Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin
<p><strong>Background:</strong>Penicillins differ structurally among themselves by the lateral chains. At the same time, they have differences in their pharmacological action that can be associated to modifications included in the betalactamic ring and/or effects localized in the s...
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Centro Provincial de Información de Ciencias Médicas. Cienfuegos
2009-09-01
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| Series: | Medisur |
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| Online Access: | http://medisur.sld.cu/index.php/medisur/article/view/788 |
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| author | Elso Manuel Cruz Cruz Eslhey María Sánchez Domínguez |
| author_facet | Elso Manuel Cruz Cruz Eslhey María Sánchez Domínguez |
| author_sort | Elso Manuel Cruz Cruz |
| collection | DOAJ |
| description | <p><strong>Background:</strong>Penicillins differ structurally among themselves by the lateral chains. At the same time, they have differences in their pharmacological action that can be associated to modifications included in the betalactamic ring and/or effects localized in the same chains. Making it clear would be a contribution to the search of the most adequate structural and electronic characteristics to design better penicillins. <br /><strong>Objective:</strong>To compare structural properties, density of the atomic charges and the frontier orbitals of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin. <strong><br />Method:</strong>The molecular structures were optimized with PM3 semiempirical calculi. The molecular properties were calculated according to the Density Functional Theory, at a B3LYP/6-31G(d) level. The density of the atomic charges and the frontier orbitals were analyzed. The effect of the substituents on the properties of the betalactamic ring was evaluated. <strong><br />Results:</strong> The structural parameters of the betalactamic ring do not change as consequence of the modifications in the lateral chain linked to carbon 6. The ring has a marked tendency to planarity. There are no variations in the density of the positive charge of the carbonylic carbon. <strong><br />Conclusions:</strong> The structures and electronic properties of the betalactamic ring, structural basis of these antibiotics, do not have significant modifications among modelled penicillins.</p> |
| format | Article |
| id | doaj-art-39f760613c1145b39874b7c1efac91b2 |
| institution | Kabale University |
| issn | 1727-897X |
| language | Spanish |
| publishDate | 2009-09-01 |
| publisher | Centro Provincial de Información de Ciencias Médicas. Cienfuegos |
| record_format | Article |
| series | Medisur |
| spelling | doaj-art-39f760613c1145b39874b7c1efac91b22025-01-30T21:28:41ZspaCentro Provincial de Información de Ciencias Médicas. CienfuegosMedisur1727-897X2009-09-0174246253512Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillinElso Manuel Cruz Cruz0Eslhey María Sánchez Domínguez1Facultad de Ciencias Médicas “Dr. Zoilo E. Marinello Vidaurreta”.Facultad de Ciencias Médicas “Dr. Zoilo E. Marinello Vidaurreta”.<p><strong>Background:</strong>Penicillins differ structurally among themselves by the lateral chains. At the same time, they have differences in their pharmacological action that can be associated to modifications included in the betalactamic ring and/or effects localized in the same chains. Making it clear would be a contribution to the search of the most adequate structural and electronic characteristics to design better penicillins. <br /><strong>Objective:</strong>To compare structural properties, density of the atomic charges and the frontier orbitals of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin. <strong><br />Method:</strong>The molecular structures were optimized with PM3 semiempirical calculi. The molecular properties were calculated according to the Density Functional Theory, at a B3LYP/6-31G(d) level. The density of the atomic charges and the frontier orbitals were analyzed. The effect of the substituents on the properties of the betalactamic ring was evaluated. <strong><br />Results:</strong> The structural parameters of the betalactamic ring do not change as consequence of the modifications in the lateral chain linked to carbon 6. The ring has a marked tendency to planarity. There are no variations in the density of the positive charge of the carbonylic carbon. <strong><br />Conclusions:</strong> The structures and electronic properties of the betalactamic ring, structural basis of these antibiotics, do not have significant modifications among modelled penicillins.</p>http://medisur.sld.cu/index.php/medisur/article/view/788penicilinasestructura molecularmodelos moleculares |
| spellingShingle | Elso Manuel Cruz Cruz Eslhey María Sánchez Domínguez Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin Medisur penicilinas estructura molecular modelos moleculares |
| title | Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin |
| title_full | Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin |
| title_fullStr | Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin |
| title_full_unstemmed | Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin |
| title_short | Molecular modelling of four penicillins: bencylpenicillin, phenoxymethylpenicillin, ampicillin and amoxicillin |
| title_sort | molecular modelling of four penicillins bencylpenicillin phenoxymethylpenicillin ampicillin and amoxicillin |
| topic | penicilinas estructura molecular modelos moleculares |
| url | http://medisur.sld.cu/index.php/medisur/article/view/788 |
| work_keys_str_mv | AT elsomanuelcruzcruz molecularmodellingoffourpenicillinsbencylpenicillinphenoxymethylpenicillinampicillinandamoxicillin AT eslheymariasanchezdominguez molecularmodellingoffourpenicillinsbencylpenicillinphenoxymethylpenicillinampicillinandamoxicillin |