The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach
The coordination of one and two aflatoxin B<sub>1</sub> (AFB<sub>1</sub>, a potent carcinogen) molecules with chlorophyll a (<b>chl a</b>) was studied at a theoretical level. Calculations were performed using the M06-2X method in conjunction with the 6-311G(d,p) b...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-05-01
|
| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/23/11/6068 |
| _version_ | 1797493153551351808 |
|---|---|
| author | Alma Vázquez-Durán Guillermo Téllez-Isaías Maricarmen Hernández-Rodríguez René Miranda Ruvalcaba Joel Martínez María Inés Nicolás-Vázquez Juan Manuel Aceves-Hernández Abraham Méndez-Albores |
| author_facet | Alma Vázquez-Durán Guillermo Téllez-Isaías Maricarmen Hernández-Rodríguez René Miranda Ruvalcaba Joel Martínez María Inés Nicolás-Vázquez Juan Manuel Aceves-Hernández Abraham Méndez-Albores |
| author_sort | Alma Vázquez-Durán |
| collection | DOAJ |
| description | The coordination of one and two aflatoxin B<sub>1</sub> (AFB<sub>1</sub>, a potent carcinogen) molecules with chlorophyll a (<b>chl a</b>) 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<sub>1</sub> and <b>chl a</b> molecules. The energy difference between molecular orbitals of AFB<sub>1</sub> and <b>chl a</b> allowed for the establishment of an intermolecular interaction. A charge transfer from AFB<sub>1</sub> to the central cation of <b>chl a</b> was shown. The energies of the optimized structures for <b>chl a</b> show two configurations, unfolded and folded, with a difference of 15.41 kcal/mol. <b>Chl a</b> 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<sub>1</sub>. The complexes of maximum stability were <b>chl a 1</b>-α-E-AFB<sub>1</sub> and <b>chl a 2</b>-β-E-AFB<sub>1</sub>, at −36.4 and −39.2 kcal/mol, respectively. Additionally, with two AFB<sub>1</sub> molecules were <b>chl a 1</b>-D-2AFB<sub>1</sub> and <b>chl a 2</b>-E-2AFB<sub>1</sub>, at −60.0 and −64.8 kcal/mol, respectively. Finally, biosorbents containing chlorophyll could improve AFB<sub>1</sub> adsorption. |
| first_indexed | 2024-03-10T01:15:55Z |
| format | Article |
| id | doaj.art-3255f4f645404035a38de7f2b2984148 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T01:15:55Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-3255f4f645404035a38de7f2b29841482023-11-23T14:09:02ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-05-012311606810.3390/ijms23116068The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical ApproachAlma Vázquez-Durán0Guillermo Téllez-Isaías1Maricarmen Hernández-Rodríguez2René Miranda Ruvalcaba3Joel Martínez4María Inés Nicolás-Vázquez5Juan Manuel Aceves-Hernández6Abraham Méndez-Albores7Unidad de Investigación Multidisciplinaria L14 (Alimentos, Micotoxinas, y Micotoxicosis), Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de Mexico 54714, MexicoDepartment of Poultry Science, University of Arkansas, Fayetteville, AR 72701, USALaboratorio de Cultivo Celular, Sección de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Ciudad de Mexico 11340, MexicoDepartamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Avenida 1o de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli, Estado de Mexico 54740, MexicoFacultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, San Luis Potosi 78210, MexicoDepartamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Avenida 1o de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli, Estado de Mexico 54740, MexicoUnidad de Investigación Multidisciplinaria L14 (Alimentos, Micotoxinas, y Micotoxicosis), Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de Mexico 54714, MexicoUnidad de Investigación Multidisciplinaria L14 (Alimentos, Micotoxinas, y Micotoxicosis), Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de Mexico 54714, MexicoThe coordination of one and two aflatoxin B<sub>1</sub> (AFB<sub>1</sub>, a potent carcinogen) molecules with chlorophyll a (<b>chl a</b>) 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<sub>1</sub> and <b>chl a</b> molecules. The energy difference between molecular orbitals of AFB<sub>1</sub> and <b>chl a</b> allowed for the establishment of an intermolecular interaction. A charge transfer from AFB<sub>1</sub> to the central cation of <b>chl a</b> was shown. The energies of the optimized structures for <b>chl a</b> show two configurations, unfolded and folded, with a difference of 15.41 kcal/mol. <b>Chl a</b> 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<sub>1</sub>. The complexes of maximum stability were <b>chl a 1</b>-α-E-AFB<sub>1</sub> and <b>chl a 2</b>-β-E-AFB<sub>1</sub>, at −36.4 and −39.2 kcal/mol, respectively. Additionally, with two AFB<sub>1</sub> molecules were <b>chl a 1</b>-D-2AFB<sub>1</sub> and <b>chl a 2</b>-E-2AFB<sub>1</sub>, at −60.0 and −64.8 kcal/mol, respectively. Finally, biosorbents containing chlorophyll could improve AFB<sub>1</sub> adsorption.https://www.mdpi.com/1422-0067/23/11/6068chlorophyll aaflatoxin B<sub>1</sub>intermolecular interactionsmolecular modelingdensity functional theoryM06-2X functional |
| spellingShingle | Alma Vázquez-Durán Guillermo Téllez-Isaías Maricarmen Hernández-Rodríguez René Miranda Ruvalcaba Joel Martínez María Inés Nicolás-Vázquez Juan Manuel Aceves-Hernández Abraham Méndez-Albores The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach International Journal of Molecular Sciences chlorophyll a aflatoxin B<sub>1</sub> intermolecular interactions molecular modeling density functional theory M06-2X functional |
| title | The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach |
| title_full | The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach |
| title_fullStr | The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach |
| title_full_unstemmed | The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach |
| title_short | The Ability of Chlorophyll to Trap Carcinogen Aflatoxin B<sub>1</sub>: A Theoretical Approach |
| title_sort | ability of chlorophyll to trap carcinogen aflatoxin b sub 1 sub a theoretical approach |
| topic | chlorophyll a aflatoxin B<sub>1</sub> intermolecular interactions molecular modeling density functional theory M06-2X functional |
| url | https://www.mdpi.com/1422-0067/23/11/6068 |
| work_keys_str_mv | AT almavazquezduran theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT guillermotellezisaias theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT maricarmenhernandezrodriguez theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT renemirandaruvalcaba theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT joelmartinez theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT mariainesnicolasvazquez theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT juanmanuelaceveshernandez theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT abrahammendezalbores theabilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT almavazquezduran abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT guillermotellezisaias abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT maricarmenhernandezrodriguez abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT renemirandaruvalcaba abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT joelmartinez abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT mariainesnicolasvazquez abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT juanmanuelaceveshernandez abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach AT abrahammendezalbores abilityofchlorophylltotrapcarcinogenaflatoxinbsub1subatheoreticalapproach |