Spectroscopy and photophysics of styrylquinoline-type HIV-1 integrase inhibitors and its oxidized forms studied by steady state and time resolved absorption and fluorescence
Identifieur interne : 000D81 ( Istex/Checkpoint ); précédent : 000D80; suivant : 000D82Spectroscopy and photophysics of styrylquinoline-type HIV-1 integrase inhibitors and its oxidized forms studied by steady state and time resolved absorption and fluorescence
Auteurs : Rolande Burdujan [France] ; Jean D'Angelo [France] ; Didier Desmaële [France] ; Fatima Zouhiri [France] ; Patrick Tauc [France] ; Jean-Claude Brochon [France] ; Christian Auclair [France] ; Jean-François Mouscadet [France] ; Pascal Pernot [France] ; Francis Tfibel [France] ; Mironel Enescu [France] ; Marie-Pierre Fontaine-Aupart [France]Source :
- Physical Chemistry Chemical Physics [ 1463-9076 ] ; 2001.
English descriptors
- Teeft :
- Absorbance, Absorption, Absorption spectra, Absorption spectrum, Aqueous solution, Catechol, Catechol group, Catechol part, Catechol transition, Chem, Chromophore, Delay times, Dioxane, Dmso, Drug concentration, Emission spectra, Ethanol, Excitation, Excitation spectrum, Excitation wavelength, Ground state, Intramolecular electron transfer, Kinetic parameters, Laser, Laser pulse, Moiety, Nanosecond, Orthoquinone, Photochem, Photolysis, Photophysical properties, Phys, Picosecond, Protonated form, Protonation, Protonation state, Quinoline, Quinoline moiety, Rotamer, Rotamers, Semiquinone, Singlet, Singlet state, Solvent, Solvent polarity, Spectral evolution, Spectrum, Steady state, Subpicosecond, Subpicosecond laser photolysis, Transient, Transient absorbance, Transient absorption spectrum, Transient spectra, Uorescence, Uorescence decay, Uorescence emission, Uorescence excitation spectra, Uorescence intensity, Uorescence lifetime, Uorescence properties, Uorescence spectra.
Abstract
The geometric and electronic structure in solution of a new 2-styrylquinoline-type inhibitor of the HIV1-integrase was examined for the first time by following changes in the photophysical properties of the chromophore using steady state as well as time resolved absorption and fluorescence methods. The results obtained under different conditions of pH and solvent revealed that there are at least two rotamers in the ground state which exhibit different photophysical and photochemical properties. Picosecond fluorescence and absorption measurements gave evidence for a very short (∽20–30 ps) singlet excited state lifetime for one conformer and a much longer one for the other conformer, from a few hundreds of picoseconds up to nanoseconds, depending on the solvent characteristics. At physiological pH, the longer lived conformer can also undergo oxygen oxidation or photooxidation giving rise to the formation of the semiquinone radical and ultimately to a stable orthoquinone species. The role played by the singlet excited state of the rotamer on the photooxidation process is also detailed using picosecond and nanosecond absorption measurements.
Url:
DOI: 10.1039/b102555b
Affiliations:
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Marie Pierre" uniqKey="Fontaine Aupart M" first="Marie-Pierre" last="Fontaine-Aupart">Marie-Pierre Fontaine-Aupart</name><affiliation wicri:level="1"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Photophysique Moléculaire, 91405, UPR 3361 CNRS, Uniersité Paris-Sud, Orsay Cedex</wicri:regionArea><wicri:noRegion>Orsay Cedex</wicri:noRegion><wicri:noRegion>Orsay Cedex</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">France</country></affiliation></author></analytic><monogr></monogr><series><title level="j">Physical Chemistry Chemical Physics</title><title level="j" type="abbrev">Phys. Chem. Chem. Phys.</title><idno type="ISSN">1463-9076</idno><idno type="eISSN">1463-9084</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="2001">2001</date><biblScope unit="volume">3</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="3797">3797</biblScope><biblScope unit="page" to="3804">3804</biblScope></imprint><idno type="ISSN">1463-9076</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1463-9076</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Absorbance</term><term>Absorption</term><term>Absorption spectra</term><term>Absorption spectrum</term><term>Aqueous solution</term><term>Catechol</term><term>Catechol group</term><term>Catechol part</term><term>Catechol transition</term><term>Chem</term><term>Chromophore</term><term>Delay times</term><term>Dioxane</term><term>Dmso</term><term>Drug concentration</term><term>Emission spectra</term><term>Ethanol</term><term>Excitation</term><term>Excitation spectrum</term><term>Excitation wavelength</term><term>Ground state</term><term>Intramolecular electron transfer</term><term>Kinetic parameters</term><term>Laser</term><term>Laser pulse</term><term>Moiety</term><term>Nanosecond</term><term>Orthoquinone</term><term>Photochem</term><term>Photolysis</term><term>Photophysical properties</term><term>Phys</term><term>Picosecond</term><term>Protonated form</term><term>Protonation</term><term>Protonation state</term><term>Quinoline</term><term>Quinoline moiety</term><term>Rotamer</term><term>Rotamers</term><term>Semiquinone</term><term>Singlet</term><term>Singlet state</term><term>Solvent</term><term>Solvent polarity</term><term>Spectral evolution</term><term>Spectrum</term><term>Steady state</term><term>Subpicosecond</term><term>Subpicosecond laser photolysis</term><term>Transient</term><term>Transient absorbance</term><term>Transient absorption spectrum</term><term>Transient spectra</term><term>Uorescence</term><term>Uorescence decay</term><term>Uorescence emission</term><term>Uorescence excitation spectra</term><term>Uorescence intensity</term><term>Uorescence lifetime</term><term>Uorescence properties</term><term>Uorescence spectra</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">The geometric and electronic structure in solution of a new 2-styrylquinoline-type inhibitor of the HIV1-integrase was examined for the first time by following changes in the photophysical properties of the chromophore using steady state as well as time resolved absorption and fluorescence methods. The results obtained under different conditions of pH and solvent revealed that there are at least two rotamers in the ground state which exhibit different photophysical and photochemical properties. Picosecond fluorescence and absorption measurements gave evidence for a very short (∽20–30 ps) singlet excited state lifetime for one conformer and a much longer one for the other conformer, from a few hundreds of picoseconds up to nanoseconds, depending on the solvent characteristics. At physiological pH, the longer lived conformer can also undergo oxygen oxidation or photooxidation giving rise to the formation of the semiquinone radical and ultimately to a stable orthoquinone species. The role played by the singlet excited state of the rotamer on the photooxidation process is also detailed using picosecond and nanosecond absorption measurements.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Île-de-France</li></region><settlement><li>Orsay</li></settlement></list><tree><country name="France"><noRegion><name sortKey="Burdujan, Rolande" sort="Burdujan, Rolande" uniqKey="Burdujan R" first="Rolande" last="Burdujan">Rolande Burdujan</name></noRegion><name sortKey="Auclair, Christian" sort="Auclair, Christian" uniqKey="Auclair C" first="Christian" last="Auclair">Christian Auclair</name><name sortKey="Brochon, Jean Claude" sort="Brochon, Jean Claude" uniqKey="Brochon J" first="Jean-Claude" last="Brochon">Jean-Claude Brochon</name><name sortKey="Burdujan, Rolande" sort="Burdujan, Rolande" uniqKey="Burdujan R" first="Rolande" last="Burdujan">Rolande Burdujan</name><name sortKey="D Angelo, Jean" sort="D Angelo, Jean" uniqKey="D Angelo J" first="Jean" last="D'Angelo">Jean D'Angelo</name><name sortKey="Desmaele, Didier" sort="Desmaele, Didier" uniqKey="Desmaele D" first="Didier" last="Desmaële">Didier Desmaële</name><name sortKey="Enescu, Mironel" sort="Enescu, Mironel" uniqKey="Enescu M" first="Mironel" last="Enescu">Mironel Enescu</name><name sortKey="Enescu, Mironel" sort="Enescu, Mironel" uniqKey="Enescu M" first="Mironel" last="Enescu">Mironel Enescu</name><name sortKey="Fontaine Aupart, Marie Pierre" sort="Fontaine Aupart, Marie Pierre" uniqKey="Fontaine Aupart M" first="Marie-Pierre" last="Fontaine-Aupart">Marie-Pierre Fontaine-Aupart</name><name sortKey="Fontaine Aupart, Marie Pierre" sort="Fontaine Aupart, Marie Pierre" uniqKey="Fontaine Aupart M" first="Marie-Pierre" last="Fontaine-Aupart">Marie-Pierre Fontaine-Aupart</name><name sortKey="Mouscadet, Jean Francois" sort="Mouscadet, Jean Francois" uniqKey="Mouscadet J" first="Jean-François" last="Mouscadet">Jean-François Mouscadet</name><name sortKey="Pernot, Pascal" sort="Pernot, Pascal" uniqKey="Pernot P" first="Pascal" last="Pernot">Pascal Pernot</name><name sortKey="Tauc, Patrick" sort="Tauc, Patrick" uniqKey="Tauc P" first="Patrick" last="Tauc">Patrick Tauc</name><name sortKey="Tfibel, Francis" sort="Tfibel, Francis" uniqKey="Tfibel F" first="Francis" last="Tfibel">Francis Tfibel</name><name sortKey="Tfibel, Francis" sort="Tfibel, Francis" uniqKey="Tfibel F" first="Francis" last="Tfibel">Francis Tfibel</name><name sortKey="Zouhiri, Fatima" sort="Zouhiri, Fatima" uniqKey="Zouhiri F" first="Fatima" last="Zouhiri">Fatima Zouhiri</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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