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Tytuł pozycji:

Ketoprofen-Based Ionic Liquids: Synthesis and Interactions with Bovine Serum Albumin.

Tytuł :
Ketoprofen-Based Ionic Liquids: Synthesis and Interactions with Bovine Serum Albumin.
Autorzy :
Ossowicz P; Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Piastów Ave. 42, 71-065 Szczecin, Poland.
Kardaleva P; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. Bl. 9, 1113 Sofia, Bulgaria.
Guncheva M; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. Bl. 9, 1113 Sofia, Bulgaria.
Klebeko J; Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Piastów Ave. 42, 71-065 Szczecin, Poland.
Świątek E; Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Piastów Ave. 42, 71-065 Szczecin, Poland.
Janus E; Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Piastów Ave. 42, 71-065 Szczecin, Poland.
Yancheva D; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. Bl. 9, 1113 Sofia, Bulgaria.
Angelov I; Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. Bl. 9, 1113 Sofia, Bulgaria.
Pokaż więcej
Źródło :
Molecules (Basel, Switzerland) [Molecules] 2019 Dec 25; Vol. 25 (1). Date of Electronic Publication: 2019 Dec 25.
Typ publikacji :
Journal Article
Język :
English
Journal Info :
Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
Imprint Name(s) :
Original Publication: Basel, Switzerland : MDPI, c1995-
MeSH Terms :
Ionic Liquids/*chemical synthesis
Ionic Liquids/*metabolism
Ketoprofen/*chemical synthesis
Serum Albumin, Bovine/*metabolism
Animals ; Cattle ; Cell Death/drug effects ; Cell Survival/drug effects ; Esters/chemical synthesis ; Esters/chemistry ; Fluorescence Resonance Energy Transfer ; Ionic Liquids/chemistry ; Ionic Liquids/toxicity ; Ketoprofen/chemistry ; Ketoprofen/toxicity ; Kinetics ; Macrophages/cytology ; Macrophages/drug effects ; Mice ; Protein Structure, Secondary ; RAW 264.7 Cells ; Serum Albumin, Bovine/chemistry ; Solubility ; Solvents/chemistry ; Water/chemistry
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Grant Information :
National Research Programme " Young scientists and postdoctoral students", DCM # 577 / 17.08.2018 Ministry of Education and Science of Bulgaria
Contributed Indexing :
Keywords: binding constants; bovine serum albumin; ionic liquids; ketoprofen; secondary structure
Substance Nomenclature :
0 (Esters)
0 (Ionic Liquids)
0 (Solvents)
059QF0KO0R (Water)
27432CM55Q (Serum Albumin, Bovine)
90Y4QC304K (Ketoprofen)
Entry Date(s) :
Date Created: 20191229 Date Completed: 20200527 Latest Revision: 20200527
Update Code :
20200716
PubMed Central ID :
PMC6983093
DOI :
10.3390/molecules25010090
PMID :
31881750
Czasopismo naukowe
The development of ionic liquids based on active pharmaceutical ingredients (API-ILs) is a possible solution to some of the problems of solid and/or hydrophobic drugs such as low solubility and bioavailability, polymorphism and an alternative route of administration could be suggested as compared to the classical drug. Here, we report for the first time the synthesis and detailed characterization of a series of ILs containing a cation amino acid esters and anion ketoprofen (KETO-ILs). The affinity and the binding mode of the KETO-ILs to bovine serum albumin (BSA) were assessed using fluorescence spectroscopy. All compounds bind in a distance not longer than 6.14 nm to the BSA fluorophores. The estimated binding constants (KA) are in order of 10 5 L mol -1 , which is indicative of strong drug or IL-BSA interactions. With respect to the ketoprofen-BSA system, a stronger affinity of the ILs containing l-LeuOEt, l-ValOBu, and l-ValOEt cation towards BSA is clearly seen. Fourier transformed infrared spectroscopy experiments have shown that all studied compounds induced a rearrangement of the protein molecule upon binding, which is consistent with the suggested static mechanism of BSA fluorescence quenching and formation of complexes between BSA and the drugs. All tested compounds were safe for macrophages.
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