Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity

Detalhes bibliográficos
Autor(a) principal: Guerra,Wendell
Data de Publicação: 2006
Outros Autores: Silva,Iara R., Azevedo,Elaine A., Monteiro,Ana R. de S., Bucciarelli-Rodriguez,Mônica, Chartone-Souza,Edmar, Silveira,Josianne N., Fontes,Ana P. S., Pereira-Maia,Elene C.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000800021
Resumo: This paper reports on the synthesis and characterization of three new platinum(II) complexes with oxytetracycline, doxycycline and chlortetracycline by elemental analysis, IR and 195Pt RMN spectroscopies. Doxycycline interactions with PtII ions as a function of the pH were studied by ¹H NMR. All the investigated tetracyclines form 1:1 complexes with PtII via the oxygen of the hydroxyl group and oxygen of the amide group at ring A. The minimal inhibitory concentrations (MIC) of the ligands and those of their PtII compounds were determined in two sensitive strains (E. coli HB 101 and E. coli ATCC 25922) and in a resistant one (E. coli HB101/pBR322). Platinum complex of doxycycline is twice as potent as the free antibiotic in the resistant strain. Octanol/water partition coefficients of the complexes were determined. Increasing lipophilicity enhances antimicrobial activity in the resistant strain.
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spelling Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activitytetracycline derivativesplatinum complexesantimicrobial activitybacterial resistanceThis paper reports on the synthesis and characterization of three new platinum(II) complexes with oxytetracycline, doxycycline and chlortetracycline by elemental analysis, IR and 195Pt RMN spectroscopies. Doxycycline interactions with PtII ions as a function of the pH were studied by ¹H NMR. All the investigated tetracyclines form 1:1 complexes with PtII via the oxygen of the hydroxyl group and oxygen of the amide group at ring A. The minimal inhibitory concentrations (MIC) of the ligands and those of their PtII compounds were determined in two sensitive strains (E. coli HB 101 and E. coli ATCC 25922) and in a resistant one (E. coli HB101/pBR322). Platinum complex of doxycycline is twice as potent as the free antibiotic in the resistant strain. Octanol/water partition coefficients of the complexes were determined. Increasing lipophilicity enhances antimicrobial activity in the resistant strain.Sociedade Brasileira de Química2006-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000800021Journal of the Brazilian Chemical Society v.17 n.8 2006reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532006000800021info:eu-repo/semantics/openAccessGuerra,WendellSilva,Iara R.Azevedo,Elaine A.Monteiro,Ana R. de S.Bucciarelli-Rodriguez,MônicaChartone-Souza,EdmarSilveira,Josianne N.Fontes,Ana P. S.Pereira-Maia,Elene C.eng2007-02-07T00:00:00Zoai:scielo:S0103-50532006000800021Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2007-02-07T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
title Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
spellingShingle Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
Guerra,Wendell
tetracycline derivatives
platinum complexes
antimicrobial activity
bacterial resistance
title_short Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
title_full Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
title_fullStr Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
title_full_unstemmed Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
title_sort Three new complexes of platinum(II) with doxycycline, oxytetracycline and chlortetracycline and their antimicrobial activity
author Guerra,Wendell
author_facet Guerra,Wendell
Silva,Iara R.
Azevedo,Elaine A.
Monteiro,Ana R. de S.
Bucciarelli-Rodriguez,Mônica
Chartone-Souza,Edmar
Silveira,Josianne N.
Fontes,Ana P. S.
Pereira-Maia,Elene C.
author_role author
author2 Silva,Iara R.
Azevedo,Elaine A.
Monteiro,Ana R. de S.
Bucciarelli-Rodriguez,Mônica
Chartone-Souza,Edmar
Silveira,Josianne N.
Fontes,Ana P. S.
Pereira-Maia,Elene C.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Guerra,Wendell
Silva,Iara R.
Azevedo,Elaine A.
Monteiro,Ana R. de S.
Bucciarelli-Rodriguez,Mônica
Chartone-Souza,Edmar
Silveira,Josianne N.
Fontes,Ana P. S.
Pereira-Maia,Elene C.
dc.subject.por.fl_str_mv tetracycline derivatives
platinum complexes
antimicrobial activity
bacterial resistance
topic tetracycline derivatives
platinum complexes
antimicrobial activity
bacterial resistance
description This paper reports on the synthesis and characterization of three new platinum(II) complexes with oxytetracycline, doxycycline and chlortetracycline by elemental analysis, IR and 195Pt RMN spectroscopies. Doxycycline interactions with PtII ions as a function of the pH were studied by ¹H NMR. All the investigated tetracyclines form 1:1 complexes with PtII via the oxygen of the hydroxyl group and oxygen of the amide group at ring A. The minimal inhibitory concentrations (MIC) of the ligands and those of their PtII compounds were determined in two sensitive strains (E. coli HB 101 and E. coli ATCC 25922) and in a resistant one (E. coli HB101/pBR322). Platinum complex of doxycycline is twice as potent as the free antibiotic in the resistant strain. Octanol/water partition coefficients of the complexes were determined. Increasing lipophilicity enhances antimicrobial activity in the resistant strain.
publishDate 2006
dc.date.none.fl_str_mv 2006-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000800021
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000800021
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532006000800021
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.17 n.8 2006
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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