Informacja

Drogi użytkowniku, aplikacja do prawidłowego działania wymaga obsługi JavaScript. Proszę włącz obsługę JavaScript w Twojej przeglądarce.

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.
Źródło:
Molecules (Basel, Switzerland) [Molecules] 2019 Dec 25; Vol. 25 (1). Date of Electronic Publication: 2019 Dec 25.
Typ publikacji:
Journal Article
Język:
English
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
References:
Dent Mater. 2019 Aug;35(8):1155-1165. (PMID: 31128938)
Annu Rev Chem Biomol Eng. 2014;5:527-46. (PMID: 24910920)
Crit Rev Biochem Mol Biol. 1995;30(2):95-120. (PMID: 7656562)
Chem Rev. 2015 Oct 28;115(20):11379-448. (PMID: 26426209)
Chem Commun (Camb). 2012 Jun 4;48(44):5422-4. (PMID: 22534649)
Biophys Rev. 2018 Jun;10(3):691-706. (PMID: 29700779)
Chem Rev. 2017 May 24;117(10):7132-7189. (PMID: 28125212)
Molecules. 2013 Apr 29;18(5):4986-5004. (PMID: 23629755)
ChemMedChem. 2019 May 6;14(9):907-911. (PMID: 30735308)
ACS Omega. 2019 Aug 06;4(8):13270-13278. (PMID: 31460455)
Spectrochim Acta A Mol Biomol Spectrosc. 2011 Jan;78(1):410-4. (PMID: 21147021)
Expert Opin Drug Deliv. 2013 Oct;10(10):1367-81. (PMID: 23795613)
Acta Biochim Biophys Sin (Shanghai). 2007 Aug;39(8):549-59. (PMID: 17687489)
Talanta. 2016 Apr 1;150:20-6. (PMID: 26838377)
Eur J Pharm Sci. 2020 Jan 1;141:105042. (PMID: 31634554)
Hepatol Int. 2016 Jan;10(1):124-32. (PMID: 26420218)
Mol Immunol. 2012 Oct;52(3-4):174-82. (PMID: 22677715)
AAPS PharmSciTech. 2019 Oct 24;20(8):322. (PMID: 31650263)
Molecules. 2015 Jun 18;20(6):11219-35. (PMID: 26096431)
Int J Pharm. 2018 Jul 30;546(1-2):31-38. (PMID: 29751143)
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:
20240104
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.
Zaloguj się, aby uzyskać dostęp do pełnego tekstu.

Ta witryna wykorzystuje pliki cookies do przechowywania informacji na Twoim komputerze. Pliki cookies stosujemy w celu świadczenia usług na najwyższym poziomie, w tym w sposób dostosowany do indywidualnych potrzeb. Korzystanie z witryny bez zmiany ustawień dotyczących cookies oznacza, że będą one zamieszczane w Twoim komputerze. W każdym momencie możesz dokonać zmiany ustawień dotyczących cookies