Mucoadhesive interaction of cysteine grafted poly(2-hydroxyethyl aspartamide) with pig mucin layer of surface plasmon resonance biosensor

Han Woong Park; Jong-Duk Kim

Journal of Industrial and Engineering Chemistry, Vol.15, No.4, 578-583, July, 2009

DOI10.1016/j.jiec.2009.01.016 Export Citation

Mucoadhesive interaction of cysteine grafted poly(2-hydroxyethyl aspartamide) with pig mucin layer of surface plasmon resonance biosensor

Han Woong Park, and Jong-Duk Kim^†

Department of Chemical and Bimolecular Engineering, Korea Advanced Institute of Science and Technology, 373-1 Kusong-dong, Yusong-gu, Daejon 305-701, South Korea

E-mail:

A new type of thiolated polyaspartamide was synthesized and characterized with a surface plasmon resonance (SPR) biosensor. L-Cysteine grafted poly(2-hydroxyethyl aspartamide) (PHEA)s was obtained by grafting S-(Trityl)-L-cysteine to poly(succinimide) and subsequently deprotecting Trityl groups. The degree of substitution was confirmed by 1H NMR, and elemental analysis. The amount of free thiol groups immobilized on the PHEA was determined by colorimetric reaction of thiols with Ellman’s reagent. The stability of thiol groups at different pH levels was also reported. Mucoadhesive interaction was determined by pig mucin immobilized SPR biosensor. It is concluded that cysteine grafted PHEA enhances the interaction with mucin but that the amount of free thiol groups among the grafted thiols determines the mucoadhesive properties.

Keywords:Mucoadhesion;Thiolated polymer;Polyaspartamide;SPR

[References]

Takeuchi H, Yamamoto H, Kawashima Y, Adv. Drug Deliv. Rev., 47, 39 (2001)
Jang JY, Kwon BS, Lee HE, Kim DH, Kang HK, Kang JS, Lee S, Choi GJ, J. Ind. Eng. Chem., 13(6), 1043 (2007)
Jin FL, Park SJ, J. Ind. Eng. Chem., 13(4), 608 (2007)
Jeong YI, Kim DG, Seo DH, Jang MK, Nah JW, J. Ind. Eng. Chem., 14(6), 747 (2008)
Lehr C, J. Control. Release, 65, 19 (2000)
Gum JR, Hicks JW, Toribara NW, Rothe EM, Lagace RE, Kim YS, J. Biol. Chem., 267, 21375 (1992)
Lee JW, Park JH, Robinson JR, J. Pharm. Sci., 89, 850 (2000)
Bernkop-Schnurch A, Adv. Drug Deliv. Rev., 57, 1569 (2005)
Bernkop-Schnurch A, Int. J. Pharm., 226, 185 (2001)
Bernkop-Schnurch A, Kast CE, Richtner MF, J. Control. Release, 71, 277 (2001)
Kafedjiiski K, Jetti RKR, Foger F, Hoyer H, Werle M, Hoffer M, Bernkop-Schnurch A, Int. J. Pharm., 343, 48 (2007)
Bravo-Osuna I, Vauthier C, Farabollini A, Palmieri GF, Ponchel G, Biomaterials, 28, 2233 (2007)
Cevher E, Taha MAM, Orlu M, Araman A, Drug Deliv., 15, 57 (2008)
Bernkop-Schnurch A, Leitner VM, Moser V, Drug Dev. Ind. Pharm., 30, 1 (2004)
Bilicic MB, Filipovic-Grcic J, Martinac A, Barbaric M, Zorc B, Cetina-Cizmek B, Tudja P, Int. J. Pharm., 291, 211 (2005)
Kim BY, Jeong JH, Park K, Kim JD, J. Control. Release, 102, 525 (2005)
Thongborisute J, Takeuchi H, Int. J. Pharm., 354, 204 (2008)
Kang HS, Yang SR, Kim JD, Han SH, Chang IS, Langmuir, 17(24), 7501 (2001)
Fontana A, Toniolo C, in: Patai S (Ed.), The Chemistry of Thiol Group, Part I, John Wiley & Sons, Bristol, 1974, p. 288.
Jordan CE, Frutos AG, Thiel AJ, Corn RM, Anal. Chem., 69, 4939 (1997)
Pearson JE, Kane JW, Petraki-Kallioti I, Gill A, Vadgama P, J. Immunol. Methods, 221, 87 (1998)
Jocelyn PC, Biochemistry of the SH Groups, Academic Press, London (1972)
Medina-Hernandez MJ, Catala-Icardo M, Garcia-Alvarez-Coque MC, Chromatographia, 41, 455 (1995)
Hornof MD, Kast CE, Bernkop-Schnurch A, Eur. J. Pharm. Biopharm., 55, 185 (2003)
Danehy JP, Noel CJ, J. Am. Chem. Soc., 82, 2511 (1960)
Allen A, Bell A, Mantle M, Pearson JP, in: Chantler EN, Elders JB, Elstein M(Eds.), Mucus in Health and Disease II, Plenum, New York, 1982, p. 115.

[Referenced By]

[Related Articles]

[1] Takeuchi H, Yamamoto H, Kawashima Y, Adv. Drug Deliv. Rev., 47, 39 (2001)

[2] Jang JY, Kwon BS, Lee HE, Kim DH, Kang HK, Kang JS, Lee S, Choi GJ, J. Ind. Eng. Chem., 13(6), 1043 (2007)

[3] Jin FL, Park SJ, J. Ind. Eng. Chem., 13(4), 608 (2007)

[4] Jeong YI, Kim DG, Seo DH, Jang MK, Nah JW, J. Ind. Eng. Chem., 14(6), 747 (2008)

[5] Lehr C, J. Control. Release, 65, 19 (2000)

[6] Gum JR, Hicks JW, Toribara NW, Rothe EM, Lagace RE, Kim YS, J. Biol. Chem., 267, 21375 (1992)

[7] Lee JW, Park JH, Robinson JR, J. Pharm. Sci., 89, 850 (2000)

[8] Bernkop-Schnurch A, Adv. Drug Deliv. Rev., 57, 1569 (2005)

[9] Bernkop-Schnurch A, Int. J. Pharm., 226, 185 (2001)

[10] Bernkop-Schnurch A, Kast CE, Richtner MF, J. Control. Release, 71, 277 (2001)

[11] Kafedjiiski K, Jetti RKR, Foger F, Hoyer H, Werle M, Hoffer M, Bernkop-Schnurch A, Int. J. Pharm., 343, 48 (2007)

[12] Bravo-Osuna I, Vauthier C, Farabollini A, Palmieri GF, Ponchel G, Biomaterials, 28, 2233 (2007)

[13] Cevher E, Taha MAM, Orlu M, Araman A, Drug Deliv., 15, 57 (2008)

[14] Bernkop-Schnurch A, Leitner VM, Moser V, Drug Dev. Ind. Pharm., 30, 1 (2004)

[15] Bilicic MB, Filipovic-Grcic J, Martinac A, Barbaric M, Zorc B, Cetina-Cizmek B, Tudja P, Int. J. Pharm., 291, 211 (2005)

[16] Kim BY, Jeong JH, Park K, Kim JD, J. Control. Release, 102, 525 (2005)

[17] Thongborisute J, Takeuchi H, Int. J. Pharm., 354, 204 (2008)

[18] Kang HS, Yang SR, Kim JD, Han SH, Chang IS, Langmuir, 17(24), 7501 (2001)

[19] Fontana A, Toniolo C, in: Patai S (Ed.), The Chemistry of Thiol Group, Part I, John Wiley & Sons, Bristol, 1974, p. 288.

[20] Jordan CE, Frutos AG, Thiel AJ, Corn RM, Anal. Chem., 69, 4939 (1997)

[21] Pearson JE, Kane JW, Petraki-Kallioti I, Gill A, Vadgama P, J. Immunol. Methods, 221, 87 (1998)

[22] Jocelyn PC, Biochemistry of the SH Groups, Academic Press, London (1972)

[23] Medina-Hernandez MJ, Catala-Icardo M, Garcia-Alvarez-Coque MC, Chromatographia, 41, 455 (1995)

[24] Hornof MD, Kast CE, Bernkop-Schnurch A, Eur. J. Pharm. Biopharm., 55, 185 (2003)

[25] Danehy JP, Noel CJ, J. Am. Chem. Soc., 82, 2511 (1960)

[26] Allen A, Bell A, Mantle M, Pearson JP, in: Chantler EN, Elders JB, Elstein M(Eds.), Mucus in Health and Disease II, Plenum, New York, 1982, p. 115.