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Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters

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2014
28-253-1-PB.pdf (2.385Mb)
Authors
Cvijetić, Ilija
Petrović, D.D.
Verbić, Tatjana
Juranić, Ivan
Drakulić, Branko
Article (Published version)
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Abstract
Interactions of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic acid (compound 1) and its mono-Me ester (compound 2) with the human serum albumin (HSA) have been studied by fluorescence spectroscopy. Comp. 1 exerts antiproliferative activity toward human tumor cells and significant selectivity (tumor vs. healthy cells) in vitro. Competitive binding study with warfarin and ibuprofen as binding site probes, revealed that one molecule of comp. 1 selectively binds to HSA Sudlow site I (warfarin site) with moderate binding constant (Kb = (2.8 ± 0.5) × 104 M-1 at 37 ± 1 °C), while comp. 2 binds to Sudlow site II (Kb = (3.2 ± 0.9) × 104 M-1 at 37 ± 1 °C). Fluorescence quenching at different temperatures was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. Energy resonance transfer between HSA and comp. 1 was examined according to Förster's non-radiative energy transfer theory. Distance of about 10 Å between ligand and Trp214 (HSA)... was obtained. Docking studies confirmed HSA Sudlow site I as a preferable comp. 1 binding site, and Sudlow site II as comp. 2 binding site. Molecular dynamics simulations proved the stability of comp. 1/HSA complex. © 2014 by the authors.

Keywords:
Competitive binding / Fluorescence spectroscopy / Molecular docking / Molecular dynamics
Source:
ADMET and DMPK, 2014, 2, 2, 126-142
Projects:
  • High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)

DOI: 10.5599/admet.2.2.28

ISSN: 1848-7718

Scopus: 2-s2.0-85047052441
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2669
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