Properties of novel surfactin-derived biosurfactants obtained through solid-phase synthesis

Universidade Federal do Rio de Janeiro. Instituto de Bioquímica Médica Leopoldo de Meis. Laboratório Est. e Reg. de Proteínas e ATPaes. Programa de Biologia Estrutural. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Toxinologia. Rio de Janeiro, RJ, Brasil.
Universidade Federal do Rio de Janeiro. Campus de Macaé. Departamento de Microbiologia. Macaé, RJ, Brasil.
Universidade Federal de São João del Rei. Departamento de Bioquímica. Laboratório de Bioquímica Celular. São João del Rei, MG, Brasil.
Universidade Federal do Rio de Janeiro. Instituto de Bioquímica Médica Leopoldo de Meis. Rio de Janeiro, RJ, Brasil.
Universidade Federal de São João del Rei. Departamento de Bioquímica. Laboratório de Bioquímica Celular. São João del Rei, MG, Brasil.
Universidade Federal do Rio de Janeiro. Centro Nacional de Biologia Estrutural e Bioimagem. Programa de Biologia Estrutural. Rio de Janeiro, RJ, Brasil.
Universidade Federal do Rio de Janeiro. Instituto de Bioquímica Médica Leopoldo de Meis. Laboratório Est. e Reg. de Proteínas e ATPaes. Programa de Biologia Estrutural. Rio de Janeiro, RJ, Brasil.
Universidade Federal do Rio de Janeiro. Instituto de Bioquímica Médica Leopoldo de Meis. Laboratório Est. e Reg. de Proteínas e ATPaes. Programa de Biologia Estrutural. Rio de Janeiro, RJ, Brasil.

Abstract

Eight molecules, four peptides (SPs) and four lipopeptides (LPs) derived by rational design from surfactin, a well-known secreted biosurfactant from Bacillus subtilis, were produced employing Fmoc-based solid-phase synthesis. These new peptides were tested to evaluate their potential biosurfactant and biological activities, aiming at possible applications in industrial, biological, pharmaceutical, and medical use. Five molecules (SP1, SP2, SP4, LP5, and LP8) presented potential for medical uses, mainly due to their drug delivery properties as suggested by their synergistic activity with the antibiotic vancomycin against Staphylococcus aureus. All synthetic peptides showed low toxicity against Vero cell cultures, in assays of hemolysis, and in different cytotoxicity assays. In addition, we found that three peptides (SP1, LP6, and LP7) had potential technological and industrial use because of their emulsifying capacity, low toxicity, and ability to physically stabilize solutions. These novel molecules retained some properties of the parental molecule (surfactin, which was originally obtained through nonribosomal synthesis in Bacillus subtilis) but have the advantage of being linear peptides, which can be produced at large scales through the use of conventional heterologous protein expression protocols.

Keywords in Portuguese

Biosurfactantes
Entrega de drogas
Peptídeos lineares
Lipopeptídeos
Peptídeos
Design racional
Síntese em fase sólida
Efeito sinérgico
Surfactina

Keywords

Biosurfactants
Drug delivery
Linear peptides
Lipopeptides
Peptide
Rational design
Solid-phase synthesis
Surfactin
Synergetic effext

Publisher

Wiley

Citation

VAZQUEZ, Leonardo; et al. Properties of novel surfactin-derived biosurfactants obtained through solid-phase synthesis. J. Pep. Sci., v.24, e3129, 13p, 2018.

DOI

10 .1002/psc.3129

ISSN

1075-2617

Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/31510

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Copyright

Restricted access

Embargo date

2030-01-01

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