Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds.

2.50
Hdl Handle:
http://hdl.handle.net/2336/21832
Title:
Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds.
Authors:
Thorsteinsson, Thorsteinn; Másson, Már; Kristinsson, Karl G; Hjálmarsdóttir, Martha A; Hilmarsson, Hilmar; Loftsson, Thorsteinn
Citation:
J. Med. Chem. 2003, 46(19):4173-81
Issue Date:
11-Sep-2003
Abstract:
A series of soft quaternary ammonium antimicrobial agents, which are analogues to currently used quaternary ammonium preservatives such as cetyl pyridinium chloride and benzalkonium chloride, were synthesized. These soft analogues consist of long alkyl chain connected to a polar headgroup via chemically labile spacer group. They are characterized by facile nonenzymatic and enzymatic degradation to form their original nontoxic building blocks. However, their chemical stability has to be adequate in order for them to have antimicrobial effects. Stability studies and antibacterial and antiviral activity measurements revealed relationship between activity, lipophilicity, and stability. Their minimum inhibitory concentration (MIC) was as low as 1 microg/mL, and their viral reduction was in some cases greater than 6.7 log. The structure-activity studies demonstrate that the bioactive compounds (i.e., MIC for Gram-positive bacteria of <10 microg/mL) have an alkyl chain length between 12 and 18 carbon atoms, with a polar headgroup preferably of a small quaternary ammonium group, and their acquired inactivation half-life must be greater than 3 h at 60 degrees C.
Description:
To access publisher full text version of this article. Please click on the hyperlink in Additional Links field
Additional Links:
http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/jm030829z

Full metadata record

DC FieldValue Language
dc.contributor.authorThorsteinsson, Thorsteinn-
dc.contributor.authorMásson, Már-
dc.contributor.authorKristinsson, Karl G-
dc.contributor.authorHjálmarsdóttir, Martha A-
dc.contributor.authorHilmarsson, Hilmar-
dc.contributor.authorLoftsson, Thorsteinn-
dc.date.accessioned2008-03-28T13:12:24Z-
dc.date.available2008-03-28T13:12:24Z-
dc.date.issued2003-09-11-
dc.date.submitted2008-03-28-
dc.identifier.citationJ. Med. Chem. 2003, 46(19):4173-81en
dc.identifier.issn0022-2623-
dc.identifier.pmid12954069-
dc.identifier.doi10.1021/jm030829z-
dc.identifier.urihttp://hdl.handle.net/2336/21832-
dc.descriptionTo access publisher full text version of this article. Please click on the hyperlink in Additional Links fielden
dc.description.abstractA series of soft quaternary ammonium antimicrobial agents, which are analogues to currently used quaternary ammonium preservatives such as cetyl pyridinium chloride and benzalkonium chloride, were synthesized. These soft analogues consist of long alkyl chain connected to a polar headgroup via chemically labile spacer group. They are characterized by facile nonenzymatic and enzymatic degradation to form their original nontoxic building blocks. However, their chemical stability has to be adequate in order for them to have antimicrobial effects. Stability studies and antibacterial and antiviral activity measurements revealed relationship between activity, lipophilicity, and stability. Their minimum inhibitory concentration (MIC) was as low as 1 microg/mL, and their viral reduction was in some cases greater than 6.7 log. The structure-activity studies demonstrate that the bioactive compounds (i.e., MIC for Gram-positive bacteria of <10 microg/mL) have an alkyl chain length between 12 and 18 carbon atoms, with a polar headgroup preferably of a small quaternary ammonium group, and their acquired inactivation half-life must be greater than 3 h at 60 degrees C.en
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.relation.urlhttp://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/jm030829zen
dc.subject.meshAlkylationen
dc.subject.meshAnimalsen
dc.subject.meshAnti-Bacterial Agentsen
dc.subject.meshAnti-Infective Agentsen
dc.subject.meshBenzalkonium Compoundsen
dc.subject.meshCercopithecus aethiopsen
dc.subject.meshCetylpyridiniumen
dc.subject.meshDrug Stabilityen
dc.subject.meshEnterococcus faecalisen
dc.subject.meshEscherichia colien
dc.subject.meshHydrophobicityen
dc.subject.meshMicrobial Sensitivity Testsen
dc.subject.meshPseudomonas aeruginosaen
dc.subject.meshQuaternary Ammonium Compoundsen
dc.subject.meshSimplexvirusen
dc.subject.meshStaphylococcus aureusen
dc.subject.meshStructure-Activity Relationshipen
dc.subject.meshVero Cellsen
dc.titleSoft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds.en
dc.typeArticleen
dc.identifier.journalJournal of medicinal chemistryen

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