186
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Improved Solubility of Morin Using p-sulphonatocalix[4]arene as Encapsulating Agent: HPLC Analysis and their Molecular Modelling

, , , & ORCID Icon
Pages 609-621 | Received 28 Jan 2018, Accepted 07 Apr 2018, Published online: 07 May 2018

References

  • P. W. Dhore, V. S. Dave, S. D. Saoji, Y. S. Bobde, C. Mack, and N. A. Raut, “Enhancement of the Aqueous Solubility and Permeability of a Poorly Water Soluble Drug Ritonavir via Lyophilized Milk-Based Solid Dispersions,” Pharmaceutical Development and Technology 22, no. 1 (2017): 90–102. doi:10.1080/10837450.2016.1193193.
  • K. S. Raghavan, G. A. Nemeth, D. B. Gray, and M. A. Hussain, “Solubility Enhancement of a Bisnaphthalimide Tumoricidal Agent, DMP 840, Through Complexation,” Pharmaceutical Development and Technology 1, no. 3 (1996): 231–8. doi:10.3109/10837459609022591.
  • M. Plaza, T. Pozzo, J. Liu, K. Z. Gulshan Ara, C. Turner, and E. Nordberg Karlsson, “Substituent Effects on in Vitro Antioxidizing Properties, Stability, and Solubility in Flavonoids,” Journal of Agricultural and Food Chemistry 62, no. 15 (2014): 3321–33. doi:10.1021/jf405570u.
  • C. Jullian, T. Orosteguis, F. Pérez-Cruz, P. Sánchez, F. Mendizabal, and C. Olea-Azar, “Complexation of Morin with Three Kinds of Cyclodextrin: A Thermodynamic and Reactivity Study,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 71, no. 1 (2008): 269–75. doi:10.1016/j.saa.2007.12.020.
  • S. V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic, and M. G. Simic, “Flavonoids as Antioxidants,” Journal of the American Chemical Society 116, no. 11 (1994): 4846–51. doi:10.1021/ja00090a032.
  • K. Khan, S. Badshah, N. Ahmad, H. Rashid, and Y. Mabkhot, “Inclusion Complexes of a New Family of Non-Ionic Amphiphilic Dendrocalix[4]arene and Poorly Water-Soluble Drugs Naproxen and Ibuprofen,” Molecules 22, no. 5 (2017): 783. doi:10.3390/molecules22050783.
  • L. G. Naso, L. Lezama, T. Rojo, S. B. Etcheverry, M. Valcarcel, M. Roura, C. Salado, E. G. Ferrer, and P. A. Williams, “Biological Evaluation of Morin and its New Oxovanadium (IV) Complex as Antio-Xidant and Specific Anti-Cancer Agents,” Chemico-Biological Interactions 206, no. 2 (2013): 289–301. doi:10.1016/j.cbi.2013.10.006.
  • B. H. Havsteen, “The Biochemistry and Medical Significance of the Flavonoids,” Pharmacology & Therapeutics 96, no. 2–3 (2002): 67–202. doi:10.1016/S0163-7258(02)00298-X.
  • S. Baumgartner, J. Kristl, F. Vrečer, P. Vodopivec, and B. Zorko, “Optimisation of Floating Matrix Tablets and Evaluation of their Gastric Residence Time,” International Journal of Pharmaceutics 195, no. 1–2 (2000): 125–35. doi:10.1016/S0378-5173(99)00378-6.
  • Y. Wang, G. Zhang, J. Yan, and D. Gong, “Inhibitory Effect of Morin on Tyrosinase: Insights from Spectroscopic and Molecular Docking Studies,” Food Chemistry 163 (2014): 226–33. doi:10.1016/j.foodchem.2014.04.106.
  • T. Tanaka, K. Kawabata, M. Kakumoto, H. Makita, J. Ushida, S. Honjo, A. Hara, H. Tsuda, and H. Mori, “Modifying Effects of a Flavonoid Morin on Azoxymethane-Induced Large Bowel Tumorigenesis in Rats,” Carcinogenesis 20, no. 8 (1999): 1477–84. doi:10.1093/carcin/20.8.1477.
  • S.-H. Fang, Y.-C. Hou, W.-C. Chang, S.-L. Hsiu, P.-D. L. Chao, and B.-L. Chiang, “Morin Sulfates/Glucuronides Exert Anti-Inflammatory Activity on Activated Macrophages and Decreased the Incidence of Septic Shock,” Life Science 74, no. 6 (2003): 743–56. doi:10.1016/j.lfs.2003.07.017.
  • B. S. Reddy, K. Tokumo, N. Kulkarni, C. Aligia, and G. Kelloff, “Inhibition of Colon Carcinogenesis by Prostaglandin Synthesis Inhibitors and Related Compounds,” Carcinogenesis 13, no. 6 (1992): 1019–23. doi:10.1093/carcin/13.6.1019.
  • J. Zhang, Q. Peng, S. Shi, Q. Zhang, X. Sun, T. Gong, and Z. Zhang, “Preparation, Characterization, and in Vivo Evaluation of a Self-Nanoemulsifying Drug Delivery System (SNEDDS) Loaded with Morin-Phospholipid Complex,” International Journal of Nanomedicine 6 (2011): 3405–14.
  • T. Loftsson, “Drug Solubilization by Complexation,” International Journal of Pharmaceutics 531, no. 1 (2017): 276–80. doi:10.1016/j.ijpharm.2017.08.087.
  • K. T. Savjani, A. K. Gajjar, and J. K. Savjani, “Drug Solubility: Importance and Enhancement Techniques,” ISRN Pharmaceutics 2012 (2012): 1–10. doi:10.5402/2012/195727.
  • G.-S. Wang, H.-Y. Zhang, D. Li, P.-Y. Wang, and Y. Liu, “Characterisation and Antiproliferative Activity of Irinotecan and Sulphonatocalixarene Inclusion Complex,” Supramolecular Chemistry 23, no. 6 (2011): 441–6. doi:10.1080/10610278.2010.544736.
  • G.-S. Wang, H.-Y. Zhang, F. Ding, and Y. Liu, “Preparation and Characterization of Inclusion Complexes of Topotecan with Sulfonatocalixarene,” Journal of Inclusion Phenomena and Macrocyclic Chemistry 69, no. 1–2 (2011): 85–89. doi:10.1007/s10847-010-9817-1.
  • Q. Li, D. S. Guo, H. Qian, and Y. Liu, “Complexation of p‐Sulfonatocalixarenes with Local Anaesthetics Guests: Binding Structures, Stabilities, and Thermodynamic Origins,” European Journal of Organic Chemistry 2012, no. 21 (2012): 3962–71. doi:10.1002/ejoc.201200515.
  • D.-S. Guo, H.-Q. Zhang, F. Ding, and Y. Liu, “Thermodynamic Origins of Selective Binding Affinity Between p-sulfonatocalix [4, 5] arenes with Biguanidiniums,” Organic & Biomolecular Chemistry 10, no. 8 (2012): 1527–36. doi:10.1039/c2ob06313a.
  • L. Shangguan, Q. Chen, B. Shi, and F. Huang, “Enhancing the Solubility and Bioactivity of Anticancer Drug Tamoxifen by Water-Soluble pillar[6]arene-based Host-Guest Complexation,” Chemical Communications 53, no. 70 (2017): 9749–52. doi:10.1039/C7CC05305C.
  • S. Memon, and M. Yilmaz, “A Complimentary Study of Calixarene based Bifunctional Receptors for Alkali or Transition Metal Cations and Cr2O72− Anions,” Journal of Molecular Structure 595, no. 1 (2001): 101–9. doi:10.1016/S0022-2860(01)00509-9.
  • C. D. Gutsche, Monographs in Supramolecular Chemistry, vol. 6, Calixarenes Revisited, (Cambridge: The Royal Society of Chemistry United Kingdom 1998).
  • A. A. Bhatti, I. Qureshi, N. Memon, and S. Memon, “Evaluation of Perchlorate Sorption Behavior of calix [4]arene Appended Resin,” Journal of Inclusion Phenomena and Macrocyclic Chemistry 76, no. 1–2 (2013): 55–60. doi:10.1007/s10847-012-0172-2.
  • Y. Xue, Y. Guan, A. Zheng, and H. Xiao, “Amphoteric calix [8]arene-based Complex for pH-Triggered Drug Delivery,” Colloids and Surfaces B: Biointerfaces 101 (2013): 55–60. doi:10.1016/j.colsurfb.2012.06.022.
  • S. Shinkai, T. Arimura, K. Araki, H. Kawabata, H. Satoh, T. Tsubaki, O. Manabe, and J. Sunamoto, “Syntheses and Aggregation Properties of New Water-Soluble Calixarenes,” Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1989): 2039–45. doi:10.1039/p19890002039.
  • C. D. Gutsche, and I. Alam, “Calixarenes. 23. The Complexation and Catalytic Properties of Water Soluble Calixarenes,” Tetrahedron 44, no. 15 (1988): 4689–94. doi:10.1016/S0040-4020(01)86171-8.
  • D.-S. Guo, and Y. Liu, “Supramolecular Chemistry of p-sulfonatocalix [n] arenes and its Biological Applications,” Accounts of Chemical Research 47, no. 7 (2014): 1925–34. doi:10.1021/ar500009g.
  • Y. Zhou, H. Li, and Y.-W. Yang, “Controlled Drug Delivery Systems Based on Calixarenes,” Chinese Chemical Letters 26, no. 7 (2015): 825–8. doi:10.1016/j.cclet.2015.01.038.
  • W. Yang, and M. M. de Villiers, “The Solubilization of the Poorly Water Soluble Drug Nifedipine by Water Soluble 4-sulphonic calix [n] arenes,” European Journal of Pharmaceutics and Biopharmaceutics 58, no. 3 (2004): 629–36. doi:10.1016/j.ejpb.2004.04.010.
  • Â. de Fátima, S. A. Fernandes, and A. A. Sabino, “Calixarenes as New Platforms for Drug Design,” Current Drug Discovery Technologies 6, no. 2 (2009): 151–70. doi:10.2174/157016309788488302.
  • P. Jiang, H.-W. Sun, R.-X. Shen, J. Shi, and C.-M. Lai, “Molecular Mechanics Study of β-cyclodextrin 6-O-monobenzoate Inclusion Complexes,” Journal of Molecular Structure: THEOCHEM 528, no. 1–3 (2000): 211–7. doi:10.1016/S0166-1280(99)00492-3.
  • C. D. Gutsche, M. Iqbal, and D. Stewart, “Calixarenes. 19. Syntheses Procedures for p-tert-butylcalix [4]arene,” The Journal of Organic Chemistry 51, no. 5 (1986): 742–5. doi:10.1021/jo00355a033.
  • S. Shinkai, K. Araki, T. Tsubaki, T. Arimura, and O. Manabe, “New Syntheses of Calixarene-p-sulphonates and p-nitrocalixarenes,” Journal of the Chemical Society, Perkin Transactions 1 (1987): 2297–9. doi:10.1039/p19870002297.
  • P. Job, “Job's Method of Continuous Variation,” Annali Di Chimica 9 (1928): 113–203.
  • H. A. Benesi, and J. Hildebrand, “A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons,” Journal of the American Chemical Society 71, no. 8 (1949): 2703–7. doi:10.1021/ja01176a030.
  • T. Higuchi, and K. Connors, “Advances in Analytical Chemistry and Instrumentation,” Interscience, New York 4 (1965): 117–212.
  • M. L. Maheshwari, A. A. Memon, S. Memon, U. U. R. Mughal, A. Dayo, N. Memon, M. A. Ghoto, and M. K. Leghari, “Optimization of HPLC Method for Determination of Cefixime Using 2-Thiophenecarboxaldehyde as Derivatizing Reagent: A New Approach,” Saudi Pharmaceutical Journal 23, no. 4 (2015): 444–52. doi:10.1016/j.jsps.2015.01.016.
  • D. C. Harris, Quantitative Chemical Analysis, 6th ed. (USA: W.H. Freeman and Company, 2007).
  • M. T. Faucci, F. Melani, and P. Mura, “Computer-aided Molecular Modeling Techniques for Predicting the Stability of Drug–Cyclodextrin Inclusion Complexes in Aqueous Solutions,” Chemical Physics Letters 358, no. 5–6 (2002): 383–90. doi:10.1016/S0009-2614(02)00410-4.
  • A. C. A. H. J. E. Guyton, “Secretory Functions of the Alimentary Tract,” in Textbook of Medical Physiology, edited by A.C. Guyton, 9th ed. (Philadelphia: WB Saunders Company, 1996), 709–25.
  • A. A. Deshpande, C. Rhodes, and M. Danish, “Intravaginal Drug Delivery,” Drug Development and Industrial Pharmacy 18, no. 11–12 (1992): 1225–79. doi:10.3109/03639049209046329.
  • P. Gupta, K. Vermani, and S. Garg, “Hydrogels: From Controlled Release to pH-responsive Drug Delivery,” Drug Discovery Today 7, no. 10 (2002): 569–79. doi:10.1016/S1359-6446(02)02255-9.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.