Drug–Membrane Interaction as Revealed by Spectroscopic Methods: The Role of Drug Structure in the Example of Rifampicin, Levofloxacin and Rapamycin

Le-Deygen, Irina M.; Safronova, Anastasia; Mamaeva, Polina V.; Kolmogorov, Ilya M.; Skuredina, Anna A.; Kudryashova, Еlena V.

doi:10.3390/biophysica2040032

Cited by 13 publications

(21 citation statements)

References 36 publications

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“…The inclusion of rifampicin in the composition of polymeric micelles is accompanied by an increase in the intensity of peaks of aromatic C–H oscillations, while the intensity of peaks corresponding to oscillations of aliphatic CH 2 in OA residues decreases, and their maximum shifts towards smaller wavenumbers ( Figure 4 d), what also causes ordering in micelles is the filling for micelles. Similar low-frequency shifts are described in work [ 49 ] for rapamycin when loaded into liposomes. Rapamycin, a large hydrophobic molecule, was actively embedded in the bilayer of liposomes, which led to the ordering of acyl chains [ 49 ].…”

Section: Resultssupporting

confidence: 80%

“…Similar low-frequency shifts are described in work [ 49 ] for rapamycin when loaded into liposomes. Rapamycin, a large hydrophobic molecule, was actively embedded in the bilayer of liposomes, which led to the ordering of acyl chains [ 49 ]. C–O–C bonds in chitosan (1080 cm −1 ) are also sensitive to micelle formation ( Figure 4 ).…”

Section: Resultssupporting

confidence: 80%

“…Oscillations in the acetyl group of chitosan are “quenched” and make a small contribution. Bands of OA carbonyl groups ( Figure 2 , 1720–1750 cm −1 ) have multicomponents [ 20 , 24 , 49 , 50 ]. High-frequency components correspond to low-hydrated groups, and low-frequency components correspond to highly hydrated groups.…”

Section: Resultsmentioning

confidence: 99%

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Chitosan or Cyclodextrin Grafted with Oleic Acid Self-Assemble into Stabilized Polymeric Micelles with Potential of Drug Carriers

Zlotnikov

Streltsov

Belogurova

et al. 2023

Life

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Polymeric micelles combining the advantages of biocompatible poly- and oligosaccharides with classical micellar amphiphilic systems represent a promising class of drug carriers. In this work, micelles based on chitosan (or cyclodextrin) and oleic acid with various modification degrees were synthesized—the most optimal grafting degree is 15–30% in terms of CMC. According to NTA data, micelles have a hydrodynamic diameter of the main fraction of 60–100 nm. The inclusion of the antibacterial agents: moxifloxacin or rifampicin in micelles was studied by FTIR spectroscopy and fluorescence spectroscopy using a pyrene label (using monomer-excimer approach). When aromatic molecules are incorporated into micelles, the absorption bands of C-H bonds of the fatty tails of micelles shift towards smaller wavenumbers, indicating a stabilization of the micelles structure, and the microenvironment of the drug molecule changes according to the low frequencies shift and intensity changes in oscillation frequencies of 1450 cm−1 corresponding to aromatic fragment. Loading of moxifloxacin and rifampicin into micelles leads to a change in the fluorescent properties: a shift of the maximum of fluorescence emission to the long-wavelength region and an increase in the fluorescence anisotropy due to a drastic increase in the hydrodynamic volume of the fluorophore-containing rotating fragment. Using the pyrene label, the critical micelle concentrations were determined: from 4 to 30 nM depending on the polymer composition. Micellar systems enhance the effect of the antibiotic by increasing the penetration into bacterial cells and storing the drug in a protective coat. As а part of the supramolecular structure, the antibiotic remains active for more than four days, while in free form, the activity decreases after two days. In pharmacokinetic experiments, in vivo moxifloxacin in micellar systems show 1.7 times more efficiency compared to free form; moreover, two times higher maximal concentration in the blood is achieved. The advantage of polymer micellar systems in comparison with simple cyclodextrins and chitosan, which do not so significantly contribute to the antibacterial and pharmacokinetic parameters, was shown. Thus, polymeric micelles are one of the key approaches to improving the effectiveness of antibacterial drugs and solving the problems of resistant bacterial infections and multidrug resistance.

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Section: Resultssupporting

confidence: 80%

Section: Resultssupporting

confidence: 80%

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Chitosan or Cyclodextrin Grafted with Oleic Acid Self-Assemble into Stabilized Polymeric Micelles with Potential of Drug Carriers

Zlotnikov

Streltsov

Belogurova

et al. 2023

Life

Self Cite

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“…The interaction of CaP-particles with the chitosan “coat” is also clearly indicated by the dramatic intensity decrease in the 1260–1220 cm −1 region after particle covering. This is the main analytically significant band in CaP-particles—absorption band of the valent oscillations of the phosphate group (1220–1260 cm −1 ) [ 54 ], the main site of CaP-particles interaction with cationic groups of chitosan and the protein, SOD1 [ 53 , 54 , 55 ]. At the same time, the intensity of the absorption peak observed for CaP-particles at 950 cm −1 (corresponding to C⎯N bonds vibrations in chitosan [ 52 ]) increased as a result of chitosan covering, whereas the incorporation of SOD and enalaprilat into the particles resulted in a decrease in the intensity.…”

Section: Resultsmentioning

confidence: 99%

Chitosan-Covered Calcium Phosphate Particles Co-Loaded with Superoxide Dismutase 1 and ACE Inhibitor: Development, Characterization and Effect on Intraocular Pressure

et al. 2023

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Improvement of the efficiency of drug penetration into the eye tissues is still an actual problem in ophthalmology. One of the most promising solutions is drug encapsulation in carriers capable of overcoming the cornea/sclera tissue barrier. Formulations on the base of antioxidant enzyme, superoxide dismutase 1 (SOD1), and an inhibitor of angiotensin-converting enzyme, enalaprilat, were prepared by simultaneous inclusion of both drugs into calcium phosphate (CaP) particles in situ with subsequent covering of the particles with 5 kDa chitosan. The formulations obtained were characterized by dynamic light scattering and scanning electron microscopy. Hybrid CaP-chitosan particles co-loaded with SOD1 and enalaprilat had a mean hydrodynamic diameter of 120–160 nm and ζ-potential +20 ± 1 mV. The percentage of the inclusion of SOD1 and enalaprilat in hybrid particles was 30% and 56%, respectively. The ability of SOD1 and enalaprilat to reduce intraocular pressure (IOP) was examined in vivo in normotensive Chinchilla rabbits. It was shown that topical instillations of SOD1/enalaprilat co-loaded hybrid particles were much more effective in decreasing IOP compared to free enzyme or free enalaprilat and even to the same particles that contained a single drug. Thus, the proposed formulations demonstrate potential as prospective therapeutic agents for the treatment of glaucoma.

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“…ATR-FTIR studies were used to investigate the mechanism of interaction between RIF and the membrane of neutral (dipalmitoylphosphatidylcholine) and anionic (dipalmitoylphosphatidylcholine:cardiolipin) liposomes. It was found that the main binding sites were phosphate and carbonyl groups of the lipids [ 158 ].…”

Section: Sensors and Analytical Methods For The Investigation Of Rifa...mentioning

confidence: 99%

State of the Art on Developments of (Bio)Sensors and Analytical Methods for Rifamycin Antibiotics Determination

Noor

David

Jinga

et al. 2023

Sensors

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This review summarizes the literature data reported from 2000 up to the present on the development of various electrochemical (voltammetric, amperometric, potentiometric and photoelectrochemical), optical (UV-Vis and IR) and luminescence (chemiluminescence and fluorescence) methods and the corresponding sensors for rifamycin antibiotics analysis. The discussion is focused mainly on the foremost compound of this class of macrocyclic drugs, namely rifampicin (RIF), which is a first-line antituberculosis agent derived from rifampicin SV (RSV). RIF and RSV also have excellent therapeutic action in the treatment of other bacterial infectious diseases. Due to the side-effects (e.g., prevalence of drug-resistant bacteria, hepatotoxicity) of long-term RIF intake, drug monitoring in patients is of real importance in establishing the optimum RIF dose, and therefore, reliable, rapid and simple methods of analysis are required. Based on the studies published on this topic in the last two decades, the sensing principles, some examples of sensors preparation procedures, as well as the performance characteristics (linear range, limits of detection and quantification) of analytical methods for RIF determination, are compared and correlated, critically emphasizing their benefits and limitations. Examples of spectrometric and electrochemical investigations of RIF interaction with biologically important molecules are also presented.

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Drug–Membrane Interaction as Revealed by Spectroscopic Methods: The Role of Drug Structure in the Example of Rifampicin, Levofloxacin and Rapamycin

Cited by 13 publications

References 36 publications

Chitosan or Cyclodextrin Grafted with Oleic Acid Self-Assemble into Stabilized Polymeric Micelles with Potential of Drug Carriers

Chitosan or Cyclodextrin Grafted with Oleic Acid Self-Assemble into Stabilized Polymeric Micelles with Potential of Drug Carriers

Chitosan-Covered Calcium Phosphate Particles Co-Loaded with Superoxide Dismutase 1 and ACE Inhibitor: Development, Characterization and Effect on Intraocular Pressure

State of the Art on Developments of (Bio)Sensors and Analytical Methods for Rifamycin Antibiotics Determination

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