Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Autor: María Pilar Vinardell, Montserrat Mitjans, Rodrigo O. Brito, J. Enrique Rodríguez-Borges, Paula Gomes, Maria João Araújo, Maria Rosa Infante, M. T. Garcia, Isabel Ribosa, Sandra G. Silva, Maria Luísa do Vale, Eduardo F. Marques
Přispěvatelé: Faculdade de Ciências
Jazyk: angličtina
Rok vydání: 2009
Předmět:
Anions
Chemical Phenomena
Context (language use)
02 engineering and technology
010402 general chemistry
Eye
01 natural sciences
Micelle
Hemolysis
Surface-Active Agents
Colloid and Surface Chemistry
Pulmonary surfactant
Microscopy
Electron
Transmission
Cations
Amphiphile
Toxicity Tests
Acute
Organic chemistry
Animals
Humans
Surface Tension
Materials engineering [Engineering and technology]
Denaturation (biochemistry)
Engenharia dos materiais [Ciências da engenharia e tecnologias]
Physical and Theoretical Chemistry
Amino Acids
Micelles
chemistry.chemical_classification
Vesicle
Materials engineering
Surfaces and Interfaces
General Medicine
021001 nanoscience & nanotechnology
0104 chemical sciences
Amino acid
chemistry
Daphnia
Drug delivery
Irritants
Engenharia dos materiais
0210 nano-technology
Biotechnology
Zdroj: Repositório Científico de Acesso Aberto de Portugal
Repositório Científico de Acesso Aberto de Portugal (RCAAP)
instacron:RCAAP
Popis: The design of efficient liposomal systems for drug delivery is of considerable biomedical interest. In this context, vesicles prepared from cationic/anionic surfactants may offer several advantages, mainly due to their spontaneity in formation and long-term stability. There is also an impending need to produce less toxic, more biocompatible amphiphiles, while maintaining the desirable aggregation properties. In this work, we present data for acute toxicity to Daphnia magna (IC(50)), and potential ocular irritation (HC(50)) for some newly prepared ionic surfactants with dodecyl chains, derived from the amino acids tyrosine (Tyr), serine (Ser), hydroxyproline (Hyp) and lysine (Lys). The micellization behavior of the compounds, evaluated from surface tension measurements, is presented and compared to more conventional ionic amphiphiles. Two types of spontaneouly formed catanionic vesicles, composed either by a dodecyltrimethylammonium bromide (DTAB)/Lys-derivative and or Ser-/Lys-derivative mixture, have also been tested for their ecotoxicity and hemolytic potential. All the micelle-forming surfactants as well as the vesicle-containing mixtures are found to have lower ecotoxicity than the reference surfactant DTAB. Moreover, the results from hemolysis and hemoglobin denaturation tests show that the Tyr- and Lys-derivatives are moderately irritant, whereas the Hyp- and Ser- ones are just slightly irritant. Even more significantly, the vesicle-containing mixtures exhibit lower hemolytic activity than the neat surfactants, a positive result for their potential use in liposomal formulations.
Databáze: OpenAIRE
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