Phenylboronic acid-conjugated cationic methylcellulose for hepatocellular carcinoma-targeted drug/gene co-delivery systems

Ju Hyeon Jeon; Jae Hong Park; Tae-il Kim

Journal of Industrial and Engineering Chemistry, Vol.75, 148-157, July, 2019

DOI10.1016/j.jiec.2019.03.016 Export Citation

Phenylboronic acid-conjugated cationic methylcellulose for hepatocellular carcinoma-targeted drug/gene co-delivery systems

Ju Hyeon Jeon¹, Jae Hong Park¹, and Tae-il Kim^{1, 2, †}

¹Department of Biosystems & Biomaterials Science and Engineering, College of Agriculture and Life Sciences, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea
²Research Institute of Agriculture and Life Sciences, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea

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Phenylboronic acid-conjugated cationic methylcellulose (MCPEI-PBA) was synthesized and character- ized for hepatocellular carcinoma-targeted drug/gene co-delivery systems. MCPEI-PBA was obtained by reductive amination of polyethylenimine 2k to oxidized methylcellulose and conjugation of PBA. MCPEIPBA could form nano-aggregates via B-N coordinate bonding and hydrophobic interaction and also form positively charged and nano-sized polyplexes. Cytotoxicity of MCPEI-PBA was low and MCPEI-PBA showed higher transfection efficiency than PEI25k in hepatocellular carcinoma. Galactose pretreatment experiment suggested its specific interaction with asialoglycoprotein receptors. MCPEI-PBA could encapsulate doxorubicin (Dox) efficiently. Finally, MCPEI-PBA/Dox/pJDK-apoptin complexes showed high anticancer activity due to the combinatorial effect of Dox and expressed apoptin.

Keywords:Drug/gene co-delivery;Methylcellulose;Phenylboronic acid;Nano-aggregates;Hepatocellular carcinoma-targeting

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[2] Yang Z, Gao D, Cao Z, Zhang C, Cheng D, Liu J, Shuai X, Biomater. Sci., 3, 1035 (2015)

[3] Khan M, Ong ZY, Wiradharma N, Attia ABE, Yang YY, Adv. Healthc. Mater., 1, 373 (2012)

[4] Thorn CF, Oshiro C, Marsh S, Hernandez-Boussard T, McLeod H, Klein TE, Altman RB, Pharmacogenet. Genomics, 21, 440 (2011)

[5] Nasatto PL, Pignon F, Silveira JLM, Duarte MER, Noseda MD, Rinaudo M, Polymers, 7, 777 (2015)

[6] Liang HF, Hong MH, Ho RM, Chung CK, Lin YH, Chen CH, Sung HW, Biomacromolecules, 5(5), 1917 (2004)

[7] Wang Y, Lapitsky Y, Kang CE, Shoichet MS, J. Control. Release, 140, 218 (2009)

[8] Gupta D, Tator CH, Shoichet MS, Biomaterials, 27, 2370 (2006)

[9] Hirrien M, Chevillard C, Desbrieres J, Axelos MAV, Rinaudo M, Polymer, 39(25), 6251 (1998)

[10] Kim K, Ryu K, Kim TI, Carbohydr. Polym., 110, 268 (2014)

[11] Sanjoh M, Miyahara Y, Kataoka K, Matsumoto A, Anal. Sci., 30, 111 (2014)

[12] Ryu JH, Lee GJ, Shih YRV, Kim TI, Varghese S, Curr. Med. Chem., 26, 1 (2019)

[13] Lorand JP, Edwards JO, J. Org. Chem., 23, 769 (1959)

[14] Springsteen G, Wang B, Tetrahedron, 58, 5291 (2002)

[15] Nishiyabu R, Kubo Y, James TD, Fossey JS, Chem. Commun., 47, 1124 (2011)

[16] Choi JY, Ryu K, Lee GJ, Kim K, Kim TI, Biomacromolecules, 16(9), 2715 (2015)

[17] Maddika S, Mendoza FJ, Hauff K, Zamzow CR, Paranjothy T, Los M, Cancer Biol. Ther., 5, 10 (2006)

[18] Bae Y, Rhim HS, Lee S, Ko KS, Han J, Choi JS, J. Pharm. Sci., 106, 1618 (2017)

[19] Alvisi G, Poon IK, Jans DA, Drug Resist. Update, 9, 40 (2006)

[20] Argiris K, Panethymitaki C, Tavassoli M, Exp. Biol. Med., 236, 524 (2011)

[21] Ray GB, Chakraborty I, Moulik SP, J. Colloid Interface Sci., 294(1), 248 (2006)

[22] Kur-Kowalska K, Przybyt M, Ziołczyk P, Sowinski P, Miller E, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 129, 320 (2014)

[23] James TD, Sandanayake KR, Shinkai S, Nature, 374(6520), 345 (1995)

[24] Gabrielson NP, Pack DW, Biomacromolecules, 7(8), 2427 (2006)

[25] Ji M, Li P, Sheng N, Liu L, Pan H, Wang C, Cai L, Ma Y, ACS Appl. Mater. Interfaces, 8, 9565 (2016)

[26] Zauner W, Ogris M, Wagner E, Adv. Drug Deliv. Rev., 30, 97 (1998)

[27] Yang W, Fan H, Gao X, Gao S, Karnati VVR, Ni W, Hooks WB, Carson J, Weston B, Wang B, Chem. Biol., 11, 439 (2004)

[28] D’Souza AA, Devarajan PV, J. Control. Release, 203, 126 (2015)

[29] Zhang X, Zhang Z, Su X, Cai M, Zhuo R, Zhong Z, Biomaterials, 34, 10296 (2013)

[30] Wang X, Tang H, Wang C, Zhang J, Wu W, Jiang X, Theranostics, 6, 1378 (2016)

[31] Wang C, Zhang Z, Chen B, Gu L, Li Y, Yu SJ, Colloid Interface Sci., 516, 332 (2018)

[32] Naicker K, Ariatti M, Singh M, Colloids Surf. B: Biointerfaces, 122, 482 (2014)

[33] Kim SH, Goto M, Akaike T, J. Biol. Chem., 276, 35312 (2001)

[34] Geffen I, Fuhrer C, Leitinger B, Weiss M, Huggel K, Griffiths G, Spiess M, J. Biol. Chem., 268, 20772 (1993)

[35] Zhou B, Zhao L, Shen M, Zhao J, Shi X, J. Mater. Chem. B, 5, 1542 (2017)

[36] Wang X, Zhen X, Wang J, Zhang J, Wu W, Jiang X, Biomaterials, 34, 4667 (2013)

[37] Swain SM, Whaley FS, Ewer MS, Cancer, 97, 2869 (2003)

[38] Gillet JP, Gottesman MM, Methods Mol. Biol., 596, 47 (2010)

[39] Amirmahani N, Mahmoodi NO, Galangash MM, Ghavidast A, J. Ind. Eng. Chem., 55, 21 (2017)