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Free radical formation in salicylic acid and heating parameters – application of EPR, UV-Vis, TGA and colorimetry examination to optimize thermal sterilization

100%
Ramos P., Pilawa B.
Acta Poloniae Pharmaceutica - Drug Research
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2020
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vol. 77
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issue 3
431-441
EN
Salicylic acid heated at different temperatures and times was examined by an X-band (9.3 GHz) EPR spectroscopy, UV-Vis spectrophotometry, TGA and colorimetry test to optimize its thermal sterilization process. Free radical formation (~1018 spin/g) during thermal sterilization of salicylic acid according to the pharmaceutical norms at temperature 120oC and time of 120 minutes was compared with those for heating at the new tested temperatures and times: 130oC and 60 minutes, and 140oC and 30 minutes. It was obtained that the relatively lower free radical concentrations characterized salicylic acid heated at temperatures (times): 120oC (120 minutes), and 130oC (60 minutes), than at temperature (time) 140oC (30 minutes). So treatment at temperature 120oC during 120 minutes, and temperature 130oC during 60 minutes, were recommended as the optimal for thermal sterilization of salicylic acid. Salicylic acid should not be sterilized at temperature 140oC during 30 minutes, because of the highest free radical formation. Free radical systems of thermally treated salicylic acid revealed complex character. Fast spin-lattice relaxation processes existed in heated salicylic acid. Strong dipolar interactions characterized all the heated salicylic acid samples. EPR spectroscopy, UV-Vis spectrophotometry, thermogravimetry, and color measurement may be helpful besides microbiological analysis to optimize thermal sterilization conditions of salicylic acid.
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EPR examination of free radicals thermally formed invaselinum flavum

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Ramos P., Pilawa B.
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issue 3
443-447
EN
The popular pharmaceutical base used in pharmacy – vaselinum flavum – was studied by an X-band (9.3 GHz) EPR spectrometer in the range of microwave power of 2.2–70 mW. The samples were sterilized in hot air oven at temperatures: 160°C (120 min), 170°C (60 min), and 180°C (30 min). The aim of this work was to determine properties and free radical concentrations in vaselinum flavum thermally sterilized at different conditions. The changes in free radical system in vaselinum flavum during storage were analyzed. Free radicals were found in all the heated samples. The lowest free radical concentration was obtained for vaselinum flavum heated at 180°C for 30 min; so these parameters are proposed for the thermal sterilization of this pharmaceutical base. Interactions with oxygen decreased free radical concentration in vaselinum flavum during storage. Strong quenching of free radicals in vaselinum flavum was observed after 2 days for the samples sterilized at temperatures 160 and 180°C. Such an effect for vaselinum flavum heated at temperature 170°C was observed later, 13 days after sterilization. Fast spin-lattice relaxation processes exist in thermally sterilized vaselinum flavum. The EPR lines of heated vaselinum flavum were homogeneously broadened. EPR spectroscopy and its use for examining the thermal sterilization process in pharmacy was confirmed.
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Effect of UV irradiation on free radicals in synthetic melanin and melanin biopolymer fromSepia officinalis– EPR examination

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Zdybel M., Pilawa B.
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issue 3
483-488
EN
Free radicals in synthetic melanin and melanin from Sepia officinalis were studied by electron paramagnetic resonance (EPR) spectroscopy. The effect of time of ultraviolet (UV) irradiation on free radicals in these melanins was tested. The samples were exposed to UV during 15, 30, and 60 minutes. EPR spectra were measured with microwaves from an X-band (9.3 GHz) in the range of microwave power of 2.2–70 mW. The performed EPR examinations indicate that high concentrations (~1021–1022 spin/g) of o-semiquinone free radicals with g factors of 2.0039–2.0045 exist in all the tested samples. For nonirradiated samples, free radical concentration was higher in natural melanin than in synthetic melanin. UV irradiation caused the increase of free radical concentrations in synthetic melanin samples and this effect depends on the time of irradiation. The largest free radical formation in the both melanins was obtained for 60 min of UV irradiation. Free radical concentrations after the UV irradiation of melanins during 30 min were lower than during irradiation by 15 min, and probably this effect was the result of recombination of the radiatively formed free radicals. EPR lines of the tested samples broadened with increasing microwave power, so these lines were homogeneously broadened. The two types of melanins differed in the time of spin-lattice relaxation processes. Slower spin-lattice relaxation processes exist in melanin from Sepia officinalis than in synthetic melanin. UV irradiation did not change the time of spin-lattice relaxation processes in the tested melanins. The performed studies confirmed the usefulness of EPR spectroscopy in cosmetology and medicine.
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EPR study of free radicals formed in fusidic acid and neomycin under UV irradiation

81%
Pierzchała E., Ramos P., Pilawa B.
Acta Poloniae Pharmaceutica - Drug Research
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2019
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vol. 76
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issue 2
215-223
EN
Free radicals in UV irradiated antibiotics used in dermatology were examined. Concentrations of free radicals in fusidic acid and neomycin, were determined. EPR spectra of the tested antibiotics were measured by electron paramagnetic resonance spectrometer with magnetic modulation of 100 kHz and numerical acquisition system the Rapid Scan Unit. The influence of microwave powers in the range of 2.2-70 mW on the spectra was obtained. Amplitudes (A) and linewidths (ΔBpp) of the EPR spectra, were analysed. The EPR spectra were homogeneously broadened. Fast spin-lattice relaxation processes existed in UV irradiated fusidic acid and neomycin, which EPR spectra were not saturated up to 70 mW. The influence of the time of UV irradiation on free radicals in the samples was observed. The samples were irradiated by UVA (315-400 nm) in the 30, 60, and 90 minute period. Free radical concentrations in the tested antibiotics exposed to UV were proportional to the amplitudes (A) of the EPR spectra. The highest amplitudes (A) were observed for the UV irradiated antibiotics during 60 minutes. The higher amplitudes (A) characterized fusidic acid than neomycin. Fusidic acid and neomycin used to treat bacterial infection of skin under UV irradiation may produce free radical toxic effects. The stronger photosensitivity characterized fusidic acid relatively to neomycin. EPR spectroscopy is the useful method to examine free radicals formed in antibiotics during photolysis.
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Microwave saturation of EPR spectra of oxidised coal

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Pilawa B., Więckowski A., Pietrzak R., Wachowska H.
Open Chemistry
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2007
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vol. 5
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issue 1
330-340
EN
Microwave saturation of multi-component EPR spectra of oxidized lignite Mequinenza (Spain) with a carbon content of 65.1 wt % and with a high sulphur content of 10.3 wt % was studied. The coal was oxidized with nitric acid (NHO3), peroxyacetic acid (PAA), and in O2/Na2CO3 system. Three different groups of paramagnetic centres exist in the coal samples analyzed. The EPR spectrum of the demineralised coal was a superposition of broad Gauss (ΔB pp = 0.75 mT), broad Lorentz 1 (ΔB pp = 0.42 mT) and narrow Lorentz 3 lines (ΔB pp = 0.08 mT). The three EPR components with linewidths: 0.58–0.77 mT (Gauss line), 0.30–0.39 mT (Lorentz 1 line) and 0.05–0.06 mT (Lorentz 3 line) were recorded for the oxidized coal. The g-values were obtained for the samples studied in the ranges 2.0043–2.0046 (Gauss lines), 2.0035–2.0038 (Lorentz 1 lines) and 2.0032–2.0034 (Lorentz 3 lines). The broad Gauss and Lorentz 1 lines saturate at low microwave powers. The narrow Lorentz 3 lines of demineralised coal were not saturated at microwave power from the range considered. After the coal oxidation with HNO3, PAA and in O2/Na2CO3 system, the microwave saturation of the narrow Lorentz 3 lines was also observed, which indicated a degradation of the multi-ring aromatic structures upon oxidation. [...]
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Zastosowanie spektroskopii EPR do badania wolnych rodników generowanych termicznie w drotawerynie

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Ramos P., Pilawa B., Adamski M.
Annales Academiae Medicae Silesiensis
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2014
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vol. 68
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issue 1
28-37
EN
INTRODUCTION Microorganisms should be removed from drugs during their production, however, sterilization processes should not produce free radicals. Free radicals in drotaverine were studied. The applicability of thermal sterilization for drotaverine was investigated. MATERIAL AND METHODS Drotaverine heated to 160oC was examined by the EPR method. Free radical concentration, their distribution in the sample, the complex character of the free radical system and magnetic spin-spin interactions in the drug were determined. Changes in the free radical concentration in drotaverine during storage after sterilization also were examined. The sterilization conditions were chosen according to pharmakopeal norms. The analysed drug was sterilized in dry hot air. RESULTS EPR lines were not obtained for drotaverine before sterilization. It was demonstrated that drotaverine after thermal sterilization at temperature 160oC contains free radicals and exhibits EPR spectra. The free radical concen-tration in drotaverine changes with storage time after thermal treatment. Interactions with oxygen are probably responsible for this effect. The free radicals are homogeneously distributed in drotaverine since characteristic correlations between the amplitudes and linewidths of the EPR lines and microwave power were observed. The free radicals are closely located to one another in drotaverine and they strongly interact in a dipolar manner, which cause broadening of the EPR spectra. Continuous microwave saturation of the EPR spectra revealed that slow spin-lattice relaxation processes occur in thermally sterilized drotaverine. The shape of the EPR spectra and asymmetry parameters of the test drug change with increasing microwave power, indicating the complex nature of the free radicals in the sample. CONCLUSIONS Drotaverine should not be thermally sterilized because of free radical formation. The obtained results confirmed the usefulness of EPR spectroscopy to examine thermally sterilized drugs. The EPR method may be used as a supplement to microbiological tests.
PL
WSTĘP Leki wymagają usunięcia drobnoustrojów podczas ich produkcji, jednak procesy sterylizacji nie powinny generować wolnych rodników. Zbadano wolne rodniki w drotawerynie. Sprawdzono, czy sterylizacja termiczna może być w tym przypadku stosowana. MATERIAŁY I METODY Zbadano drotawerynę ogrzewaną w 160oC metodą EPR. Wyznaczono koncentrację wolnych rodników, określono sposób ich rozmieszczenia w ogrzanej próbce, złożoność układu wolnorodnikowego oraz oddziaływania magnetyczne spin-spin. Zbadano również zmiany koncentracji wolnych rodników w drotawerynie podczas przechowywania leku po sterylizacji. Warunki sterylizacji termicznej wybrano zgodnie z obowiązującymi normami farmakopealnymi. Lek sterylizowano suchym gorącym powietrzem. WYNIKI Nie uzyskano linii EPR dla drotaweryny przed sterylizacją. Wykazano, że drotaweryna po sterylizacji termicznej w temp. 160oC zawiera wolne rodniki i wykazuje widma EPR. Koncentracja wolnych rodników w drotawerynie zmienia się wraz z czasem przechowywania leku po obróbce termicznej. Za efekt ten odpowiadają prawdopodobnie oddziaływania z tlenem. Wolne rodniki w drotawerynie rozmieszczone są jednorodnie, ponieważ zaobserwowano charakterystyczne dla tego przypadku zależności amplitudy i szerokości linii EPR od mocy mikrofalowej. Wolne rodniki w drotawerynie są położone blisko siebie i silnie oddziałują dipolowo, co powoduje poszerzenie widm EPR. Ciągłe nasycenie mikrofalowe widm EPR wykazało, że w drotawerynie sterylizowanej termicznie zachodzą wolne procesy relaksacji spin-sieć. Kształt widm EPR i parametry asymetrii testowanego leku zmieniają się wraz ze wzrostem mocy mikrofalowej, co wskazuje na złożony charakter układu wolnych rodników w próbce. WNIOSKI Drotaweryna nie powinna być sterylizowana termicznie ze względu na generowanie wolnych rodników. Uzyskane rezultaty potwierdziły przydatność spektroskopii EPR do badania leków sterylizowanych termicznie. Metoda EPR może być wykorzystana jako uzupełnienie testów mikrobiologicznych.
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Effect of microwave power on EPR spectra of natural and synthetic dental biocompatible materials

81%
Adamczyk J., Ramos P., Pilawa B.
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issue 3
449-453
EN
Paramagnetic centers in the two exemplary synthetic and natural dental biocompatible materials applied in implantology were examined by the use of an X-band (9.3 GHz) electron paramagnetic resonance (EPR) spectroscopy. The EPR spectra were measured in the range of microwave power 2.2–70 mW. The aims of this work were to compare paramagnetic centers concentrations in different dental biocompatible materials and to determine the effect of microwave power on parameters of their EPR spectra. It is the very first and innovatory examination of paramagnetic centers in these materials. It was pointed out that paramagnetic centers existed in both natural (~1018 spin/g) and synthetic (~1019 spin/g) dental biocompatible materials, but the lower free radical concentration characterized the natural sample. Continuous microwave saturation of EPR spectra indicated that faster spin-lattice relaxation processes existed in synthetic dental biocompatible materials than in natural material. Linewidths (ΔBpp) of the EPR spectra of the natural dental material slightly increased for the higher microwave powers. Such effect was not observed for the synthetic material. The broad EPR lines (ΔBpp): 2.4 mT, 3.9 mT, were measured for the natural and synthetic dental materials, respectively. Probably strong dipolar interactions between paramagnetic centers in the studied samples may be responsible for their line broadening. EPR spectroscopy is the useful experimental method in the examination of paramagnetic centers in dental biocompatible materials.
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Effect of microwave power on EPR spectra of thermally sterilizedeucerinum anhydricum

81%
Ramos P., Pepliński P., Pilawa B.
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issue 3
439-442
EN
Free radicals formed during thermal sterilization of eucerinum anhydricum – the pharmaceutical base were examined by an X-band (9.3 GHz) spectrometer. Eucerinum anhydricum was sterilized at different physical conditions according to the Polish Pharmacopeia norms. The samples were heated at temperatures: 160°C (120 min), 170°C (60 min), and 180°C (30 min). The aim of this study is to compare free radical concentration and effect of microwave power on EPR spectra of eucerinum anhydricum base thermally sterilized at different temperatures and periods of time. The effect of time storage on the free radicals in the heated samples was tested. Free radical concentrations in the sample stored 15 min strongly decreased with the increasing of sterilization temperature, probably as the result of recombination. Storage caused strong decrease of free radical concentrations in the samples, probably as the result of interactions with oxygen. It was observed to be independent of sterilization conditions from 2 days of storage and longer. Because of the lowest free radical concentration, for eucerinum anhydricum thermal sterilization at 180°C for 30 min is recommended. The sterilized samples should be stored at inert atmosphere without oxygen molecules. Fast spin-lattice relaxation processes existed in sterilized eucerinum anhydricum. The character of changes of amplitudes and linewidths of EPR lines with increasing of microwave power was the same for different storage times. The parameters of thermal sterilization and storage time influenced free radical concentration in eucerinum anhydricum, but magnetic spin-lattice interactions were unchanged. The usefulness of EPR spectroscopy in optimization of thermal sterilization process of eucerinum anhydricum was confirmed.
9
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Impact of UVC radiation on interaction of selected antifungal drugs (azole derivatives) with model DPPH free radical

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Ramos P., Pepliński P., Pilawa B.
Annales Academiae Medicae Silesiensis
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2020
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issue 74
77-90
EN
INTRODUCTION: Fungal lesions are accompanied by inflammation, during which large amounts of free radicals are formed. Antifungal drugs, which have an additional antioxidant effect, could contribute to a faster recovery. An important role in ensuring effective and safe pharmacotherapy of fungal lesions is played by proper drug storage and appro-priate patient actions during treatment. Ultraviolet radiation can generate free radicals in a drug due to photolysis. A drug containing free radicals may cause toxic effects in the body. The aim of the study was to research the antioxidant properties of selected antifungal drugs of azole derivatives. Addi-tionally, the impact of UVC radiation on the tested drugs and their interaction with the DPPH free radical was studied. MATERIAL AND METHODS: The tested azole samples were exposed to 24-hour UVC radiation. The interaction of drug samples with a model DPPH free radical, before and after exposure to UV radiation, was studied. UV-Vis spectroscopy and colourimetry in the CIE Lab colour analysis system were used as the research techniques. RESULTS: Among the initial samples of the tested drugs only ketoconazole interacted with the DPPH free radical, causing its extinction. Exposure to UVC radiation increased the antioxidant properties in ketoconazole and miconazole. The CIE Lab parameters, UV spectra and interaction kinetics of those two drugs with DPPH were different after UVC exposure, which may indicate changes in ketoconazole and miconazole. The highest stability to ultraviolet radiation was shown by fluconazole, whose CIE Lab parameters, UV spectra and interaction with DPPH did not change after exposure of the sample to light radiation. CONCLUSIONS: The research using UV-Vis spectrophotometry and colourimetry enabled the impact of UVC radiation on selected antifungal drugs to be evaluated, including evaluation of their interaction with the model DPPH free radical. It is recommended to protect ketoconazole and miconazole from exposure to light. It is also advisable to protect patients from the sun during pharmacotherapy with these drugs.
PL
WSTĘP: Zmianom grzybiczym towarzyszy stan zapalny, w trakcie którego wytwarzane są duże ilości wolnych rodników. Leki działające przeciwgrzybiczo, wykazujące dodatkowo działanie antyoksydacyjne, mogłyby się przyczynić do szybszego powrotu do zdrowia. Ważną rolę w zapewnieniu skutecznej i bezpiecznej farmakoterapii zmian grzybiczych odgrywają prawidłowe przechowywanie leku oraz odpowiednie postępowanie pacjenta w trakcie leczenia. Promieniowanie ultrafioletowe może generować wolne rodniki w leku w procesie fotolizy. Lek zawierający wolne rodniki może powodować efekty toksyczne w organizmie. Celem pracy było zbadanie właściwości antyoksydacyjnych wybranych leków przeciwgrzybiczych pochodnych azoli. Dodatkowo sprawdzono wpływ promieniowania UVC (ultraviolet C) na badane leki oraz ich oddziaływanie z modelowym wolnym rodnikiem DPPH (2,2-Diphenyl-1-picrylhydrazyl). MATERIAŁ I METODY: Badane próbki azoli poddano 24-godzinnej ekspozycji na promieniowanie UVC. Zbadano oddziaływanie próbek leków z modelowym wolnym rodnikiem DPPH przed i po naświetlaniu ich promieniowaniem ultrafioletowym. Jako techniki badawcze zastosowano spektroskopię UV-Vis (ultraviolet-visible) oraz kolorymetrię w układzie analizy barwy CIE Lab. WYNIKI: Spośród wyjściowych próbek badanych leków tylko ketokonazol oddziaływał z wolnym rodnikiem DPPH, powodując jego wygaszenie. Ekspozycja na promieniowanie UVC powodowała wzrost właściwości antyoksydacyjnych w ketokonazolu oraz w mikonazolu. Parametry CIE Lab, widma UV oraz kinetyka oddziaływania z DPPH obu leków były odmienne po naświetlaniu promieniowaniem UVC, co może wskazywać na zmiany zachodzące w ketokonazolu i mikonazolu. Największą stabilność na promieniowanie ultrafioletowe wykazywał flukonazol, którego parametry CIE Lab, widma UV oraz oddziaływanie z DPPH nie zmieniły się po naświetlaniu próbki. WNIOSKI: Badania z zastosowaniem spektrofotometrii UV-Vis oraz kolorymetrii pozwoliły na ocenę wpływu promieniowania UVC na wybrane leki przeciwgrzybicze, w tym na ocenę ich oddziaływania z modelowym wolnym rodnikiem DPPH. Zaleca się ochronę ketokonazolu i mikonazolu przed światłem. Wskazana jest również ochrona przed słońcem pacjentów w trakcie farmakoterapii tymi lekami.
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Can angiotensin-converting enzyme inhibitors interfere with the free radicals? Measurement of antioxidant capacity using DPPH radical reduction examined by UV-VIS method

71%
Ramos P., Juszczak A., Szczołko W., Pilawa B., Stanisz B. J.
Acta Poloniae Pharmaceutica - Drug Research
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2019
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vol. 76
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issue 2
233-239
EN
A negative impact of radicals on human’s health is responsible for growing research interest in antioxidant properties of substances, which protect organisms from the damaging influence of these reactive species. Angiotensin-converting enzyme inhibitors (ACE-I) are the most popular drugs used in cardiovascular diseases. There are a lot of clinical reports that ACE-I have antioxidant properties, due to the fact, that prolonged use improves conditions of patients with neurodegenerative disorders and slow inflammatory processes. The paper shows the antioxidant properties of a selected ACE-I: cilazapril, ramipril, imidapril, lisinopril, perindopril, and quinapril. Among numerous methods for antioxidant activity estimation, DPPH reduction is the most popular and commonly used one due to its ease, speed, sensitivity and the usage of stable radicals. UV-Vis spectrophotometry was used to examine interactions of chosen ACE-I with model-free radicals. Absorption of UV-Vis spectra of DPPH (reference), and DPPH interacting with the tested ACE-I were compared. For all tested ACE-I kinetics of their interaction with DPPH, up to 30 minutes, were obtained. The strongest interaction with DPPH was observed for imidapril and cilazapril and the lowest interaction for lisinopril. Studies have shown usefulness UV-Vis spectrophotometry for obtaining information on interactions of ACE-I with model-free radicals.
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Continuous microwave saturation of EPR spectra of melanin complexes at different temperatures

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Zdybel M., Pilawa B., Buszman E., Wrzesniok D., Krzyminiewski R., Kruczynski Z.
Polish Journal of Medical Physics And Engineering
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2011
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vol. 17
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issue 2
85-94
EN
Paramagnetic centers in DOPA-melanin and complexes of DOPA-melanin with netilmicin and Cu(II) were studied by the use of an X-band (9.3 GHz) electron paramagnetic resonance (EPR) spectroscopy. Measurements of continuous microwave saturation of EPR spectra at temperatures: 125 K, 175 K, 225 K, 275 K, were performed. Homogeneous broadening of all the examined EPR spectra was observed. EPR spectra of DOPA-melanin-Cu(II) complexes saturated at higher microwave powers than the others tested melanin samples. Fast spin-lattice relaxation exists in DOPA-melanin-Cu(II) complexes. Slow spin-lattice relaxation processes exist in melanin's paramagnetic centers of DOPA-melanin and its complexes with netilmicin, and its complexes with both netilimicin and Cu(II). EPR spectra of all the tested samples saturated at higher microwave powers with increasing of the measuring temperature. Faster spin-lattice relaxation processes occurs in DOPA-melanin and its complexes with netilmicin and Cu(II) at higher temperature.
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THE INFLUENCE OF STORAGE TEMPERATURE AND UV-IRRADIATION ON FREE RADICAL SCAVENGING PROPERTIES OF ETHANOLIC EXTRACTS OF PROPOLIS

52%
Komosińska-Vassev K., Olczyk P., Ramos P., Mencner L., Derkacz A., Waluga E., Krysik K., Olczyk K., Pilawa B.
Acta Poloniae Pharmaceutica - Drug Research
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2018
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vol. 74
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issue 6
1833-1840
EN
The free radical scavenging activity of ethanolic extracts of propolis (EEP) at the concentrations of 3%, 7%, and 10% was examined. The impact of storage temperature and exposure to ultraviolet (UV) light on the interactions of extracts of propolis with the model DPPH free radicals was also determined. The quenching of an X-band electron paramagnetic resonance spectra of DPPH free radicals by the extracts stored at room temperature, heated at the temperature of 50 oC and exposed to UV-irradiation, were compared. The examined propolis ethanolic extracts revealed an antioxidative character. The storage of the samples at a higher temperature (50 oC) caused a decrease of the scavenging activity equaling to 7% and 10% EEP. UV-irradiation of the 3% EEP increased the quenching of DPPH free radical lines. The reverse effect was observed for the 7% and 10% propolis extracts. The 3% ethanolic extract of propolis is more stable for storage at 50ºC, and less than other analyzed EEP susceptible for UV-irradiation. Alterations of the antioxidative properties of the analyzed EEP and changes in the kinetics of their interactions with free radicals, indicate that 3%, 7%, and 10% propolis extracts should not be exposed to the temperature of 50 oC and UV-irradiation.
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