Preparation and Spectroscopic Characterization of Ternary Inclusion Complexes of Ascorbyl Palmitate and Urea with γ-Cyclodextrin

A three-component inclusion complex of ascorbyl palmitate (ASCP), urea (UR), and γ-cyclodextrin (γCD) with a molar ratio of 1/12 has been prepared for the first time using the evaporation method (EVP method) and the grinding and mixing method (GM method). Also, we investigated changes in the physicochemical properties of the three-component complexes. The powder X-ray diffraction (PXRD) measurements showed ASCP, UR, and γCD characteristic peaks in the physical mixture (PM) (AU (ASCP/UR = 1/12)/γCD = 1/2). In GM (AU (ASCP/UR = 1/12)/γCD = 1/1), new diffraction peaks were observed around 2θ = 7.5° and 16.6°, while characteristic peaks derived from EVP (ASCP/UR = 1/12) were observed at 2θ = 23.4° and 24.9°. On the other hand, new diffraction peaks at 2θ = 7.4° and 16.6° were observed in GM (1/2). In the differential scanning calorimeter (DSC) measurement, an endothermic peak at around 83 °C was observed in the GM (1/1) sample, which is thought to originate from the phase transition of urea from the hexagonal to the tetragonal form. An endothermic peak around 113.9 °C was also observed for EVP (ASCP/UR = 1/12). However, no characteristic phase transition-derived peak or EVP (ASCP/UR = 1/12)-derived endothermic peak was observed in GM (1/2). Near infrared (NIR) spectroscopy of GM (1/2) showed no shift in the peak derived from the CH group of ASCP. The peaks derived from the NH group of UR shifted to the high and low wavenumber sides at 5032 cm−1 and 5108 cm−1 in EVP (ASCP/UR = 1/12). The peak derived from the OH group of γCD shifted, and the peak derived from the OH group of ASCP broadened at GM (1/2). These results suggest that AU (ASCP/UR = 1/12)/γCD prepared by the mixed grinding method formed inclusion complexes at the molar ratio (1/2).

[1]  P. Sakdiset,et al.  Chemical Permeation Enhancers for Topically-Applied Vitamin C and Its Derivatives: A Systematic Review , 2022, Cosmetics.

[2]  H. Todo,et al.  Preparation, Characterization, Solubility, and Antioxidant Capacity of Ellagic Acid-Urea Complex , 2022, Materials.

[3]  C. Garnero,et al.  Cyclodextrin Multicomponent Complexes: Pharmaceutical Applications , 2021, Pharmaceutics.

[4]  T. Loftsson,et al.  Characterization and Evaluation of Ternary Complexes of Ascorbic Acid with γ-Cyclodextrin and Poly(vinyl Alcohol) , 2020, International journal of molecular sciences.

[5]  Y. Inoue,et al.  Characterization of Inclusion Complex of Coenzyme Q10 with the New Carrier CD-MOF-1 Prepared by Solvent Evaporation , 2018, AAPS PharmSciTech.

[6]  Y. Inoue,et al.  Usefulness of Urea as a Means of Improving the Solubility of Poorly Water-Soluble Ascorbyl Palmitate , 2017, International journal of medicinal chemistry.

[7]  Keiichi Motoyama,et al.  Potential Use of Cyclodextrins as Drug Carriers and Active Pharmaceutical Ingredients. , 2017, Chemical & pharmaceutical bulletin.

[8]  R. Bini,et al.  High-Pressure High-Temperature Structural Properties of Urea , 2017 .

[9]  Y. Inoue,et al.  STUDY ON COMPLEXATION OF ASCORBIC ACID DERIVATIVES WITH γ-CYCLODEXTRIN , 2017 .

[10]  R. Neubert,et al.  The effect of urea and taurine as hydrophilic penetration enhancers on stratum corneum lipid models. , 2016, Biochimica et biophysica acta.

[11]  István Antal,et al.  Comparative evaluation of the effect of cyclodextrins and pH on aqueous solubility of apigenin. , 2016, Journal of pharmaceutical and biomedical analysis.

[12]  Y. Inoue,et al.  Effect of γ-cyclodextrin derivative complexation on the physicochemical properties and antimicrobial activity of hinokitiol , 2015, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[13]  A. Madan,et al.  Studies on urea co-inclusion complexes of simvastatin for improvement of pharmaceutical characteristics , 2015, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[14]  Anders Nordin,et al.  NIR provides excellent predictions of properties of biocoal from torrefaction and pyrolysis of biomass , 2014 .

[15]  Fan Yang,et al.  Improvement in solubility and bioavailability of puerarin by mechanochemical preparation , 2013, Drug development and industrial pharmacy.

[16]  M. Longhi,et al.  Binding of Sulfamethazine to β-cyclodextrin and Methyl-β-cyclodextrin , 2013, AAPS PharmSciTech.

[17]  S. Degoutin,et al.  Multilayered textile coating based on a β-cyclodextrin polyelectrolyte for the controlled release of drugs. , 2013, Carbohydrate polymers.

[18]  Pumori Saokar Telang.  Vitamin C in dermatology , 2013, Indian dermatology online journal.

[19]  Lingyu Huang,et al.  Stability studies of ascorbic acid 2-glucoside in cosmetic lotion using surface response methodology. , 2013, Bioorganic & medicinal chemistry letters.

[20]  W. Shinoda,et al.  Regioselective recognition of a [60]fullerene-bisadduct by cyclodextrin. , 2013, The Journal of organic chemistry.

[21]  Hailiang Nie,et al.  Aqueous solubility and stability enhancement of astilbin through complexation with cyclodextrins. , 2013, Journal of agricultural and food chemistry.

[22]  Zhengyu Jin,et al.  Preparation of the β-cyclodextrin-vitamin C (β-CD-Vc) inclusion complex under high hydrostatic pressure (HHP). , 2012, Carbohydrate polymers.

[23]  P. Szabó-Révész,et al.  DSC, X-ray and FTIR studies of a gemfibrozil/dimethyl-β-cyclodextrin inclusion complex produced by co-grinding. , 2012, Journal of pharmaceutical and biomedical analysis.

[24]  T. Yano,et al.  The enhancement of the oral bioavailability of γ-tocotrienol in mice by γ-cyclodextrin inclusion. , 2011, The Journal of nutritional biochemistry.

[25]  M. Sheraz,et al.  Photostability and Interaction of Ascorbic Acid in Cream Formulations , 2011, AAPS PharmSciTech.

[26]  Nathalie Dupuy,et al.  Evaluation of multiblock NIR/MIR PLS predictive models to detect adulteration of diesel/biodiesel blends by vegetal oil , 2011 .

[27]  K. Higashi,et al.  Simultaneous dissolution of naproxen and flurbiprofen from a novel ternary gamma-cyclodextrin complex. , 2010, Chemical & pharmaceutical bulletin.

[28]  A. Katrusiak,et al.  H-Bond Breaking in High-Pressure Urea , 2009 .

[29]  T. Fukami,et al.  Effectiveness of mechanochemical treatment with cyclodextrins on increasing solubility of glimepiride. , 2009, Die Pharmazie.

[30]  A. Segall,et al.  Stability of vitamin C derivatives in topical formulations containing lipoic acid, vitamins A and E , 2008, International journal of cosmetic science.

[31]  J. Yao,et al.  Inclusion Complex of Spironaphthoxazine with γ-Cyclodextrin and Its Photochromism Study , 2007 .

[32]  M. Ichihashi,et al.  A new lipophilic pro-vitamin C, tetra-isopalmitoyl ascorbic acid (VC-IP), prevents UV-induced skin pigmentation through its anti-oxidative properties. , 2006, Journal of dermatological science.

[33]  H. Trommer,et al.  Overcoming the Stratum Corneum: The Modulation of Skin Penetration , 2006, Skin Pharmacology and Physiology.

[34]  T. Tsuno,et al.  Analytical characterization of a ferulic acid/γ-cyclodextrin inclusion complex , 2006 .

[35]  Gupta Ym,et al.  Raman and X-Ray Scattering Studies of High-Pressure Phases of Urea , 2005 .

[36]  M. White.  Origins of thermodynamic stability of urea:alkane inclusion compounds , 1998 .

[37]  Jiro Shimada,et al.  Conformation of cyclomaltooligosaccharide (“cycloamylose”) of dp21 in aqueous solution , 1997 .

[38]  J. Shimada,et al.  Conformation of Novel Cycloamylose: Topological Aspects and Simulations , 1996 .

[39]  T. Saito,et al.  Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. , 1984, The Journal of biological chemistry.

[40]  Masahiko,et al.  Effects of oxethazaine and gamma-cyclodextrin complex formation on intestinal contractions , 2016 .

[41]  Jianbin Chao,et al.  Investigation of the inclusion behavior of chlorogenic acid with hydroxypropyl-β-cyclodextrin. , 2012, International journal of biological macromolecules.