Publicação
Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir
| Resumo: | The derivatization of ACV with amino acids has been used for the development of ACV prodrugs. In fact, the valine derivative of ACV – valacyclovir – is a pro-drug of widespread use in herpes treatment. Mitra and co-workers have recently reported the synthesis and properties of novel dipeptide prodrugs of ACV, two of which are included in the present work (3c and 3d) [1,2]. The compounds 3a-f prepared were screened for their in vitro antimicrobial activity against Gram positive (Bacillus cereus, Bacillus subtilis) and Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and also for their fungicidal activity using Candida albicans. The antimicrobial activities were evaluated by diameter measurement of haloes formed by growth inhibition caused by compounds 3 at different concentrations in DMSO [3]. Compounds 3 exhibited antimicrobial activity preferentially against Gram-positive bacteria and were all inactive against Pseudomonas aeruginosa. The minimal inhibitory concentrations (MIC) could be determined for some of the compounds in the concentration range assayed. Further dilutions are being done for MIC determination of most compounds against B. cereus and B. subtilis. The determined MIC were significantly lower than those of typical standards such as ampicilline, cloramphenicol or cyclohexamide. The parent drug, ACV, was also assayed and found to be less active than the corresponding dipeptide ester derivatives. These results suggest that compounds 3 might be activated by bacterial peptidases or actively transported through bacterial cell membrane. |
|---|---|
| Autores principais: | Pereira, Cláudia S.G.P. |
| Outros Autores: | Santos, Cledir; Barreira, João C.M.; Moreira, Rui; Ferreira, Isabel C.F.R.; Estevinho, Leticia M.; Gomes, Paula |
| Ano: | 2005 |
| País: | Portugal |
| Tipo de documento: | documento de conferência |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| _version_ | 1863850680450547712 |
|---|---|
| author | Pereira, Cláudia S.G.P. |
| author2 | Santos, Cledir Barreira, João C.M. Moreira, Rui Ferreira, Isabel C.F.R. Estevinho, Leticia M. Gomes, Paula |
| author2_role | author author author author author author |
| author_facet | Pereira, Cláudia S.G.P. Santos, Cledir Barreira, João C.M. Moreira, Rui Ferreira, Isabel C.F.R. Estevinho, Leticia M. Gomes, Paula |
| author_role | author |
| contributor_name_str_mv | Biblioteca Digital do IPB |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Pereira, Cláudia S.G.P.\"},{\"Person.name\":\"Santos, Cledir\"},{\"Person.name\":\"Barreira, João C.M.\",\"Person.identifier.orcid\":\"0000-0003-1233-0990\"},{\"Person.name\":\"Moreira, Rui\"},{\"Person.name\":\"Ferreira, Isabel C.F.R.\",\"Person.identifier.orcid\":\"0000-0003-4910-4882\"},{\"Person.name\":\"Estevinho, Leticia M.\",\"Person.identifier.orcid\":\"0000-0002-9249-1948\"},{\"Person.name\":\"Gomes, Paula\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Biblioteca Digital do IPB |
| datacite.creators.creator.creatorName.fl_str_mv | Pereira, Cláudia S.G.P. Santos, Cledir Barreira, João C.M. Moreira, Rui Ferreira, Isabel C.F.R. Estevinho, Leticia M. Gomes, Paula |
| datacite.date.Accepted.fl_str_mv | 2005-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2011-03-23T11:42:18Z |
| datacite.date.embargoed.fl_str_mv | 2011-03-23T11:42:18Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.titles.title.fl_str_mv | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| dc.contributor.none.fl_str_mv | Biblioteca Digital do IPB |
| dc.creator.none.fl_str_mv | Pereira, Cláudia S.G.P. Santos, Cledir Barreira, João C.M. Moreira, Rui Ferreira, Isabel C.F.R. Estevinho, Leticia M. Gomes, Paula |
| dc.date.Accepted.fl_str_mv | 2005-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2011-03-23T11:42:18Z |
| dc.date.embargoed.fl_str_mv | 2011-03-23T11:42:18Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10198/3724 |
| dc.language.none.fl_str_mv | eng |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.title.fl_str_mv | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_c94f |
| description | The derivatization of ACV with amino acids has been used for the development of ACV prodrugs. In fact, the valine derivative of ACV – valacyclovir – is a pro-drug of widespread use in herpes treatment. Mitra and co-workers have recently reported the synthesis and properties of novel dipeptide prodrugs of ACV, two of which are included in the present work (3c and 3d) [1,2]. The compounds 3a-f prepared were screened for their in vitro antimicrobial activity against Gram positive (Bacillus cereus, Bacillus subtilis) and Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and also for their fungicidal activity using Candida albicans. The antimicrobial activities were evaluated by diameter measurement of haloes formed by growth inhibition caused by compounds 3 at different concentrations in DMSO [3]. Compounds 3 exhibited antimicrobial activity preferentially against Gram-positive bacteria and were all inactive against Pseudomonas aeruginosa. The minimal inhibitory concentrations (MIC) could be determined for some of the compounds in the concentration range assayed. Further dilutions are being done for MIC determination of most compounds against B. cereus and B. subtilis. The determined MIC were significantly lower than those of typical standards such as ampicilline, cloramphenicol or cyclohexamide. The parent drug, ACV, was also assayed and found to be less active than the corresponding dipeptide ester derivatives. These results suggest that compounds 3 might be activated by bacterial peptidases or actively transported through bacterial cell membrane. |
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| identifier.url.fl_str_mv | http://hdl.handle.net/10198/3724 |
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| institution | Instituto Politécnico de Bragança |
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| person_str_mv | Pereira, Cláudia S.G.P. Santos, Cledir Barreira, João C.M. Barreira, João C.M. http://orcid.org/0000-0003-1233-0990 0000-0003-1233-0990 Moreira, Rui Ferreira, Isabel C.F.R. Ferreira, Isabel C.F.R. https://www.ciencia-id.pt/9418-CF95-9919 9418-CF95-9919 http://orcid.org/0000-0003-4910-4882 0000-0003-4910-4882 Estevinho, Leticia M. Estevinho, Leticia M. https://www.ciencia-id.pt/BA14-09D6-A406 BA14-09D6-A406 http://orcid.org/0000-0002-9249-1948 0000-0002-9249-1948 Gomes, Paula |
| publishDate | 2005 |
| reponame_str | Biblioteca Digital do IPB |
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| spelling | engenThe derivatization of ACV with amino acids has been used for the development of ACV prodrugs. In fact, the valine derivative of ACV – valacyclovir – is a pro-drug of widespread use in herpes treatment. Mitra and co-workers have recently reported the synthesis and properties of novel dipeptide prodrugs of ACV, two of which are included in the present work (3c and 3d) [1,2]. The compounds 3a-f prepared were screened for their in vitro antimicrobial activity against Gram positive (Bacillus cereus, Bacillus subtilis) and Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and also for their fungicidal activity using Candida albicans. The antimicrobial activities were evaluated by diameter measurement of haloes formed by growth inhibition caused by compounds 3 at different concentrations in DMSO [3]. Compounds 3 exhibited antimicrobial activity preferentially against Gram-positive bacteria and were all inactive against Pseudomonas aeruginosa. The minimal inhibitory concentrations (MIC) could be determined for some of the compounds in the concentration range assayed. Further dilutions are being done for MIC determination of most compounds against B. cereus and B. subtilis. The determined MIC were significantly lower than those of typical standards such as ampicilline, cloramphenicol or cyclohexamide. The parent drug, ACV, was also assayed and found to be less active than the corresponding dipeptide ester derivatives. These results suggest that compounds 3 might be activated by bacterial peptidases or actively transported through bacterial cell membrane.application/pdfporSynthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovirPereira, Cláudia S.G.P.Santos, CledirPersonalBarreira, João C.M.DSpacehttp://dspace.org/items/4629b12c-39b0-4da8-8b8d-6efba5cf2d81DSpacehttp://dspace.org/items/4629b12c-39b0-4da8-8b8d-6efba5cf2d81BarreiraJoão C.M.ORCIDhttp://orcid.org0000-0003-1233-0990Researcher IDhttps://www.researcherid.comD-8269-2013Scopus Author IDhttps://www.scopus.com54895546900Moreira, RuiPersonalFerreira, Isabel C.F.R.DSpacehttp://dspace.org/items/bd0d1537-2e03-41fb-b27a-140af9c35db8DSpacehttp://dspace.org/items/bd0d1537-2e03-41fb-b27a-140af9c35db8FerreiraIsabel C.F.R.Ciência IDhttps://www.ciencia-id.pt9418-CF95-9919ORCIDhttp://orcid.org0000-0003-4910-4882Researcher IDhttps://www.researcherid.comE-8500-2013Scopus Author IDhttps://www.scopus.com36868826600PersonalEstevinho, Leticia M.DSpacehttp://dspace.org/items/4a1d5ba2-1854-4ca5-89a4-73f35e964df9DSpacehttp://dspace.org/items/4a1d5ba2-1854-4ca5-89a4-73f35e964df9EstevinhoLetícia M.Ciência IDhttps://www.ciencia-id.ptBA14-09D6-A406ORCIDhttp://orcid.org0000-0002-9249-1948Scopus Author IDhttps://www.scopus.com6506577664Scopus Author IDhttps://www.scopus.com57211945650Gomes, PaulaHostingInstitutionOrganizationalBiblioteca Digital do IPBe-mailmailto:dspace@ipb.ptdspace@ipb.ptISSNIsPartOf0036-87092011-03-23T11:42:18Z20052005-01-01T00:00:00ZHandlehttp://hdl.handle.net/10198/3724http://purl.org/coar/access_right/c_abf2open access178606 bytesother research producthttp://purl.org/coar/resource_type/c_c94fconference objecthttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://bibliotecadigital.ipb.pt/bitstreams/04c2a351-1cb9-4d74-b46e-b1c17edf7f61/downloadSupplement 1, Scientia Pharmaceutica, 73 (2) 2005- Abstracts of the Contributions of the Joint Meeting on Medicinal ChemistryViena, Áustria |
| spellingShingle | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir Pereira, Cláudia S.G.P. |
| title | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| title_full | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| title_fullStr | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| title_full_unstemmed | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| title_short | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| title_sort | Synthesis and antimicrobial activity of dipeptide esters of the anti-rectroviral drug acyclovir |
| url | http://hdl.handle.net/10198/3724 |
| visible | 1 |