Preparation of redox-sensitive β-CD-based nanoparticles with controlled release of curcumin for improved therapeutic effect on liver cancer in vitro

Dae Hyeok Yang; Hyun Joo Kim; Jae Kwang Kim; Heung Jae Chun; Kyeongsoon Park

Journal of Industrial and Engineering Chemistry, Vol.45, 156-163, January, 2017

DOI10.1016/j.jiec.2016.09.018 Export Citation

Preparation of redox-sensitive β-CD-based nanoparticles with controlled release of curcumin for improved therapeutic effect on liver cancer in vitro

Dae Hyeok Yang¹, Hyun Joo Kim^{1, 2}, Jae Kwang Kim³, Heung Jae Chun^{1, 2, †}, and Kyeongsoon Park⁴

¹Institute of Cell and Tissue Engineering, College of Medicine, The Catholic University of Korea, Seoul 06591, Republic of Korea
²Department of Biomedical Sciences, College of Medicine, The Catholic University of Korea, Seoul 06591, Republic of Korea
³Department of Internal Medicine, Bucheon St. Mary’s Hospital, College of Medicine, The Catholic University of Korea, Bucheon-si, Gyeonggi-do 14647, Republic of Korea
⁴Division of Bio-imaging, Chuncheon Center, Korea Basic Science Institute, Chuncheon-si, Gangwon-do 24341, Republic of Korea

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A redox-sensitive beta-cyclodextrin nanoparticle (β-CD NP) system was prepared for the controlled release of curcumin (CUR), and its therapeutic efficacy on liver cancer was compared with that of CUR in vitro. 1-Dodecanethiol (DDT) was conjugated to per-6-thiol-β-CD by disulfide bond formation though an oxidation reaction (β-CD-ss-DDT). Rhodamine B (RhoB) was included into the β-CD-ss-DDT cavity by inclusion complex formation (β-CD-ss-DDT-ic-RhoB). CUR was encapsulated into β-CD-ss-DDT-ic-RhoB aggregates by self-assembly through dialysis method. The composition, morphology, size distribution and zeta potential of β-CD-ss-DDT-ic-RhoB NPs were characterized by proton nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM) and dynamic light scattering (DLS), respectively. It was found that CUR was released from β-CDss-DDT-ic-RhoB/CUR NPs due to the dissociation of β-CD-ss-DDT through a reduction reaction. β-CD-ss-DDT-ic-RhoB/CUR NPs had a higher cellular uptake ratio and a greater anticancer effect on mouse hepatoma Hepa 1-6 cells than CUR, mainly attributed to the improved water-solubility of CUR after encapsulating it in the NPs. Our findings suggest that β-CD-ss-DDT-ic-RhoB NPs can be used as nanocarriers for delivering CUR into cancer cells, thereby serving as a clinical therapeutic agent for liver cancer treatment.

Keywords:Beta-cyclodextrin nanoparticle (β-CD NP);system;Curcumin;Redox-sensitive;Disulfide bond formation;Liver cancer

[References]

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[Referenced By]

[1] DeVita VT, Chu E, Cancer Res., 68, 8643 (2008)

[2] Kalepu S, Nekkanti V, Acta Pharmacol. Sin. B, 5, 442 (2015)

[3] Narvekar M, Xue HY, Eoh JY, Wong HL, AAPS PharmSciTech, 15, 822 (2014)

[4] Fermeglia M, Ferrone M, Lodi A, Pricl S, Carbohydr. Polym., 53, 15 (2003)

[5] Mizusako H, Tagami T, Hattori K, Ozeki T, J. Pharm. Sci., 104, 2934 (2015)

[6] Zerkoune L, Angelova A, Lesieur S, Nanomaterials, 4, 741 (2014)

[7] Perez-Tomas R, Curr. Med. Chem., 13, 1859 (2006)

[8] Gottesman MM, Fojo T, Bates SE, Nat. Rev. Cancer, 2, 48 (2002)

[9] Nobili S, Lippi D, Witort E, Donnini M, Bausi L, Mini E, Capaccioli S, Pharmacol. Res., 59, 365 (2009)

[10] Newman DJ, Cragg GM, J. Nat. Prod., 70, 461 (2007)

[11] Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB, Mol. Pharm., 4, 807 (2007)

[12] Kolivoska V, Mohos M, Pobelov IV, Rohrbach S, Yoshida K, Hong WJ, Fu YC, Moreno-Garcia P, Meszaros G, Broekmann P, Hromadova M, Sokolova R, Valasek M, Wandlowski T, Chem. Commun., 50, 11757 (2014)

[13] Kalyanasundaram K, Thomas JK, J. Am. Chem. Soc., 99, 2039 (1977)

[14] Liu Y, Chen Y, Liu SX, Guan XD, Wada T, Inoue Y, Org. Lett., 3, 1657 (2001)

[15] Lincoln SF, Coates JH, Schiller RL, J. Incl. Phenom., 5, 709 (1987)

[16] Nah JW, Paek YW, Jeong YI, Kim DW, Cho CS, Kim SH, Kim MY, Arch. Pharm. Res., 21, 418 (1998)

[17] Lee JY, Chung SJ, Cho HJ, Kim DD, Adv. Funct. Mater., 25(24), 3705 (2015)

[18] Beig A, Agbaria R, Dahan A, PLOS ONE, 8, e68237 (2013)

[19] He C, Hu Y, Yin L, Tang C, Yin C, Biomaterials, 31, 3657 (2010)

[20] Kanapathipillai M, Brock A, Ingber DE, Adv. Drug Deliv. Rev., 79-80, 107 (2014)

[21] Mura S, Nicolas J, Couvreur P, Nat. Mater., 12(11), 991 (2013)

[22] Nagahama K, Sano Y, Kumano T, Bioorg. Med. Chem. Lett., 25, 2519 (2015)

[23] Hasegawa T, Kondo Y, Koizumi Y, Sugiyama T, Takeda A, Ito S, Hamada F, Bioorg. Med. Chem., 17, 6015 (2009)

[24] Tsai SW, Liaw JW, Kao YC, Huang MY, Lee CY, Rau LR, Huang CY, Wei KC, Ye TC, PLOS ONE, 8, e76545 (2013)

[25] Du Q, Deng S, Shen KP, Hu B, Pharm. Clin. Chin. Mater. Med., 27, 28 (2011)