Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
- Autores
- Vega Hissi, Esteban Gabriel; Estrada, Mario Rinaldo; Lavecchia, Martín José; Pis Diez, Reinaldo
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis.
Centro de Química Inorgánica - Materia
-
Química
Computational analysis
Unconjugated bilirrubin
Pka - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- http://creativecommons.org/licenses/by-nc-sa/4.0/
- Repositorio
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/104345
Ver los metadatos del registro completo
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Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarificationVega Hissi, Esteban GabrielEstrada, Mario RinaldoLavecchia, Martín JoséPis Diez, ReinaldoQuímicaComputational analysisUnconjugated bilirrubinPkaThe pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis.Centro de Química Inorgánica2013-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://sedici.unlp.edu.ar/handle/10915/104345enginfo:eu-repo/semantics/altIdentifier/url/http://hdl.handle.net/11336/4389info:eu-repo/semantics/altIdentifier/issn/0021-9606info:eu-repo/semantics/altIdentifier/doi/10.1063/1.4773586info:eu-repo/semantics/altIdentifier/hdl/11336/4389info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:22:42Zoai:sedici.unlp.edu.ar:10915/104345Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:22:43.233SEDICI (UNLP) - Universidad Nacional de La Platafalse |
dc.title.none.fl_str_mv |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
title |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
spellingShingle |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification Vega Hissi, Esteban Gabriel Química Computational analysis Unconjugated bilirrubin Pka |
title_short |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
title_full |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
title_fullStr |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
title_full_unstemmed |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
title_sort |
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification |
dc.creator.none.fl_str_mv |
Vega Hissi, Esteban Gabriel Estrada, Mario Rinaldo Lavecchia, Martín José Pis Diez, Reinaldo |
author |
Vega Hissi, Esteban Gabriel |
author_facet |
Vega Hissi, Esteban Gabriel Estrada, Mario Rinaldo Lavecchia, Martín José Pis Diez, Reinaldo |
author_role |
author |
author2 |
Estrada, Mario Rinaldo Lavecchia, Martín José Pis Diez, Reinaldo |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
Química Computational analysis Unconjugated bilirrubin Pka |
topic |
Química Computational analysis Unconjugated bilirrubin Pka |
dc.description.none.fl_txt_mv |
The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis. Centro de Química Inorgánica |
description |
The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-11 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Articulo http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://sedici.unlp.edu.ar/handle/10915/104345 |
url |
http://sedici.unlp.edu.ar/handle/10915/104345 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://hdl.handle.net/11336/4389 info:eu-repo/semantics/altIdentifier/issn/0021-9606 info:eu-repo/semantics/altIdentifier/doi/10.1063/1.4773586 info:eu-repo/semantics/altIdentifier/hdl/11336/4389 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) |
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openAccess |
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http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) |
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application/pdf |
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SEDICI (UNLP) - Universidad Nacional de La Plata |
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