From conventional towards new – natural surfactants in drug delivery systems design: current status and perspectives

Bibliography

• Corrigan OI, Healy AM. Surfactants in pharmaceutical products and systems, in Encyclopedia of pharmaceutical technology. M Dekker, New York; 2002
   Google Scholar
• Müller-Goymann CC. Physicochemical characterization of colloidal drug delivery systems such as reverse micelles, vesicles, liquid crystals and nanoparticles for topical administration. Eur J Pharm Biopharm 2004;58:343-56
   PubMed Web of Science ®Google Scholar
• Ashton P, Walters KA, Brain KR, Surfactant effects in percutaneous absorption. II. Effects on protein and lipid structure of the stratum corneum. Int J Pharm 1992;87:265-9
   Google Scholar
• European Pharmacopoeia 6.0, European Directorate for Quality of Medicines, Council of Europe, Strasbourg, France; 2008
   Google Scholar
• United States Pharmacopeia/National Formulary (USP/NF); 2009
   Google Scholar
• British Pharmacopoeia 2009 (BP 2009), British Pharmacopoeia Commission, The Stationery Office, London, UK; 2009
   Google Scholar
• Deutsche Arzneibuch 2006 (DAB 2006), German Federal Institute for Drugs and Medicines, Bonn, 2006
   Google Scholar
• Bárány E, Lindberg M, Lodén M. Unexpected skin barrier influence from nonionic emulsifiers. Int J Pharm 2000;195:189-95
   PubMedGoogle Scholar
• OECD (2008). OECD Guideline for the Testing of Chemicals, Draft Proposal for a New Guideline: In Vitro Skin Irritation: Human Skin Model Test. Available from: http://www.oecd.org/searchResult/0,3400,en-2649-201185-1-1-1-1-1,00.html [Last accessed 31 August 2009]
   Google Scholar
• Bárány E. Human in vivo skin irritancy testing, in dry skin and moisturizers. CRC Press LLC, Boca Raton; 2000
   Google Scholar
• Fluhr JW, Kuss O, Diepgen T, Testing for irritation with a multifactorial approach: comparison of eight non-invasive measuring techniques on five different irritation types. Br J Dermatol 2001;145:696-703
   PubMed Web of Science ®Google Scholar
• Aikens PA, Friberg SE. Emulsifiers, in dry skin and moisturizers. CRC Press LLC, Boca Raton; 2000
   Google Scholar
• Eccleston GM. . Functions of mixed emulsifiers and emulsifying waxes in dermatological lotions and creams. Colloids Surf A Physicochem Eng Aspects 1997;123/124:169-182
   Web of Science ®Google Scholar
• Al-Bawab A, Friberg SE. Some pertinent factors in skin care emulsions. Adv Colloid Interface Sci 2006;123-126:313-322
   PubMed Web of Science ®Google Scholar
• Williams AC, Barry BB. Penetration enhancers. Adv Drug Deliv Rev 2004;56:603-18
   PubMed Web of Science ®Google Scholar
• Holmberg K. Natural surfactants. Cur Opin Colloid Interface Sci 2001;6:148-59
   Web of Science ®Google Scholar
• Stubenrauch K. Sugar surfactants – aggregation, interfacial, and adsorption phenomena. Cur Opin Colloid Interface Sci 2001;6:160-70
   Web of Science ®Google Scholar
• Johansson I, Svensson M. Surfactants based on fatty acids and other natural hydrophobes. Cur Opin Colloid Interface Sci 2001;6:178-88
   Web of Science ®Google Scholar
• Hill K. Alkyl polyglycosides: where ‘green’ meets performance. HPC Focus Surfactants 2008;2:18-22
   Google Scholar
• Nickel D, Förster T, von Rybinski W. Physicochemical properties of alkyl polyglycosides, in Alkyl polyglycosides. Weinheim: VCH; 1997
   Google Scholar
• von Rybinski W, Hill K. Alkyl polyglycosides – properties and applications of a new class of surfactants. Angew Chem Int Ed Engl 1998;37:1328-45
   PubMed Web of Science ®Google Scholar
• Zhang R, Marone PA, Thiyagarajan P, Tiede DM. Structure and molecular fluctuations of n-alkyl-beta-D-glycopyranoside micelles determined by X-ray and neutron scattering. Langmuir 1999;15:7510-9
   Web of Science ®Google Scholar
• Sierra ML, Svensson M. Mixed micelles containing alkyl glycosides: effect of the chain length and the polar head group. Langmuir 1999;15:2301-6
   Web of Science ®Google Scholar
• Boyd BJ, Drummond CJ, Krodkiewska I, Grieser F. How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behavior and the air-water interfacial adsorption of glucose-based surfactants. Langmuir 2000;16:7359-67
   Web of Science ®Google Scholar
• Vill V, von Minden HM, Koch MHJ, Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part I: monosaccharide headgroups. Chem Phys Lipids 2000;104(1):75-91
   PubMed Web of Science ®Google Scholar
• von Minden HM, Brandenburg K, Seydel U, Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part II: disaccharide headgroups. Chem Phys Lipids 2000;106(2):157-79
   PubMed Web of Science ®Google Scholar
• Satam RM, Sawant MR. A study of the solubilization of polar oily materials by alkyl polyglucoside and sodium dodecyl sulfate in mixed surfactant system. J Dispersion Sci Technol 2006;27(2):179-84
   Web of Science ®Google Scholar
• Fanun M. Liquid crystal structural variability on water/mixed nonionic surfactants/caprylic-capric triglyceride systems. J Dispersion Sci Technol 2009;30(3):289-96
   Web of Science ®Google Scholar
• Fukuda K, Olsson U, Ueno M. Microemulsions formed by alkyl polyglucoside and alkyl glycerol ether with weakly charged films. Colloid Surf B Biointerfaces 2001;20:129-35
   PubMed Web of Science ®Google Scholar
• Kluge K, Sottmann T, Stubenrauch C, Strey R. Temperature-insensitive microemulsions formulated from octyl monglucoside and alcohols: potential candidates for applications. Tenside Surf Det 2001;38:30-40
   Web of Science ®Google Scholar
• Mitsubishi Kagaku Food Corporation. Application of sugar esters. 2007. Available from: http://www.mfc.co.jp/english/infor.htm/ [Last accessed 31 August 2009]
   Google Scholar
• Garti N, Clement V, Leser M, Sucrose ester microemulsions. J Mol Liq 1999;80:253-96
   Web of Science ®Google Scholar
• Fanun M, Wachtel E, Antalek B, A study of the microstructure of four-component sucrose ester microemulsions by SAXS and NMR. Colloid Surf A Physicochem Eng Aspects 2001;180:173-86
   Web of Science ®Google Scholar
• Matthies W, Jackwerth B, Krächter H-U. Dermatological properties of alkyl polyglycosides, in Alkyl polyglycosides. Weinheim: VCH; 1997
   Google Scholar
• Mehling A, Hensen H. Comparative studies on the irritation potential of surfactants. Exog Dermatol 2004;3:191-200
   Google Scholar
• Mehling A, Kleber M, Hensen H. Comparative studies on the ocular and dermal irritation potential of surfactants. Food Chem Toxicol 2007;45:747-58
   PubMed Web of Science ®Google Scholar
• Aulmann W, Sterzel W. Toxicology of alkyl polyglycosides, in Alkyl polyglycosides. Weinheim: VCH; 1997
   Google Scholar
• Messinger H, Aulmann W, Kleber M, Koehl W. Investigations on the effects of alkyl polyglycosides on development and fertility. Food Chem Toxicol 2007;45:1357-82
   Google Scholar
• Hadgraft J. Skin deep. Eur J Pharm Biopharm 2004;58:291-9
   PubMed Web of Science ®Google Scholar
• Refai H, Müller-Goymann CC. The influence of dilution of topical semisolid preparations on hydrocortisone permeation through excised human stratum corneum. Eur J Pharm Biopharm 2002;54:143-50
   PubMed Web of Science ®Google Scholar
• Available from: http://www.seppic.com [Last accessed 31 August 2009]
   Google Scholar
• Savic S, Tamburic S, Savic M, Vehicle-controlled effect of urea on normal and SLS-irritated skin. Int J Pharm 2004;271:269-80
   PubMed Web of Science ®Google Scholar
• Savic S, Vuleta G, Daniels R, Müller-Goymann CC. Colloidal microstructure of binary systems and model creams stabilized with an alkylpolyglucoside non-ionic emulsifier. Colloid Polymer Sci 2005;283:439-51
   Web of Science ®Google Scholar
• Savic S, Vuleta G, Milic J, Structural characterisation of multiphase emulsion systems based on an alkylpolyglucoside non-ionic emulsifier. RISG La Rivista Italiana Delle Sostanze Grasse 2005;82(5):236-44
   Web of Science ®Google Scholar
• Fairhust C, Fuller S, Gray J, Holmes MC. Lyotropic surfactant liquid crystals, in Handbook of liquid crystals. Volume 3. Weinheim: Wiley-VCH; 1998
   Google Scholar
• Müller-Goymann CC, Drug delivery – liquid crystals in, in Encyclopedia of pharmaceutical technology. Volume 1. Marcel Dekker, New York; 2002
   Google Scholar
• Eccleston GM, Behan-Martin MK, Jones GR, Towns-Andrews E. Synchrotron X-ray investigations into the lamellar gel phase formed in pharmaceutical creams prepared with cetrimide and fatty alcohols. Int J Pharm 2000;203:127-39
   PubMed Web of Science ®Google Scholar
• Junginger HE. Multiphase emulsions, in Surfactants in cosmetics. Marcel Dekker, New York; 1997
   Google Scholar
• Mondain-Monval O. Freeze fracture TEM investigations in liquid crystals. Curr Opin Colloid Interf Sci 2005;10:250-5
   Web of Science ®Google Scholar
• Makai M, Csanyi E, Nemeth Z, Structure and drug release of lamellar liquid crystals containing glycerol. Int J Pharm 2003;256:95-107
   PubMed Web of Science ®Google Scholar
• Erös I, Kónya M, Csóka I. Study of the structure of coherent emulsions. Int J Pharm 2003;256:75-84
   PubMedGoogle Scholar
• Makai M, Csanyi E, Dékány I, Structural properties of nonionic surfactant/glycerol/paraffin lyotropic liquid crystals. Colloid Polym Sci 2003;281:839-44
   Web of Science ®Google Scholar
• Korhonen M, Lehtonen J, Hellen L, Rheological properties of three component creams containing sorbitan monoesters as surfactants. Int J Pharm 2002;247:103-14
   PubMed Web of Science ®Google Scholar
• Robles-Vasquez O, Corona-Galvan S, Soltero JFA, Rheology of lyotropic liquid crystals of Aerosol OT. II. High concentration regime. J Colloid Interface Sci 1993;160:65-71
   Web of Science ®Google Scholar
• Nemeth Z, Halasz L, Palinkas J, Rheological behaviour of a lamellar liquid crystalline surfactant-water system. Colloid Surf A 1998;145:107-19
   Web of Science ®Google Scholar
• Masmoudi H, Piccerelle P, Le Dréau Y, Kister J. A rheological method to evalauate the physical stability of highly viscous pharmaceutical oil-in-water emulsions. Pharm Res 2006;23(8):1937-1947
   PubMed Web of Science ®Google Scholar
• Savic S, Tamburic S, Kovacevic A, Natural surfactant-based emulsion systems: the influence of common pharmaceutical excipients on colloidal structure and physical stability. J Dispersion Sci Technol 2008;29:1276-87
   Web of Science ®Google Scholar
• Baudonnet L, Grossiord J-L, Rodriguez F. Physicochemical characterization and in vitro release of salicylic acid from o/w emulsions prepared with Montanov 68®: effect of formulation parameters. Drug Dev Ind Pharm 2004;30 (9):975-984
   PubMed Web of Science ®Google Scholar
• Savić SD, Savić MM, Vesić SA, Vehicles based on a sugar surfactant: colloidal structure and its impact on in vitro/in vivo hydrocortisone permeation. Int J Pharm 2006;320:86-95
   PubMed Web of Science ®Google Scholar
• Savic S, Savic M, Tamburic S, An alkylpolyglucoside surfactant as a prospective pharmaceutical excipient for topical formulations: the influence of oil polarity on the colloidal structure and hydrocortisone in vitro/in vivo permeation. Eur J Pharm Sci 2007;30:441-50
   PubMed Web of Science ®Google Scholar
• Vucinic-Milankovic N, Savic S, Vuleta G, Vucinic S. The physicochemical characterization and in vitro/in vivo evaluation of natural surfactants-based emulsions as vehicles for diclofenac diethylamine. Drug Dev Ind Pharm 2007;33:1-14
   Google Scholar
• Savic S, Tamburic S, Jancic B, The impact of urea on the colloidal structure of alkylpolyglucoside-based emulsions: physicochemical and in vitro/in vivo characterization, in Colloids in cosmetic and personal care. Weinheim: Wiley-VCH; 2008
   Google Scholar
• Savic S, Weber C, Tamburic S, Topical vehicles based on natural surfactants/fatty alcohols mixed emulsifier: the influence of two polyolos on the colloidal structure and in vitro/in vivo skin performance. J Pharm Sci 2009;98(6):2073-90
   PubMed Web of Science ®Google Scholar
• Savic S, Weber C, Savic M, Müller-Goymann C. Natural surfactant-based topical vehicles for two model drugs: influence of different lipophilic excipients on in vitro/in vivo skin performance. Int J Pharm 2009;381:220-30
   PubMed Web of Science ®Google Scholar
• Ponec M. Skin constructs for replacement of skin tissues for in vitro testing. Adv Drug Del Rev 2002;54(Suppl 1):S19-30
   PubMedGoogle Scholar
• Schmook FP, Meingassner JG, Billich A. Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm 2001;215:51-6
   PubMed Web of Science ®Google Scholar
• Hoffmann C, Müller-Goymann CC. Use of artificial skin constructs in permeation studies of clindamycin phosphate. Pharmazie 2005;60:350-3
   PubMed Web of Science ®Google Scholar
• Schäfer-Korting M, Bock U, Diembeck W, The use of reconstructed human epidermis for skin absorption testing: results of the validation study. ATLA 2008;36:161-87
   Google Scholar
• Bolzinger MA, Briançon S, Pelletier J, Percutaneous release of caffeine from microemulsions, emulsions and gel dosage forms. Eur J Pharm Biopharm 2008;68:446-51
   PubMed Web of Science ®Google Scholar
• Fang JY, Leu YL, Fang CL, Chiu HC. In vitro and in vivo evaluations of the efficacy and safety of skin permeation enhancers using flurbiprofen as a model drug. Int J Pharm 2003;255:153-66
   PubMed Web of Science ®Google Scholar
• Roberts MS, Walker M. Water: the most natural penetration enhancer, in Pharmaceutical skin enhancement. New York: Marcel Dekker; 1993
   Google Scholar
• Lodèn M. Role of topical emollients and moisturizers in the treatment of dry skin barrier disorders. Am J Clin Dermatol 2003;4:771-88
   PubMed Web of Science ®Google Scholar
• Gloor M, Gehring W. O/W emulsions compromise the stratum corneum barrier and improve drug penetration. Pharmazie 2003;58:709-15
   PubMed Web of Science ®Google Scholar
• Adams WP, Singh GJP. Guidance: topical dermatologic corticosteroids: in vivo bioequivalence, Division of Bioequivalence, Office of Generic Drugs, Food and Drug Administration, 1995
   Google Scholar
• Lehmann L, Keipert S, Gloor M. Effects of microemulsions on the stratum corneum and hydrocortisone penetration. Eur J Pharm Biopharm 2001;52:129-36
   PubMed Web of Science ®Google Scholar
• Clarys P, Alewaeters K, Lambrecht R, Barel AO. Skin color measurements: comparison between three instruments: the Chromameter®, the DermaSpectrometer® and the Mexameter®. Skin Res Technol 2000;6:230-8
   PubMed Web of Science ®Google Scholar
• Fullerton A, Fischer T, Lahti A, Guidelines for measurement of skin colour and erythema. A report from the Standardization Group of the European Society of Contact Dermatitis. Contact Dermatitis 1996;35:1-10
   PubMed Web of Science ®Google Scholar
• Haigh JM, Meyer E, Smith EW, Kanfer I. The human skin blanching assay for in vivo topical corticosteroid assessment. I. Reproducibility of the assay. Int J Pharm 1997;152:179-83
   Google Scholar
• Levin J, Maibach H. The correlation between transepidermal water loss and percutaneous absorption: an overview. J Control Release 2005;103:291-9
   PubMed Web of Science ®Google Scholar
• Zhai H, Maibach HI. Effects of skin occlusion on percutaneous absorption: an overview. Skin Pharmacol Appl Skin Physiol 2001;14:1-10
   PubMedGoogle Scholar
• Panchagnula R, Salve PS, Thomas NS, Transdermal delivery of naloxone: Effect of water, propylene glycol, ethanol and their binary combinations on permeation through rat skin. Int J Pharm 2001;219:95-105
   PubMed Web of Science ®Google Scholar
• Trottet L, Merly C, Mirza M, Effect of finite doses of propylene glycol on enhancement of in vitro percutaneous permeation of loperamide hydrochloride. Int J Pharm 2004;274:213-9
   PubMed Web of Science ®Google Scholar
• Herkenne C, Naik A, Kalia YN, Effect of propylene glycol on ibuprofen absorption into human skin in vivo. J Pharm Sci 2008;97:185-97
   PubMed Web of Science ®Google Scholar
• Weyermann J, Lochmann D, Zimmer A. A practical note on the use of cytotoxicity assays. Int J Pharm 2005;288:369-76
   PubMed Web of Science ®Google Scholar
• Vinardell MP, Mitjans M. Alternative methods for eye and skin irritation tests: an overview. J Pharm Sci 2008;97:46-59
   PubMed Web of Science ®Google Scholar
• Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res 2003;20(8):1267-73
   PubMed Web of Science ®Google Scholar
• Quintanar-Ganem A, Quintanar-Guerrero D, Falson-Rieg F, Buri P. Ex vivo oral mucosal permeation of lidocaine hydrochloride with sucrose fatty acid esters as absorption enhancers. Int J Pharm 1998;173:203-10
   Google Scholar
• Manconi M, Sinico C, Valenti D, Niosomes as carriers for tretinoin III. A study into the in vitro cutaneous delivery of vesicle-incorporated tretinoin. Int J Pharm 2006;311:11-9
   PubMed Web of Science ®Google Scholar
• Rentel C-O, Bouwstra JA, Naisbett B, Junginger HE. Niosomes as a novel peroral vaccine delivery system. Int J Pharm 1999;186:161-7
   PubMed Web of Science ®Google Scholar
• Csóka G, Marton S, Zelko R, Application of sucrose fatty acid esters in transdermal therapeutic systems. Eur J Pharm Biopharm 2007;65:233-7
   PubMed Web of Science ®Google Scholar
• Patel AR, Joshi VY. Evaluation of SLS: APG mixed surfactant systems as carrier for solid dispersion. AAPS PharmSciTech 2008;9(2):583-90
   PubMed Web of Science ®Google Scholar
• Patel AR, Kulkami S, Nandeker TD, Vavia PR. Evaluation of alkyl polyglucoside as an alternative surfactant in the preparation of peptide-loaded nanoparticles. J Microencapsul 2008;25(8):531-40
   PubMed Web of Science ®Google Scholar
• Graf A, Ablinger E, Peters S, Microemulsions containing lecithin and sugar-based surfactants: nanoparticle templates for delivery of proteins and peptides. Int J Pharm 2008;350:351-60
   PubMed Web of Science ®Google Scholar
• Youan BB, Hussian A, Nguyen NT. Evaluation of sucrose esters as alternative surfactants in microencapsulation of proteins by the solvent evaporation method. AAPS PharmSciTech 2003;5:222-30
   Google Scholar
• Ullrich S, Metz H, Mäder K. Sucrose ester nanodispersions: Microviscosity and viscoelastic properties. Eur J Pharm Biopharm 2008;70:550-5
   PubMed Web of Science ®Google Scholar
• Pouton CW. Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. Eur J Pharm Sci 2006;29:278-87
   PubMed Web of Science ®Google Scholar
• Pakpayat N, Nielloud F, Fortuné R, Formulation of ascorbic acid microemulsions with alkyl polyglycosides. Eur J Pharm Biopharm 2009;72:444-52
   PubMed Web of Science ®Google Scholar