Spectroscopic Studies of Amino Acid Ionic Liquid-Supported Schiff Bases

Ossowicz, Paula; Januś, Ewa; Schroeder, Grzegorz; Rozwadowski, Zbigniew

doi:10.3390/molecules18054986

Cited by 33 publications

(27 citation statements)

References 36 publications

(56 reference statements)

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“…Additionally, evidence for the ionic structure is the carbonyl carbon signal, which is shied about 2 ppm upeld (to about 179 ppm) in ibuprofen derivatives compared to the chemical shi value for this carbon in the parent ibuprofen (181.16 ppm). [39][40][41] The characteristic IR absorption bands for [ValOR][IBU] also conrmed the ionic structure. The FTIR spectra for ibuprofen, Lvaline ester, L-valine ester hydrochloride, and ester ibuprofenate are presented for comparison in Fig.…”

Section: Synthesis Identication and Characterisation Of The [Valor]mentioning

confidence: 99%

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

et al. 2020

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New ibuprofen derivatives were made via conjugation with L-valine alkyl esters (ValOR), where R was changed from an ethyl to a hexyl group. The ionic structure was confirmed using NMR and FTIR. Specific rotation, solubility in commonly used solvents, thermal properties including phase transitions temperatures, and thermal stability were also determined. The ionic structure with a protonated amine group on an L-valine ester and melting points below 100 C allowed inclusion of these ibuprofen derivatives into the pharmaceutically active protic ionic liquids. The ibuprofen salt solubility in deionised water and two buffer solutions at pH 5.4 and 7.4 were established and compared with the parent acid solubility. The octanol/water (buffer) partition coefficient, permeation through porcine skin, and accumulation in the skin were also measured. Ibuprofen pairing with L-valine alkyl esters [ValOR][IBU], caused higher solubility and a greater drug molecule absorption through biological membranes. log P was lower for ibuprofen salts than for the acid and it increased with a longer L-valine ester cation alkyl chain. In vitro porcine skin tests showed that ibuprofen salts with a propyl or isopropyl ester in L-valine are particularly relevant for topical application. They provide transport for ibuprofen through the skin at much higher rate than the unmodified acid and a higher permeated ibuprofen concentration, which can improve efficacy. Thus, synthesised ibuprofen derivatives could be used as drug carriers in transdermal systems to provide better drug bioavailability, and they can be also be the source of exogenous L-valine.

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Section: Synthesis Identication and Characterisation Of The [Valor]mentioning

confidence: 99%

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

et al. 2020

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“…As given in Figure 3, the azomethine carbon signal for the ligand appears at 157.594 ppm [33]. The signal for the carbon of carbonyl group (C-3) appears at 172.668 ppm in the spectrum of ligand [34]. Aromatic carbons showed signals in the range of 115-145 ppm.…”

Section: 23mentioning

confidence: 92%

Spectral Investigation andIn VitroAntibacterial Evaluation of Ni^IIand Cu^IIComplexes of Schiff Base Derived from Amoxicillin andα-Formylthiophene (αft)

Chaudhary

Mishra

2015

Journal of Chemistry

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Two new metal complexes of general formula M(Haαft)2[M =NiIIandCuII] of asymmetrical Schiff base ligand (HL = Haαft) derived from amoxicillin andα-formylthiophene have been prepared and characterized by various physicochemical and spectral techniques. Molar conductance measurement indicates nonelectrolytic nature of the metal complexes. FT-IR spectral study reveals the ligation of metal ions at two different nitrogen [NN] donor sites of Haαft. FT-IR and electronic absorption spectral evidences suggest distorted tetrahedral and square planar geometry forCuIIandNiIIcomplexes, respectively. The structure optimization by molecular mechanics (MM) force field calculation through ArgusLab 4.0.1 version software also supports the concerned geometry of the complexes. The cell dimensions as suggested by XRPD study,a(6.753 Å),b(13.904 Å),c(20.122 Å),α(142.76°),β(106.580°), andγ(72.4343°) forCuIIanda(24.2547 Å),b(6.6371 Å),c(5.5047 Å) (α=β=γ= 90°) forNiIIcomplexes, are in good agreement with their triclinic and orthorhombic crystal systems. Particle size calculation by Scherrer’s formula indicates nanocrystalline nature of the complexes. The antibacterial sensitivity study suggests promising activities of Haαft (Ligand) and M(Haαft)2complexes against four clinical pathogenic bacteria, namely,E. coli,P. vulgaris,P. aeruginosa, andS. aureus, though being less active than the standard drug amikacin.

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“…On the 13 C-NMR spectra of all obtained KETO-ILs, there is not observed the characteristic signal for imine with a chemical shift between 162 and 164 ppm. Moreover, in FTIR spectra there are not the characteristic bands for Schiff bases, neither the vibrational band of N-H at 3355 cm −1 nor C=N stretching vibration band at 1657 cm −1 [25].…”

Section: Synthesis Of the Amino-acid Ester-ketoprofenatementioning

confidence: 94%

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

et al. 2019

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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.

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Spectroscopic Studies of Amino Acid Ionic Liquid-Supported Schiff Bases

Cited by 33 publications

References 36 publications

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Spectral Investigation andIn VitroAntibacterial Evaluation of Ni^IIand Cu^IIComplexes of Schiff Base Derived from Amoxicillin andα-Formylthiophene (αft)

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

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Spectroscopic Studies of Amino Acid Ionic Liquid-Supported Schiff Bases

Cited by 33 publications

References 36 publications

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Spectral Investigation andIn VitroAntibacterial Evaluation of NiIIand CuIIComplexes of Schiff Base Derived from Amoxicillin andα-Formylthiophene (αft)

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

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Spectral Investigation andIn VitroAntibacterial Evaluation of Ni^IIand Cu^IIComplexes of Schiff Base Derived from Amoxicillin andα-Formylthiophene (αft)