Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives
The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic na...
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| Format: | Article |
| Language: | English |
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Wiley
2011-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2011/731090 |
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| author | Jose Isagani B. Janairo Gerardo C. Janairo Derrick Ethelbhert C. YU |
| author_facet | Jose Isagani B. Janairo Gerardo C. Janairo Derrick Ethelbhert C. YU |
| author_sort | Jose Isagani B. Janairo |
| collection | DOAJ |
| description | The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic nature can result to poor bioavailabilty, low absorption and poor systemic circulation. In silico simulations revealed that this setback can be overcome by introduction of hydroxyl group to the tertiary carbon of ent-kaurenoic acid employing m-CPBA catalyzed hydroxylation, thus, unleashing its full drug potency. Moreover, molecular similarity analyses derived from semi-empirical calculations between ent-kaurenoic acid and a set of kaurane diterpenoids showed differences in hydrophobic complementarity, size and electronic properties despite possessing nearly identical molecular frameworks, thus, arriving in a generalization for their observed mechanistic differences on acting on different targets. |
| format | Article |
| id | doaj-art-104b4a9bac3f46d9a4906bf6d47ba913 |
| institution | Kabale University |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2011-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | E-Journal of Chemistry |
| spelling | doaj-art-104b4a9bac3f46d9a4906bf6d47ba9132025-02-03T01:13:05ZengWileyE-Journal of Chemistry0973-49452090-98102011-01-018270371010.1155/2011/731090Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and DerivativesJose Isagani B. Janairo0Gerardo C. Janairo1Derrick Ethelbhert C. YU2Materials Science and Nanotechnology Unit, Center for Natural Sciences and Environmental Research, De La Salle University, 2401 Taft Avenue, Manila, PhilippinesMaterials Science and Nanotechnology Unit, Center for Natural Sciences and Environmental Research, De La Salle University, 2401 Taft Avenue, Manila, PhilippinesDepartment of Chemistry, De La Salle University, 2401 Taft Avenue, Manila, PhilippinesThe physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic nature can result to poor bioavailabilty, low absorption and poor systemic circulation. In silico simulations revealed that this setback can be overcome by introduction of hydroxyl group to the tertiary carbon of ent-kaurenoic acid employing m-CPBA catalyzed hydroxylation, thus, unleashing its full drug potency. Moreover, molecular similarity analyses derived from semi-empirical calculations between ent-kaurenoic acid and a set of kaurane diterpenoids showed differences in hydrophobic complementarity, size and electronic properties despite possessing nearly identical molecular frameworks, thus, arriving in a generalization for their observed mechanistic differences on acting on different targets.http://dx.doi.org/10.1155/2011/731090 |
| spellingShingle | Jose Isagani B. Janairo Gerardo C. Janairo Derrick Ethelbhert C. YU Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives E-Journal of Chemistry |
| title | Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives |
| title_full | Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives |
| title_fullStr | Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives |
| title_full_unstemmed | Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives |
| title_short | Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives |
| title_sort | semi empirical predictions on the structure and properties of ent kaurenoic acid and derivatives |
| url | http://dx.doi.org/10.1155/2011/731090 |
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