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1.
Materials (Basel) ; 14(12)2021 Jun 09.
Artigo em Inglês | MEDLINE | ID: mdl-34207691

RESUMO

Nowadays, we consume very large amounts of medicinal substances. Medicines are used to cure, halt, or prevent disease, ease symptoms, or help in the diagnosis of illnesses. Some medications are used to treat pain. Ibuprofen is one of the most popular drugs in the world (it ranks third). This drug enters our water system through human pharmaceutical use. In this article, we describe and compare the biodegradation of ibuprofen and ibuprofen derivatives-salts of L-valine alkyl esters. Biodegradation studies of ibuprofen and its derivatives have been carried out with activated sludge. The structure modifications we received were aimed at increasing the biodegradation of the drug used. The influence of the alkyl chain length of the ester used in the biodegradation of the compound was also verified. The biodegradation results correlated with the lipophilic properties (log P).

2.
Int J Mol Sci ; 22(12)2021 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-34200719

RESUMO

The potential of bacterial cellulose as a carrier for the transport of ibuprofen (a typical example of non-steroidal anti-inflammatory drugs) through the skin was investigated. Ibuprofen and its amino acid ester salts-loaded BC membranes were prepared through a simple methodology and characterized in terms of structure and morphology. Two salts of amino acid isopropyl esters were used in the research, namely L-valine isopropyl ester ibuprofenate ([ValOiPr][IBU]) and L-leucine isopropyl ester ibuprofenate ([LeuOiPr][IBU]). [LeuOiPr][IBU] is a new compound; therefore, it has been fully characterized and its identity confirmed. For all membranes obtained the surface morphology, tensile mechanical properties, active compound dissolution assays, and permeation and skin accumulation studies of API (active pharmaceutical ingredient) were determined. The obtained membranes were very homogeneous. In vitro diffusion studies with Franz cells were conducted using pig epidermal membranes, and showed that the incorporation of ibuprofen in BC membranes provided lower permeation rates to those obtained with amino acids ester salts of ibuprofen. This release profile together with the ease of application and the simple preparation and assembly of the drug-loaded membranes indicates the enormous potentialities of using BC membranes for transdermal application of ibuprofen in the form of amino acid ester salts.


Assuntos
Aminoácidos/química , Anti-Inflamatórios não Esteroides/farmacologia , Celulose/química , Ésteres/química , Ibuprofeno/farmacologia , Absorção Cutânea/efeitos dos fármacos , Pele/efeitos dos fármacos , Administração Cutânea , Animais , Anti-Inflamatórios não Esteroides/administração & dosagem , Anti-Inflamatórios não Esteroides/química , Bactérias/metabolismo , Sistemas de Liberação de Medicamentos , Ibuprofeno/administração & dosagem , Ibuprofeno/química , Suínos
3.
Molecules ; 26(6)2021 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-33808584

RESUMO

Novel biocompatible compounds that stabilize proteins in solution are in demand for biomedical and/or biotechnological applications. Here, we evaluated the effect of six ionic liquids, containing mono- or dicholinium [Chol]1or2 cation and anions of charged amino acids such as lysine [Lys], arginine [Arg], aspartic acid [Asp], or glutamic acid [Glu], on the structure, thermal, and storage stability of the Rapana thomasiana hemocyanin (RtH). RtH is a protein with huge biomedicinal potential due to its therapeutic, drug carrier, and adjuvant properties. Overall, the ionic liquids (ILs) induce changes in the secondary structure of RtH. However, the structure near the Cu-active site seems unaltered and the oxygen-binding capacity of the protein is preserved. The ILs showed weak antibacterial activity when tested against three Gram-negative and three Gram-positive bacterial strains. On the contrary, [Chol][Arg] and [Chol][Lys] exhibited high anti-biofilm activity against E. coli 25213 and S. aureus 29213 strains. In addition, the two ILs were able to protect RtH from chemical and microbiological degradation. Maintained or enhanced thermal stability of RtH was observed in the presence of all ILs tested, except for RtH-[Chol]2[Glu].


Assuntos
Aminoácidos/química , Gastrópodes/química , Hemocianinas/química , Líquidos Iônicos/química , Animais
4.
Molecules ; 25(1)2019 Dec 25.
Artigo em Inglês | MEDLINE | ID: mdl-31881750

RESUMO

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 105 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.


Assuntos
Líquidos Iônicos/síntese química , Líquidos Iônicos/metabolismo , Cetoprofeno/síntese química , Soroalbumina Bovina/metabolismo , Animais , Bovinos , Morte Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Ésteres/síntese química , Ésteres/química , Transferência Ressonante de Energia de Fluorescência , Líquidos Iônicos/química , Líquidos Iônicos/toxicidade , Cetoprofeno/química , Cetoprofeno/toxicidade , Cinética , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Secundária de Proteína , Células RAW 264.7 , Soroalbumina Bovina/química , Solubilidade , Solventes/química , Água/química
5.
Molecules ; 24(18)2019 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-31500119

RESUMO

Ionic liquids based on different l-amino acids (glycine, l-valine, l-leucine, l-isoleucine, l-histidine, l-methionine, l-tyrosine, l-tryptophan, l-arginine, and l-threonine) and different cations (tetrabutylammonium (TBA), tributylmethylammonium (tBMA), didecyldimethylammonium (DDA), (2-hydroxyethyl)trimethylammonium (choline) (Chol), alkyl(C12-C14) dimethylbenzylammonium (benzalkonium) (BA), dodecyltrimethylammonium (DDTMA), hexadecyltrimethylammonium (HDTMA), octadecyltrimethylammonium (ODTMA) and 1-ethyl-3-methylimidazolium (EMIM)) have been synthesized and characterized by NMR and FTIR. Viscosity, specific rotation, surface activity, thermal stability (TG), and phase transformations (DSC) have been determined and compared with available data. Furthermore, benzalkonium, didecyldimethylammonium, dodecyltrimethylammonium, hexadecyltrimethylammonium, and octadecyltrimethylammonium amino acid ionic liquids have been shown to exhibit surface activity. The dissolution of cellulose in amino acid ionic liquids (AAILs) composed of various cations was also investigated. Cellulose was only dissolved in EMIM salts of amino acids. In particular, the influence of the cation type on selected physicochemical and spectroscopic properties were discussed. The article is a mini review on amino acid ionic liquids.


Assuntos
Aminoácidos/química , Imidazóis/química , Líquidos Iônicos/química , Compostos de Amônio Quaternário/química , Cátions/química , Celulose/química , Espectroscopia de Ressonância Magnética , Relação Estrutura-Atividade
6.
Int J Biol Macromol ; 82: 798-805, 2016 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26478091

RESUMO

This is the first study on the surface modification of a hemocyanin from marine snail Rapana thomasiana (RtH) with series of imidazolium-based amino acid ionic liquids [emim][AA]. We monitored the induced by [emim][AA] conformational changes in RtH molecule and evaluated the effect of these ionic liquids (ILs) on the protein thermal stability. The cytotoxicity of all obtained RtH-[emim][AA] complexes was assessed toward breast cancer cells (MCF-7) and murine fibroblasts (3T3). As a whole, even small amounts of the tested ILs altered the secondary structure of RtH. The thermal denaturation of RtH in presence of [emim][AA] displayed multi-component transitions, which were shifted toward lower temperatures in comparison to those estimated for the native RtH. The profiles of the RtH-IL calorimetric curves show a clear dependence on the structure of the added salts. In addition, all RtH-[emim][AA] complexes exhibited an enhanced antiprofilerative activity of toward MCF-7 cells in comparison to that of the native RtH. The best results are observed for RtH-[emim][Leu], RtH-[emim][Trp] or RtH-[emim][Ile], which applied in concentration of 700 µg/mL inhibited the MCF-7 cell viability (for 24h) by 66, 63 and 53%, respectively. In addition, these IL-RtH complexes were less cytotoxic to 3T3 cells, i.e. they exhibited some cell specificity.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Gastrópodes , Hemocianinas/química , Hemocianinas/farmacologia , Líquidos Iônicos/química , Células 3T3 , Animais , Neoplasias da Mama , Sobrevivência Celular/efeitos dos fármacos , Feminino , Fibroblastos/efeitos dos fármacos , Fibroblastos/metabolismo , Humanos , Líquidos Iônicos/síntese química , Células MCF-7 , Camundongos , Estabilidade Proteica , Espectroscopia de Infravermelho com Transformada de Fourier , Termodinâmica
7.
Molecules ; 18(5): 4986-5004, 2013 Apr 29.
Artigo em Inglês | MEDLINE | ID: mdl-23629755

RESUMO

Amino acid ionic liquid-supported Schiff bases, derivatives of salicylaldehyde and various amino acids (L-threonine, L-valine, L-leucine, L-isoleucine and L-histidine) have been investigated by means of various spectroscopic techniques (NMR, UV-Vis, IR, MS) and deuterium isotope effects on ¹³C-NMR chemical shifts. The results have shown that in all studied amino acid ionic liquid-supported Schiff bases (except the L-histidine derivative) a proton transfer equilibrium exists and the presence of the COO⁻ group stabilizes the proton transferred NH-form.


Assuntos
Aldeídos/química , Aminoácidos/química , Bases de Schiff/química , Análise Espectral/métodos
8.
J Colloid Interface Sci ; 365(1): 191-7, 2012 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-21978404

RESUMO

The epoxidation of 1,4-bis(allyloxy)butane (DiBan) with hydrogen peroxide as an oxidant in the presence of o-phosphoric acid and sodium tungstate as an epoxidation catalyst was carried out in an organic solvent/aqueous solution two-phase medium. A few different phase-transfer catalysts were used in the process. The effect of the stirring speed, nature of solvent, the type of PT catalyst and molar ratio of H(2)O(2):DiBan, DiBan:Na(2)WO(4):H(3)PO(4) on the DiBan conversion as the function of time was studied. Based on the experimental results, a pseudo-first-order expression for the reaction rate was applied and most efficient conditions epoxidation were developed.

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