Pregled bibliografske jedinice broj: 268369
Binding of ring-substituted indole-3-acetic acids to human serum albumin
Binding of ring-substituted indole-3-acetic acids to human serum albumin // Bioorganic & Medicinal Chemistry, 15 (2007), 13; 4595-4600 (međunarodna recenzija, članak, znanstveni)
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Naslov
Binding of ring-substituted indole-3-acetic acids to human serum albumin
Autori
Šoškić, Milan ; Magnus, Volker
Izvornik
Bioorganic & Medicinal Chemistry (0968-0896) 15
(2007), 13;
4595-4600
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
indole-3-acetic acid; human serum albumin; high-performance liquid chromatography; octanol-water partition coefficient; QSPR (quantitative structure-property relationships)
Sažetak
The plant hormone, indole-3-acetic acid (IAA), and its ring-substituted derivatives have recently attracted attention as promising pro-drugs in cancer therapy. Here we present relative binding constants to human serum albumin for IAA and 34 of its derivatives, as obtained using the immobilized protein bound to a support suitable for high-performance liquid chromatography. We also report their octanol-water partition coefficients (log Kow) computed from retention data on a C18-coated silica gel column. A four-parameter QSPR (quantitative structure-property relationships) model, based on physico-chemical properties is put forward, which accounts for more than 96% of the variations in the binding affinities of these compounds. The model confirms the importance of lipophilicity as a global parameter governing interaction with serum albumin, but also assigns significant roles to parameters specifically related to the molecular topology of ring-substituted IAAs. Bulky substituents at ring-position 6 increase affinity, those at position 2 obstruct binding, while no steric effects were noted at other ring-positions. Electron-withdrawing substituents at position 5 enhance binding, but have no obvious effect at other ring positions.
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
Citiraj ovu publikaciju:
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::
- Chemical Abstracts
- Excerpta Medica
- Biochemistry and Biophysics Citation Index
- Chemical Citation Index
- BIOSIS
- Beilstein Database
- Cancerlit
- EMBASE
- Elsevier BIOBASE/Current Advances in Biological Sciences
- MEDLINE
- Pascal
- Research Alert
- SCISEARCH
- Scopus
- TOXFILE