Polydopamine coating in organic solvent for material-independent immobilization of water-insoluble molecules and avoidance of substrate hydrolysis

Inseong You; Hyejin Jeon; Kyueui Lee; Minjae Do; Young Chang Seo; Haesung A. Lee; Haeshin Lee

Journal of Industrial and Engineering Chemistry, Vol.46, 379-385, February, 2017

DOI10.1016/j.jiec.2016.11.007 Export Citation

Polydopamine coating in organic solvent for material-independent immobilization of water-insoluble molecules and avoidance of substrate hydrolysis

Inseong You¹, Hyejin Jeon², Kyueui Lee², Minjae Do², Young Chang Seo², Haesung A. Lee², and Haeshin Lee^{2, 3, †}

¹Graduate School of Nanoscience & Technology, Korea Advanced Institute of Science and Technology (KAIST), 291 University Rd., Daejeon 305-701, Republic of Korea
²Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), 291 University Rd., Daejeon 305-701, Republic of Korea
³KAIST School of Molecular Science, KAIST, 291 University Rd., Daejeon 305-701, Republic of Korea

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Polydopamine (pDA) coating is the first material-independent surface chemistry utilized in energy storage systems, environmental technology, and biomaterial science. However, the conventional coating method requires use of aqueous solutions, which restrict immobilization of water-insoluble molecules onto surfaces, and the coating cannot be applied to degradable polyester substrates. Herein, methods to form pDA in organic protic solvents (o-pDA) with fast coating kinetics resulting in ~50 nm in thickness just for 4 h. One-step immersion of surfaces in a one-pot mixture of a water-insoluble molecule, dopamine, and piperidine results in o-pDA coating with robust surface immobilization of molecules of interest.

Keywords:Polydopamine;Surface functionalization;One-step coating;Organic Solvents;Drug immobilization

[References]

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Lee H, Lee BP, Messersmith PB, Nature, 448, 338 (2007)
Sileika TS, Kim HD, Maniak P, Messersmith PB, ACS Appl. Mater. Interfaces, 3, 4602 (2011)
Feng J, Sun M, Xu L, Li J, Liu X, Jiang S, J. Sep. Sci., 34, 2482 (2011)
Zheng TT, Zhang R, Zou L, Zhu JJ, Analyst, 137, 1316 (2012)
Yang SH, Kang SM, Lee KB, Chung TD, Lee H, Choi IS, J. Am. Chem. Soc., 133(9), 2795 (2011)
Wei Q, Li B, Yi N, Su B, Yin Z, Zhang F, Li J, Zhao C, J. Biomed. Mater. Res., 96A, 38 (2011)
Ku SH, Lee JS, Park CB, Langmuir, 26(19), 15104 (2010)
Chien HW, Kuo WH, Wang MJ, Tsai SW, Tsai WB, Langmuir, 28(13), 5775 (2012)
Kang SM, You I, Cho WK, Shon HK, Lee TG, Choi IS, Lee H, Angew. Chem.-Int. Edit., 49, 9401 (2010)
Lee M, Rho J, Lee DE, Hong S, Choi SJ, Messersmith PB, Lee H, ChemPlusChem, 77, 987 (2012)
Ko JW, Kim JH, Park CB, J. Mater. Chem. A, 1, 241 (2013)
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Zhou YS, Yang DZ, Chen XM, Xu Q, Lu FM, Nie J, Biomacromolecules, 9(1), 349 (2008)
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Liebscher J, Mrowczynski R, Scheidt HA, Filip C, Hadade ND, Turcu R, Bende A, Beck S, Langmuir, 29(33), 10539 (2013)
Hong S, Na YS, Choi S, Song IT, Kim WY, Lee H, Adv. Funct. Mater., 22(22), 4711 (2012)
Niles AL, Moravec RA, Hesselberth PE, Scurria MA, Daily WJ, Riss TL, Anal. Biochem., 366, 197 (2007)
Wu MC, Lin LY, Lee SS, King CR, Laser Focus World, 35, 64 (1996)
Kovacs GT, Petersen K, Albin M, Anal. Chem., 68, 407A (1996)
Briceno G, Chang HY, Sun XD, Schultz PG, Xiang XD, Science, 270(5234), 273 (1995)
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Bryzek J, Peterson K, McCulley W, IEEE Spectr., 31, 20 (1994)
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Wink T, van Zuilen SJ, Bult A, van Bennkom WP, Analyst, 122, R43 (1997)
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[Referenced By]

[1] Lee H, Dellatore SM, Miller WM, Science, 318, 426 (2007)

[2] Lee H, Lee BP, Messersmith PB, Nature, 448, 338 (2007)

[3] Sileika TS, Kim HD, Maniak P, Messersmith PB, ACS Appl. Mater. Interfaces, 3, 4602 (2011)

[4] Feng J, Sun M, Xu L, Li J, Liu X, Jiang S, J. Sep. Sci., 34, 2482 (2011)

[5] Zheng TT, Zhang R, Zou L, Zhu JJ, Analyst, 137, 1316 (2012)

[6] Yang SH, Kang SM, Lee KB, Chung TD, Lee H, Choi IS, J. Am. Chem. Soc., 133(9), 2795 (2011)

[7] Wei Q, Li B, Yi N, Su B, Yin Z, Zhang F, Li J, Zhao C, J. Biomed. Mater. Res., 96A, 38 (2011)

[8] Ku SH, Lee JS, Park CB, Langmuir, 26(19), 15104 (2010)

[9] Chien HW, Kuo WH, Wang MJ, Tsai SW, Tsai WB, Langmuir, 28(13), 5775 (2012)

[10] Kang SM, You I, Cho WK, Shon HK, Lee TG, Choi IS, Lee H, Angew. Chem.-Int. Edit., 49, 9401 (2010)

[11] Lee M, Rho J, Lee DE, Hong S, Choi SJ, Messersmith PB, Lee H, ChemPlusChem, 77, 987 (2012)

[12] Ko JW, Kim JH, Park CB, J. Mater. Chem. A, 1, 241 (2013)

[13] Wang Y, Liu L, Li M, Xu S, Gao F, Biosens. Bioelectron., 30, 107 (2011)

[14] Kang SM, Hwang NS, Yeom J, Park SY, Messersmith PB, Choi IS, Langer R, Anderson DG, Lee H, Adv. Funct. Mater., 22(14), 2949 (2012)

[15] Nijhuis AW, Van Den Beucken JJ, Boerman OC, Jansen JA, Leeuwenburgh SC, Tissue Eng. Part C Methods, 19, 610 (2013)

[16] Yue Q, Wang M, Sun Z, Wang C, Wang C, Deng Y, Zhao D, J. Mater. Chem. B, 1, 6085 (2013)

[17] Vecchia DN, Avolio R, Alfe M, Errico ME, Napolitano A, d'Ischia M, Adv. Funct. Mater., 23, 1331 (2012)

[18] Zhou YS, Yang DZ, Chen XM, Xu Q, Lu FM, Nie J, Biomacromolecules, 9(1), 349 (2008)

[19] Majewska A, Furmanowa M, Sliwinska E, Glowniak K, Guzewska J, Kuras M, Zobel A, Acta Soc. Bot. Pol., 69, 185 (2000)

[20] Mu L, Feng SS, J. Control. Release, 86, 33 (2003)

[21] Miller K, Wang M, Gralow J, Dickler M, Cobleigh M, Perez EA, Shenkier T, Cella D, Davidson NE, N. Engl. J. Med., 357, 2666 (2007)

[22] Liebscher J, Mrowczynski R, Scheidt HA, Filip C, Hadade ND, Turcu R, Bende A, Beck S, Langmuir, 29(33), 10539 (2013)

[23] Hong S, Na YS, Choi S, Song IT, Kim WY, Lee H, Adv. Funct. Mater., 22(22), 4711 (2012)

[24] Niles AL, Moravec RA, Hesselberth PE, Scurria MA, Daily WJ, Riss TL, Anal. Biochem., 366, 197 (2007)

[25] Wu MC, Lin LY, Lee SS, King CR, Laser Focus World, 35, 64 (1996)

[26] Kovacs GT, Petersen K, Albin M, Anal. Chem., 68, 407A (1996)

[27] Briceno G, Chang HY, Sun XD, Schultz PG, Xiang XD, Science, 270(5234), 273 (1995)

[28] Bryzek J, Sensors, 4 (1996)

[29] Bryzek J, Peterson K, McCulley W, IEEE Spectr., 31, 20 (1994)

[30] Clark RA, Hietpas PB, Ewing AG, Anal. Chem., 69, 259 (1997)

[31] Wink T, van Zuilen SJ, Bult A, van Bennkom WP, Analyst, 122, R43 (1997)

[32] Bain CD, Troughton EB, Tao YT, Evall J, Whitesides GM, Nuzzo RG, J. Am. Chem. Soc., 111, 321 (1989)

[33] Love JC, Estroff LA, Kriebel JK, Nuzzo RG, Whitesides GM, Chem. Rev., 105(4), 1103 (2005)