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Pregled bibliografske jedinice broj: 368980

Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine


Šoškić, Milan; Magnus, Volker
Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine // EuroQSAR-08 The 17th European Symposium on Quantitative Structure-Activity Relationships & Omics Technologies and Systems Biology
Uppsala, Švedska, 2008. (poster, međunarodna recenzija, sažetak, znanstveni)


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Naslov
Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine

Autori
Šoškić, Milan ; Magnus, Volker

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
EuroQSAR-08 The 17th European Symposium on Quantitative Structure-Activity Relationships & Omics Technologies and Systems Biology / - , 2008

Skup
The 17th European Symposium on Quantitative Structure-Activity Relationships & Omics Technologies and Systems Biology

Mjesto i datum
Uppsala, Švedska, 21.09.2008. - 26.09.2008

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
indole derivatives; 3; 5-dinitrobenzoylphenylglycine; high performance liquid chromatography; quantitative structure-activity relationship

Sažetak
Aromatic interactions play an important role in ligand-receptor interactions in biological systems. The importance of such interactions in auxin recognition by the potential receptor, ABP1, is strongly suggested by a recent crystallographic study which showed that the indole moiety of the amino acid residue Trp-151 is part of the active site accommodating the synthetic auxin, naphthalene-1-acetic acid. Here we use high performance liquid chromatography to study the affinity of about 50 indole derivatives (most of them with auxin activity) to immobilized 3, 5-dinitrobenzoyl-phenylglycine which is expected to act as a pi-electron acceptor because the electron density in its aromatic ring system is significantly less than in the indole nucleus. To verify the retention mechanism, a QSPR (quantitative structure-property relationship) analysis was performed. A five-parameter model was obtained which accounted for more than 95% of the variations in the relative binding constants. The model confirmed that binding affinity is significantly influenced by the electron density in the indole nucleus. Thus, for indoles with small ring-substituents, their inductive effects predominantly determined the binding constants: electron-withdrawing substituents reduced affinity, while electron-donating substituents increased it. The presence of ring-substituents with hydrogen-bonding capacity further strengthened binding to the acceptor phase. On the other hand, bulky substituents generally decreased affinity, presumably by interfering with the interaction of the indoles with the stationary phase. The relative binding constants of dihalogenated indole-3-acetic acids were essentially determined by their substitution pattern. Indole-3-acetic acids bound more strongly than the corresponding 3-unsubstituted indoles, presumably as a result of additional hydrogen bonding and/or dipole-dipole interaction involving the carboxyl group.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekti:
098-0982913-2829 - Molekularna regulacija biljnog razvitka (Salopek-Sondi, Branka, MZOS ) ( CroRIS)
178-0982929-2259 - Molekulsko prepoznavanje biljnih regulatora rasta (Šoškić, Milan, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Agronomski fakultet, Zagreb

Profili:

Avatar Url Milan Šoškić (autor)

Avatar Url Volker Magnus (autor)


Citiraj ovu publikaciju:

Šoškić, Milan; Magnus, Volker
Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine // EuroQSAR-08 The 17th European Symposium on Quantitative Structure-Activity Relationships & Omics Technologies and Systems Biology
Uppsala, Švedska, 2008. (poster, međunarodna recenzija, sažetak, znanstveni)
Šoškić, M. & Magnus, V. (2008) Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine. U: EuroQSAR-08 The 17th European Symposium on Quantitative Structure-Activity Relationships & Omics Technologies and Systems Biology.
@article{article, author = {\v{S}o\v{s}ki\'{c}, Milan and Magnus, Volker}, year = {2008}, keywords = {indole derivatives, 3, 5-dinitrobenzoylphenylglycine, high performance liquid chromatography, quantitative structure-activity relationship}, title = {Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine}, keyword = {indole derivatives, 3, 5-dinitrobenzoylphenylglycine, high performance liquid chromatography, quantitative structure-activity relationship}, publisherplace = {Uppsala, \v{S}vedska} }
@article{article, author = {\v{S}o\v{s}ki\'{c}, Milan and Magnus, Volker}, year = {2008}, keywords = {indole derivatives, 3, 5-dinitrobenzoylphenylglycine, high performance liquid chromatography, quantitative structure-activity relationship}, title = {Interactions of indole derivatives with immobilized 3, 5-dinitrobenzoylphenylglycine}, keyword = {indole derivatives, 3, 5-dinitrobenzoylphenylglycine, high performance liquid chromatography, quantitative structure-activity relationship}, publisherplace = {Uppsala, \v{S}vedska} }




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