Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery

Carbohydrate Polymers

Volumn 128, Issue , 2015, Pages 207-219

  Polyakov, Nikolay E ^a   Kispert, Lowell D ^b  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

Antioxidant activity; Arabinogalactan; Carotenoids; Cyclodextrins; Free radicals; Glycyrrhizin; Inclusion complexes; Oligosaccharides; Oxidation stability; Photostability; Polysaccharides; Water solubility

Indexed keywords

AGENTS; ANTIOXIDANTS; BIOCHEMISTRY; BIOCOMPATIBILITY; CHEMICAL ANALYSIS; CYCLODEXTRINS; DIGITAL STORAGE; FOOD PROCESSING; FREE RADICALS; HYDROCARBON REFINING; METAL IONS; OLIGOSACCHARIDES; OXYGEN; POLYSACCHARIDES; SOLUBILITY; STABILITY;

ANTI-OXIDANT ACTIVITIES; ARABINOGALACTAN; CAROTENOIDS; GLYCYRRHIZIN; INCLUSION COMPLEX; OXIDATION STABILITY; PHOTO-STABILITY; WATER SOLUBILITIES;

PIGMENTS;

ARABINOGALACTAN; BIOMATERIAL; CAROTENOID; CYCLODEXTRIN; GALACTAN; GLYCYRRHIZIC ACID; WATER;

CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

BIOCOMPATIBLE MATERIALS; CAROTENOIDS; CYCLODEXTRINS; GALACTANS; GLYCYRRHIZIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY; WATER;

EID: 84929458727     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.04.016     Document Type: Review

References (94)

1. F. Acevedo, M. Rubilar, I. Jofre, M. Villarroel, P. Navarrete, and M. Esparza Oil bodies as a potential microencapsulation carrier for astaxanthin stabilisation and safe delivery Journal of Microencapsulation 31 5 2014 488 500
2. A. Al-Agamey, G.M. Lowe, D.J. McGarvey, A. Mortensen, D.M. Phillip, and T.G. Truscott Carotenoid radical chemistry and antioxidant/pro-oxidant properties Archives of Biochemistry and Biophysics 430 2004 37 48
3. I.E. Apanasenko, O. Selyutina, N.E. Yu Polyakov, L.P. Suntsova, E.S. Meteleva, and A.V. Dushkin Solubilization and stabilization of macular carotenoids by water soluble oligosaccharides and polysaccharides Archives of Biochemistry and Biophysics 572 2015 58 65 10.1016/j.abb.2014.12.010
4. A. Ascenso, S. Pinho, C. Eleuterio, F.G. Praca, B. Lopes, and M.V. Bentley Lycopene from tomatoes: Vesicular nanocarrier formulations for dermal delivery Journal of Agricultural and Food Chemistry 61 30 2013 7284 7293
5. J. Bacardit, J. Stötzner, E. Chamarro, and S. Esplugas Effect of salinity on the photo-fenton process Industrial & Engineering Chemistry Research 46 2007 7615 7619
6. P.S. Bailey The reactions of ozone with organic compounds Chemical Reviews 58 1958 925 1010
7. Bartlett, M. R., Mastaloudis, A., Smidt, C. R., Poole, S. J.; (2010). Nanosized carotenoid cyclodextrin complexes. Patent US 7781572 B2.
8. H.H. Billsten, V. Sundstrom, and T. Polivka Self-assembled aggregates of the carotenoid zeaxanthin: Time-resolved study of excited states Journal of Physical Chemistry A 109 2005 1521 1529
9. S.N. Borisenko, A.V. Lekar, A.A. Milov, E.V. Vetrova, and N.I. Borisenko Mass-spectrometry and quantum-chemical study of self-association processes of glycyrrhizinic acid molecules Chemistry of Plant Materials 2 2013 85 92 (in Russian)
10. H.-J. Buschmann, and E. Schollmayer Applications of cyclodextrins in cosmetic products: A review Journal of Cosmetic Science 53 2002 185 191
11. C. Bustos-Garza, J. Yanez-Fernandez, and B.E. Barragan-Huerta Thermal and pH stability of spray-dried encapsulated astaxanthin oleoresin from Haematococcus pluvialis using several encapsulation wall materials Food Research International 54 1 2013 641 649
12. A.R. Casy, A.D. Cooper, T.M. Jefferies, R.M. Gaskell, D. Greatbanks, and R. Pickford HPLC and 1H-NMR study of chiral recognition in some thromboxane antagonists induced by β-cyclodextrin Journal of Pharmaceutical and Biomedical Analysis 9 1991 787 792
13. S. Chistyachenko Yu, A.V. Dushkin, N.E. Polyakov, M.V. Khvostov, T.G. Tolstikova, and G.A. Tolstikov Polysaccharide arabinogalactan from larch Larix sibirica as carrier for molecules of salicylic and acetylsalicylic acid: Preparation, physicochemical and pharmacological study Drug Delivery 2014 10.3109/10717544.2014.884655
14. K.A. Connors The stability of cyclodextrin complexes in solution Chemical Reviews 97 1996 1325 1357
15. P.J. D'Adamo Larch arabinogalactan is a novel immune modulator Journal of Naturopathic Medical 6 1996 33 37
16. M.E. Davis, and M.E. Brewster Cyclodextrin-based pharmaceutics: Past, present and future Nature Reviews Drug Discovery 3 12 2005 1023 1035
17. V.E. De Oliveira, E.W.C. Almeida, H.V. Castro, H.G.M. Edwards, H.F. Dos Santos, and L.F.C. de Oliveira Carotenoids and beta-Cyclodextrin inclusion complexes: Raman spectroscopy and theoretical investigation Journal of Physical Chemistry A 115 30 2011 8511 8519
18. E.G. Donhowe, and F. Kong Beta-carotene: Digestion, microencapsulation, and in vitro bioavailability Food and Bioprocess Technology 7 2 2014 338 354
19. A.V. Dushkin Mechanochemical synthesis of organic compounds and rapidly soluble materials M. Sopicka-Lizer, High-energy ball milling. Mechanochemical processing of nanopowders 2010 Woodhead Publishing Limited Oxford 249 273
20. A.V. Dushkin, E.S. Meteleva, T.G. Tolstikova, G.A. Tolstikov, N.E. Polyakov, and E.N. Medvedeva Mechanochemical preparation and pharmacological activities of water-soluble intermolecular complexes of arabinogalactan with medicinal agents Russian Chemical Bulletin 6 2008 1299 1307
21. J. Fenoll, P. Hellin, C.M. Martinez, P. Flores, and S. Navarro Semiconductor-sensitized photodegradation of s-triazine and chloroacetanilide herbicides in leaching water using TiO2 and ZnO as catalyst under natural sunlight Journal of Photochemistry and Photobiology A: Chemistry 238 2012 81 87
22. A.L. Focsan, M.K. Bowman, T.A. Konovalova, P. Molnar, J. Deli, and D.A. Dixon Pulsed EPR and DFT characterization of radicals produced by photo-oxidation of zeaxanthin and violaxanthin on silica-alumina Journal of Physical Chemistry B 112 2008 1806 1819
23. A.L. Focsan, M.K. Bowman, J. Shamshina, M.D. Krzyaniak, A. Magyar, and N.E. Polyakov EPR study of the astaxanthin n-octanoic acid monoester and diester radicals on silica-alumina Journal of Physical Chemistry B 116 2012 13200 13210
24. P.I. Francz, H.K. Biesalski, and I. Pfitzner Carotenoid: Methyl-b-cyclodextrin formulations: An improved method for supplementation of cultured cells Biochimica et Biophysica Acta 1474 2000 163 168
25. Y.L. Gao, S. Webb, and L.D. Kispert Deprotonation of carotenoid radical cation and formation of a didehydrodimer Journal of Physical Chemistry B 107 2003 13237 13240
26. Y. Gao, and L.D. Kispert Reaction of carotenoids and ferric chloride: Equilibria, isomerisation, and products Journal of Physical Chemistry B 107 2003 5333 5338
27. S.M.T. Gharibzahedi, S.H. Razavi, and M. Mousavi Characterizing the natural canthaxanthin/2-hydroxypropyl-beta-cyclodextrin inclusion complex Carbohydrate Polymers 101 2014 1147 1153
28. O.Yu Gluschenko, N.E. Polyakov, and T.V. Leshina NMR relaxation study of cholesterol binding with plant metabolites Applied Magnetic Resonance 41 2011 283 294
29. M. Gomes, L. Martins, N. Petito, V.G. Costa, D.Q. Falcao, and K.G. de Lima Araujo Inclusion complexes of red bell pepper pigments with beta-cyclodextrin: Preparation, characterisation and application as natural colorant in yogurt Food Chemistry 148 2014 428 436
30. D. Greatbanks, and R. Pickford Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements Magnetic Resonance in Chemistry 25 1987 208 215
31. V.N. Gusakov, V.N. Maistrenko, and P.P. Safiullin Thermodynamics of formation of molecular complexes of aromatic nitro derivatives with lincomycin and β-glycyrrhizic acid Russian Journal of General Chemistry 71 2001 1307 1316
32. L.K. Henry, N.L. Puspitasari-Nienaber, M. Jaren-Galan, R.B. van Breemen, G.L. Catignani, and S.J. Schwartz Effects of ozone and oxygen on the degradation of carotenoids in an aqueous model system Journal of Agricultural and Food Chemistry 48 2000 5008 5013
33. Z. Hou, Y. Liu, F. Lei, and J. Gao Investigation into the in vitro release properties of beta-carotene in emulsions stabilized by different emulsifiers LWT - Food Science and Technology 59 2 2014 867 873
34. M.L.-N. Jose, R.-B. Pilar, and G.-C. Francisco Cyclodextrins and antioxidants Critical Reviews in Food Science and Nutrition 54 2 2014 251 276
35. R. Katoh, and A. Furube Electron injection efficiency in dye-sensitized solar cells Journal of Photochemistry and Photobiology C: Photochemistry Reviews 20 2014 1 16
36. L.D. Kispert, T. Konovalova, and Y. Gao Carotenoid radical cations and dications: EPR, optical, and electrochemical studies Archives of Biochemistry and Biophysics 430 2004 49 60
37. L.D. Kispert, and N.E. Polyakov Carotenoid radicals: Cryptochemistry of natural colorants Chemistry Letters 39 3 2010 148 155
38. G. Kodis, P.A. Liddell, A.L. Moore, T.A. Moore, and D. Gust Synthesis and photochemistry of a carotene-porphyrin-fullerene model photosynthetic reaction center Journal of Physical Organic Chemistry 17 2004 724 734
39. T.A. Konovalova, S.A. Dikanov, M.K. Bowman, and L.D. Kispert Detection of anisotropic hyperfine components of chemically prepared carotenoid radical cations: 1D and 2D ESEEM and pulsed ENDOR study Journal of Physical Chemistry B 105 2001 8361 8368
40. V.S. Kornievskaya, A.I. Kruppa, N.E. Polyakov, and T.V. Leshina Effect of glycyrrhizic acid on lappaconitine phototransformation Journal of Physical Chemistry B 111 2007 11447 11452
41. N.I. Krinsky, and E.J. Johnson Carotenoid actions and their relation to health and disease Molecular Aspects of Medicine 26 6 2005 459 516
42. I. Lancrajan, H.A. Diehl, C. Socaciu, M. Engelke, and M. Zorn-Kruppa Chemistry and physics of lipids Chemistry and Physics of Lipids 112 2001 1 10
43. J.T. Landrum Carotenoids: Physical, chemical, and biological functions and properties 2009 CRC Press Boca Raton, FL
44. D.W. Lawlor Photosynthesis: Metabolism, control and physiology 1987 Wiley New York, NY
45. J.A. Lemire, J.J. Harrison, and R.J. Turner Antimicrobial activity of metals: Mechanisms, molecular targets and applications Nature Reviews Microbiology 11 2013 371 384 10.1038/nrmicro3028
46. D.Z. Liu, Y.L. Gao, and L.D. Kispert Electrochemical properties of natural carotenoids Journal of Electroanalytical Chemistry 488 2000 140 150
47. E.A. Lopez, J.M. Bosque-Sendra, L.C. Rodriguez, A.M.G. Campana, and J.J. Aaron Applying non-parametric statistical methods to the classical measurements of inclusion complex binding constants Analytical and Bioanalytical Chemistry 375 2003 414 423
48. D. Luxsuwong, R. Indranupakorn, and P. Wongtrakul Preparation of vesicles entrapped lycopene extract Journal of Oleo Science 63 6 2014 645 652
49. V.N. Maistrenko, V.N. Gusakov, I.A. Rusakov, I. Murinov Yu, and G.A. Tolstikov Complexation of glycyrrhizinic acid with 5-nitro-8-oxiquinoline and trinitroglycerine Doklady Akademii Nauk 335 1994 329 331
50. J.A. Mares Carotenoids and eye disease: Epidemiological evidences N.I. Krinsky, S.T. Mayne, H. Sies, Carotenoids in health and disease 2004 Marcel Dekker New York, NY 427 444
51. J.L. McHale Hierarchal light harvesting aggregates and their potential for solar energy applications Journal of Physical Chemistry Letters 3 2012 587 597
52. A. Mele, R. Mendichi, and A. Selva Non-covalent associations of... for the formation of large aggregates by light scattering and NMR spectroscopy Carbohydrate Research 310 1998 261 267
53. A. Mele, R. Mendichi, A. Selva, P. Molnar, and G. Toth Non-covalent associations of cyclomaltooligosaccharides (cyclo-dextrins) with carotenoids in water. A study on the alpha- and beta-cyclodextrin/psi,psi-carotene (lycopene) systems by light scattering, ionspray ionization and tandem mass spectrometry Carbohydrate Research 337 2002 1129 1136
54. P. Odonmazig, A. Ebringerova, E. Machova, and J. Alfoldi Structural and molecular properties of the arabinogalactan isolated from Mongolian larchwood (Larix dahurica L.) Carbohydrate Research 252 1994 317 324
55. E.A. Offord, J.-C. Gautier, O. Avanti, C. Scaletta, F. Runge, and K. Kramer Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts Free Radical Biology and Medicine 32 2002 1293 1303
56. P. Palozza, G. Calviello, S. Serini, N. Maggiano, P. Lanza, and F.O. Ranelletti Beta-carotene at high concentrations induces apoptosis by enhancing oxy-radical production in human adenocarcinoma cells Free Radical Biology and Medicine 30 2001 1000 1007
57. I. Pfitzner, P.I. Francz, and H.K. Biesalski Carotenoid:methyl-β-cyclodextrin formulations: An improved method for supplementation of cultured cells Biochimica et Biophysica Acta - General Subjects 1474 2 2000 163 168 10.1016/S0304-4165(00)00014-3
58. E. Pinho, M. Grootveld, G. Soares, and M. Henriques Cyclodextrins as encapsulation agents for plant bioactive compounds Carbohydrate Polymers 101 2014 121 135
59. N.E. Polyakov, V.K. Khan, M.B. Taraban, and T.V. Leshina Complex of calcium receptor blocker nifedipine with glycyrrhizic acid Journal of Physical Chemistry B 112 2008 4435 4440
60. N.E. Polyakov, V.K. Khan, M.B. Taraban, T.V. Leshina, N.F. Salakhutdinov, and G.A. Tolstikov Complexation of lappaconitine with glycyrrhizinic acid. Structure, stability and reactivity studies Journal of Physical Chemistry B 109 2005 24526 24530
61. N.E. Polyakov, and L.D. Kispert Water soluble supramolecular complexes of β-carotene and other carotenoids. Beta carotene: Dietary sources L. Haugen, T. Bjornson, Cancer and cognition 2009 Nova Science Publishers New York 191 230
62. N.E. Polyakov, V.V. Konovalov, T.V. Leshina, O.A. Luzina, N.F. Salakhutdinov, and T.A. Konovalova One-electron transfer product of quinone addition to carotenoids. EPR and optical absorption studies Journal of Photochemistry and Photobiology A: Chemistry 141 2001 117 126
63. N.E. Polyakov, A.I. Kruppa, T.V. Leshina, T.A. Konovalova, and L.D. Kispert One-electron transfer product of quinone addition to carotenoids. EPR and optical absorption studies Free Radical Biology and Medicine 31 2001 43 52
64. N.E. Polyakov, and T.V. Leshina Glycyrrhizic acid as a novel drug delivery vector: Synergy of drug transport and efficacy The Open Conference Proceedings Journal 2 2011 64 72
65. N.E. Polyakov, T.V. Leshina, T.A. Konovalova, E.O. Hand, and L.D. Kispert Inclusion complexes of carotenoids with cyclodextrins. 1H NMR, EPR and optical studies Free Radical Biology and Medicine 36 2004 872 880
66. N.E. Polyakov, T.V. Leshina, T.A. Konovalova, and L.D. Kispert Carotenoids as scavengers of free radicals in a Fenton reaction: Antioxidants or pro-oxidants? Free Radical Biology and Medicine 31 2001 398 404
67. N.E. Polyakov, T.V. Leshina, E.S. Meteleva, A.V. Dushkin, T.A. Konovalova, and L.D. Kispert Water soluble complexes of carotenoids with arabinogalactan Journal of Physical Chemistry B 113 2009 275 282
68. N.E. Polyakov, T.V. Leshina, E.S. Meteleva, A.V. Dushkin, T.A. Konovalova, and L.D. Kispert Enhancement of photocatalytic activity of TiO2 nanoparticles by water soluble complexes of carotenoids Journal of Physical Chemistry B 114 2010 14200 14204
69. N.E. Polyakov, T.V. Leshina, E. Hand, A. Petrenko, and L.D. Kispert Beta-ionone cyclodextrins inclusion complexes. NMR study and photolysis Journal of Photochemistry and Photobiology A: Chemistry 161 2004 261 267
70. N.E. Polyakov, T.V. Leshina, N.F. Salakhutdinov, and L.D. Kispert Host-guest complexes of carotenoids with beta-glycyrrhizic acid Journal of Physical Chemistry B 110 2006 6991 6998
71. N.E. Polyakov, T.V. Leshina, N.F. Salakhutdinov, T.A. Konovalova, and L.D. Kispert Antioxidant and redox properties of supramolecular complexes of carotenoids with β-glycyrrhizic acid Free Radical Biology and Medicine 40 2006 1804 1809
72. N.E. Polyakov, A. Magyar, and L.D. Kispert Photochemical and optical properties of water-soluble xanthophyll antioxidants: Aggregation vs. complexation Journal of Physical Chemistry B 117 2013 10173 10182
73. M.V. Rekharsky, and Y. Inoue Complexation thermodynamics of cyclodextrins Chemical Reviews 98 1998 1875 1917
74. A.V. Ruban, P. Horton, and A.J. Young Aggregation of higher plant xanthophylls: Differences in absorption spectra and in the dependency on solvent polarity Journal of Photochemistry and Photobiology B: Biology 21 1993 229 234
75. M.R.A. Silva, A.G. Trovó, and R.F.P. Nogueira Degradation of the herbicide tebuthiuron using solar photo-Fenton process and ferric citrate complex at circumneutral pH Journal of Photochemistry and Photobiology A: Chemistry 191 2007 187 192
76. R. Solarska, I. Rutkowska, R. Morand, and J. Augustynski Photoanodic reactions occurring at nanostructured titanium dioxide films Electrochimica Acta 51 2006 2230 2236
77. R. Stancanelli, L.D. Løjkner, K.L. Larsen, M. Guardo, C. Cannavà, and S. Tommasini Structural and spectroscopic features of lutein/butanoyl-β-cyclodextrin nanoassemblies Journal of Pharmaceutical and Biomedical Analysis 71 2012 214 218 10.1016/j.jpba.2012.07.034
78. J. Szejtli, and T. Osa J.L. Atwood, J.E.D. Davies, D.D. MacNicol, F. Vögtle, Comprehensive supramolecular chemistry vol. 3 1996 Elsevier Sci. Ltd Oxford, UK 5 41
79. L. Szente, K. Mikuni, H. Hashimoto, and J. Szejtli Stabilization and solubilization of lipophilic natural colorants with cyclodextrins Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 32 1998 81 89
80. A. Tachaprutinun, T. Udomsup, C. Luadthong, and S. Wanichwecharungruang Preventing the thermal degradation of astaxanthin through nanoencapsulation International Journal of Pharmaceutics 374 2009 119 124
81. C. Tan, J. Xue, S. Abbas, Y. Guan, B. Feng, and X. Zhang Liposome as a delivery system for carotenoids: Comparative antioxidant activity of carotenoids as measured by ferric reducing antioxidant power, DPPH assay and lipid peroxidation Journal of Agricultural and Food Chemistry 62 28 2014 6726 6735
82. S.A. Tanumihardjo Carotenoids and human health 2013 Humana Press New York, NY
83. V.A. Timoshnikov, T. Kobzeva, N.E. Polyakov, and G.J. Kontoghiorghes Inhibition of Fe2+ and Fe3+ induced hydroxyl radical production by the iron chelating drug deferiprone Free Radical Biology and Medicine 78 2015 118 122 10.1016/j.freeradbiomed.2014.10.513
84. T.G. Tolstikova, M.V. Khvostov, and A.O. Bryzgalov The Complexes of drugs with carbohydrate-containing plant metabolites as pharmacologically promising agents Mini-Reviews in Medicinal Chemistry 9 2009 1317 1328
85. T. Toniazzo, I.F. Berbel, S. Cho, C.S. Fávaro-Trindade, I.C. Moraes, and S.C. Pinho Beta-carotene-loaded liposome dispersions stabilized with xanthan and guar gums: Physico-chemical stability and feasibility of application in yogurt LWT - Food Science and Technology 59 2 2014 1265 1273
86. H.H. Tonnesen Photostability of drugs and drug formulations 2nd ed. 2004 CRC Press Boca Raton, FL
87. E. Tykarska, S. Sobiak, and M. Gdaniec Supramolecular organization of neutral and ionic forms of pharmaceutically relevant glycyrrhizic acid - Amphiphile self-assembly and inclusion of small drug molecules Crystal Growth and Design 12 2012 2133 2137
88. C. Walling Intermediates in the reactions of Fenton type reagents Accounts of Chemical Research 31 1998 55 157
89. C. Wang, C.J. Berg, C.C. Hsu, B.A. Merrill, and M.J. Tauber Characterization of carotenoid aggregates by steady-state optical spectroscopy Journal of Physical Chemistry B 116 2012 10617 10630
90. C. Wang, and M.J. Tauber High-yield singlet fission in a carotenoid aggregate observed by picosecond resonance Raman spectroscopy Journal of the American Chemical Society 132 2010 13988 13991
91. K.D. Welch, T.Z. Davis, M.E. Van Eden, and S.D. Aust Deleterious iron-mediated oxidation of biomolecules Free Radical Biology and Medicine 32 2001 577 583
92. Y. Yamamoto, and Y. Inoue NMR studies of cyclodextrin inclusion complex Journal of Carbohydrate Chemistry 8 1989 29 46
93. C. Yuan, L. Du, Z. Jin, and X. Xu Storage stability and antioxidant activity of complex of astaxanthin with hydroxypropyl-beta-cyclodextrin Carbohydrate Polymers 91 1 2013 385 389
94. C. Yuan, Z. Jin, and X. Xu Inclusion complex of astaxanthin with hydroxypropyl-beta-cyclodextrin: UV, FTIR, H1 NMR and molecular modeling studies Carbohydrate Polymers 89 2 2012 492 496