Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry
A theoretical study of the ciprofloxacin interactions with glucuronic acid, arabinose, glucosamine, and rhamnose is presented. The most stable complexes were obtained through genetic algorithms starting from the neutral and zwitterion species of ciprofloxacin. The energy at the semiempirical level P...
- Autores:
-
Coba-Jiménez, Ludis
Guerra, Mayamarú
Maza, Julio
Deluque-Gómez, Julio
Cubillán, Néstor
- Tipo de recurso:
- Fecha de publicación:
- 2022
- Institución:
- Universidad Tecnológica de Bolívar
- Repositorio:
- Repositorio Institucional UTB
- Idioma:
- eng
- OAI Identifier:
- oai:repositorio.utb.edu.co:20.500.12585/12201
- Acceso en línea:
- https://hdl.handle.net/20.500.12585/12201
- Palabra clave:
- Molecular Dynamics;
Carbohydrate Conformation;
Cellobiose
LEMB
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by-nc-nd/4.0/
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Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
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Maza, |
| title |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| spellingShingle |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry Molecular Dynamics; Carbohydrate Conformation; Cellobiose LEMB |
| title_short |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| title_full |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| title_fullStr |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| title_full_unstemmed |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| title_sort |
Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry |
| dc.creator.fl_str_mv |
Coba-Jiménez, Ludis Guerra, Mayamarú Maza, Julio Deluque-Gómez, Julio Cubillán, Néstor |
| dc.contributor.author.none.fl_str_mv |
Coba-Jiménez, Ludis Guerra, Mayamarú Maza, Julio Deluque-Gómez, Julio Cubillán, Néstor |
| dc.subject.keywords.spa.fl_str_mv |
Molecular Dynamics; Carbohydrate Conformation; Cellobiose |
| topic |
Molecular Dynamics; Carbohydrate Conformation; Cellobiose LEMB |
| dc.subject.armarc.none.fl_str_mv |
LEMB |
| description |
A theoretical study of the ciprofloxacin interactions with glucuronic acid, arabinose, glucosamine, and rhamnose is presented. The most stable complexes were obtained through genetic algorithms starting from the neutral and zwitterion species of ciprofloxacin. The energy at the semiempirical level PM7 of the optimal structures of the complexes was the genetic algorithm‘s fitness function. The resulting complexes’ geometry was optimized at M062X−D3/6-311++G** level of theory, and non-covalent interactions were assessed through the reduced density gradient and quantum theory of atoms in molecules. The results show that the zwitterion species of ciprofloxacin favorably complex carbohydrates and can induce proton exchange between them. The molecular complexes from proton exchange are the most stable, followed by the complexes formed by the contact of the zwitterion species and the carbohydrate. The complexes formed by both neutral species were the least stable. The medium strength and strong (assisted by charge) hydrogen bonds, the XH⋅⋅⋅π and lone-pair⋅⋅π interactions, were mainly present in the complexes. Proton exchange processes strengthen the interactions mentioned above. © 2022 Wiley-VCH GmbH |
| publishDate |
2022 |
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2022 |
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2023-07-19T21:19:59Z |
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2023-07-19T21:19:59Z |
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2023 |
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http://purl.org/coar/version/c_b1a7d7d4d402bcce |
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http://purl.org/coar/resource_type/c_6501 |
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Coba‐Jiménez, L., Maza, J., Guerra, M., Deluque‐Gómez, J., & Cubillán, N. (2022). Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry. ChemistrySelect, 7(2), e202103836. |
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https://hdl.handle.net/20.500.12585/12201 |
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10.1002/slct.202103836 |
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Universidad Tecnológica de Bolívar |
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Repositorio Universidad Tecnológica de Bolívar |
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Coba‐Jiménez, L., Maza, J., Guerra, M., Deluque‐Gómez, J., & Cubillán, N. (2022). Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry. ChemistrySelect, 7(2), e202103836. 10.1002/slct.202103836 Universidad Tecnológica de Bolívar Repositorio Universidad Tecnológica de Bolívar |
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https://hdl.handle.net/20.500.12585/12201 |
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eng |
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eng |
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Coba-Jiménez, Ludisa74218d9-e5bf-4533-97c1-fa33ccf7476eGuerra, Mayamarú5af72308-bd11-495a-86d4-0817f8961b6cMaza, Julio599ccf29-8723-4821-be7a-79f78c0a9c19Deluque-Gómez, Julio3fad6b64-ebe6-41cd-b378-12e209a35d76Cubillán, Néstor81ec06c5-9433-4b0c-9e60-ef40644183c82023-07-19T21:19:59Z2023-07-19T21:19:59Z20222023Coba‐Jiménez, L., Maza, J., Guerra, M., Deluque‐Gómez, J., & Cubillán, N. (2022). Interaction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum Chemistry. ChemistrySelect, 7(2), e202103836.https://hdl.handle.net/20.500.12585/1220110.1002/slct.202103836Universidad Tecnológica de BolívarRepositorio Universidad Tecnológica de BolívarA theoretical study of the ciprofloxacin interactions with glucuronic acid, arabinose, glucosamine, and rhamnose is presented. The most stable complexes were obtained through genetic algorithms starting from the neutral and zwitterion species of ciprofloxacin. The energy at the semiempirical level PM7 of the optimal structures of the complexes was the genetic algorithm‘s fitness function. The resulting complexes’ geometry was optimized at M062X−D3/6-311++G** level of theory, and non-covalent interactions were assessed through the reduced density gradient and quantum theory of atoms in molecules. The results show that the zwitterion species of ciprofloxacin favorably complex carbohydrates and can induce proton exchange between them. The molecular complexes from proton exchange are the most stable, followed by the complexes formed by the contact of the zwitterion species and the carbohydrate. The complexes formed by both neutral species were the least stable. The medium strength and strong (assisted by charge) hydrogen bonds, the XH⋅⋅⋅π and lone-pair⋅⋅π interactions, were mainly present in the complexes. Proton exchange processes strengthen the interactions mentioned above. © 2022 Wiley-VCH GmbHapplication/pdfenghttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://purl.org/coar/access_right/c_abf2ChemistrySelectInteraction of Ciprofloxacin with Arabinose, Glucosamine, Glucuronic Acid and Rhamnose: Insights from Genetic Algorithm and Quantum ChemistryMaza,info:eu-repo/semantics/articleinfo:eu-repo/semantics/drafthttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/version/c_b1a7d7d4d402bccehttp://purl.org/coar/resource_type/c_2df8fbb1Molecular Dynamics;Carbohydrate Conformation;CellobioseLEMBCartagena de IndiasUnemo, M., Golparian, D., Eyre, D.W. Antimicrobial Resistance in Neisseria gonorrhoeae and Treatment of Gonorrhea (2019) Methods in Molecular Biology, 1997, pp. 37-58. 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Cited 14 times. link.springer.de/link/service/journals/00244/index.htm doi: 10.1007/s00244-020-00789-wWang, K., Gao, D., Xu, J., Cai, L., Cheng, J., Yu, Z., Hu, Z., (...), Yu, J. Interaction of ciprofloxacin with the activated sludge of the sewage treatment plant (Open Access) (2018) Environmental Science and Pollution Research, 25 (35), pp. 35064-35073. Cited 8 times. http://www.springerlink.com/content/0944-1344 doi: 10.1007/s11356-018-3413-0Xie, P., Chen, C., Zhang, C., Su, G., Ren, N., Ho, S.-H. Revealing the role of adsorption in ciprofloxacin and sulfadiazine elimination routes in microalgae (2020) Water Research, 172, art. no. 115475. Cited 124 times. www.elsevier.com/locate/watres doi: 10.1016/j.watres.2020.115475Yu, J.-H., Lee, B., Jeong, D., Jung, S. Solubility and bioavailability enhancement of ciprofloxacin by induced oval-shaped mono-6-deoxy-6-aminoethylamino-β-cyclodextrin (2017) Carbohydrate Polymers, 163, pp. 118-128. 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