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1.
J Clin Med ; 12(15)2023 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-37568458

RESUMO

BACKGROUND: An adequate interlesion distance (ILD) applied during point-by-point pulmonary vein (PV) isolation for atrial fibrillation (AF) has never been established. We hypothesized that maximum tolerated ILD may differ between PV regions and may influence long-term ablation outcomes. METHODS: A total of 260 AF patients underwent PV isolation with 3D electroanatomical platform. Postablation, ILD values were classified into 5 groups (6-5.5 mm, 5.5-5.0 mm, 5.0-4.5 mm, 4.5-4.0 mm and <4.0 mm); the number of tags in each group was calculated and correlated with postablation AF recurrence (AFR). All measurements were performed globally for the entire encirclement around each individual PV and regionally for designated PV anatomic segments. RESULTS: Single-procedure freedom from AF was 81% for paroxysmal and 66% for persistent AF at 12 months. Global analysis showed that AFR was not related to median ILD nor the number of lesions within each ILD tag group for any PV. Segmental analysis showed that AFR was not related to median ILD. However, the presence of tags from the 5.5-6.0 mm ILD group located on the posterior aspect of right upper PV (RUPV) correlated with AFR. This was confirmed in a multivariable logistic regression model. CONCLUSIONS: Maximum tolerated ILD of 6.0 mm translated into well-accepted ablation results. However, the study suggests that it may be inadequate at the posterior aspect of RUPV.

2.
Med Chem ; 17(5): 533-544, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-31729945

RESUMO

BACKGROUND: Stilbene phytalexis (1,2-diphenyloethylen) and benzamide are beneficial for human health. To increase the stilbene ring activity, a new series of its derivatives containing benzamide structure was synthesized and evaluated for their in vitro antioxidant power. METHODS: 1H nuclear magnetic resonance, mass spectroscopy, and chromatographic analyses were used to confirm the successful synthesis. The antioxidant properties were determined by the elimination of O2˙-, HO˙ , DPPH˙ , ABTS+˙ radicals, total antioxidant status (TAS) and the ferric reducing antioxidant activities (TAC) measurements. RESULTS: Stilbenebenzamide compounds showed a wide spectrum of antioxidant ability; however, their total antioxidant power was weaker than those of butylated hydroxytoluene (BHT), ascorbic acid, and resveratrol. The highest antiradical activity towards O2˙ and HO˙ was shown by the compounds with structures containing amine group (SBEBA, SBA) (O2˙: 37.7 - 38.0% and 40.8 - 43.5%, HO˙ : 29.8%, 28.7% inhibition, respectively) at1.25 mM concentration. The antiradical power of SBEBA (0.29) in DPPH˙ assay was lower than those of resveratrol (1.83), ascorbic acid (3.63) and BHT (4.09). The TAS values of the synthesized compounds ranged from 152.9±5.3 to 240.2±6.7µM trolox equivalent/gram (TE/g) and were much lower than those of BHT (1304±43.0), reservatrol (1360±29.0) and ascorbic acid (2782±39.7) µM TE/g. Similarly, the TAC values ranging from 29.7±0.9 to 41.5±1.6 µM TE were weaker than that of resveratrol (239.2 ±6.7 µM TE/g). CONCLUSION: The results suggest that the presence of the hydroxyl group in the stilbene ring should be considered in the further design of stilbenebenzamide compounds to enhance their antioxidant activity.


Assuntos
Benzamidas/química , Sequestradores de Radicais Livres/química , Estilbenos/química , Benzamidas/síntese química , Sequestradores de Radicais Livres/síntese química , Estilbenos/síntese química
3.
Bioorg Chem ; 95: 103513, 2020 01.
Artigo em Inglês | MEDLINE | ID: mdl-31884144

RESUMO

BACKGROUND: A series of eight new flavone derivatives containing a piperazine chain with different substitution were synthesized and their structures were determined. METHODS: Their antiradical and antioxidant activities were evaluated using superoxide anion radical, hydroxyl radical, 2,2-diphenyl-1-picrylhydrazyl radical, 2,2'-azino-di(3-ethylbenzthiazoline sulphonate) radical cation (ABTS+) scavenging (as measure total antioxidant status TAS), ferric reducing antioxidant power (TAC), and hydrogen peroxide decomposition. The antioxidant activities of the synthesized compounds were compared with standard antioxidants trolox, ascorbic acid, butylated hydroxytoluene (BHT) as positive controls, reference antibiotics (doxycycline, dicloxacillin), and medicinal plants (Menthae piperita, Cistus incanus). Chemiluminescence, spectrophotometry, electron spin resonance (ESR) spectroscopy in conjunction with 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as the spin trap were the measurement techniques. RESULTS: The results show that the synthesized compounds exhibit weak, albeit a wide spectrum of antiradical and antioxidant activities. The TAS values were measured as trolox equivalents, ranging from 209.6 ± 6.1 to 391.1 ± 8.2 µM TE/g; the TAC values were in ranges from 10.8 ± 0.5 to 49.5 ± 0.5 µM TE/g being higher than that of dicloxacillin (241.0 ± 16.5 and 9.73 ± 0.8 µM TE/g, respectively), but lower than ascorbic acid, BHT, doxycycline, and medicinal plants. Best antioxidant activities were found for the piperazinyl analogues with methoxy group on phenyl piperazine ring. CONCLUSION: We suggest that the synthesized compounds may be used as lead molecules for optimization of molecular structure to maximize the antioxidant potency.


Assuntos
Antioxidantes/farmacologia , Flavonas/farmacologia , Piperazina/farmacologia , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Relação Dose-Resposta a Droga , Flavonas/síntese química , Flavonas/química , Peróxido de Hidrogênio/antagonistas & inibidores , Radical Hidroxila/antagonistas & inibidores , Estrutura Molecular , Picratos/antagonistas & inibidores , Piperazina/química , Relação Estrutura-Atividade , Superóxidos/antagonistas & inibidores
4.
Free Radic Res ; 53(5): 497-521, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-31039624

RESUMO

The body of evidence from the past three decades demonstrates that oxidative stress can be involved in several diseases. This study aims to summarise the current state of knowledge on the association between oxidative stress and the pathogenesis of some characteristic to the biological systems diseases and aging process. This review also presents the effect of physical activity on redox homeostasis. There is strong evidence from studies for participation of reactive oxygen and nitrogen species in pathogenesis of acute and chronic diseases based on animal models and human studies. Elevated levels of pro-oxidants and various markers of the oxidative stress and cells and tissues damage linked with pathogenesis of cancer, atherosclerosis, neurodegenerative diseases hypertension, diabetes mellitus, cardiovascular disease, atherosclerosis, reproductive system diseases, and aging were reported. Evidence confirmed that inflammation contributes widely to multiple chronic diseases and is closely linked with oxidative stress. Regular moderate physical activity regulates oxidative stress enhancing cellular antioxidant defence mechanisms, whereas acute exercise not preceded by training can alter cellular redox homeostasis towards higher level of oxidative stress. Future studies are needed to clarify the multifaceted effects of reactive oxygen/nitrogen species on cells and tissues and to continue study on the biochemical roles of antioxidants and physical activity in prevention of oxidative stress-related tissue injury.


Assuntos
Envelhecimento/metabolismo , Doenças Cardiovasculares/metabolismo , Diabetes Mellitus/metabolismo , Exercício Físico , Doenças Urogenitais Femininas/metabolismo , Doenças Urogenitais Masculinas/metabolismo , Neoplasias/metabolismo , Doenças Neurodegenerativas/metabolismo , Animais , Doenças Cardiovasculares/fisiopatologia , Diabetes Mellitus/fisiopatologia , Feminino , Doenças Urogenitais Femininas/fisiopatologia , Homeostase/fisiologia , Humanos , Masculino , Doenças Urogenitais Masculinas/fisiopatologia , Neoplasias/fisiopatologia , Doenças Neurodegenerativas/fisiopatologia , Oxirredução , Estresse Oxidativo , Espécies Reativas de Nitrogênio/metabolismo , Espécies Reativas de Oxigênio/metabolismo
5.
Future Med Chem ; 10(19): 2293-2308, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-30273015

RESUMO

AIM: Synthesis of novel 2(2-hydroxyphenyl) pyrimidine/benzothiazole piperazinyl-substituted flavones end evaluate their antioxidant activity. RESULTS: Six novel 2-(2-hydroxyphenyl) pyrimidine/benzothiazole-substituted flavones were synthesized, their structures were confirmed by elementary and spectral analyses. The compounds were evaluated for their in vitro antioxidant potency by employing various antioxidant assays. CONCLUSION: All tested compounds acted as scavengers of free radicals like hydroxyl (15-45%), 2,2-diphenyl-1-picrylhydrazyl• (17-48%) at 1.25 and 0.5 mM concentrations respectively. The total antioxidant status activity values of the compounds ranged from 234.1 to 464.1 µm trolox equivalent/g, the total antioxidant capacity - from 24.9 to 52.7 µm trolox equivalent per gram. Compounds incorporating the benzothiazole group on the piperazine ring were more effective antioxidants than those with the 2-(2-hydroxyphenyl) pyrimidine group.


Assuntos
Antioxidantes/síntese química , Benzotiazóis/química , Flavonas/química , Pirimidinas/química , Antioxidantes/química , Espectroscopia de Ressonância de Spin Eletrônica , Compostos Férricos/química , Flavonas/síntese química , Radical Hidroxila/química , Medições Luminescentes , Superóxidos/química
6.
Med Chem ; 14(4): 372-386, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29205120

RESUMO

BACKGROUND: A new series of 13 piperazinyl flavone derivatives has been synthesized and examined for their in vitro antiradical and antioxidant activities in response to the pharmacy industry's increasing demand for new non-toxic anti-inflammatory and anticancer drugs. METHOD: Their antioxidant activity was evaluated by the reactive oxygen species (ROS) scavenging assays, 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH•) and 2,2'-azino-bis(3- ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS+•) scavenging assays, and the ferric reducing antioxidant potency (TAC) method, and was compared to known positive controls, herbal infusions, and penicillins. Chemiluminescence, spectrophotometry, electron spin resonance (ESR) and 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as the spin trap were the measurement techniques. RESULT: It was seen that synthesized compounds have a wide spectrum of antioxidant property. Some of the test compounds proved to be extremely efficient scavengers of H2O2 exhibiting, in some cases, EC50 of about 2 µM. The values of antioxidant status (TAS) were in the range of 49 ± 3.9 to 1283 ± 51.3 µM TE/g (TE = Trolox equivalent) and were lower than that of butylated hydroxytoluene (BHT) (1304 ± 43.2 µM TE/g) and green tea (1356 ± 40.0 µM TE/g), but for several synthesized compounds, they were higher than chamomille infusion and penicillins. Ferric reducing antioxidant powers (TAC) for the piperazinyl flavone derivatives were in the range 7 ± 0.5 to 104 ± 0.6 µM TE/g and were weaker than that of BHT (217 ± 5.3 µM TR/g ). CONCLUSION: Carboxylic or hydroxamic acid substituted piperazinyl flavones are potentially active as antioxidants, thus may be suggested as pharmacologically interesting ones.


Assuntos
Flavonas/farmacologia , Sequestradores de Radicais Livres/farmacologia , Piperazinas/farmacologia , Ácido Ascórbico/farmacologia , Hidroxitolueno Butilado/farmacologia , Camellia sinensis , Dicloxacilina/farmacologia , Flavonas/síntese química , Flavonas/química , Sequestradores de Radicais Livres/síntese química , Sequestradores de Radicais Livres/química , Matricaria , Penicilina G/farmacologia , Piperazinas/síntese química , Piperazinas/química , Extratos Vegetais/farmacologia , Relação Estrutura-Atividade , Chás de Ervas
7.
Luminescence ; 32(8): 1431-1441, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28569387

RESUMO

Flavones exhibit a variety of beneficial effects and are well known for their medicinal importance in several diseases, including cardiovascular, neurodegenerative and cancer. The inclusion of the piperazine ring to the flavone backbone is an important strategy in drug discovery but only a few studies have synthesized piperazinyl flavone compounds to test their biological activity. While there is a major focus on the antioxidant properties of drugs in therapy of several diseases of inflammatory origin, we synthesized a series of the novel piperazinyl flavone analogues bearing the phenyl ring with different substituents. The analogues were evaluated for in vitro antioxidant activity against superoxide anion radical, hydroxyl radical, 2,2-diphenyl-1-picrylhydrazyl radical, and hydrogen peroxide scavenging properties. The total antioxidant status based on the absorbance of the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS+• ) and total antioxidant capacity using the Fe(III)-ferrozine complex were also monitored. The results of the above studies showed that the compounds synthesized were found possessed moderate radical scavenging potential, and that their interaction with reactive oxygen species is complex and depends on their structural conformation and the type of substituent R in the piperazine ring being attached. Best antiradical activity were found for the compounds with methoxy groups on the phenyl ring of substituent R, whereas the presence of methoxy or trifluoromethyl groups in substituent R resulted in higher ABTS+• and ion Fe(III) reduction. These compounds are promising molecules to be used for their antioxidant properties and may be regarded, after improvement of the antioxidant potential, to control diseases of free radical etiology.


Assuntos
Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Flavonas/farmacologia , Peróxido de Hidrogênio/antagonistas & inibidores , Picratos/antagonistas & inibidores , Piperazinas/farmacologia , Superóxidos/antagonistas & inibidores , Antioxidantes/síntese química , Antioxidantes/química , Flavonas/síntese química , Flavonas/química , Radicais Livres/antagonistas & inibidores , Estrutura Molecular , Piperazina , Piperazinas/síntese química , Piperazinas/química
8.
Luminescence ; 32(3): 434-442, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27511803

RESUMO

The aim of this study was to characterize the antioxidant activity of penicillin G (PG), ampicillin (AMP), oxacillin (OX) and dicloxacillin (DOX) through their reactivity towards reactive oxygen species (superoxide anion radical, O2•̅; hydroxyl radical, HO• ; peroxyl radical, ROO• ; hydrogen peroxide, H2 O2 ; DPPH• ) using various in vitro antioxidant assays with chemiluminescence (CL) and spectrophotometry as measurement techniques. In hydroxyl radical assays , PG, OX and AMP were found to inhibit the CL signal arising from the Fenton-like reaction in a dose-dependent manner with IC50  = 0.480 ± 0.020 mM, IC50  = 0.569 ± 0.021 mM, and IC50  = 0.630 ± 0.019 mM, respectively. The highest reactivity of PG among the tested penicillins towards the HO radical was confirmed in the deoxyribose degradation assay. In the ABAP-derived ROO radical assay, the radical-scavenging ability of the test penicillins was in the following order: AMP > PG > DOX > OX. The number of reduced DPPH radicals by the drugs tested was <1 being the biggest for PG. The weak antioxidant capacity of the test penicillins was confirmed in the trolox antioxidant capacity assay (0.075 ± 0.004; 0.093 ± 0.006; 0.123 ± 0.005; 0.126 ± 0.004) for OX, AMP, DOX, PG, respectively. Use of luminol as a CL probe for estimation of penicillin reactivity towards H2 O2 showed that only AMP was able to quench light emission; the remaining antibiotics demonstrated a strong enhancing effect. All the examined compounds showed a weak antioxidant potential when estimated using the ferric-ferrozine assay. This study is the first to report the evaluation of test penicillins as antioxidants under the same reaction conditions.


Assuntos
Ampicilina/química , Dicloxacilina/química , Sequestradores de Radicais Livres/química , Oxacilina/química , Penicilina G/química , Estrutura Molecular
9.
Luminescence ; 31(6): 1201-6, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-26799817

RESUMO

Isoflavones genistein and daidzein are nonsteroidal phytoestrogens occurring mainly in soybean foods. These phytoestrogens possess estrogenic properties and show a variety of health benefits as anti-inflammatory agents. However, the mechanism of their action has not been identified in detail. The aim of this study is to characterize the antioxidant powers of genistein, daidzein and daidzein metabolite-equol through their activities to scavenge superoxide anion radical (O(•) 2 (-) ), hydroxyl radical (HO(•) ), 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(•) ) and hydrogen peroxide (H2 O2 ) using chemiluminescence and spectrophotometry techniques. Potassium superoxide in dimethyl sulphoxide (DMSO) and 18-crown-6 ether were used as a source of O(•) 2 (-) . Hydroxyl radicals were produced using the Fenton reaction. In free radical assays, genistein had the IC50 values (an amount of antioxidant concentration required to decrease the initial radical concentration by 50%) 0.391 ± 0.012 mM for O(•) 2 (-) , 0.621 ± 0.028 mM for HO(•) and 1.89 ± 0.16 mM for DPPH(•) . The IC50 values for daidzein for these free radicals were 1.924 ± 0.011 mM, 0.702 ± 0.012 mM and 2.81 ± 0.03 mM, respectively. Equol was the most active the free radical scavenger with IC50  = 0.451 ± 0.018 mM for HO(•) and IC50  = 1.36 ± 0.11 mM for DPPH(•) . All tested compounds exerted a significant effect on the H2 O2 : IC50  = 18.1 ± 1.1 µM for genistein, IC50  = 2.1 ± 0.5 µM for daidzein, and IC50  = 1.06 ± 0.2 µM for equol. These findings show that genistein, daidzein and equol are effective free radical scavengers and possess high antioxidant power in vitro. Copyright © 2016 John Wiley & Sons, Ltd.


Assuntos
Antioxidantes/química , Genisteína/química , Isoflavonas/química , Fitoestrógenos/química , Antioxidantes/metabolismo , Genisteína/metabolismo , Isoflavonas/metabolismo , Luminescência , Fitoestrógenos/metabolismo
10.
Luminescence ; 30(7): 1153-8, 2015 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-25754627

RESUMO

Pyruvic acid and its derivatives occurring in most biological systems are known to exhibit several pharmacological properties, such as anti-inflammatory, neuroprotective or anticancer, many of which are suggested to originate from their antioxidant and free radical scavenger activity. The therapeutic potential of these compounds is a matter of particular interest, due to their mechanisms of action, particularly their possible antioxidant behaviour. Here, we report the results of a study of the effect of pyruvic acid (PA), ethyl pyruvate (EP) and sodium pyruvate (SP) on reactions generating reactive oxygen species (ROS), such as superoxide anion radicals, hydroxyl radicals and singlet oxygen, and their total antioxidant capacity. Chemiluminescence (CL) and spectrophotometry techniques were employed. The pyruvate analogues studied were found to inhibit the CL signal arising from superoxide anion radicals in a dose-dependent manner with IC50 = 0.0197 ± 0.002 mM for EP and IC50 = 69.2 ± 5.2 mM for PA. These compounds exhibited a dose-dependent decrease in the CL signal of the luminol + H2O2 system over the range 0.5-10 mM with IC50 values of 1.71 ± 0.12 mM for PA, 3.85 ± 0.21 mM for EP and 22.91 ± 1.21 mM for SP. Furthermore, these compounds also inhibited hydroxyl radical-dependent deoxyribose degradation in a dose-dependent manner over the range 0.5-200 mM, with IC50 values of 33.2 ± 0.3 mM for SP, 116.1 ± 6.2 mM for EP and 168.2 ± 6.2 mM for PA. All the examined compounds also showed antioxidant capacity when estimated using the ferric-ferrozine assay. The results suggest that the antioxidant activities of pyruvate derivatives may reflect a direct effect on scavenging ROS and, in part, be responsible for their pharmacological actions.


Assuntos
Antioxidantes/química , Ácido Pirúvico/química , Espécies Reativas de Oxigênio/química , Antioxidantes/farmacologia , Relação Dose-Resposta a Droga , Modelos Lineares , Luminescência , Estrutura Molecular , Ácido Pirúvico/farmacologia , Espécies Reativas de Oxigênio/antagonistas & inibidores
11.
Luminescence ; 30(5): 556-63, 2015 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-25377006

RESUMO

Fifteen chromonylrhodamine derivatives (CRs) were synthesized and the antioxidant activity levels were evaluated for the first time. The antioxidant activity potencies of these chromone derivatives were evaluated towards superoxide anion radicals, hydroxyl radicals and 2,2-diphenyl-1-picrylhydrazyl radicals. Also, the total antioxidant capacity of the tested compounds was measured using the ferric-ferrozine assay. The antioxidant activities were investigated using a chemiluminescence (CL) assay, spectrophotometry measurements, direct electron paramagnetic resonance (EPR) and the EPR spin-trapping technique. The 5,5-dimethyl- 1-pyrroline-1-oxide (DMPO) was applied as spin trap. Eleven of the 15 chromone compounds exhibited a decrease in the CL accompanying the superoxide anion radical produced in anhydrous dimethylsulfoxide (DMSO), ranging from 71-94% at concentration of 1 mmol /L; four of these compounds enhanced light emission in the range 231-672%. Similarly, these compounds caused 28-58% inhibition in the intensity of the DMPO-OOH radical EPR signal and the DMPO-OH radical (from 12-48%). Furthermore, three of these compounds showed very good antioxidant response towards the DPPH radical (EC50 : 0.51-0.56 µmol/L) and the high reduction potentials. These findings demonstrate that the chromone compounds tested may be considered as effective free radicals scavengers, a finding that is of great pharmacological importance.


Assuntos
Antioxidantes/química , Cromonas/química , Rodanina/química , Antioxidantes/farmacologia , Compostos de Bifenilo/química , Óxidos N-Cíclicos/química , Espectroscopia de Ressonância de Spin Eletrônica , Sequestradores de Radicais Livres/química , Radical Hidroxila/química , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Medições Luminescentes , Picratos/química , Superóxidos/química
12.
Luminescence ; 29(8): 1107-12, 2014 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-24733694

RESUMO

A series of flavonyl-2,4-thiazolidinedione, imidazolidinedione and rhodanine derivatives were tested for their antioxidant activity as scavengers of oxygen free radicals. Free radical scavenging activities, including superoxide anion radical O2•, hydroxyl radical (HO(•)) and 2,2'-diphenyl-1-picrylhydrazyl free radical have been evaluated using chemiluminescence, electron paramagnetic resonance and spin trapping with 5,5-dimethyl-1-pyrroline-1-oxide as a spin trap. Potassium superoxide in dimethylsulfoxide and 18-crown-6 ether were used for the production of O2•. Hydroxyl radical was generated using the Fenton reaction. Ten of the eleven examined compounds exhibited decrease in chemiluminescence, but there were large differences in the decrease, ranging from 16% to 89%; also, two of these compounds increased light emission by about 200%. On the contrary, all compounds tested exhibited 30-68% scavenging HO(•) and 25-96% scavenging the DPPH(•) radical respectively. Possible mechanisms are proposed to explain the results.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Flavonas/química , Compostos de Bifenilo/química , Espectroscopia de Ressonância de Spin Eletrônica , Flavonas/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Radical Hidroxila , Luminescência , Picratos/química , Superóxidos/química
13.
Luminescence ; 29(7): 846-53, 2014 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-24482260

RESUMO

Recent reviews evidence that the naturally occurring compounds containing the chromone skeleton exhibit antiradical activities, providing protection against oxidative stress. The antioxidant activities of 13 new synthesized chromonyl-2,4-thiazolidinediones, chromonyl-2,4-imidazolidinediones and chromonyl-2-thioxoimidzolidine-4-ones were evaluated using in vitro antioxidant assays, including superoxide anion radical (O2(-•)), hydroxyl radical (HO(•)), 2,2-diphenyl-1-picryl-hydrazyl free radical (DPPH(•)) scavenging capacity and total antioxidant capacity ferric ion reducing activity. Superoxide anion radical was produced using potassium superoxide/18-crown-6-ether dissolved in dimethylsulfoxide, and the Fenton-like reaction (Fe(II) + H2O2) was a generator of hydroxyl radicals. Chemiluminescence, spectrophotometry, electron paramagnetic resonance (EPR) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin trap were the measurement techniques. The results showed that the majority of the chromone derivatives tested showed a strong scavenging effect towards free radicals, similar to the chemiluminescence reaction with superoxide anion radical with a high activity, inhibition of the DMPO-OOH radical EPR signal (24-58%), the DMPO-OH radical EPR signal (4-75%) and DPPH radical EPR signal (6-100%) at 1 mmol/L. Several of the examined compounds exhibited the high reduction potentials. The results obtained show that the new synthesized chromone derivatives may directly scavenger reactive oxygen species and thus may play a protective role against oxidative damage.


Assuntos
Antioxidantes/farmacologia , Cromonas/farmacologia , Antioxidantes/síntese química , Antioxidantes/química , Cromonas/síntese química , Cromonas/química , Radicais Livres/antagonistas & inibidores , Estrutura Molecular , Estresse Oxidativo/efeitos dos fármacos , Superóxidos/antagonistas & inibidores
14.
J Fluoresc ; 23(6): 1319-27, 2013 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-23860947

RESUMO

The antioxidant properties of 11 new synthesized chromonyl-2,4-thiazolidinediones and chromonyl-2,4-imidazolidinediones (CBs) were investigated. The antioxidant activities and mechanisms of the CBs interaction with reactive oxygen species (ROS) were clarified using various in vitro antioxidant assay methods including superoxide anion radical (O2(•-)), hydroxyl radical (HO(•)), 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH(•)) scavenging activity and the iron (II)-ferrozine complex formation. The potassium superoxide/18-crown-6 ether dissolved in dimethylsulfoxide (DMSO) was applied as a source of superoxide anion radical. Hydroxyl radicals were produced in the Fenton-like reaction Fe(II)+H2O2. Chemiluminescence, spectrophotometry, and electron paramagnetic resonance (EPR) spectroscopy using 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as spin trap were applied as the measurement techniques. The CBs examined that exhibited good free radical scavenging activity also showed strong total antioxidant power capacity. Possible mechanisms of antioxidation are proposed to explain the differences in the experimental results between the chromone derivatives with imidazolidine-2,4-dione ring and those with thiazolidine-2,4-dione ring. In conclusion, some of the new CBs are promising to be applied as inhibitors of free radicals.


Assuntos
Antioxidantes/química , Cromonas/química , Imidazolidinas/química , Tiazolidinedionas/química , Antioxidantes/síntese química , Cromonas/síntese química , Radicais Livres/química , Imidazolidinas/síntese química , Estrutura Molecular , Espécies Reativas de Oxigênio/química , Tiazolidinedionas/síntese química
15.
Luminescence ; 28(4): 450-5, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-23319391

RESUMO

The direct effect of the four catecholamines (adrenaline, noradrenaline, dopamine and isoproterenol) on superoxide anion radicals (O2•) was investigated. The reaction between 18-crown-6-ether and potassium superoxide in dimethylsulfoxide was used as a source of O2•. The reactivity of catecholamines with O2• was examined using chemiluminescence, reduction of nitroblue tetrazolium and electron paramagnetic resonance spin-trapping techniques. 5,5-Dimethyl-1-pyrroline-N-oxide was included as the spin trap. The results showed that the four catecholamines were effective and efficient in inhibiting chemiluminescence accompanying the potassium superoxide/18-crown-6-ether system in a dose-dependent manner over the range 0.05-2 mM in the following order: adrenaline > noradrenaline > dopamine > isoproterenol, with, IC50 = 0.15 ± 0.02 mM 0.21 ± 0.03 mM, 0.27 ± 0.03 mM and 0.50 ± 0.04 mM, respectively. The catecholamines examined also exhibited a strong scavenging effect towards O2• when evaluated this property by the inhibition of nitroblue tetrazolium reduction (56-73% at 1 M concentration). A very similar capacity of O2• scavenging was monitored in the 5,5-dimethyl-1-pyrroline-N-oxide spin-trapping assay. The results suggest that catecholamines tested may involve a direct effect on scavenging O2- radicals.


Assuntos
Catecolaminas/química , Sequestradores de Radicais Livres/química , Superóxidos/química , Ânions/química , Éteres de Coroa/química , Luminescência , Estrutura Molecular
16.
Luminescence ; 27(4): 249-55, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-22887986

RESUMO

Tetracyclines are the second most common antibiotic family in medicine usage. These antibiotics exhibit antioxidant potential; however, the exact mechanism remains unclear. The antiradical activity of the seven tetracyclines (TCs; tetracycline, chlortetracycline, oxytetracycline, doxocycline, methacycline, demeclocycline, minocycline) was determined using the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH(•)) and hydroxyl radicals (HO(•)) generated in a Fenton reaction. Electron spin resonance (ESR), ESR spin-trapping, chemiluminescence and spectrophotometry techniques were applied. It was found that the TCs showed high DPPH antiradical activity in the range 26-96% at 2.5 mmol/L concentration. The second-order rate constants for the reaction between HO(•) and TCs were calculated, in the range (3.6-9.6) × 10(9) L/mol/s. The tetracycline compounds also exhibited a strong decrease in light emission (range 61-85% at concentration of 1 mmol/L). This study also showed that TCs promote the generation of singlet oxygen in the presence of H(2)O(2) and Fe(II)/Fe(III) ions. Our findings suggest direct scavenging activity of the examined tetracyclines towards free radicals, and may be relevant to therapeutic strategy.


Assuntos
Antibacterianos/química , Antioxidantes/química , Tetraciclina/química , Compostos de Bifenilo/química , Espectroscopia de Ressonância de Spin Eletrônica , Cinética , Oxirredução , Picratos/química
17.
Luminescence ; 27(6): 473-7, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-22238226

RESUMO

The direct effects of the four catecholamines (CATs), adrenaline (A), noradrenaline (NA), dopamine (D) and isoproterenol (I), on free radicals were investigated using the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH(•)) and hydroxyl radial (HO(•)). The CATs examined were found to inhibit the ESR signal intensity of DPPH(•) in a dose-dependent manner over the range 0.1-2.5 mmol/L in the following order: NA > A > I > D, with IC50= 0.30 ± 0.03 for noradrenaline and IC50= 0.86 ± 0.02 for dopamine. Hydroxyl radicals were produced using a Fenton reaction in the presence of the spin trap 5,5-dimethyl-1-pyrroline N-oxide (DMPO), and ESR technique was applied to detect the CATs reactivity toward the radicals. The reaction rates constant (k(r)) of CATs with HO(•) were found to be in the order of 10(9) L/mol/s, and the k(r) value for noradrenaline was the highest (k(r)= 8.4 × 10(9) L/mol/s). The CATs examined exhibited also a strong decrease in the light emission (62-73% at 1 mmol/L concentration and 79-89% at 2 mmol/L concentration) from a Fenton-like reaction. These reactions may be relevant to the biological action of these important polyphenolic compounds.


Assuntos
Catecolaminas/química , Catecolaminas/farmacologia , Sequestradores de Radicais Livres/química , Radical Hidroxila/química , Compostos de Bifenilo/química , Relação Dose-Resposta a Droga , Espectroscopia de Ressonância de Spin Eletrônica , Sequestradores de Radicais Livres/farmacologia , Concentração Inibidora 50 , Picratos/química
18.
Luminescence ; 26(3): 202-7, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21681910

RESUMO

The purpose of this study was to identify the antioxidant activity of 16 compounds isolated from Piper cubeba (CNCs) through the extent of their capacities to scavenge free radicals, hydroxyl radical (HO(•)), superoxide anion radical O•(2)(-) and 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(•)), in different systems. Electron paramagnetic resonance (EPR) and 5,5-dimethyl-1-pyrroline-N-oxide, DMPO, as the spin trap, and chemiluminescence techniques were applied. Using the Fenton-like reaction [Fe(II) + H(2)O(2)], CNCs were found to inhibit DMPO-OH radical formation ranging from 5 to 57% at 1.25 mmol L(-1) concentration. The examined CNCs also showed a high DPPH antiradical activity (ranging from 15 to 99% at 5 mmol L(-1) concentration). Furthermore, the results indicated that seven of the 16 tested compounds may catalyse the conversion of superoxide radicals generated in the potassium superoxide/18-crown-6 ether system, thus showing superoxide dismutase-like activity. The data obtained suggest that radical scavenging properties of CNCs might have potential application in many plant medicines.


Assuntos
Sequestradores de Radicais Livres/química , Radicais Livres/química , Piper/química , Extratos Vegetais/química , Sequestradores de Radicais Livres/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/isolamento & purificação
19.
Luminescence ; 26(6): 611-5, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21413138

RESUMO

The tetracycline family antibiotics are widely used as human and veterinary treatments. The drugs are effective as antibiotics and also show antimicrobial and non-microbial action. However, the antioxidant properties of tetracyclines have not been characterized in aprotic media. To better understand their biological functions, the in vitro superoxide anion radical (O2•¯) scavenging activities of tetracycline, chlortetracycline, oxytetracycline, doxycycline and methacycline were characterized, along with a very efficient O2•¯ scavenger, tiron, in dimethyl sulphoxide (DMSO), using ultra-weak chemiluminescence (CL). We found that tetracycline, chlortetracycline and doxycycline efficiently inhibited CL from the O2•¯-generating system at concentration levels of 0.02-1.0 mmol/L. Methacycline and oxytetracycline were the O2•¯ scavengers at concentration levels of 0.01-0.1 mmol/L, whereas when their concentration was lowered the drugs were capable of generating O2•¯, leading to CL enhancement. For all the data obtained in this study, the scavenging activity for the compounds tested decreased in the following order: tetracycline > doxycycline > chlortetracycline > tiron methacycline > oxytetracycline. These results indicate that the tetracycline drugs directly alter O2•¯ redox chemistry in aprotic media.


Assuntos
Antibacterianos/química , Sequestradores de Radicais Livres/química , Superóxidos/química , Tetraciclinas/química
20.
Luminescence ; 26(6): 598-603, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21370385

RESUMO

A chemiluminescent technique was applied to determine antioxidative activities of adriamycin, farmorubicin, mitomycin C and bleomycin against superoxide anion radical (O(2)(•)) in aprotic medium. The antioxidant capacity was expressed as the decrease in light emission from the O(2)(•) solution by and antibiotic. A KO(2) solution in dimethyl sulphoxide (DMSO) and 18-crown-6 ether were used for the generation of O(2)(•). The results showed that the examined compounds decreased the chemiluminescence (CL) sum from the O(2)(•)-generating system in a dose-dependent manner. Among the antibiotics examined, adriamycin, farmorubicin and bleomycin exhibited antioxidant activity almost comparable to that of 1,2-dihydroxy benzene-3,5-disulphonic acid (tiron), an efficient of the O(2)(•) inhibitor. Mitomycin C was two-times less effective as tiron in decreasing the initial CL intensity. The proposed assay with usage of ultraweak CL technique and the KO(2)-DMSO-crown ether system was useful for the evaluation of antioxidant activity in aprotic solvents.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Superóxidos/antagonistas & inibidores , Relação Dose-Resposta a Droga , Luminescência
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