Acidic pH-stimulated tiotropium release from porous poly(lactic-co-glycolic acid) microparticles containing 3-diethylaminopropyl-conjugated hyaluronate

Sol Kim; Dong Sup Kwag; Dong Jin Lee; Eun Seong Lee

Macromolecular Research, Vol.24, No.2, 176-181, February, 2016

DOI10.1007/s13233-016-4022-8 Export Citation

Acidic pH-stimulated tiotropium release from porous poly(lactic-co-glycolic acid) microparticles containing 3-diethylaminopropyl-conjugated hyaluronate

Sol Kim, Dong Sup Kwag, Dong Jin Lee, and Eun Seong Lee^†

Department of Biotechnology, The Catholic University of Korea, 43-1 Yeokgok 2-dong, Wonmi-gu, Bucheon, Gyeonggi, 14662, Korea

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In this study, we developed porous poly(lactide-co-glycolide) (PLGA) microparticles (PM) exhibiting pH-activated drug release properties. The PMs were prepared via the water-in-oil-in-water (W1/O/W2) multi-emulsion method using PLGA, 3-diethylaminopropyl amine (DEAP)-conjugated hyaluronate (HA) (HA-DEAP), and an anti-cholinergic model drug (tiotropium). Here, HA-DEAP was incorporated into the PMs; it acted as a drug release activator, accelerating drug release. In vitro drug release studies revealed that the tiotropium was released from the PMs as their pores were destabilized by eletrostatic interactions between the carboxyl groups (negatively charged) of the HA molecules and the tertiary amine groups (positively charged) of the DEAP moieties under acidic environments. This PLGA microparticle system, which contains a HA-DEAP, could provide unique advantages in treating chronic obstructive pulmonary disease (COPD) with chronic respiratory acidosis.

Keywords:porous microparticles;poly(lactide-co-glycolide);tiotropium;3-diethylaminopropyl;respiratory acidosis

[References]

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Vogelmeier CF, Asijee GM, Kupas K, Beeh KM, N. Engl. J. Med., 364, 1093 (2011)
Dolovich MB, Dhand R, Lancet, 377, 1032 (2011)
Svedsater H, Dale P, Garrill K, Walker R, Woepse MW, BMC Pulm. Med., 13, 72 (2013)
Hickey J, J. Pharm. Sci., 102, 1165 (2013)
De Savi C, Cox RJ, Warner DJ, Cook AR, Dickinson MR, McDonough A, Morrill LC, Parker B, Andrews G, Young SS, Gilmour PS, Riley R, Dearman MS, J. Med. Chem., 57, 4661 (2014)
Lee SH, Teo J, Heng D, Zhao Y, Ng WK, Chan HK, Tan RB, J. Pharm. Sci., 103, 1115 (2014)
Magnussen H, Watz H, Zimmermann I, Macht S, Greguletz R, Falques M, Jarreta D, Garcia GE, Respir. Med., 103, 1832 (2009)
Geller DE, Respir. Care, 54, 658 (2009)
Labiris NR, Dolovich MB, Br. J. Clin. Pharmacol., 56, 588 (2003)
Chrystyn H, Safioti G, Keegstra JR, Gopalan G, Int. J. Pharm., 491, 268 (2015)
Durham PG, Zhang Y, German N, Mortensen N, Dhillon J, Mitchison DA, Fourie PB, Hickey AJ, Mol. Pharm., 15, 2574 (2015)
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Ungaro F, d’Angelo I, Miro A, La Rotonda MI, Quaglia F, J. Pharm. Pharmacol., 64, 1217 (2012)
Cipolla D, Gonda I, Chan HK, Ther. Deliv., 4, 1047 (2013)
Mura S, Hillaireau H, Nicolas J, Kerdine-Romer S, Le Droumaguet B, Delomenie C, Nicolas V, Pallardy M, Tsapis N, Fattal E, Biomacromolecules, 12(11), 4136 (2011)
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Ben-Jebria A, Chen D, Eskew ML, Vanbever R, Langer R, Edwards DA, Pharm. Res., 16, 555 (1999)
Dhand R, Curr. Opin. Crit. Care, 13, 27 (2007)
Kim I, Byeon HJ, Kim TH, Lee ES, Oh KT, Shin BS, Lee KC, Youn YS, Biomaterials, 33, 5574 (2012)
Chen D, Jiang X, Huang Y, Zhang C, Ping Q, J. Bioact. Compat. Polym., 25, 527 (2010)
Bae YS, Yazaydin AO, Snurr RQ, Langmuir, 26(8), 5475 (2010)
Kim SW, Oh KT, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 116, 359 (2014)
Lee JO, Lee MJ, Kim D, Lee ES, J. Bioact. Compat. Polym., 29, 368 (2014)
Yoo NY, Youn YS, Oh NM, Oh KT, Lee DK, Cha KH, Oh YT, Lee ES, Colloids Surf. B: Biointerfaces, 88, 419 (2011)
Lee JO, Oh KT, Kim D, Lee ES, J. Mater. Chem. B, 2, 6363 (2014)
Baik HJ, Oh NM, Oh YT, Yoo NY, Park SY, Oh KT, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 84, 585 (2011)
Oh NM, Oh KT, Baik HJ, Lee BR, Lee AH, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 78, 120 (2010)
Oh NM, Kwag DS, Oh KT, Youn YS, Lee ES, Biomaterials, 33, 1884 (2012)

[Referenced By]

[1] Wise RA, Anzueto A, Cotton D, Dahl R, Devins T, Disse B, Dusser D, Joseph E, Kattenbeck S, Koenen-Bergmann M, Pledger G, Calverley P, N. Engl. J. Med., 369, 1491 (2013)

[2] Vogelmeier CF, Asijee GM, Kupas K, Beeh KM, N. Engl. J. Med., 364, 1093 (2011)

[3] Dolovich MB, Dhand R, Lancet, 377, 1032 (2011)

[4] Svedsater H, Dale P, Garrill K, Walker R, Woepse MW, BMC Pulm. Med., 13, 72 (2013)

[5] Hickey J, J. Pharm. Sci., 102, 1165 (2013)

[6] De Savi C, Cox RJ, Warner DJ, Cook AR, Dickinson MR, McDonough A, Morrill LC, Parker B, Andrews G, Young SS, Gilmour PS, Riley R, Dearman MS, J. Med. Chem., 57, 4661 (2014)

[7] Lee SH, Teo J, Heng D, Zhao Y, Ng WK, Chan HK, Tan RB, J. Pharm. Sci., 103, 1115 (2014)

[8] Magnussen H, Watz H, Zimmermann I, Macht S, Greguletz R, Falques M, Jarreta D, Garcia GE, Respir. Med., 103, 1832 (2009)

[9] Geller DE, Respir. Care, 54, 658 (2009)

[10] Labiris NR, Dolovich MB, Br. J. Clin. Pharmacol., 56, 588 (2003)

[11] Chrystyn H, Safioti G, Keegstra JR, Gopalan G, Int. J. Pharm., 491, 268 (2015)

[12] Durham PG, Zhang Y, German N, Mortensen N, Dhillon J, Mitchison DA, Fourie PB, Hickey AJ, Mol. Pharm., 15, 2574 (2015)

[13] Rytting E, Nguyen J, Wang X, Kissel T, Expert Opin. Drug Deliv., 5, 629 (2008)

[14] Kurmi BD, Kayat J, Gajbhiye V, Tekade RK, Jain NK, Expert Opin. Drug Deliv., 7, 781 (2010)

[15] Ungaro F, d’Angelo I, Miro A, La Rotonda MI, Quaglia F, J. Pharm. Pharmacol., 64, 1217 (2012)

[16] Cipolla D, Gonda I, Chan HK, Ther. Deliv., 4, 1047 (2013)

[17] Mura S, Hillaireau H, Nicolas J, Kerdine-Romer S, Le Droumaguet B, Delomenie C, Nicolas V, Pallardy M, Tsapis N, Fattal E, Biomacromolecules, 12(11), 4136 (2011)

[18] Ungaro F, d’Angelo I, Coletta C, d’Emmanuele di Villa Bianca, Sorrentino R, Perfetto B, Tufano MA, Miro A, La Rotonda MI, Quaglia F, J. Control. Release, 157, 149 (2012)

[19] De Stefano D, Ungaro F, Giovino C, Polimeno A, Quaglia F, Carnuccio R, J. Gene Med., 13, 200 (2011)

[20] Ben-Jebria A, Chen D, Eskew ML, Vanbever R, Langer R, Edwards DA, Pharm. Res., 16, 555 (1999)

[21] Dhand R, Curr. Opin. Crit. Care, 13, 27 (2007)

[22] Kim I, Byeon HJ, Kim TH, Lee ES, Oh KT, Shin BS, Lee KC, Youn YS, Biomaterials, 33, 5574 (2012)

[23] Chen D, Jiang X, Huang Y, Zhang C, Ping Q, J. Bioact. Compat. Polym., 25, 527 (2010)

[24] Bae YS, Yazaydin AO, Snurr RQ, Langmuir, 26(8), 5475 (2010)

[25] Kim SW, Oh KT, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 116, 359 (2014)

[26] Lee JO, Lee MJ, Kim D, Lee ES, J. Bioact. Compat. Polym., 29, 368 (2014)

[27] Yoo NY, Youn YS, Oh NM, Oh KT, Lee DK, Cha KH, Oh YT, Lee ES, Colloids Surf. B: Biointerfaces, 88, 419 (2011)

[28] Lee JO, Oh KT, Kim D, Lee ES, J. Mater. Chem. B, 2, 6363 (2014)

[29] Baik HJ, Oh NM, Oh YT, Yoo NY, Park SY, Oh KT, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 84, 585 (2011)

[30] Oh NM, Oh KT, Baik HJ, Lee BR, Lee AH, Youn YS, Lee ES, Colloids Surf. B: Biointerfaces, 78, 120 (2010)

[31] Oh NM, Kwag DS, Oh KT, Youn YS, Lee ES, Biomaterials, 33, 1884 (2012)