Toxicity is one of the main concern limiting the use of surfactants. Many efforts have been devoted to the development of new amphiphilic molecules characterized by a lower toxicological profile and environmental impact. N-acyl amino acids are a class of anionic surfactants that can find applications in different technological fields as an alternative to sulphate-based surfactants (e.g., sodium dodecyl sulphate). The understanding of the relationship between chemical structure and toxicological profile is fundamental for the disclosure of the full potential of these amphiphiles. With this aim, two series of N-acyl surfactants, with different length of the hydrophobic tails and serine or alanine as polar head, were synthesized and fully characterized. The correlation between the surface and toxicological parameters allowed highlighting the role exerted by the length of the hydrocarbon chain and the polar head on cytotoxicity. The length of the hydrocarbon chain mainly influences surface properties and toxicological parameters, while the amino acid polar head plays a key role only on cellular toxicity. Overall, our data suggest that minor differences in the polar head, not affecting significantly CMC values, may have a strong impact on cytotoxicity.

Correlation among chemical structure, surface properties and cytotoxicity of N-acyl alanine and serine surfactants

PERINELLI, DIEGO ROMANO;CESPI, MARCO;GIORGIONI, Gianfabio;BONACUCINA, Giulia;PALMIERI, Giovanni Filippo
2016-01-01

Abstract

Toxicity is one of the main concern limiting the use of surfactants. Many efforts have been devoted to the development of new amphiphilic molecules characterized by a lower toxicological profile and environmental impact. N-acyl amino acids are a class of anionic surfactants that can find applications in different technological fields as an alternative to sulphate-based surfactants (e.g., sodium dodecyl sulphate). The understanding of the relationship between chemical structure and toxicological profile is fundamental for the disclosure of the full potential of these amphiphiles. With this aim, two series of N-acyl surfactants, with different length of the hydrophobic tails and serine or alanine as polar head, were synthesized and fully characterized. The correlation between the surface and toxicological parameters allowed highlighting the role exerted by the length of the hydrocarbon chain and the polar head on cytotoxicity. The length of the hydrocarbon chain mainly influences surface properties and toxicological parameters, while the amino acid polar head plays a key role only on cellular toxicity. Overall, our data suggest that minor differences in the polar head, not affecting significantly CMC values, may have a strong impact on cytotoxicity.
2016
File in questo prodotto:
File Dimensione Formato  
Correlation among chemical structure_EJPB_2016.pdf

solo gestori di archivio

Tipologia: Versione Editoriale
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 2.24 MB
Formato Adobe PDF
2.24 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/393717
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 28
  • ???jsp.display-item.citation.isi??? 26
social impact