LrgpV1, Main, Exploration, bibRecord, 000A94

Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers

Identifieur interne : 000A94 ( Main/Exploration ); précédent : 000A93; suivant : 000A95

Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers

Auteurs : Cédric Rouxel [France] ; Marina Charlot [France] ; Youssef Mir [France] ; Céline Frochot [France] ; Olivier Mongin [France] ; Mireille Blanchard-Desce [France]

Source :

New Journal of Chemistry [ 1144-0546 ] ; 2011.

RBID : Hal:hal-00777839

English descriptors

mix :
- 2-PHOTON PHOTODYNAMIC THERAPY, ABSORPTION, EXCITATION CROSS-SECTIONS, FLUORESCENCE EXCITATION, METAL-IONS, OPTICAL-DATA STORAGE, ORGANIC NANODOTS, PHOTOPHYSICAL PROPERTIES, SINGLET OXYGEN, STRUCTURE-PROPERTY RELATIONSHIPS.

Abstract

This study aims at designing dual-role biphotonic chromophores that could be used for photodynamic therapy (PDT) while maintaining some fluorescence in order to locate them, thus allowing selective irradiation of cancer cells when combined with targeting. Quadrupolar two-photon absorbing fluorophores were synthesized from the symmetrical functionalization of a fluorene core bearing elongated conjugated rods made from arylene-vinylene or arylene-ethynylene building blocks in order to test modifications which could increase singlet oxygen production ability while retaining some fluorescence and high two-photon absorption (TPA) cross-sections in the biological spectral range of interest. All chromophores show a polar emissive excited state whose dipole moment is highly dependent on the nature of the conjugated linker. Interestingly, the largest TPA responses in the NIR region as well as singlet oxygen quantum yield are correlated with the smallest dipole moment of the emissive excited-state. The molecular optimization study led to a multifunctional biphotonic chromophore combining high TPA cross-sections in the whole spectral range of interest (700-900 nm), reasonable singlet oxygen production efficiency, significant remaining fluorescence, and alcohol end-groups for further covalent grafting. This compound offers thus interesting potentialities for highly selective spatially-resolved two-photon PDT by incorporation in nanostructures.

Url:

https://hal.archives-ouvertes.fr/hal-00777839

DOI: 10.1039/c1nj20073a

Affiliations:

Links toward previous steps (curation, corpus...)

to stream Hal, to step Corpus: 000149
to stream Hal, to step Curation: 000149
to stream Hal, to step Checkpoint: 000A32
to stream Main, to step Merge: 000C18
to stream Main, to step Curation: 000A94

Le document en format XML

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<orgName type="acronym">UL</orgName>
<date type="start">2012-01-01</date>
<desc><address><addrLine>34 cours Léopold - CS 25233 - 54052 Nancy cedex</addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://www.univ-lorraine.fr/</ref>
</desc>
</org>
</tutelle>
<tutelle name="UMR7274" active="#struct-441569" type="direct"><org type="institution" xml:id="struct-441569" status="VALID"><idno type="ISNI">0000000122597504</idno>
<idno type="IdRef">02636817X</idno>
<orgName>Centre National de la Recherche Scientifique</orgName>
<orgName type="acronym">CNRS</orgName>
<date type="start">1939-10-19</date>
<desc><address><country key="FR"></country>
</address>
<ref type="url">http://www.cnrs.fr/</ref>
</desc>
</org>
</tutelle>
</tutelles>
</hal:affiliation>
<country>France</country>
<placeName><settlement type="city">Nancy</settlement>
<settlement type="city">Metz</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Lorraine (région)</region>
</placeName>
<orgName type="university">Université de Lorraine</orgName>
</affiliation>
</author>
<author><name sortKey="Mongin, Olivier" sort="Mongin, Olivier" uniqKey="Mongin O" first="Olivier" last="Mongin">Olivier Mongin</name>
<affiliation wicri:level="1"><hal:affiliation type="laboratory" xml:id="struct-136861" status="OLD"><orgName>Chimie et Photonique Moléculaires</orgName>
<orgName type="acronym">CPM</orgName>
<desc><address><addrLine>bat. 10A et bat. 10C 263 Av du général Leclerc 35042 RENNES CEDEX</addrLine>
<country key="FR"></country>
</address>
</desc>
<listRelation><relation active="#struct-105160" type="direct"></relation>
<relation name="UMR6510" active="#struct-441569" type="direct"></relation>
</listRelation>
<tutelles><tutelle active="#struct-105160" type="direct"><org type="institution" xml:id="struct-105160" status="VALID"><orgName>Université de Rennes 1</orgName>
<orgName type="acronym">UR1</orgName>
<desc><address><addrLine>2 rue du Thabor - CS 46510 - 35065 Rennes cedex</addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://www.univ-rennes1.fr/</ref>
</desc>
</org>
</tutelle>
<tutelle name="UMR6510" active="#struct-441569" type="direct"><org type="institution" xml:id="struct-441569" status="VALID"><idno type="ISNI">0000000122597504</idno>
<idno type="IdRef">02636817X</idno>
<orgName>Centre National de la Recherche Scientifique</orgName>
<orgName type="acronym">CNRS</orgName>
<date type="start">1939-10-19</date>
<desc><address><country key="FR"></country>
</address>
<ref type="url">http://www.cnrs.fr/</ref>
</desc>
</org>
</tutelle>
</tutelles>
</hal:affiliation>
<country>France</country>
<placeName><settlement type="city">Rennes</settlement>
<region type="region" nuts="2">Région Bretagne</region>
</placeName>
<orgName type="university">Université de Rennes 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université européenne de Bretagne</orgName>
</affiliation>
</author>
<author><name sortKey="Blanchard Desce, Mireille" sort="Blanchard Desce, Mireille" uniqKey="Blanchard Desce M" first="Mireille" last="Blanchard-Desce">Mireille Blanchard-Desce</name>
<affiliation wicri:level="1"><hal:affiliation type="laboratory" xml:id="struct-136861" status="OLD"><orgName>Chimie et Photonique Moléculaires</orgName>
<orgName type="acronym">CPM</orgName>
<desc><address><addrLine>bat. 10A et bat. 10C 263 Av du général Leclerc 35042 RENNES CEDEX</addrLine>
<country key="FR"></country>
</address>
</desc>
<listRelation><relation active="#struct-105160" type="direct"></relation>
<relation name="UMR6510" active="#struct-441569" type="direct"></relation>
</listRelation>
<tutelles><tutelle active="#struct-105160" type="direct"><org type="institution" xml:id="struct-105160" status="VALID"><orgName>Université de Rennes 1</orgName>
<orgName type="acronym">UR1</orgName>
<desc><address><addrLine>2 rue du Thabor - CS 46510 - 35065 Rennes cedex</addrLine>
<country key="FR"></country>
</address>
<ref type="url">http://www.univ-rennes1.fr/</ref>
</desc>
</org>
</tutelle>
<tutelle name="UMR6510" active="#struct-441569" type="direct"><org type="institution" xml:id="struct-441569" status="VALID"><idno type="ISNI">0000000122597504</idno>
<idno type="IdRef">02636817X</idno>
<orgName>Centre National de la Recherche Scientifique</orgName>
<orgName type="acronym">CNRS</orgName>
<date type="start">1939-10-19</date>
<desc><address><country key="FR"></country>
</address>
<ref type="url">http://www.cnrs.fr/</ref>
</desc>
</org>
</tutelle>
</tutelles>
</hal:affiliation>
<country>France</country>
<placeName><settlement type="city">Rennes</settlement>
<region type="region" nuts="2">Région Bretagne</region>
</placeName>
<orgName type="university">Université de Rennes 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université européenne de Bretagne</orgName>
</affiliation>
</author>
</analytic>
<idno type="DOI">10.1039/c1nj20073a</idno>
<series><title level="j">New Journal of Chemistry</title>
<idno type="ISSN">1144-0546</idno>
<imprint><date type="datePub">2011</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="mix" xml:lang="en"><term>2-PHOTON PHOTODYNAMIC THERAPY</term>
<term>ABSORPTION</term>
<term>EXCITATION CROSS-SECTIONS</term>
<term>FLUORESCENCE EXCITATION</term>
<term>METAL-IONS</term>
<term>OPTICAL-DATA STORAGE</term>
<term>ORGANIC NANODOTS</term>
<term>PHOTOPHYSICAL PROPERTIES</term>
<term>SINGLET OXYGEN</term>
<term>STRUCTURE-PROPERTY RELATIONSHIPS</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">This study aims at designing dual-role biphotonic chromophores that could be used for photodynamic therapy (PDT) while maintaining some fluorescence in order to locate them, thus allowing selective irradiation of cancer cells when combined with targeting. Quadrupolar two-photon absorbing fluorophores were synthesized from the symmetrical functionalization of a fluorene core bearing elongated conjugated rods made from arylene-vinylene or arylene-ethynylene building blocks in order to test modifications which could increase singlet oxygen production ability while retaining some fluorescence and high two-photon absorption (TPA) cross-sections in the biological spectral range of interest. All chromophores show a polar emissive excited state whose dipole moment is highly dependent on the nature of the conjugated linker. Interestingly, the largest TPA responses in the NIR region as well as singlet oxygen quantum yield are correlated with the smallest dipole moment of the emissive excited-state. The molecular optimization study led to a multifunctional biphotonic chromophore combining high TPA cross-sections in the whole spectral range of interest (700-900 nm), reasonable singlet oxygen production efficiency, significant remaining fluorescence, and alcohol end-groups for further covalent grafting. This compound offers thus interesting potentialities for highly selective spatially-resolved two-photon PDT by incorporation in nanostructures.</div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Grand Est</li>
<li>Lorraine (région)</li>
<li>Région Bretagne</li>
</region>
<settlement><li>Metz</li>
<li>Nancy</li>
<li>Rennes</li>
</settlement>
<orgName><li>Université de Lorraine</li>
<li>Université de Rennes 1</li>
<li>Université européenne de Bretagne</li>
</orgName>
</list>
<tree><country name="France"><region name="Région Bretagne"><name sortKey="Rouxel, Cedric" sort="Rouxel, Cedric" uniqKey="Rouxel C" first="Cédric" last="Rouxel">Cédric Rouxel</name>
</region>
<name sortKey="Blanchard Desce, Mireille" sort="Blanchard Desce, Mireille" uniqKey="Blanchard Desce M" first="Mireille" last="Blanchard-Desce">Mireille Blanchard-Desce</name>
<name sortKey="Charlot, Marina" sort="Charlot, Marina" uniqKey="Charlot M" first="Marina" last="Charlot">Marina Charlot</name>
<name sortKey="Frochot, Celine" sort="Frochot, Celine" uniqKey="Frochot C" first="Céline" last="Frochot">Céline Frochot</name>
<name sortKey="Mir, Youssef" sort="Mir, Youssef" uniqKey="Mir Y" first="Youssef" last="Mir">Youssef Mir</name>
<name sortKey="Mongin, Olivier" sort="Mongin, Olivier" uniqKey="Mongin O" first="Olivier" last="Mongin">Olivier Mongin</name>
</country>
</tree>
</affiliations>
</record>

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Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers

Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers

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