble cedex 9, UMR 5250, CNRS/Universit Joseph Fourier, BP 53, France</affiliation>
<affiliation>E-mail: martine.demeunynck@ujf-grenoble.fr</affiliation>
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<originInfo><publisher>The Royal Society of Chemistry.</publisher>
<dateIssued encoding="w3cdtf">2009</dateIssued>
<copyrightDate encoding="w3cdtf">2009</copyrightDate>
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<abstract>The present article reports on the design and the synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders. It is shown that bispyrimidinoacridines represent an interesting compromise between easy synthetic access and efficiency in terms of quadruplex interaction (both affinic and selective), as judged by G4-FID assay and molecular modelling. The present study also highlights that control of the -stacking interactions taking place between the ligand and the accessible G-tetrad of a quadruplex-DNA is indeed essential for good recognition but not exclusively (key role of direct and water-mediated H-bonds). The introduction of additional amino side chains, valuable in the acridine series, results here in steric perturbations of the ligand/quadruplex recognition and lowers the quadruplex/duplex selectivity.</abstract>
<note type="footnote" displayLabel="fn1">Electronic supplementary information (ESI) available: Tables collecting the data obtained for energy calculations for the three major tautomers of compound 12 and the calculated pKa values of compounds 12 and 18; HPLC analysis. See DOI: 10.1039/b912716j</note>
<note>The design and synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders are reported.</note>
<relatedItem type="host"><titleInfo><title>Organic & Biomolecular Chemistry</title>
</titleInfo>
<titleInfo type="abbreviated"><title>Org. Biomol. Chem.</title>
</titleInfo>
<genre type="journal">journal</genre>
<originInfo><publisher>The Royal Society of Chemistry.</publisher>
</originInfo>
<identifier type="ISSN">1477-0520</identifier>
<identifier type="eISSN">1477-0539</identifier>
<identifier type="coden">OBCRAK</identifier>
<identifier type="RSC sercode">OB</identifier>
<part><date>2009</date>
<detail type="volume"><caption>vol.</caption>
<number></number>
</detail>
<detail type="issue"><caption>no.</caption>
<number>24</number>
</detail>
<extent unit="pages"><start>5219</start>
<end>5228</end>
<total>10</total>
</extent>
</part>
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<identifier type="istex">38CA4F05590C6A15B3B5068479E51610520039C5</identifier>
<identifier type="DOI">10.1039/b912716j</identifier>
<identifier type="ms-id">b912716j</identifier>
<accessCondition type="use and reproduction" contentType="copyright">This journal is © The Royal Society of Chemistry</accessCondition>
<recordInfo><recordContentSource>RSC Journals</recordContentSource>
<recordOrigin>The Royal Society of Chemistry</recordOrigin>
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Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

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