Development of a carboxymethyl chitosan functionalized nanoemulsion formulation for increasing aqueous solubility, stability and skin permeability of astaxanthin using low-energy method

References

• Acosta EJ, Bhakta AS. The HLD-NAC model for mixtures of ionic and nonionic surfactants. J Surfactants Deterg, 2009;12:7–19.
   Web of Science ®Google Scholar
• Ahmad N, Ahmad R, Alam MA, Samim M, Iqbal Z, Ahmad FJ. Quantification and evaluation of thymoquinone loaded mucoadhesive nanoemulsion for treatment of cerebral ischemia. Int J Biol Macromol, 2016;88:320–32.
   PubMed Web of Science ®Google Scholar
• Aljuffali IA, Hsu CY, Lin YK, Fang JY. Cutaneous delivery of natural antioxidants: the enhancement approaches. Curr Pharm Des, 2015;21:2745–57.
   PubMed Web of Science ®Google Scholar
• Ambati RR, Siew Moi P, Ravi S, Aswathanarayana RG. Astaxanthin: sources, extraction, stability, biological activities and its commercial applications—a review. Marine Drugs, 2014;12:128–52.
   PubMed Web of Science ®Google Scholar
• Anarjan N, Tan CP, Nehdi IA, Ling TC. Colloidal astaxanthin: preparation, characterisation and bioavailability evaluation. Food Chem, 2012;135:1303–9.
   PubMed Web of Science ®Google Scholar
• Anitha A, Divya Rani VV, Krishna R, Sreeja V, Selvamurugan N, Nair SV, Tamura H, Jayakumar R. Synthesis, characterization, cytotoxicity and antibacterial studies of chitosan, O-carboxymethyl and N,O-carboxymethyl chitosan nanoparticles. Carbohydr Polym, 2009;78:672–7.
   Web of Science ®Google Scholar
• Atrux-Tallau N, Lasselin J, Han S-H, Delmas T, Bibette J. Quantitative analysis of ligand effects on bioefficacy of nanoemulsion encapsulating depigmenting active. Colloids Surf B: Biointerf, 2014;122:390–5.
   PubMed Web of Science ®Google Scholar
• Breithaupt DE. Identification and quantification of astaxanthin esters in shrimp (Pandalus borealis) and in a microalga (Haematococcus pluvialis) by liquid chromatography-mass spectrometry using negative ion atmospheric pressure chemical ionization. J Agric Food Chem, 2004;52:3870–5.
   PubMed Web of Science ®Google Scholar
• Bromberg L, Alakhov V. Effects of polyether-modified poly(acrylic acid) microgels on doxorubicin transport in human intestinal epithelial Caco-2 cell layers. J Controll Release, 2003;88:11–22.
   PubMed Web of Science ®Google Scholar
• Chanamai R, Mcclements DJ. Depletion flocculation of beverage emulsions by gum arabic and modified starch. J Food Sci, 2001;66:457–63.
   Web of Science ®Google Scholar
• Chen X, Chen R, Guo Z, Li C, Li P. The preparation and stability of the inclusion complex of astaxanthin with β-cyclodextrin. Food Chem, 2007;101:1580–4.
   Web of Science ®Google Scholar
• Cho YH, Mcclements DJ. Theoretical stability maps for guiding preparation of emulsions stabilized by protein-polysaccharide interfacial complexes. Langmuir, 2009;25:6649–57.
   PubMed Web of Science ®Google Scholar
• Etoh H, Suhara M, Tokuyama S, Kato H, Nakahigashi R, Maejima Y, Ishikura M, Terada Y, Maoka T. Auto-oxidation products of astaxanthin. J Oleo Sci, 2012;61:17–21.
   PubMed Web of Science ®Google Scholar
• Feng C, Wang Z, Jiang C, Kong M, Zhou X, Li Y, Cheng X, Chen X. Chitosan/o-carboxymethyl chitosan nanoparticles for efficient and safe oral anticancer drug delivery: in vitro and in vivo evaluation. Int J Pharm, 2013;457:158–67.
   PubMed Web of Science ®Google Scholar
• Guan Y, Wu J, Zhong Q. Eugenol improves physical and chemical stabilities of nanoemulsions loaded with β-carotene. Food Chem, 2016;194:787–96.
   PubMed Web of Science ®Google Scholar
• Guerin M, Huntley ME, Olaizola M. Haematococcus astaxanthin: applications for human health and nutrition. Trends Biotechnol, 2003;21:210–6.
   PubMed Web of Science ®Google Scholar
• Guttoff M, Saberi AH, Mcclements DJ. Formation of vitamin D nanoemulsion-based delivery systems by spontaneous emulsification: factors affecting particle size and stability. Food Chem, 2015;171:117–22.
   PubMed Web of Science ®Google Scholar
• Haj-Ahmad R, Khan H, Arshad MS, Rasekh M, Hussain A, Walsh S, Li X, Chang M-W, Ahmad Z. Microneedle coating techniques for transdermal drug delivery. Pharmaceutics, 2015;7:486–502.
   PubMed Web of Science ®Google Scholar
• Hama S, Uenishi S, Yamada A, Ohgita T, Tsuchiya H, Yamashita E, Kogure K. Scavenging of hydroxyl radicals in aqueous solution by astaxanthin encapsulated in liposomes. Biol Pharm Bull, 2012;35:2238–42.
   PubMed Web of Science ®Google Scholar
• Hansali F, Wu M, Bendedouch D, Marie E. n-Butyl cyanoacrylate miniemulsion polymerization via the phase inversion composition method. Colloids Surf A: Physicochem Eng Aspects, 2012;393:133–8.
   Web of Science ®Google Scholar
• Harwansh RK, Mukherjee PK, Kar A, Bahadur S, Al-Dhabi NA, Duraipandiyan V. Enhancement of photoprotection potential of catechin loaded nanoemulsion gel against UVA induced oxidative stress. J Photochem Photobiol B, 2016;160:318–29.
   PubMed Web of Science ®Google Scholar
• Higuera-Ciapara I, Felix-Valenzuela L, Goycoolea FM, Argüelles-Monal W. Microencapsulation of astaxanthin in a chitosan matrix. Carbohydr Polym, 2004;56:41–5.
   Web of Science ®Google Scholar
• Hong L, Han D, Li MX, Zhang P, Liu CG. Development and validation of an ultraviolet–visible spectrophotometric method for determination of phenylethyl resorcinol in new topical nanoemulsions. Int J Cosmet Sci, 2017;39:337–43.
   PubMed Web of Science ®Google Scholar
• Jahanzad F, Crombie G, Innes R, Sajjadi S. Catastrophic phase inversion via formation of multiple emulsions: a prerequisite for formation of fine emulsions. Chem Eng Res Des, 2009;87:492–8.
   Web of Science ®Google Scholar
• Jimtaisong A, Saewan N. Utilization of carboxymethyl chitosan in cosmetics. Int J Cosmet Sci, 2014;36:12–21.
   PubMed Web of Science ®Google Scholar
• Kim DM, Hyun SS, Yun P, Lee CH, Byun SY. Identification of an emulsifier and conditions for preparing stable nanoemulsions containing the antioxidant astaxanthin. Int J Cosmet Sci, 2012;34:64–73.
   PubMed Web of Science ®Google Scholar
• Komaiko JS, Mcclements DJ. Formation of food-grade nanoemulsions using low-energy preparation methods: a review of available methods. Compr Rev Food Sci Food Saf, 2016;15:331–52.
   PubMed Web of Science ®Google Scholar
• Kong M, Chen XG, Kweon DK, Park HJ. Investigations on skin permeation of hyaluronic acid based nanoemulsion as transdermal carrier. Carbohydr Polym, 2011;86:837–43.
   Web of Science ®Google Scholar
• Lauterbach A, Müller-Goymann CC. Applications and limitations of lipid nanoparticles in dermal and transdermal drug delivery via the follicular route. Eur J Pharm Biopharm, 2015;97(Part A):152–63.
   PubMed Web of Science ®Google Scholar
• Liu X, Mcclements DJ, Cao Y, Xiao H. Chemical and physical stability of astaxanthin-enriched emulsion-based delivery systems. Food Biophys, 2016;11:302–10.
   Web of Science ®Google Scholar
• Luo Y, Teng Z, Wang Q. Development of zein nanoparticles coated with carboxymethyl chitosan for encapsulation and controlled release of vitamin D3. J Agric Food Chem, 2012;60:836–43.
   PubMed Web of Science ®Google Scholar
• Luo Y, Wang TTY, Teng Z, Chen P, Sun J, Wang Q. Encapsulation of indole-3-carbinol and 3,3′-diindolylmethane in zein/carboxymethyl chitosan nanoparticles with controlled release property and improved stability. Food Chem, 2013;139:224–30.
   PubMed Web of Science ®Google Scholar
• Martínez-Delgado AA, Khandual S, Villanueva–Rodríguez SJ. Chemical stability of astaxanthin integrated into a food matrix: effects of food processing and methods for preservation. Food Chem, 2017;225:23–30.
   PubMed Web of Science ®Google Scholar
• Mayer S, Weiss J, Mcclements DJ. Behavior of vitamin E acetate delivery systems under simulated gastrointestinal conditions: lipid digestion and bioaccessibility of low-energy nanoemulsions. J Colloid Interface Sci, 2013a;404:215–22.
   PubMed Web of Science ®Google Scholar
• Mayer S, Weiss J, Mcclements DJ. Vitamin E-enriched nanoemulsions formed by emulsion phase inversion: factors influencing droplet size and stability. J Colloid Interface Sci, 2013b;402:122–30.
   PubMed Web of Science ®Google Scholar
• Mcclements DJ. 2005. Food emulsions: principles, practices, and techniques. Boca Raton: CRC Press.
   Google Scholar
• Mcclements DJ. Emulsion design to improve the delivery of functional lipophilic components. Annu Rev Food Sci Technol, 2010;1:241–69.
   PubMed Web of Science ®Google Scholar
• Mcclements DJ. Edible nanoemulsions: fabrication, properties, and functional performance. Soft Matter, 2011;7:2297–316.
   Web of Science ®Google Scholar
• Mcclements DJ, Xiao H. Potential biological fate of ingested nanoemulsions: influence of particle characteristics. Food Funct, 2012;3:202–20.
   PubMed Web of Science ®Google Scholar
• Miller CA. Spontaneous emulsification produced by diffusion—a review. Colloids Surf, 1988;29:89–102.
   Google Scholar
• Mohd AMM, Julianto T, Majeed A. Development and stability evaluation of astaxanthin nanoemulsion. Asian J Pharm Clin Res, 2011;4:142–8.
   Google Scholar
• Mortensen A, Skibsted LH. Kinetics of photobleaching of β-carotene in chloroform and formation of transient carotenoid species absorbing in the near infrared. Free Rad Res, 1996;25:355–68.
   PubMed Web of Science ®Google Scholar
• Nejadmansouri M, Hosseini SMH, Niakosari M, Yousefi GH, Golmakani MT. Physicochemical properties and oxidative stability of fish oil nanoemulsions as affected by hydrophilic lipophilic balance, surfactant to oil ratio and storage temperature. Colloids Surf A: Physicochem Eng Aspects, 2016;506:821–32.
   Web of Science ®Google Scholar
• Ostertag F, Weiss J, Mcclements DJ. Low-energy formation of edible nanoemulsions: Factors influencing droplet size produced by emulsion phase inversion. J Colloid Interface Sci, 2012;388:95–102.
   PubMed Web of Science ®Google Scholar
• Pignatello R, Impallomeni G, Pistarà V, Cupri S, Graziano ACE, Cardile V, Ballistreri A. New amphiphilic derivatives of poly(ethylene glycol) (PEG) as surface modifiers of colloidal drug carriers. III. Lipoamino acid conjugates with carboxy- and amino-PEG5000 polymers. Mater Sci Eng C Mater Biol Appl, 2015;46:470–81.
   PubMed Web of Science ®Google Scholar
• Piorkowski DT, Mcclements DJ. Beverage emulsions: recent developments in formulation, production, and applications. Food Hydrocoll, 2014;42:5–41.
   Web of Science ®Google Scholar
• Qian C, Decker EA, Xiao H, Mcclements DJ. Physical and chemical stability of β-carotene-enriched nanoemulsions: influence of pH, ionic strength, temperature, and emulsifier type. Food Chem, 2012;132:1221–9.
   PubMed Web of Science ®Google Scholar
• Ranga R, Sarada AR, Baskaran V, Ravishankar GA. Identification of carotenoids from green alga Haematococcus pluvialis by HPLC and LC-MS (APCI) and their antioxidant properties. J Microbiol Biotechnol, 2009;19:1333–41.
   PubMed Web of Science ®Google Scholar
• Rao J, Mcclements DJ. Food-grade microemulsions, nanoemulsions and emulsions: fabrication from sucrose monopalmitate and lemon oil. Food Hydrocoll, 2011;25:1413–23.
   Web of Science ®Google Scholar
• Rebiha M, Moulai-Mostefa N, Hadjsadok A. Investigations of the effects of xanthan and sodium caseinate on the formation and stability of an oil-in-water emulsion stabilized by a nonionic surfactant using a response surface method. J Dispers Sci Technol, 2012;33:429–36.
   Web of Science ®Google Scholar
• Reisinger K, Hoffmann S, Alépée N, Ashikaga T, Barroso J, Elcombe C, Gellatly N, Galbiati V, Gibbs S, Groux H, et al. Systematic evaluation of non-animal test methods for skin sensitisation safety assessment. Toxicol in Vitro, 2015;29:259–70.
   PubMed Web of Science ®Google Scholar
• Saberi AH, Fang Y, Mcclements DJ. Fabrication of vitamin E-enriched nanoemulsions: factors affecting particle size using spontaneous emulsification. J Colloid Interface Sci, 2013;391:95–102.
   PubMed Web of Science ®Google Scholar
• Salvia-Trujillo L, Decker EA, Mcclements DJ. Influence of an anionic polysaccharide on the physical and oxidative stability of omega-3 nanoemulsions: antioxidant effects of alginate. Food Hydrocoll, 2016;52:690–8.
   Web of Science ®Google Scholar
• Scott RC, Walker M, Dugard PH. In vitro percutaneous absorption experiments: A technique for the production of intact epidermal membranes from rat skin. J Soc Cosmet Chem, 1986;37:35–41.
   Web of Science ®Google Scholar
• Shi Y, Cao X-W, Tang F, Du H-R, Wang Y-Z, Qiu X-Q, Yu H-P, Lu B. In vitro toxicity of surface water disinfected by different sequential treatments. Water Res, 2009;43:218–28.
   PubMed Web of Science ®Google Scholar
• Sperling RA, Parak WJ. Surface modification, functionalization and bioconjugation of colloidal inorganic nanoparticles. Philos Trans A Math Phys Eng Sci, 2010;368:1333–83.
   PubMed Web of Science ®Google Scholar
• Takeungwongtrakul S, Benjakul S. Astaxanthin degradation and lipid oxidation of Pacific white shrimp oil: kinetics study and stability as affected by storage conditions. Int Aquat Res, 2016;8:15–27.
   Google Scholar
• Tamjidi F, Shahedi M, Varshosaz J, Nasirpour A. Design and characterization of astaxanthin-loaded nanostructured lipid carriers. Innov Food Sci Emerg Technol, 2014;26:366–74.
   Web of Science ®Google Scholar
• Thanou M, Nihot MT, Jansen M, Verhoef JC, Junginger HE. Mono-N-carboxymethyl chitosan (MCC), a polyampholytic chitosan derivative, enhances the intestinal absorption of low molecular weight heparin across intestinal epithelia in vitro and in vivo. J Pharm Sci, 2001;90:38–46.
   PubMed Web of Science ®Google Scholar
• Wissing SA, Müller RH. Solid lipid nanoparticles as carrier for sunscreens: in vitro release and in vivo skin penetration. J Control Release, 2002;81:225–33.
   PubMed Web of Science ®Google Scholar
• Woo JO, Misran M, Lee PF, Tan LP. Development of a controlled release of salicylic acid loaded stearic acid-oleic acid nanoparticles in cream for topical delivery. Sci World J, 2014;2014:205703.
   Web of Science ®Google Scholar
• Yang Y, Lu Y, Wu Q-Y, Hu H-Y, Chen Y-H, Liu W-L. Evidence of ATP assay as an appropriate alternative of MTT assay for cytotoxicity of secondary effluents from WWTPs. Ecotoxicol Environ Saf, 2015;122:490–496.
   PubMed Web of Science ®Google Scholar
• Yu M, Ma H, Lei M, Li N, Tan F. In vitro/in vivo characterization of nanoemulsion formulation of metronidazole with improved skin targeting and anti-rosacea properties. Eur J Pharm Biopharm, 2014;88:92–103.
   PubMed Web of Science ®Google Scholar
• Yuan C, Du L, Jin Z, Xu X. Storage stability and antioxidant activity of complex of astaxanthin with hydroxypropyl-β-cyclodextrin. Carbohydr Polym, 2013;91:385–389.
   PubMed Web of Science ®Google Scholar
• Zaru M, Manca M-L, Fadda AM, Antimisiaris SG. Chitosan-coated liposomes for delivery to lungs by nebulisation. Colloids Surf B: Biointerfaces, 2009;71:88–95.
   PubMed Web of Science ®Google Scholar
• Zhao L, Zhao G, Chen F, Wang Z, Wu J, Hu X. Different effects of microwave and ultrasound on the stability of (all-E)-astaxanthin. J Agric Food Chem, 2006;54:8346–8351.
   PubMed Web of Science ®Google Scholar
• Zhou W, Liu W, Zou L, Liu W, Liu C, Liang R, Chen J. Storage stability and skin permeation of vitamin C liposomes improved by pectin coating. Colloids Surf B Biointerfaces, 2014;117:330–337.
   PubMed Web of Science ®Google Scholar
• Zhu A, Chan-Park MB, Dai S, Li L. The aggregation behavior of O-carboxymethylchitosan in dilute aqueous solution. Colloids Surf B Biointerfaces, 2005;43:143–149.
   PubMed Web of Science ®Google Scholar
• Zhu A, Jin W, Yuan L, Yang G, Yu H, Wu H. O-Carboxymethylchitosan-based novel gatifloxacin delivery system. Carbohydr Polym, 2007;68:693–700.
   Web of Science ®Google Scholar