Highly Enhanced Loading Quality of Curcumin onto Carboxylated Folate Graphene Oxide

Document Type : Article

Authors

1 School of Chemical Engineering, College of Engineering, University of Tehran, Tehran, Iran

2 School of Chemical Engineering, College of Engineering, University of Tehran, Tehran, Iran.

Abstract

This research focuses on loading of curcumin (Cur) anticancer drug onto nanocarriers, based on graphene oxide (GO), and improvement of loading efficiency. Surface of synthesized GO was modified by citric acid (CA) and functionalized by folic acid (FA) as a targeting agent. The functionalized GO by CA (CGO) and FA (GO-FA) were analyzed by Fourier transform infrared (FTIR). Furthermore FA was conjugated to the composite of CGO to prepare stabilized and targeted GO. The CGO-FA composite was characterized by FTIR and scanning electron microscopy (SEM) analysis. Thereafter, Cur as hydrophobic drug was loaded onto GO, CGO, GO-FA, and CGO-FA. Loaded Cur onto GO was characterized by SEM, FTIR and UV-Vis spectrophotometry. To increase the loading efficiency of Cur, the effects of water and ethanol as solvents and the weight ratios of initial Cur to GO (Cur/GO) were evaluated on the loading efficiency by response surface methodology. Comparing the loaded drug efficiencies onto different carriers demonstrated maximum loading onto CGO compared with the other carriers at optimal conditions. The optimized condition was concluded at 25.6% water in solution and 1.66 ratio of Cur/GO to achieve 112.5% loading efficiency and 13.5 ratio of loading efficiency/weight of initial Cur, respectively.

Keywords

Main Subjects


References
1. Orecchioni, M., Cabizza, R., Bianco, A., and Delogu,
L.G. \Graphene as cancer theranostic tool: progress
and future challenges", Theranostics, 5(7), p. 710
(2015).
2. Gomez, M.L., Malmierca, E., de Gorgolas, M., and
Casado, E. \Cancer in developing countries: the next
most preventable pandemic, The global problem of
cancer", Critical Reviews in Oncology/Hematology,
88(1), pp. 117-122 (2013).
3. Yang, K., Zhang, S., Zhang, G., Sun, X., Lee, S.T.,
and Liu, Z. \Graphene in mice: Ultrahigh in vivo
tumor uptake and ecient photothermal therapy",
Nano Letters, 10(9), pp. 3318-3323 (2010).
4. Liu, J., Cui, L., and Losic, D. \Graphene and graphene
oxide as new nanocarriers for drug delivery applications",
Acta Biomaterialia, 9(12), pp. 9243-9257
(2013).
5. Miao, W., Shim, G., Lee, S., Lee, S., Choe, Y.S., and
Oh, Y.K. \Safety and tumor tissue accumulation of
pegylated graphene oxide nanosheets for co-delivery
of anticancer drug and photosensitizer", Biomaterials,
34(13), pp. 3402-3410 (2013).
6. Sahoo, N.G., Bao, H., Pan, Y., Pal, M., Kakran, M.,
Cheng, H.K., Li, L., and Tan, L.P. \Functionalized
carbon nanomaterials as nanocarriers for loading and
delivery of a poorly water-soluble anticancer drug: A
comparative study", Chem. Communications, 47(18),
pp. 5235-5237 (2011).
7. Goncalves, G., Vila, M., Portoles, M.T., Vallet-Regi,
M., Gracio, J., and Marques, P.A. \Nano-graphene
oxide: A potential multifunctional platform for cancer
therapy", Advanced Healthcare Materials, 2(8), pp.
1072-1090 (2013).
8. Liu, Z., Robinson, J.T., Sun, X., and Dai, H. \PEgylated
nanographene oxide for delivery of waterinsoluble
cancer drugs", J. of the American Chem.
Soc., 130(33), pp. 10876-10877 (2008).
9. Zhou, H., Zhang, B., Zheng, J., Yu, M., Zhou, T.,
Zhao, K., andWei, T. \The inhibition of migration and
invasion of cancer cells by graphene via the impairment
of mitochondrial respiration", Biomaterials, 35(5), pp.
1597-1607 (2014).
10. Dreyer, D.R. Park, S., Bielawski, C.W., and Ruo ,
R.S. \The chemistry of graphene oxide", Chem. Soc.
Reviews, 39(1), pp. 228-240 (2010).
11. Nurunnabi, M., Khatun, Z., Huh, K.M., Park, S.Y.,
Lee, D.Y., Cho, K.J., and Lee, Y.K. \In vivo biodistribution
and toxicology of carboxylated graphene quantum
dots", ACS Nano, 7(8), pp. 6858-6867 (2013).
12. Wang, X., Sun, X., Lao, J., He, H., Cheng, T.,
Wang, M., and Huang, F. \Multifunctional graphene
quantum dots for simultaneous targeted cellular imaging
and drug delivery", Colloids and Surfaces B:
Biointerfaces, 122, pp. 638-644 (2014).
13. Zhang, L., Xia, J., Zhao, V., Liu, L., and Zhang,
Z. \Functional graphene oxide as a nanocarrier for
controlled loading and targeted delivery of mixed
anticancer drugs", Small, 6(4), pp. 537-544 (2010).
14. Kurien, B.T. and Sco eld, R.H. \Heat-solubilized
curcumin should be considered in clinical trials for increasing
bioavailability", Clinical Cancer Res., 15(2),
p. 747 (2009).
15. Liang, G., Shao, L.,Wang, Y., Zhao, C., Chu, Y., Xiao,
J., Zhao, Y., Li, X., and Yang, S. \Exploration and
synthesis of curcumin analogues with improved structural
stability both in vitro and in vivo as cytotoxic
agents", Bioorganic & Medicinal Chemistry, 17(6), pp.
2623-2631 (2009).
16. Anand, P., Kunnumakkara, A.B., Newman, R.A., and
Aggarwal, B.B. \Bioavailability of curcumin: Problems
and promises", Molecular Pharmaceutics, 4(6),
pp. 807-818 (2007).
17. Some, S., Gwon, A.R., Hwang, E., Bahn, G.H., Yoon,
Y., Kim, Y., and Lee, H. \Cancer therapy using ultrahigh
hydrophobic drug-loaded graphene derivatives",
Scienti c Reports, 4, pp. 6314-6322 (2014).
18. Maity, A.R., Chakraborty, A., Mondal, A., and Jana,
N.R. \Carbohydrate coated, folate functionalized colloidal
graphene as a nanocarrier for both hydrophobic
and hydrophilic drugs", Nanoscale, 6(5), pp. 2752-2758
(2014).
19. Kianpour, B., Ebrahimi, A., Salehi, Z., and Fatemi,
S. \Evaluating the e ect of graphite source and operating
conditions on the synthesis of graphene oxide",
Chemical and Petroleum Engineering, 50(2), pp. 37-45
(2017).
20. Kianpour, B., Salehi, Z., Ebrahimi, A., and Fatemi, S.
\Comparison of two synthesis methods for graphene
oxide: the e ect of operating conditions", 3rd International
Conference on Nanotechnology (ICN2015),
August 27-28, Istanbul, Turkey (2015).
21. Ebrahimi, A., Salehi, Z., Kianpour, B., and Fatemi, S.
\Evaluation of graphite source in
uence on synthesis
of graphene oxide", 3rd International Conference on
Nanotechnology (ICN2015), August 27-28, Istanbul,
Turkey (2015).
22. Pavia, D., Lampman, G., Kriz, G., and Vyvyan, J.
\Introduction to spectroscopy", Cengage Learning, 4th
Ed., Chap. 2, pp. 15-88 (2008).
23. Hatamie, S., Akhavan, O., Sadrnezhaad, S.K., Ahadian,
M.M., Shirolkar, M.M., and Wang, H.Q.
\Curcumin-reduced graphene oxide sheets and their
e ects on human breast cancer cells", Materials Sci.
and Eng. C, 55, pp. 482-489 (2015).
24. Snee, R.D. \Experimental designs for quadratic models
in constrained mixture spaces", Technometrics, 17(2),
pp. 149-159 (1975).
1394 B. Kianpour et al./Scientia Iranica, Transactions C: Chemistry and ... 25 (2018) 1384{1394
25. Marquardt, D.W. and Snee, R.D. \Test statistics for
mixture models", Technometrics, 16(4), pp. 533-537
(1974).
26. Ghadiri, M., Fatemi, S., Vatanara, A., Doroud, D.,
Najafabadi, A.R., Darabi, M., and Rahimi, A.A.
\Loading hydrophilic drug in solid lipid media as
nanoparticles: Statistical modeling of entrapment ef-
ciency and particle size", Int. J. of Pharmaceutics,
424(1), pp. 128-137 (2012).
27. Xu, D.H., Wang, S., Mei, X.T., Luo, X.J., and Xu,
S.B. \Studies on solubility enhancement of curcumin
by polyvinylpyrrolidione K30", Zhong Yao Cai, J.
of Chinese Medicinal Materials, 31(3), pp. 438-442
(2008).