pH-triggered intracellular release of doxorubicin from polyaspartamide-encapsulated mesoporous silica nanoparticles

Cheolwon Lim; Eun-Bum Cho; Dukjoon Kim

Korean Journal of Chemical Engineering, Vol.36, No.1, 166-172, January, 2019

DOI10.1007/s11814-018-0185-7 Export Citation

pH-triggered intracellular release of doxorubicin from polyaspartamide-encapsulated mesoporous silica nanoparticles

Cheolwon Lim, Eun-Bum Cho¹, and Dukjoon Kim^†

School of Chemical Engineering, Sungkyunkwan University, Suwon, Gyeonggi 16419, Korea
¹Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul 01811, Korea

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Mesoporous silica nanoparticles (MSNs) conjugating doxorubicin (DOX) via a pH-sensitive cleavable linkage, hydrazine (HYD) were synthesized. MSN-HYD-DOX were encapsulated with the polyaspartamide (PASPAM) grafted with the hydrophilic o-(2-aminoethyl)-o'-methylpoly(ethylene glycol) (PEG) and the cell permeating ligand, biotin (Biotin). The chemical structure of the synthesized MSN-HYD-DOX and PASPAM-g-PEG/Biotin was confirmed using FT-IR and 1H-NMR spectroscopy. The mean diameter of the MSN-HYD-DOX@PASPAM-g-PEG/Biotin nanoparticle was 142 nm and 121 nm, respectively, examined by dynamic light scattering (DLS) and transmission electron microscope (TEM). The HYD bond was effectively cleaved in acidic condition, and thus DOX was released much faster at pH 5.0 than at pH 7.4. The cell viability in MSN-HYD-DOX@PASPAM-g-PEG/Biotin system was much lower than that of the free DOX drug because of efficient intracellular drug delivery associated with the biotin ligand.

Keywords:Mesoporous Silica Nanoparticle;Polysuccinimide;Hydrazone Bond;Doxorubicin

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Matsumura Y, Drug Delivery System, 29, 39 (2014)
Couvreur P, Adv. Drug Deliv. Rev., 65, 21 (2013)
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Teng X, Cheng S, Meng R, Zheng S, Yang L, Ma Q, Jiang W, He J, J. Nanosci. Nanotechnol., 15, 3773 (2015)
Moon JR, Kim MW, Kim D, Jeong JH, Kim JH, Colloid Polym. Sci., 289, 63 (2011)
Kim M, Shin SW, Lim CW, Kim J, Um SH, Kim D, Biomater. Sci., 5, 305 (2017)
Lee M, Jeong J, Kim D, Biomacromolecules, 16, 136 (2014)
Piatkowski M, Bogdal D, Raclavsky K, Int. J. Polym. Anal. Charact., 20, 714 (2015)
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Gil ES, Hudson SM, Prog. Polym. Sci, 29, 1173 (2004)
Patil R, Portilla-Arias J, Ding H, Konda B, Rekechenetskiy A, Inoue S, Black KL, Holler E, Ljubimova JY, Int. J. Mol. Sci., 13(9), 11681 (2012)
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[Related Articles]

[1] Anand P, Kunnumakara AB, Sundaram C, Harikumar KB, Tharakan ST, Lai OS, Sung B, Aggarwal BB, Pharm. Res., 25, 2097 (2008)

[2] Lim CW, Park JH, Ahn CH, Kim D, J. Mater. Chem. B, 3, 2978 (2015)

[3] Akbarzadeh A, Rezaei-Sadabady R, Davaran S, Joo SW, Zarghami N, Hanifehpour Y, Samiei M, Kouhi M, Nejati-Koshki K, Nanoscale Res. Lett., 8, 102 (2013)

[4] Kesharwani P, Jain K, Jain NK, Prog. Polym. Sci, 39, 268 (2014)

[5] Kango S, Kalia S, Celli A, Njuguna J, Habibi Y, Kumar R, Prog. Polym. Sci, 38, 1232 (2013)

[6] Prabhakar U, Maeda H, Jain RK, Sevick-Muraca EM, Cancer Res., 73, 2412 (2013)

[7] Matsumura Y, Drug Delivery System, 29, 39 (2014)

[8] Couvreur P, Adv. Drug Deliv. Rev., 65, 21 (2013)

[9] Wang Y, Zhao Q, Han N, Bai L, Li J, Liu J, Che E, Hu L, Zhang Q, Jiang T, Nanomedicine: NBM, 11, 313 (2015)

[10] Tarn D, Ashley CE, Xue M, Carnes EC, Zink JI, Brinker CJ, Accounts Chem. Res., 46, 792 (2013)

[11] Yu S, Wu G, Gu X, Wang J, Wang Y, Gao H, Ma J, Colloids Surf. B: Biointerfaces, 103, 15 (2013)

[12] Teng X, Cheng S, Meng R, Zheng S, Yang L, Ma Q, Jiang W, He J, J. Nanosci. Nanotechnol., 15, 3773 (2015)

[13] Moon JR, Kim MW, Kim D, Jeong JH, Kim JH, Colloid Polym. Sci., 289, 63 (2011)

[14] Kim M, Shin SW, Lim CW, Kim J, Um SH, Kim D, Biomater. Sci., 5, 305 (2017)

[15] Lee M, Jeong J, Kim D, Biomacromolecules, 16, 136 (2014)

[16] Piatkowski M, Bogdal D, Raclavsky K, Int. J. Polym. Anal. Charact., 20, 714 (2015)

[17] Craparo EF, Cavallaro G, Bondi ML, Mandracchia D, Giammona G, Biomacromolecules, 7(11), 3083 (2006)

[18] Bae Y, Nishiyama N, Fukushima S, Koyama H, Yasuhiro M, Kataoka K, Bioconjugate Chem., 16, 122 (2005)

[19] Gil ES, Hudson SM, Prog. Polym. Sci, 29, 1173 (2004)

[20] Patil R, Portilla-Arias J, Ding H, Konda B, Rekechenetskiy A, Inoue S, Black KL, Holler E, Ljubimova JY, Int. J. Mol. Sci., 13(9), 11681 (2012)

[21] Li X, Zhang L, Dong X, Liang J, Shi J, Microporous Mesoporous Mater., 102, 151 (2007)

[22] Paolo N, Guido A, Franco B, Francesco C, Guido G, J. Med. Chem., 16, 893 (1973)