The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B 1 : A Theoretical Approach

• Published in: International journal of molecular sciences Vol. 23; no. 11
• Main Authors: Vázquez-Durán, Alma, Téllez-Isaías, Guillermo, Hernández-Rodríguez, Maricarmen, Ruvalcaba, René Miranda, Martínez, Joel, Nicolás-Vázquez, María Inés, Aceves-Hernández, Juan Manuel, Méndez-Albores, Abraham
• Format: Journal Article
• Language: English
• Published: Switzerland 28-05-2022
• Subjects: Aflatoxin B1 - chemistry; Carcinogens; Chlorophyll; Chlorophyll A; Oxygen; aflatoxin B1; M06-2X functional; molecular modeling; density functional theory; intermolecular interactions; chlorophyll a
• ISSN: 1422-0067

The coordination of one and two aflatoxin B
(AFB
, a potent carcinogen) molecules with chlorophyll a (
) was studied at a theoretical level. Calculations were performed using the M06-2X method in conjunction with the 6-311G(d,p) basis set, in both gas and water phases. The molecular electrostatic potential map shows the chemical activity of various sites of the AFB
and
molecules. The energy difference between molecular orbitals of AFB
and
allowed for the establishment of an intermolecular interaction. A charge transfer from AFB
to the central cation of
was shown. The energies of the optimized structures for
show two configurations, unfolded and folded, with a difference of 15.41 kcal/mol.
appeared axially coordinated to the plane (α-down or β-up) of the porphyrin moiety, either with the oxygen atom of the ketonic group, or with the oxygen atom of the lactone moiety of AFB
. The complexes of maximum stability were
-α-E-AFB
and
-β-E-AFB
, at -36.4 and -39.2 kcal/mol, respectively. Additionally, with two AFB
molecules were
-D-2AFB
and
-E-2AFB
, at -60.0 and -64.8 kcal/mol, respectively. Finally, biosorbents containing chlorophyll could improve AFB
adsorption.