Biochemical and Biophysical Research Communications
Antioxidant properties of bucillamine: Possible mode of action
Section snippets
Materials and methods
All reagents were of analytical grade, obtained from Sigma Aldrich Chemical Co. (Israel). Bucillamine of high chemical purity was purchased from GreenSyn (Guangzhou) Co., Ltd., China.
Cyclic voltammetric studies were carried out by an EG&G Princeton Applied Research potentiostat galvanostat, model 263 A, using a three-electrode assembly consisting of a glassy carbon working electrode (A = 0.07 cm2), a platinum counter electrode, and a saturated calomel as a reference electrode.
Antioxidant activity
Results
The antioxidant activity of BUC and other antioxidants was evaluated by the TEAC and FRAP assays and the results are shown in Table 1. By both methods BUC had a high relative antioxidant activity, 1.46 ± 0.06 and 2.07 ± 0.01 mM, as compared with trolox 1.00 ± 0.0 and 1.75 ± 0.02, and ascorbic acid, 0.99 ± 0.02 and 1.95 ± 0.02 mM, respectively.
The scavenging activity of the DPPH radical was evaluated. As shown in Table 2, the concentration providing 50% of the radical scavenging (IC50) was determined. A lower
Discussion
The aim of this study was to evaluate the in vitro antioxidant properties and possible mode of action of the thiol-containing drug Bucillamine, the efficacy of which in the treatment of rheumatoid arthritis is well documented [22], [23], [24]. We used a panel of tests to assess its antioxidant activity, using biologically relevant oxygen-derived species to test its scavenging capacity. BUC, a di-thiol, showed effective and potent antioxidant activity albeit poor scavenging capacity against the
Acknowledgment
This study was supported in part by a Grant from the Israel Science Foundation.
References (30)
Characterization of drugs as antioxidant prophylaxis
Free. Radic. Biol. Med
(1996)- et al.
Regulation of B cell function of bucillamine, a novel disease-modifying antirheumatic drug
Clin. Immunol. Immunopathol.
(1993) - et al.
The characterization of antioxidants
Food Chem. Toxicol.
(1995) - et al.
Use of a free radical method to evaluate antioxidant activity
Lebensmittel-Wissenschaft Technol.
(1995) - et al.
The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay
Analyt. Biochem.
(1996) - et al.
In vitro antioxidant properties of morphine
Pharmacol. Res.
(2004) - et al.
The deoxyribose method: a simple “test tube” assay for determination of rate constants for reactions of hydroxyl radicals
Analyt. Biochem.
(1987) - et al.
Antioxidant properties of butein isolated from Dalbergia odorifera
Biochim. Biophys. Acta
(1998) - et al.
Thiourea protects against copper-induced oxidative damage by formation of a redox-inactive thiourea–copper complex
Free Radic. Biol. Med.
(2002) - et al.
Decrease in disease activity and concomitant increase in the percentage of peripheral blood suppressor T-cells in rheumatoid arthritis by a newly synthesized slow-acting anti-rheumatic drug (bucillamine)
Int. J. Immunopharmacol.
(1989)
In vivo total antioxidant capacity: comparison of different analytical methods
Free Radic. Biol. Med.
The antioxidant action of n-acetylcysteine: its reaction with hydrogen peroxide, hydroxyl radical, superoxide and hypochlorous acid
Free Radic. Biol. Med.
Antioxidant status in rheumatoid arthritis and role of antioxidant therapy
Clin. Chim. Acta
Pharmacological effects of SA96 (bucillamine) and its metabolites as immunomodulating drugs—the disulfide structure of SA-96 metabolites play a critical role in the pharmacological action of the drug
Int. J. Immunopharmacol.
Antioxidants in human health and disease
Ann. Rev. Nutr.
Cited by (39)
Application of thiol compounds to reduce acrylamide levels and increase antioxidant activity of French fries
2021, LWTCitation Excerpt :Moreover, while the relative antioxidant activities determined by DPPH scavenging and FRAP were in agreement, CUPRAC was different. It was thought that the reason might be the difference in reduction capacities of GSH, CYS and NAC against Fe+3 and Cu+2 radicals (Güngör, Özyürek, Güçlü, Çekiç, & Apak, 2011; Mazor, Greenberg, Shamir, Meyerstein, & Meyerstein, 2006). The amounts of total phenols of raw and fried potatoes were demonstrated in Table 2.
Prostaglandin D <inf>2</inf> -ethanolamide induces skin cancer apoptosis by suppressing the activity of cellular antioxidants
2019, Prostaglandins and Other Lipid MediatorsDetermination of antioxidant capacity of thiol-containing compounds by electron spin resonance spectroscopy based on Cu<sup>2+</sup> ion reduction
2018, TalantaCitation Excerpt :In human body, an accumulation of excess reactive oxygen species generated from metabolic processes and environmental stresses can lead to damage in proteins and DNA, thus resulting in oxidative stress [1,2]. Antioxidants can attenuate the damage caused by oxidative stress [3]. They do this by being oxidized themselves and thus antioxidants are often reducing agents such as thiols, ascorbic acid (vitamin C), or polyphenols [4].
S,S′-dinitrosobucillamine, a new nitric oxide donor, induces a better vasorelaxation than other S-nitrosothiols
2014, European Journal of PharmacologyCitation Excerpt :We have presently selected the dithiol bucillamine (BUC(SH)2) as an interesting NO carrier because it combines in its structure N-acetylcysteine and N-acetyl-d,l-penicillamine moieties at the same time (Fig. 1). Moreover, BUC(SH)2 is a commercially available drug used in rheumatoid arthritis; it presents anti-inflammatory and anti-oxidant properties through metallic ion chelation (Mazor et al., 2006), and it has undergone some preliminary investigations in experimental studies of ischemia–reperfusion (Amersi et al., 2002). We have investigated the vasorelaxant properties of BUC(NO)2 using an ex vivo aortic ring model and compared them to those of the two constitutive S-mononitrosothiols, S-nitroso-N-acetylpenicillamine (SNAP) and S-nitroso-N-acetylcysteine (NACNO), and to an equimolar mixture of SNAP plus NACNO (which mimics the number of NO moles contained in a BUC(NO)2 molecule).
Free-radical degradation of high-molecular-weight hyaluronan induced by ascorbate plus cupric ions. Testing of bucillamine and its SA981-metabolite as antioxidants
2011, Journal of Pharmaceutical and Biomedical AnalysisOxidative stress in asthma
2011, World Allergy Organization Journal