Study to explore the mechanism to form inclusion complexes of β-cyclodextrin with vitamin molecules

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Saha, Subhadeep ^a   Roy, Aditi ^a   Roy, Kanak ^a   Roy, Mahendra Nath ^a  

^a UNIVERSITY OF NORTH BENGAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; FOOD ADDITIVE; NICOTINIC ACID; SEQUESTERING AGENT; VITAMIN;

CALORIMETRY; CHEMICAL PHENOMENA; CHEMISTRY; SPECTROSCOPY;

ASCORBIC ACID; BETA-CYCLODEXTRINS; CALORIMETRY; CHEMICAL PHENOMENA; FOOD ADDITIVES; NIACIN; SEQUESTERING AGENTS; SPECTRUM ANALYSIS; VITAMINS;

EID: 84992385053     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep35764     Document Type: Article

References (62)

1. Szejtli, J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1753 (1998).
2. Saenger, W. Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. 19, 344-362 (1980).
3. Bender, M. L., Komiyama, M. Cyclodextrin Chemistry 10-15 (Springer-Verlag, 1978).
4. Szejtli, J., Osa, T. Cyclodextrins 189-203 (Elsevier, 1999).
5. Valle, E. M. M. D. Cyclodextrins and their uses: a review. Process Biochemistry 39, 1033-1046 (2004).
6. Connors, K. A. The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325-1357 (1997).
7. Kang, Y., Guo, K., Li, B. J., Zhang, S. Nanoassemblies driven by cyclodextrin based inclusion complexation. Chem. Commun. 50, 11083-11092 (2014).
8. Gao, Y. et al. Inclusion complexes of-cyclodextrin with ionic liquid surfactants. J. Phys. Chem. B 110, 8576-8581 (2006).
9. Yu, G., Jie, K., Huang, F. Supramolecular amphiphiles based on host guest molecular recognition motifs. Chem. Rev. 115, 7240-7303 (2015).
10. Zhou, Y. et al. Acetylcholine-triggered cargo release from supramolecular nanovalves based on different macrocyclic receptors. Chem. Eur. J. 20, 2998-3004 (2014).
11. Sun, Y. L. et al. Mechanized silica nanoparticles based on pillar[5]arenes for on-command cargo release. Small 9, 3224-3229 (2013).
12. Li, H. et al. Viologen-mediated assembly of and sensing with carboxylatopillar[5]arene-modified gold nanoparticles. J. Am. Chem. Soc. 135, 1570-1576 (2013).
13. Yu, G., Tang, G., Huang, F. Supramolecular enhancement of aggregation-induced emission and its application in cancer cell imaging. J. Mater. Chem. C 2, 6609-6617 (2014).
14. Yu, G., Hua, B., Han, C. Proton transfer in host-guest complexation between a difunctional pillar[5]arene and alkyldiamines. Org. Lett. 16, 2486-2489 (2014).
15. Angelos, S., Yang, Y. W., Khashab, N. M., Stoddart, J. F., Zink, J. I. Dual-controlled nanoparticles exhibiting AND logic. J. Am. Chem. Soc. 131, 11344-11346 (2009).
16. Keene, D., Price, C., Shin, M. J. S., Francis, D. P. Effect on cardiovascular risk of high density lipoprotein targeted drug treatments niacin, fibrates, and CETP inhibitors: meta-analysis of randomised controlled trials including 117411 patients. BMJ 349, doi: 10. 1136/bmj. g4379 (2014).
17. Carlson, L. A. Nicotinic acid: the broad-spectrum lipid drug. A 50th anniversary review. Journal of Internal Medicine 258, 94-114 (2005).
18. Levine, M. et al. Vitamin C pharmacokinetics in healthy volunteers: evidence for a recommended dietary allowance. Proc. Natl. Acad. Sci. 93, 3704-3709 (1996).
19. Padayatty, S. J. et al. Vitamin C as an antioxidant: evaluation of its role in disease prevention. Journal of the American College of Nutrition 22, 18-35 (2003).
20. Guorong, Z., Xiaolei, W., Xingwang, S., Tianling, S.-Cyclodextrin-ferrocene inclusion complex modified carbon paste electrode for amperometric determination of ascorbic acid. Talanta 51, 1019-1025 (2000).
21. Okazakit, M., Kuwata, K. A stopped-flow ESR study on the reactivity of some nitroxide radicals with ascorbic acid in the presence of-cyclodextrin. J. Phys. Chem. 89, 4437-4440 (1985).
22. Delicado, E. N., Ferrer, A. S., Carmona, F. G. Cyclodextrins as secondary antioxidants: synergism with ascorbic acid. J. Agric. Food Chem. 45, 2830-2835 (1997).
23. Manzanares, M. I., Solis, V., Rossi, R. H. Effect of cyclodextrins on the electrochemical behaviour of ascorbic acid on gold electrodes. Journal of Electroanalytical Chemistry 407, 141-147 (1996).
24. Silva, M. T. R., Pardave, M. P., Avendano, S. C., Romo, M. R., Angeles, G. A. Guest-host complex formed between ascorbic acid and-cyclodextrin immobilized on the surface of an electrode. Molecules 19, 5952-5964 (2014).
25. Pardave, M. P. et al. Electrochemical and spectrophotometric determination of the formation constants of the ascorbic acid-cyclodextrin and dopamine-cyclodextrin inclusion complexes. J. Incl. Phenom. Macrocycl. Chem. 69, 91-99 (2011).
26. Hu, X. et al. Preparation of the-cyclodextrin-vitamin C (-CD-Vc) inclusion complex under high hydrostatic pressure (HHP). Carbohydrate Polymers 90, 1193-1196 (2012).
27. Terekhova, I. V., Lisi, R. D., Lazzara, G., Milioto, S., Muratore, N. Volume and heat capacity studies to evidence interactions between cyclodextrins and nicotinic acid in water. Journal of Thermal Analysis and Calorimetry 92, 285-290 (2008).
28. Job, P. Formation and stability of inorganic complexes in solution. Ann. Chim. 9, 113-203 (1928).
29. Renny, J. S., Tomasevich, L. L., Tallmadge, E. H., Collum, D. B. Method of continuous variations: applications of Job plots to the study of molecular associations in organometallic chemistry. Angew. Chem. Int. Ed. 52, 11998-12013 (2013).
30. Caso, J. V. et al. Investigating the inclusion properties of aromatic amino acids complexing beta-cyclodextrins in model peptides. Amino Acids 47, 2215-2227 (2015).
31. Yang, B., Lin, J., Chen, Y., Liu, Y. Artemether/hydroxypropyl-cyclodextrin host-guest system: characterization, phase-solubility and inclusion mode. Bioorganic and Medicinal Chemistry 17, 6311-6317 (2009).
32. Servais, A. C. et al. Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins. J. Sep. Sci. 33, 1617-1624 (2010).
33. Correia, I. et al. Study of inclusion complexes of acridine with-and (2, 6-di-O-methyl)-cyclodextrin by use of solubility diagrams and NMR spectroscopy. Journal of Physical Organic Chemistry 15, 647-659 (2002).
34. Bednarek, E. et al. Complexation of steroid hormones: prednisolone, ethinyloestradiol and estriol with-cyclodextrin. An aqueous 1H NMR study. J. Chem. Soc. Perkin Trans. 2, 999-1004 (2002).
35. Sindelar, V. et al. Supramolecular assembly of 2, 7-dimethyldiazapyrenium and cucurbit[8]uril: a new fluorescent host for detection of catechol and dopamine. Chem. Eur. J. 11, 7054-7059 (2005).
36. Wang, T., Wang, M. D., Ding, C., Fu, J. Mono-benzimidazole functionalized-cyclodextrins as supramolecular nanovalves for pH-triggered release of p-coumaric acid. Chem. Commun. 50, 12469-12472 (2014).
37. Ishizu, T., Hirata, C., Yamamoto, H., Harano, K. Structure and intramolecular flexibility of-cyclodextrin complex with ( )-epigallocatechin gallate in aqueous solvent. Magnetic Resonance in Chemistry 44, 776-783 (2006).
38. Kemelbekov, U. et al. IR, UV and NMR studies of-cyclodextrin inclusion complexes of kazcaine and prosidol bases. J. Incl. Phenom. Macrocycl. Chem. 69, 181-190 (2011).
39. Stalin, T., Srinivasan, K., Sivakumar, K., Radhakrishnan, S. Preparation and characterizations of solid/aqueous phases inclusion complex of 2, 4-dinitroaniline with-cyclodextrin. Carbohydrate Polymers 107, 72-84 (2014).
40. Saha, S., Ray, T., Basak, S., Roy, M. N. NMR, surface tension and conductivity studies to determine the inclusion mechanism: thermodynamics of host-guest inclusion complexes of natural amino acids in aqueous cyclodextrins. New J. Chem. 40, 651-661 (2016).
41. Roy, A., Saha, S., Roy, M. N. Study to explore host-guest inclusion complexes of cyclodextrins with biologically active molecules in aqueous environment. Fluid Phase Equilibria 425, 252-258 (2016).
42. Roy, M. N., Saha, S., Kundu, M., Saha, B. C., Barman, S. Exploration of inclusion complexes of neurotransmitters with-cyclodextrin by physicochemical techniques. Chemical Physics Letters 655-656, 43-50 (2016).
43. Barman, S., Ekka, D., Saha, S., Roy, M. N. NMR, surface tension and conductance study to investigate host-guest inclusion complexes of three sequential ionic liquids with-cyclodextrin in aqueous media. Chemical Physics Letters 658, 43-50 (2016).
44. Pineiro, A. et al. On the characterization of host-guest complexes: surface tension, calorimetry, and molecular dynamics of cyclodextrins with a non-ionic surfactant. J. Phys. Chem. B 111, 4383-4392 (2007).
45. Gao, Y. et al. Preparation and characterization of inclusion complexes of-cyclodextrin with ionic liquid. Chem. Eur. J. 11, 5875-5880 (2005).
46. Gao, Y. et al. Inclusion complexes of-cyclodextrin with ionic liquid surfactants. J. Phys. Chem. B 110, 8576-8581 (2006).
47. Roy, M. N., Ekka, D., Saha, S., Roy, M. C. Host-guest inclusion complexes of and-cyclodextrins with-amino acids. RSC Adv. 4, 42383-42390 (2014).
48. Roy, M. N., Saha, S., Barman, S., Ekka, D. Host-guest inclusion complexes of RNA nucleosides inside aqueous cyclodextrins explored by physicochemical and spectroscopic methods. RSC Adv. 6, 8881-8891 (2016).
49. Qian, T., Yu, C., Wu, S., Shen, J. Nanoparticles coated polystyrene/reduced graphite oxide microspheres with improved dispersibility and electrical conductivity for dopamine detection. Colloids and Surfaces B: Biointerfaces 112, 310-314 (2013).
50. Cramer, F., Saenger, W., Spatz, H. Inclusion compounds. The formation of inclusion compounds of-cyclodextrin in aqueous solutions. Thermodynamics and kinetics. J. Am. Chem. Soc. 89, 14-20 (1967).
51. Benesi, H. A., Hildebrand, J. H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Chem. Soc. 71, 2703-2707 (1949).
52. Dotsikas, Y., Kontopanou, E., Allagiannis, C., Loukas, Y. L. Interaction of 6-p-toluidineylnaphthalene-2-sulphonate with-cyclodextrin. J. Pharm. Biomed. Anal. 23, 997-1003 (2000).
53. Roy, M. N., Roy, A., Saha, S. Probing inclusion complexes of cyclodextrins with amino acids by physicochemical approach. Carbohydrate Polymers 151, 458-466 (2016).
54. He, Y., Shen, X. Interaction between-cyclodextrin and ionic liquids in aqueous solutions investigated by a competitive method using a substituted 3H-indole probe. Journal of Photochemistry and Photobiology, A: Chemistry 197, 253-259 (2008).
55. Thordarson, P. Determining association constants from titration experiments in supramolecular chemistry. Chem. Soc. Rev. 40, 1305-1323 (2011).
56. Spies, M. A., Schowen, R. L. The trapping of a spontaneously "flipped-out" base from double helical nucleic acids by host-guest complexation with-cyclodextrin: the intrinsic base-flipping rate constant for DNA and RNA. J. Am. Chem. Soc. 124, 14049-14053 (2002).
57. Hamdan, A. A., Bugnon, P., Saudan, C., Lye, P. G., Merbach, A. E. High-pressure studies as a novel approach in determining inclusion mechanisms: thermodynamics and kinetics of the host-guest interactions for-cyclodextrin complexes. J. Am. Chem. Soc. 122, 592-602 (2000).
58. Hazra, S., Kumar, G. S. Physicochemical properties of inclusion complexes of sanguinarine with natural cyclodextrins: spectroscopy, calorimetry and NMR studies. RSC Adv. 5, 1873-1882 (2015).
59. Voskuhl, J. et al. Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin-nanodiamond inclusion complexes. Org. Biomol. Chem. 10, 4524-4530 (2012).
60. Kriz, Z., Koca, J., Imberty, A., Charlot, A., Velty, R. A. Investigation of the complexation of (+ )-catechin by-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques. Org. Biomol. Chem. 1, 2590-2595 (2003).
61. Ahirwar, R. et al. In silico selection of an aptamer to estrogen receptor alpha using computational docking employing estrogen response elements as aptamer-alike molecules. Scientific Reports., doi: 10. 1038/srep21285 (2016).
62. Shekaari, H., Jebali, F. Volumetric and conductometric studies of some amino acids in aqueous ionic liquid, 1-hexyl-3-methylimidazolium chloride solutions at 298. 15 K. Phys. Chem. Liq. 49, 572-587 (2011).