Publication
Correlation between octanol/water and liposome/water distribution coefficients and drug absorption of a set of pharmacologically active compounds
| dc.contributor.author | Esteves, Freddy | |
| dc.contributor.author | Moutinho, Carla | |
| dc.contributor.author | Matos, Carla | |
| dc.date.accessioned | 2019-12-24T11:47:28Z | |
| dc.date.available | 2019-12-24T11:47:28Z | |
| dc.date.issued | 2013 | |
| dc.description.abstract | Absorption and consequent therapeutic action are key issues in the development of new drugs by the pharmaceutical industry. In this sense, different models can be used to simulate biological membranes to predict the absorption of a drug. This work compared the octanol/water and the liposome/water models. The parameters used to relate the two models were the distribution coefficients between liposomes and water and octanol and water and the fraction of drug orally absorbed. For this study, 66 drugs were collected from literature sources and divided into four groups according to charge and ionization degree: neutral; positively charged; negatively charged; and partially ionized/zwitterionic. The results show a satisfactory linear correlation between the octanol and liposome systems for the neutral (R²= 0.9324) and partially ionized compounds (R²= 0.9367), contrary to the positive (R²= 0.4684) and negatively charged compounds (R²= 0.1487). In the case of neutral drugs, results were similar in both models because of the high fraction orally absorbed. However, for the charged drugs (positively, negatively, and partially ionized/zwitterionic), the liposomal model has a more-appropriate correlation with absorption than the octanol model. These results show that the neutral compounds only interact with membranes through hydrophobic bonds, whereas charged drugs favor electrostatic interactions established with the liposomes. With this work, we concluded that liposomes may be a more-appropriate biomembrane model than octanol for charged compounds. | pt_PT |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.doi | 10.3109/08982104.2012.742539 | pt_PT |
| dc.identifier.issn | 0898-2104 | |
| dc.identifier.issn | 1532-2394 | |
| dc.identifier.uri | http://hdl.handle.net/10284/8336 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | Taylor & Francis | pt_PT |
| dc.relation.publisherversion | https://www.tandfonline.com/doi/abs/10.3109/08982104.2012.742539?journalCode=ilpr20 | pt_PT |
| dc.subject | Models, Chemical | pt_PT |
| dc.subject | Octanols | pt_PT |
| dc.subject | Water | pt_PT |
| dc.subject | Liposomes | pt_PT |
| dc.title | Correlation between octanol/water and liposome/water distribution coefficients and drug absorption of a set of pharmacologically active compounds | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 93 | pt_PT |
| oaire.citation.issue | 2 | pt_PT |
| oaire.citation.startPage | 83 | pt_PT |
| oaire.citation.title | Journal of Liposome Research | pt_PT |
| oaire.citation.volume | 23 | pt_PT |
| person.familyName | Moutinho | |
| person.familyName | Matos | |
| person.givenName | Carla | |
| person.givenName | Carla | |
| person.identifier | 1536969 | |
| person.identifier.ciencia-id | B61F-F356-80C6 | |
| person.identifier.ciencia-id | 721C-DA34-256E | |
| person.identifier.orcid | 0000-0003-1310-4696 | |
| person.identifier.orcid | 0000-0003-0617-3538 | |
| person.identifier.rid | M-7142-2013 | |
| person.identifier.scopus-author-id | 16064733800 | |
| person.identifier.scopus-author-id | 7004493818 | |
| rcaap.rights | restrictedAccess | pt_PT |
| rcaap.type | article | pt_PT |
| relation.isAuthorOfPublication | cff7638e-1f33-4384-aa73-d3acc5cca5f8 | |
| relation.isAuthorOfPublication | d4b6d3e1-6d29-4fb4-97c7-abb2cf4c83b4 | |
| relation.isAuthorOfPublication.latestForDiscovery | cff7638e-1f33-4384-aa73-d3acc5cca5f8 |