Skip to main content

Advertisement

SpringerLink
Log in

Polyamide Nanocapsules and Nano-emulsions Containing Parsol® MCX and Parsol® 1789: In Vitro Release, Ex Vivo Skin Penetration and Photo-Stability Studies

  • Research Paper
  • Published:
Pharmaceutical Research Aims and scope Submit manuscript

ABSTRACT

Purpose

To prepare polyamide nanocapsules for skin photo-protection, encapsulating α-tocopherol, Parsol®MCX (ethylhexyl methoxycinnamate) and/or Parsol®1789 (butyl methoxydibenzoylmethane).

Methods

Nanocapsules were obtained by combining spontaneous emulsification and interfacial polycondensation reaction between sebacoyl chloride and diethylenetriamine. Nano-emulsions used as control were obtained by the same process without monomers. The influence of carrier on release rate was studied in vitro with a membrane-free model. Epidermal penetration of encapsulated sunscreens was ex vivo evaluated using Franz diffusion cells. Ability of encapsulated sunscreens to improve photo-stability was verified by comparing percentage of degradation after UV radiation exposure.

Results

Sunscreen-containing nanocapsules (260–400 nm) were successfully prepared; yield of encapsulation was >98%. Parsol®MCX and Parsol®1789 encapsulation led to decreased release rate by up to 60% in comparison with nano-emulsion and allowed minimum penetration through pig ear epidermis. Presence of polyamide shell protected encapsulated sunscreen filters from photo-degradation without affecting their activity.

Conclusions

Encapsulation of Parsol®MCX and Parsol®1789 into oil-core of polyamide nanocapsules allowed protection from photo-degradation, controlled release from nanocapsules, and limited penetration through pig ear epidermis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

REFERENCES

  1. Trenti R (2007) Prodotti funzionali: Fotostabilità dei filtri solari, Manuale del cosmetologo, Ed. Tecniche Nuove, Milano, 406–407

  2. Trenti R (2007) Prodotti funzionali: Prodotti solari e dopo sole, Manuale del cosmetologo, Ed. Tecniche Nuove, Milano, 402–407

  3. Proserpio G (1985) Radiazioni e loro azione sulla cute: Abbronzatura, Filtri UVB—UNA, Fattori di pigmentazione, Chimica e tecnica cosmetica, Ed. Sinerga, Pero—Milano, 406–422

  4. Wang SQ, Balagula Y, Osterwalder U. Photoprotection: a review of the current and future technologies. Dermatologic Therapy. 2010;23:31–47.

    Article  PubMed  CAS  Google Scholar 

  5. Pfluecker F, Driller HJ, Vouzellaud L, Marchio F, Guinard H, Chaudhuri R. Encapsulated sunscreen composition that does not penetrate skin, World Intellectual Property Organization patent. WO. 2003;2003011239:A2.

    Google Scholar 

  6. Alvarez-Roman R, Barré G, Guy RH, Fessi H. Biodegradable polymer nanocapsules containing a sunscreen agent: preparation and photoprotection. Eur J Pharm Biopharm. 2001;52:191–5.

    Article  PubMed  CAS  Google Scholar 

  7. Alvarez-Roman R, Kail A, Kalia YN, Guy R, Fessi H. Enhancement of topical delivery from biodegradable nanoparticles. Pharm Res. 2004;21(10):1818–25.

    Article  PubMed  CAS  Google Scholar 

  8. Chaudhuri RK (2007) Photostable organic sunscreen composition, US Patent 7166273

  9. Bouchemal K, Briançon S, Perrier E, Fessi H, Bonnet I, Zydowicz N. Synthesis and characterization of polyurethane and poly(ether urethane) nano-capsules using a new technique of interfacial polycondensation combined to spontaneous emulsification. Int J Pharm. 2004;269(1):89–100.

    Article  PubMed  CAS  Google Scholar 

  10. Bouchemal K, Couenne F, Briançon S, Fessi H, Tayakout M. Polyamides nanocapsules: modelling and wall thickness estimation. AIChE J. 2006;52(6):1–10.

    Article  Google Scholar 

  11. Bouchemal K, Couenne F, Briançon S, Fessi H, Tayakout M. Stability studies on colloidal suspensions of Polyurethane nanocapsules. J Nanosci Nanotechno. 2006;6:9–10.

    Article  Google Scholar 

  12. Bouchemal K, Briançon S, Fessi H, Chevalier Y, Bonnet I, Perrier E. Simultaneous emulsification and interfacial polycondensation for the preparation of colloidal suspension of nanocapsules. Mat Sci Eng C. 2006;26:472–80.

    Article  CAS  Google Scholar 

  13. Vauthier C, Bouchemal K. Methods for the preparation and manufacture of polymeric nanoparticles. Pharm Res. 2009;26(5):1025–58.

    Article  PubMed  CAS  Google Scholar 

  14. Laurent C, Pouget J-P, Voisin P. Modulation of DNA damage by pentoxigylline and α-tocopherol in skin fibroblasts exposed to gamma rays. Radiation Res. 2005;164:63–72.

    Article  PubMed  CAS  Google Scholar 

  15. Wu S, Gao J, Dinh QT, Chen C, Fimmel S. IL-8 production and AP-1 transactivation induced by UVA in human keratinocytes: roles of D-alpha-tocopherol. Mol Immunol. 2008;45:2288–96.

    Article  PubMed  CAS  Google Scholar 

  16. Masaki H. Role of antioxidants in the skin: Anti-aging effects. J Dermatol Sci. 2010;58:85–90.

    Article  PubMed  CAS  Google Scholar 

  17. Wu Y, Matsui MS, Chen JZS, Jin X, Shu C-M, Jin G-Y, et al. Antioxidants add protection to a broad-spectrum sunscreen. Clin Exp Dermatol. 2010;36:178–87.

    Article  PubMed  Google Scholar 

  18. Bouchemal K, Briançon S, Perrier E, Fessi H. Nano-emulsion formulation using spontaneous emulsification: solvent, oil and surfactant optimization. Int J Pharm. 2004;280(1–2):241–51.

    Article  PubMed  CAS  Google Scholar 

  19. Bouchemal K, Briançon S, Chaumont P, Fessi H, Zydowicz N. Microencapsulation of Dehydroepiandrosterone (DHEA) with poly (ortho esters) polymers by interfacial polycondensation. J Microencapsul. 2003;20(5):635–51.

    Google Scholar 

  20. Bouchemal K, Ponchel G, Mazzaferro S, Campos-Requena V-H, Gueutin C, Palmieri G-F, et al. A new approach to determine loading efficiency of Leu-enkephalin in poly(isobutylcyanoacrylate) nanoparticles coated with thiolated chitosan. J Drug Del Sci Tech. 2008;18(6):392–7.

    CAS  Google Scholar 

  21. Wissing SA, Müller RH. Solid lipid nanoparticles as carrier for sunscreens: in vitro release and in vivo skin penetration. J Control Release. 2002;81(3):225–33.

    Article  PubMed  CAS  Google Scholar 

  22. Dick IP, Scott RC. Pig ear skin as an in-vitro model for human skin permeability. J Pharm Pharmacol. 1992;44(8):640–5.

    Article  PubMed  CAS  Google Scholar 

  23. Kligman AM, Christophers E. Preparation of isolated sheets of human stratum corneum, Arch. Dermatol. 1963;88:702–5.

    CAS  Google Scholar 

  24. Puglia C, Blasi P, Rizza L, Schoubben A, Bonina F, Rossi C, et al. Lipid nanoparticles for prolonged topical delivery: An in vitro and in vivo investigation. Int J Pharm. 2008;357:295–304.

    Article  PubMed  CAS  Google Scholar 

  25. Swarbrick J, Lee G, Brom J. Drug permeation through human skin. I. Effects of storage conditions of skin. J Invest Dermatol. 1982;78:63–6.

    Article  PubMed  CAS  Google Scholar 

  26. Matts PJ, Alard V, Brown MW, Ferrero L, Gers-Barlag H, Issachar I, et al. The COLIPA in vitro UVA method: a standard and reproducible measure of sunscreen UVA protection. Int J Cosmet Sci. 2010;32:35–46.

    Article  PubMed  CAS  Google Scholar 

  27. Diffey BL, Robson J. A new substrate to measure sunscreen protection factors throughout the ultraviolet spectrum. J Soc Cosmet Chem. 1989;40:127–33.

    CAS  Google Scholar 

  28. Berset G, Gozenbach H, Christ R, Martin R, Deflandre A, Mascotto RE, et al. Proposed protocol for determination of photostability. Part I: cosmetic UV filters. Int J Cosmet Sci. 1996;18:167–77.

    Article  PubMed  CAS  Google Scholar 

  29. Davis RD, Steadman SJ, Jarrett WL, Mathias LJ. Solution 13 C NMR characterization of nylon 66: quantification of cis amide conformers, acid and amine end groups. Macromolecules. 2000;33:7088–92.

    Article  CAS  Google Scholar 

  30. Lauprêtre F, Eustache R-P, Monnerie L. High-resolution solid-state 13 C nuclear magnetic resonance investigation of local motions in model epoxy resins. Polymer. 1995;36:267–74.

    Article  Google Scholar 

  31. Skrovanek DJ, Howes SE, Painter PC, Coleman MM. Hydrogen bonding in polyamides. Macromolecules. 1985;18:1676–83.

    Article  CAS  Google Scholar 

  32. Schroeer LR, Cooper SL. Hydrogen bonding in polyamides. J Appl Phys. 1976;47:4310–7.

    Article  Google Scholar 

  33. Arimoto H. α–γ Transition of nylon 6. J Polym Sci, Part A: Polym Chem. 1964;2:2283–95.

    CAS  Google Scholar 

  34. Trifan DS, Terenzi JF. Extents of hydrogen bonding in polyamides and polyurethanes. J Polym Sci. 1958;28:443.

    Article  CAS  Google Scholar 

  35. Okada A, Kawasumi M, Tajima I, Kurauchi T, Kamigaito O. A solid state NMR study on crystalline forms of nylon 6. J Appl Polym Sci. 1989;37(5):1363–71.

    Article  CAS  Google Scholar 

  36. Illers KH, Haberkorn H, Lanbo JB. J Macromol Sci Phys B. 1972;6:129.

    Article  Google Scholar 

  37. Murthy NS. Metastable crystalline phases in nylon 6. Polym Commun. 1991;32:301–5.

    CAS  Google Scholar 

  38. Moore WH, Krimm S. Vibrational analysis of peptides, polypeptides, and proteins. I Polyglycine I Biopolymers. 1976;15:2439–64.

    CAS  Google Scholar 

  39. Ferranti V, Marchais H, Chabenat C, Orecchioni AM, Lafont O. Primidone-loaded poly-varε-caprolactone nanocapsules: incorporation efficiency and in vitro release profiles. Int J Pharm. 1999;193:107–11.

    Article  PubMed  CAS  Google Scholar 

  40. Calvo P, Vila-Jato JL, Alonso MJ. Comparative in vitro evaluation of several colloidal systems, nanoparticles, nanocapsules, and nanoemulsions, as ocular drug carriers. J Pharm Sci. 1996;85:530–6.

    Article  PubMed  CAS  Google Scholar 

  41. Müller RH, Mäder K, Gohla S. Solid lipid nanoparticles (SLN) for controlled drug delivery—a review of the state of the art. Eur J Pharm Biopharm. 2000;50:161–78.

    Article  PubMed  Google Scholar 

  42. Mathiowitz E, Cohen MD. Polyamide microcapsules for controlled release. I Characterization of the membranes. J Membrane Sci. 1989;40:1–26.

    Article  CAS  Google Scholar 

  43. Janssen LJJM, Boersma A, te Nijenhuis K. Encapsulation by interfacial polycondensation. III. Microencapsulation; the influence of process conditions on wall permeability. J Membrane Sci. 1993;79:11–26.

    Article  CAS  Google Scholar 

  44. Mathiowitz E, Cohen MD. Polyamide microcapsules for controlled release. I V. Effects of swelling. J Membrane Sci. 1989;40:55–65.

    Article  CAS  Google Scholar 

  45. Benech-Kieffer F, Wegrich P, Schwarzenbach R, Klecak G, Weber T, Leclaire J, et al. Percutaneous absorption of sunscreens in vitro: interspecies comparison, skin models and reproducibility aspects. Skin Pharmacol Appl Skin Physiol. 2000;13:324–35.

    Article  PubMed  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS & DISCLOSURES

Nicolas Tsapis, Mounia Makhoukh, Ludivine Houel were gratefully thanked for their help for microscopic observations. Claire Troufflard and France Costa-Torro were gratefully thanked for their help for NMR analyses.

Author information

Authors and Affiliations

  1. Faculty of Pharmacy, University of Paris-Sud 11 UMR CNRS 8612, 5 Rue J.B. Clément, 92296, Châtenay-Malabry cedex, France

    Ibrahim Hanno & Kawthar Bouchemal

  2. Faculty of Pharmacy Interdepartmental Centre of Cosmetic Science & Technology, University of Siena, Via della Diana, 2, 53100, Siena, Italy

    Ibrahim Hanno & Cecilia Anselmi

  3. Physicochimie Pharmacotechnie & Biopharmacie, Faculté de pharmacie, 5 Rue J.B. Clément, 92296, Châtenay-Malabry, France

    Kawthar Bouchemal

Authors
  1. Ibrahim Hanno
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cecilia Anselmi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kawthar Bouchemal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kawthar Bouchemal.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hanno, I., Anselmi, C. & Bouchemal, K. Polyamide Nanocapsules and Nano-emulsions Containing Parsol® MCX and Parsol® 1789: In Vitro Release, Ex Vivo Skin Penetration and Photo-Stability Studies. Pharm Res 29, 559–573 (2012). https://doi.org/10.1007/s11095-011-0592-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11095-011-0592-5

KEY WORDS

Search

Navigation