View in EDS

Cationic surfactants from lysine: Synthesis, micellization and biological evaluation

Saved in:
Bibliographic Details
Title: Cationic surfactants from lysine: Synthesis, micellization and biological evaluation
Authors: Pérez, Lourdes1 lpmste@cid.csic.es, Pinazo, Aurora1, Teresa García, M.1, Lozano, Marina1, Manresa, Angeles2, Angelet, Marta1, Pilar Vinardell, M.3, Mitjans, Montse3, Pons, Ramon1, Rosa Infante, M.1
Source: European Journal of Medicinal Chemistry. May2009, Vol. 44 Issue 5, p1884-1892. 9p.
Subject Terms: *Surface active agents, Organic synthesis, Biomedical materials, Lysine, Acylation, Pharmaceutical chemistry, Anti-infective agents
Abstract: Abstract: Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of Nɛ-lauroyl lysine methyl ester, Nɛ-myristoyl lysine methyl ester and Nɛ-palmitoyl lysine methyl ester) have been prepared in high yields by lysine acylation in ɛ position with three natural saturated fatty acids. The micellization process of these surfactants has been studied using the PGSE-NMR technique. The compounds were tested as antimicrobial agents against Gram-positive and Gram-negative bacteria. The surfactants show moderate antimicrobial activity against the Gram-positive bacteria but Gram-negative bacteria are resistant to these surfactants in the concentration range tested. The haemolytic activity is considerably lower than those reported for other cationic Nα-acyl amino acid analogues. The acute toxicity against Daphnia magna and biodegradability was studied. The toxicity is clearly lower than that reported for conventional cationic surfactants from quaternary ammonium and the three surfactants from lysine can be classified as ready biodegradable surfactants. [Copyright &y& Elsevier]
Copyright of European Journal of Medicinal Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: GreenFILE
FullText Text:
  Availability: 0
Header DbId: 8gh
DbLabel: GreenFILE
An: 37225900
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Cationic surfactants from lysine: Synthesis, micellization and biological evaluation
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Pérez%2C+Lourdes%22">Pérez, Lourdes</searchLink><relatesTo>1</relatesTo><i> lpmste@cid.csic.es</i><br /><searchLink fieldCode="AR" term="%22Pinazo%2C+Aurora%22">Pinazo, Aurora</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Teresa+García%2C+M%2E%22">Teresa García, M.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Lozano%2C+Marina%22">Lozano, Marina</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Manresa%2C+Angeles%22">Manresa, Angeles</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Angelet%2C+Marta%22">Angelet, Marta</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Pilar+Vinardell%2C+M%2E%22">Pilar Vinardell, M.</searchLink><relatesTo>3</relatesTo><br /><searchLink fieldCode="AR" term="%22Mitjans%2C+Montse%22">Mitjans, Montse</searchLink><relatesTo>3</relatesTo><br /><searchLink fieldCode="AR" term="%22Pons%2C+Ramon%22">Pons, Ramon</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Rosa+Infante%2C+M%2E%22">Rosa Infante, M.</searchLink><relatesTo>1</relatesTo>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: European Journal of Medicinal Chemistry. May2009, Vol. 44 Issue 5, p1884-1892. 9p.
– Name: Subject
  Label: Subject Terms
  Group: Su
  Data: *<searchLink fieldCode="DE" term="%22Surface+active+agents%22">Surface active agents</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Biomedical+materials%22">Biomedical materials</searchLink><br /><searchLink fieldCode="DE" term="%22Lysine%22">Lysine</searchLink><br /><searchLink fieldCode="DE" term="%22Acylation%22">Acylation</searchLink><br /><searchLink fieldCode="DE" term="%22Pharmaceutical+chemistry%22">Pharmaceutical chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Anti-infective+agents%22">Anti-infective agents</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Abstract: Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of Nɛ-lauroyl lysine methyl ester, Nɛ-myristoyl lysine methyl ester and Nɛ-palmitoyl lysine methyl ester) have been prepared in high yields by lysine acylation in ɛ position with three natural saturated fatty acids. The micellization process of these surfactants has been studied using the PGSE-NMR technique. The compounds were tested as antimicrobial agents against Gram-positive and Gram-negative bacteria. The surfactants show moderate antimicrobial activity against the Gram-positive bacteria but Gram-negative bacteria are resistant to these surfactants in the concentration range tested. The haemolytic activity is considerably lower than those reported for other cationic Nα-acyl amino acid analogues. The acute toxicity against Daphnia magna and biodegradability was studied. The toxicity is clearly lower than that reported for conventional cationic surfactants from quaternary ammonium and the three surfactants from lysine can be classified as ready biodegradable surfactants. [Copyright &y& Elsevier]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of European Journal of Medicinal Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=8gh&AN=37225900
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.ejmech.2008.11.003
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 9
        StartPage: 1884
    Subjects:
      – SubjectFull: Surface active agents
        Type: general
      – SubjectFull: Organic synthesis
        Type: general
      – SubjectFull: Biomedical materials
        Type: general
      – SubjectFull: Lysine
        Type: general
      – SubjectFull: Acylation
        Type: general
      – SubjectFull: Pharmaceutical chemistry
        Type: general
      – SubjectFull: Anti-infective agents
        Type: general
    Titles:
      – TitleFull: Cationic surfactants from lysine: Synthesis, micellization and biological evaluation
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Pérez, Lourdes
      – PersonEntity:
          Name:
            NameFull: Pinazo, Aurora
      – PersonEntity:
          Name:
            NameFull: Teresa García, M.
      – PersonEntity:
          Name:
            NameFull: Lozano, Marina
      – PersonEntity:
          Name:
            NameFull: Manresa, Angeles
      – PersonEntity:
          Name:
            NameFull: Angelet, Marta
      – PersonEntity:
          Name:
            NameFull: Pilar Vinardell, M.
      – PersonEntity:
          Name:
            NameFull: Mitjans, Montse
      – PersonEntity:
          Name:
            NameFull: Pons, Ramon
      – PersonEntity:
          Name:
            NameFull: Rosa Infante, M.
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 01
              M: 05
              Text: May2009
              Type: published
              Y: 2009
          Identifiers:
            – Type: issn-print
              Value: 02235234
          Numbering:
            – Type: volume
              Value: 44
            – Type: issue
              Value: 5
          Titles:
            – TitleFull: European Journal of Medicinal Chemistry
              Type: main
ResultId 1