Abstract— This investigation explores the interaction between
single walled carbon nanotubes and the linoleic acid, a polyun-
saturated fatty acid, present in low density lipoprotein, which
is highly susceptible to oxidation. Molecular models were built
and theoretical studies were performed using the PM6 semiem-
pirical method and the density functional theory. The strength
of the interaction was estimated from the interaction energy cal-
culation. Negative values of E
int
indicated that all evaluated sys-
tems are stable. Although, the interaction occurs through weak
forces, CH··· π , OH··· π and CH···N, collectively such interac-
tions are strong enough and may be considered as chemisorp-
tion.
Keywords— Carbon nanotubes, linoleic acid, lipid peroxida-
tion, density functional theory.
I I NTRODUCTION
Experimental evidence has attributed to lipid peroxida-
tion an important role in the pathogenesis of atherosclerosis.
The structural changes experienced by low-density lipopro-
tein (LDL) after oxidation can significantly increase their
atherogenic characteristics [1, 2]. About half of the content
of fatty acids in LDL consists of polyunsaturated fatty acids
(PUFAs), mainly linoleic acid (LA) [3, 4]. As consequence,
oxygenated derivatives of LA have been found in human
atherosclerotic lesions, as main peroxidation products [5, 6].
The hypothesis that antioxidants may inhibit LDL oxida-
tion and reduce the incidence of coronary events has encour-
aged the development of various investigations. Some stud-
ies have been conducted using antioxidant vitamins (beta-
carotene, vitamin C and vitamin E) and a synthetic antiox-
idant (Probucol), obtaining results in favor and against of its
use [7, 8]. On the other hand, statins are drugs widely used in
the treatment of hypercholesterolemia [9]. However, there is
some concern because a relationship between statins use and
the risk of developing other pathologies has been found [10].
Therefore, it is important the search of alternative treat-
ments to prevent or inhibit lipid peroxidation. On this direc-
tion, the use of certain nanomaterials such as carbon nan-
otubes (CNTs) could be considered. Doping and function-
alization enhance biocompatibility and solubility of these
nanomaterials, and can alter its cellular interaction pathways,
resulting in a reduction in the cytotoxic effects [11], which
has opened the possibility of its application in medicine field.
In addition, antioxidant activity has also been reported in
CNTs [12, 13], which could be useful for the treatment of
different diseases, including the atherosclerosis.
Modeling and simulation have been well established as in-
strumental in the study of CNTs [14, 15, 16]. Theoretical re-
search is based on the development of a molecular model that
allows the description, research and prediction of properties
of interest. Electronic structure methods are the fundamen-
tal level of theory used for the description of the systems
at nanoscale. These methods use the laws of quantum me-
chanics and are characterized by different levels of approach
to the solution of the Schr¨ odinger equation. Semiempirical
methods, ab initio and the density functional theory (DFT)
are classified as electronic structure methods [17].
As a first approach to the study of the inhibition of lipid
peroxidation applying CNTs, we evaluated theoretically the
interaction of the LA and perfect single walled carbon nan-
otubes (SWCNTs) and doped with nitrogen (SWCNT4N),
using the PM6 semiempirical method [18] and the DFT
[19, 20]. We took advantage of the highly cost effective
semiempirical method to perform geometry optimization of
SWCNT-LA and SWCNT4N-LA. The optimized coordi-
nates were used to perform single point calculations at DFT
level. Interaction energies were estimated and considered as
a criterion for evaluating the stability of the systems. End-
functionalization of LA with SWCNT has been reported us-
ing molecular dynamics [21], but electronic calculations are
required for an adequate estimation of the interaction.
II METHODOLOGY
To study the interaction of SWCNTs with LA, we selected
a (10,0) SWCNT, which has been commonly studied [22, 23].
Model of perfect SWCNT was built using 280 carbon atoms.
Theoretical study of the interaction between carbon nanotubes and the linoleic acid,
an atherogenic polyunsaturated fatty acid
Ana M. Torres
1
, John Bustamante
1
, Andrés M. Garay-Tapia
2
and Tapas Kar
3
1
Universidad Pontificia Bolivariana/Centro de Bioingeniería, Grupo de Dinámica Cardiovascular, Medellín, Colombia
2
Centro de Investigación en Materiales Avanzados/Grupo de Termodinámica Computacional, Monterrey, México
3
Department of Chemistry and Biochemistry/Utah State University, Logan, UT 84321, USA
© Springer Nature Singapore Pte Ltd. 2017 492
I. Torres et al. (eds.), VII Latin American Congress on Biomedical Engineering CLAIB 2016,
Bucaramanga, Santander, Colombia, October 26th -28th, 2016,
IFMBE Proceedings 60,
DOI: 10.1007/978-981-10-4086-3_124