e n v i r o n m e n t a l t o x i c o l o g y a n d p h a r m a c o l o g y 3 4 ( 2 0 1 2 ) 446–453
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Antioxidant properties of ˇ-seleno amines against lipid
peroxidation in rat brain and liver
S.M. Sabir
a,∗
, Syed M. Salman
b
, J.B.T. Rocha
c
a
Department of Eastern Medicine and Surgery, University of the Pooch Rawalakot Azad Kashmir Pakistan
b
Department of Chemistry, Abdul Wali Khan University Mardan, Khyber pakhtunkhwa, Pakistan
c
Departmento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria, CEP 97105-900,
Brazil
a r t i c l e i n f o
Article history:
Received 27 October 2011
Received in revised form
13 June 2012
Accepted 16 June 2012
Available online 26 June 2012
Keywords:
Monoselenides
Lipid peroxidation
DPPH radical scavenging activity
Pro-oxidants
Total antioxidant activity
a b s t r a c t
ˇ-Seleno amines were screened for in vitro antioxidant activity. The compounds (C1–C4)
were tested against lipid peroxidation induced by iron and sodium nitroprusside in rat
brain and liver homogenates. The compounds showed inhibition against thiobarbituric acid
reactive species (TBARS) induced by different pro-oxidants (10 M FeSO
4
and 5 M sodium
nitroprusside (SNP) in rat brain and liver homogenates. The compounds exhibited strong
antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and phosphomolybde-
num assays. The IC
50
values revealed that the ˇ-seleno amines in which the amino group was
protected with protecting groups tert-butyloxycarbonyl (Boc) and Tosyl (Ts) groups showed
better antioxidant profiles compared to the free monoselenides. The total antioxidant activ-
ity of C1, C2, C3 and C4 were found to be 85.2 ± 11.5, 114 ± 7.9, 138 ± 8.5, 125.81 ± 5.2 M/ml
of ascorbic acid respectively. Therefore, these compounds may be used as synthetic antiox-
idants.
© 2012 Elsevier B.V. All rights reserved.
1. Introduction
Antioxidant compounds that are generally used in biological
system, such as some phenols and amines (primary and sec-
ondary), exhibit their antioxidant effect through chain transfer
and chain termination mechanisms (Gugumus, 1990). The
first step of the reactive radical termination by antioxidant
compounds is the donation of hydrogen atom from the antiox-
idant molecule to the reactive radical intermediate (Zhu et al.,
1997). In line with this, several studies have demonstrated that
TBARS (thiobarbituric acid reactive substances) level monitor-
ing is a useful tool in pathological states in humans and tissues
of animal models (Dorman et al., 2003; Fraga and Oteiza,
2002). Lipid peroxidation which is a result of oxidative stress,
∗
Corresponding author. Tel.: +92 05824960007; fax: +92 05824443628.
E-mail address: mubashersabir@yahoo.com (S.M. Sabir).
contributes to the initiation and progress of liver damage
(Albano et al., 1985). It is therefore, assumed that the lipid
peroxidation product, i.e., malondialdehyde (MDA) may play
a significant role in brain and liver toxicities.
Free radicals are now accepted as important mediators of
tissue injury in several neurodegenerative diseases (Beal, 1996)
and in other pathological conditions, such as senescence (Ji
et al., 2003). In fact, free radicals can attack membrane lipids,
proteins and nucleic acids, disrupting normal cell physiology
(Halliwell, 1992). Evidence has been provided in the last two
decades that organo-chalcogens are promising pharmacolog-
ical agents and possess very interesting biological activities
(Doering et al., 2010; Parnham and Sies, 2000). Several studies
have reported a glutathione peroxidase (GPx)-mimetic activity
1382-6689/$ – see front matter © 2012 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.etap.2012.06.002