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Pregled bibliografske jedinice broj: 619660

Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study


Porobić, Ivana; Kontrec, Darko; Šoškić Milan
Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study // Bioorganic & medicinal chemistry, 21 (2013), 3; 653-659 doi:10.1016/j.bmc.2012.11.048 (međunarodna recenzija, članak, znanstveni)


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Naslov
Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study

Autori
Porobić, Ivana ; Kontrec, Darko ; Šoškić Milan

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 21 (2013), 3; 653-659

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
indole derivatives; molecularly imprinted polymers; High-performance Liquid Chromatography; Retention Factors; Quantitative structure-property relationships

Sažetak
Three molecularly imprinted polymers (MIPs) were prepared using the phytohormone indole-3-acetic acid (IAA) as a template molecule, 4-vinylpyridine (MIP-1 and MIP-2) or N, N-dimethylaminoethyl methacrylate (MIP-3) as functional monomers, ethylenglycol dimethacrylate as a cross linker and acetonitrile (MIP-1), a methanol–water mixture (MIP-2) or chloroform (MIP-3) as porogens. Retention factors for IAA and 29 indole derivatives were determined by high-performance liquid chromatography, using the molecularly imprinted polymers as stationary phases and acetonitrile as an eluent. High correlations between selectivity factors of above mentioned polymers indicate that their retention mechanisms are basically the same. A quantitative structure–property relationships analysis revealed that the presence of the terminal carboxyl group on the 3-side chain plays an essential role in the binding of the indole derivatives to the polymers. The derivatives without the carboxyl group exhibit a drastically lower affinity toward the polymers. Another factor which favors the binding is electronic density of indole nucleus. Substituents with electro-withdrawing properties enhance the binding, while electro-donating substituents have the opposite effect. The length of the 3-side chain also affects the binding. Indole-3-carboxylic acid having the carboxyl group directly attached to the ring as well as the derivatives whose side chain is longer than that of IAA bind to the polymers with a lower affinity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekt / tema
098-0982904-2910 - Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja (Vinković, Vladimir, MZOS - )
178-0982929-2259 - Molekulsko prepoznavanje biljnih regulatora rasta (Šoškić, Milan, MZOS - )

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

Profili:

Avatar Url Ivana Porobić (autor)

Avatar Url Darko Kontrec (autor)

Citiraj ovu publikaciju

Porobić, Ivana; Kontrec, Darko; Šoškić Milan
Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study // Bioorganic & medicinal chemistry, 21 (2013), 3; 653-659 doi:10.1016/j.bmc.2012.11.048 (međunarodna recenzija, članak, znanstveni)
Porobić, I., Kontrec, D. & Šoškić Milan (2013) Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study. Bioorganic & medicinal chemistry, 21 (3), 653-659 doi:10.1016/j.bmc.2012.11.048.
@article{article, year = {2013}, pages = {653-659}, DOI = {10.1016/j.bmc.2012.11.048}, keywords = {indole derivatives, molecularly imprinted polymers, High-performance Liquid Chromatography, Retention Factors, Quantitative structure-property relationships}, journal = {Bioorganic and medicinal chemistry}, doi = {10.1016/j.bmc.2012.11.048}, volume = {21}, number = {3}, issn = {0968-0896}, title = {Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid : A QSPR study}, keyword = {indole derivatives, molecularly imprinted polymers, High-performance Liquid Chromatography, Retention Factors, Quantitative structure-property relationships} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


Uključenost u ostale bibliografske baze podataka:


  • CA Search (Chemical Abstracts)
  • MEDLINE


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