Influence of surfactants on depsipeptide submicron particle formation

Eur J Pharm Biopharm. 2017 Jul:116:61-65. doi: 10.1016/j.ejpb.2016.11.011. Epub 2016 Nov 12.

Abstract

Surfactants are required for the formation and stabilization of hydrophobic polymeric particles in aqueous environment. In order to form submicron particles of varying sizes from oligo[3-(S)-sec-butylmorpholine-2,5-dione]diols ((OBMD)-diol), different surfactants were investigated. As new surfactants, four-armed star-shaped oligo(ethylene glycol)s of molecular weights of 5-20kDa functionalized with desamino-tyrosine (sOEG-DAT) resulted in smaller particles with lower PDI than with desaminotyrosyl tyrosine (sOEG-DATT) in an emulsion/solvent evaporation method. In a second set of experiments, sOEG-DAT of Mn=10kDa was compared with the commonly employed emulsifiers polyvinylalcohol (PVA), polyoxyethylene (20) sorbitan monolaurate (Tween 20), and D-α-tocopherol polyethylene glycol succinate (VIT E-TPGS) for OBMD particle preparation. sOEG-DAT allowed to systematically change sizes in a range of 300 up to 900nm with narrow polydispersity, while in the other cases, a lower size range (250-400nm, PVA; ∼300nm, Tween 20) or no effective particle formation was observed. The ability of tailoring particle size in a broad range makes sOEG-DAT of particular interest for the formation of oligodepsipeptide particles, which can further be investigated as drug carriers for controlled delivery.

Keywords: Depsipeptide; Particle size; Submicron particles; Surfactants.

MeSH terms

  • Depsipeptides / chemistry*
  • Drug Carriers / chemistry
  • Emulsifying Agents / chemistry
  • Emulsions / chemistry
  • Molecular Weight
  • Nanoparticles / chemistry
  • Particle Size
  • Polyethylene Glycols / chemistry
  • Polymers / chemistry
  • Polysorbates / chemistry
  • Polyvinyl Alcohol / chemistry
  • Solvents / chemistry
  • Surface-Active Agents / chemistry*
  • Tyrosine / chemistry
  • alpha-Tocopherol / analogs & derivatives
  • alpha-Tocopherol / chemistry

Substances

  • Depsipeptides
  • Drug Carriers
  • Emulsifying Agents
  • Emulsions
  • Polymers
  • Polysorbates
  • Solvents
  • Surface-Active Agents
  • Polyethylene Glycols
  • Tyrosine
  • Polyvinyl Alcohol
  • alpha-Tocopherol