Citation: Zhang Ru, Yuan Linlin, Sun Kaiyue, Wang Shan, Geng Lina, Zhang Jianjun. Preparation and Partition Coefficient Determination of Nano-Resveratrol Liposomes[J]. Acta Physico-Chimica Sinica, ;2020, 36(6): 190509. doi: 10.3866/PKU.WHXB201905090 shu

Preparation and Partition Coefficient Determination of Nano-Resveratrol Liposomes

  • Corresponding author: Geng Lina, genglina0102@126.com
  • Received Date: 31 May 2019
    Revised Date: 21 June 2019
    Accepted Date: 21 June 2019
    Available Online: 27 June 2019

    Fund Project: The project was supported by the National Natural Science Foundation of China (31201305) and Natural Science Foundation of Hebei Province (B2019205054)the National Natural Science Foundation of China 31201305Natural Science Foundation of Hebei Province B2019205054

  • Resveratrol is a natural polyphenol and phytoalexin with anti-inflammatory, anti-oxidant, anti-cancer, and neuroprotective effects. However, resveratrol exhibits low solubility, light sensitivity, poor absorption by oral administration, and short cycle time, which greatly limit its applications in medicine and the food industry. To overcome these limitations, a nano-resveratrol liposome (RES-Lip) was prepared. As a drug carrier, liposomes have many advantages such as good targeting properties, low toxicity, biocompatibility, and long-term sustained release. In liposomal studies, the oil-water (n-octanol-water) partition coefficient (Po/w) is often used to predict the encapsulation and drug loading efficiencies. This method focuses on the lipophilicity of the drug, reflecting its hydrophobic action while ignoring the biological properties of the biofilm. The liposome-water partition coefficient (Plip/w) reflects the structure of the biofilms and its interaction with drugs governed by factors including hydrophobicity, electrostatic forces, and hydrogen bonding. Herein, RES-Lip was successfully prepared using a rotary-evaporated film-ultrasonication method and subsequent characterization by transmission electron microscopy (TEM) and dynamic light scattering (DLS). The effects of the membrane to material ratio (lecithin to cholesterol mass ratio mPC : mChol = 5 : 1, 8 : 1, 10 : 1, and 12 : 1) and drug to lipid ratio (drug to lecithin mass ratio mRES : mPC = 1 : 25, 1 : 40, 1 : 50, and 1 : 60) of nano-resveratrol liposomes on the liposome-water partition coefficient (Plip/w) were determined. Changes in the oil-water partition coefficient (lgPo/w) and liposome-water partition coefficient (lgPlip/w) as a function of pH were also determined. In addition, the Gibbs free energy between the drug and phospholipid bilayer membrane in RES-Lip was calculated. The results showed that RES-Lip adopted a spherical vesicle structure with a particle size of approximately 100 nm. When the membrane to material ratio was 10 : 1 and the drug to lipid ratio was 1 : 40, lgPlip/w was maximized, indicating that the combined forces between RES and the phospholipid membrane were the highest at these ratios. The trends of lgPo/w and lgPlip/w as a function of pH were the same, indicating that the main interaction force between RES and the phospholipid membrane was the hydrophobic effect with secondary interaction forces of hydrogen bonding and electrostatic interaction. The Gibbs free energy between the RES and liposome membrane in RES-Lip was determined to be −17.07 kJ·mol−1.
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    1. [1]

      Arora, D.; Jaglan, S. Environ. Chem. Lett. 2018, 16 (1), 35. doi: 10.1007/s10311-017-0660-0  doi: 10.1007/s10311-017-0660-0

    2. [2]

      Yucel, C.; Karatoprak, G. S.; Aktas, Y. J. Nanosci. Nanotechnol. 2018, 18 (6), 3856. doi: 10.1166/jnn.2018.15247  doi: 10.1166/jnn.2018.15247

    3. [3]

      Elshaer, M.; Chen, Y. R.; Wang, X. J.; Tang, X. W. Life Sci. 2018, 207, 340. doi: 10.1016/j.lfs.2018.06.028  doi: 10.1016/j.lfs.2018.06.028

    4. [4]

      Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W.; Fong, H. H.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; et al. Science 1997, 275 (5297), 218. doi: 10.1126/science.275.5297.218  doi: 10.1126/science.275.5297.218

    5. [5]

      Huang, X. T.; Li, X.; Xie, M. L.; Huang, Z.; Huang, Y. X.; Wu, G. X.; Peng, Z. R.; Sun, Y. N.; Ming, Q. L.; Liu, Y. X.; et al. Chem.-Biol. Interact. 2019, 306, 29. doi: 10.1016/j.cbi.2019.04.001  doi: 10.1016/j.cbi.2019.04.001

    6. [6]

      Wang, M. L.; Li, L.; Zhang, X. W.; Liu, Y. P.; Zhu, R. Y.; Liu, L. X.; Fang, Y.; Gao, Z. R.; Gao, D. W. ACS Sustain. Chem. Eng. 2018, 6 (12), 17124. doi: 10.1021/acssuschemeng.8b04507  doi: 10.1021/acssuschemeng.8b04507

    7. [7]

      Hammoud, Z.; Gharib, R.; Fourmentin, S.; Elaissari, A.; Greige-Gerges, H. Int. J. Pharm. 2019, 561, 161. doi: 10.1016/j.ijpharm.2019.02.022  doi: 10.1016/j.ijpharm.2019.02.022

    8. [8]

      Van Tran, V.; Moon, J. Y.; Lee, Y. C. J. Control. Release 2019, 300, 114. doi: 10.1016/j.jconrel.2019.03.003  doi: 10.1016/j.jconrel.2019.03.003

    9. [9]

      Wehbe, N.; Patra, D.; Abdel-Massih, R. M.; Baydoun, E. Colloid Surf. B-Biointerfaces 2019, 173, 94. doi: 10.1016/j.colsurfb.2018.09.053  doi: 10.1016/j.colsurfb.2018.09.053

    10. [10]

      Kristl, J.; Teskac, K.; Caddeo, C.; Abramovic, Z.; Sentjurc, M. Eur. J. Pharm. Biopharm. 2009, 73 (2), 253. doi: 10.1016/j.ejpb.2009.06.006  doi: 10.1016/j.ejpb.2009.06.006

    11. [11]

      Ethemoglu, M. S.; Seker, F. B.; Akkaya, H.; Kilic, E.; Aslan, I.; Erdogan, C. S.; Yilmaz, B. Neuroscience 2017, 357, 12. doi: 10.1016/j.neuroscience.2017.05.026  doi: 10.1016/j.neuroscience.2017.05.026

    12. [12]

      Wang, H. Y.; Zhang, M. J.; Yang, Q. Cereals & Oils 2018, 31 (3), 93.  doi: 10.3969/j.issn.1008-9578.2018.03.025

    13. [13]

      Wang, Y. C.; Xu, H. L.; Fu, Q.; Ma, R.; Xiang, J. Z. China J. Chin. Mater. Med. 2011, 36 (8), 1060.  doi: 10.4268/cjcmm20110826

    14. [14]

      Wei, G.; Xv, H.; Ma, Y.; Li, S. M.; Zheng, J. M. Acta Pharm. Sin. 2001, No. 9, 707.  doi: 10.3321/j.issn:0513-4870.2001.09.018

    15. [15]

      Deng, Y. J.; Shi, S. F.; Gu, X. X. Acta Pharm. Sin. 1988, No. 7, 539.

    16. [16]

      Ma, H. Q.; Mu, J.; Liu, Y.; Zhang, H.; Ding, T.; Tian, H.; Wang, C. L.; Li, Y.; Liu, F. Northwest Pharm. J. 2019, 34 (1), 84.  doi: 10.3969/j.issn.1004-2407.2019.01.021

    17. [17]

      Mohsen-Nia, M.; Ebrahimabadi, A. H.; Niknahad, B. J. Chem. Thermodyn. 2012, 54, 393. doi: 10.1016/j.jct.2012.05.021  doi: 10.1016/j.jct.2012.05.021

    18. [18]

      Barzanti, C.; Evans, R.; Fouquet, J.; Gouzin, L.; Howarth, N. M.; Kean, G.; Levet, E.; Wang, D.; Wayemberg, E.; Yeboah, A. A.; et al. Tetrahedron Lett. 2007, 48 (19), 3337. doi: 10.1016/j.tetlet.2007.03.085  doi: 10.1016/j.tetlet.2007.03.085

    19. [19]

      van Balen, G. P.; Martinet, C. A. M.; Caron, G.; Bouchard, G.; Reist, M.; Carrupt, P. A.; Fruttero, R.; Gasco, A.; Testa, B. Med. Res. Rev. 2004, 24 (3), 299. doi: 10.1002/med.10063  doi: 10.1002/med.10063

    20. [20]

      Endo, S.; Mewburn, B.; Escher, B. I. Chemosphere 2013, 90 (2), 505. doi: 10.1016/j.chemosphere.2012.07.069  doi: 10.1016/j.chemosphere.2012.07.069

    21. [21]

      Chavez-Capilla, T.; Maher, W.; Kelly, T.; Foster, S. J. Environ. Sci. 2016, 49, 222. doi: 10.1016/j.jes.2016.08.007  doi: 10.1016/j.jes.2016.08.007

    22. [22]

      Esteves, F.; Moutinho, C.; Matos, C. J. Liposome Res. 2013, 23 (2), 83. doi: 10.3109/08982104.2012.742539  doi: 10.3109/08982104.2012.742539

    23. [23]

      Ikonen, M.; Murtomaki, L.; Kontturi, K. J. Electroanal. Chem. 2007, 602 (2), 189. doi: 10.1016/j.jelechem.2006.12.014  doi: 10.1016/j.jelechem.2006.12.014

    24. [24]

      Lu, W. G.; Chen, T. T.; Wang, P. Q.; Li, J.; Ren, D. Q. Chin. J. Pharmaceut. 2008, No. 8, 591.  doi: 10.3969/j.issn.1001-8255.2008.08.012

    25. [25]

      Zhong, H. J.; Deng, Y. J.; Wang, L. J.; Du, S. Wang, X. M.; Chen, Y. J. Shenyang Pharm. Univ. 2005, No. 2, 110.

    26. [26]

      Li, N. N.; Geng, L. N.; Wang, L.; Yuan, L. L.; Chang, Y. Z.; Zhang, J. J. Acta Phys. -Chim. Sin. 2015, 31 (11), 2043.  doi: 10.3866/PKU.WHXB201509141

    27. [27]

      Huang, C.; Mason, J. T. Proc. Natl. Acad. Sci. U. S. A. 1978, 75 (1), 308. doi: 10.1073/pnas.75.1.308  doi: 10.1073/pnas.75.1.308

    28. [28]

      Russell, C. J.; Thorgeirsson, T. E.; Shin, Y. K. Biochemistry 1996, 35 (29), 9526. doi: 10.1021/bi960614+  doi: 10.1021/bi960614+

    29. [29]

      Li, X.; Lv, H. F.; Ying, M. F.; Zhao, Y. Z.; Xu, Y. Y.; Zhao, R. Chin. J. Mod. Appl. Pharm. 2017, 34 (1), 72.  doi: 10.13748/j.cnki.issn1007-7693.2017.01.017

    30. [30]

      Suo, X. B.; Li, M. L.; Wang, Y. Q.; Qiu, J. S. Chin. Pharm. J. 2009, 44 (23), 1796.

    31. [31]

      Wang, Z. X.; Deng, Y. J.; Zhang, X. P. Acta Pharm. Sin. 2006, 41 (4), 318.  doi: 10.3321/j.issn:0513-4870.2006.04.005

    32. [32]

      Quan, D. Q.; Ge, M.; Gao, L. J. Chin. Pharm. J. 2012, 47 (12), 1001.

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