Correlation among chemical structure, surface properties and cytotoxicity of N-acyl alanine and serine surfactants.
Toxicity is one of the main concerns 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 may play a key role only on cellular toxicity. Overall, our data suggest that minor differences in the polar head, not significantly affecting CMC values, may have an impact on cytotoxicity.
School of Pharmacy, University of Camerino, 62032 Camerino, MC, Italy.
Diego Romano
DR
Perinelli
School of Pharmacy, University of Camerino, 62032 Camerino, MC, Italy.
Marco
M
Cespi
Department of Biomolecular Sciences, School of Pharmacy, University of Urbino, 61029 Urbino, PU, Italy.
Luca
L
Casettari
School of Pharmacy, Joseph Banks Laboratories, Green Lane, Lincoln LN6 7DL, UK.
Driton
D
Vllasaliu
Department of Pure and Applied Sciences, University of Urbino, Urbino 61029, Italy.
Michela
M
Cangiotti
Department of Pure and Applied Sciences, University of Urbino, Urbino 61029, Italy.
Maria Francesca
MF
Ottaviani
School of Pharmacy, University of Camerino, 62032 Camerino, MC, Italy.
Gianfabio
G
Giorgioni
School of Pharmacy, University of Camerino, 62032 Camerino, MC, Italy.
Giulia
G
Bonacucina
School of Pharmacy, University of Camerino, 62032 Camerino, MC, Italy.
Giovanni Filippo
GF
Palmieri
D000409:Alanine / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D018938:Caco-2 Cells; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004578:Electron Spin Resonance Spectroscopy; D005740:Gases; D006461:Hemolysis; D006801:Humans; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D007770:L-Lactate Dehydrogenase / Q000737:chemistry; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D012542:Scattering, Radiation; D012694:Serine / Q000737:chemistry*; D012967:Sodium Dodecyl Sulfate / Q000737:chemistry; D012997:Solvents; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*; D013696:Temperature
D000596:Amino Acids; D005740:Gases; D008823:Micelles; D012997:Solvents; D013501:Surface-Active Agents; D012967:Sodium Dodecyl Sulfate; D012694:Serine; D007770:L-Lactate Dehydrogenase; D000409:Alanine
DLS; EPR; Haemolytic assay; LDH; MTS; N-acyl amino acid, CMC