Photo-responsive liposomes decorated with hydrophobically modified poly(vinyl alcohol)-coumarin conjugate

Hee Jin Seo; Hyun Ju Cha; Tae Soo Kim; Jin-Chul Kim

Journal of Industrial and Engineering Chemistry, Vol.19, No.1, 310-315, January, 2013

DOI10.1016/j.jiec.2012.08.017 Export Citation

Photo-responsive liposomes decorated with hydrophobically modified poly(vinyl alcohol)-coumarin conjugate

Hee Jin Seo, Hyun Ju Cha, Tae Soo Kim¹, and Jin-Chul Kim^†

Division of Biotechnology & Bioengineering and Institute of Bioscience and Biotechnology, Kangwon National University, 192-1, Hyoja 2 dong, Chuncheon-si, Kangwon-do 200-701, Republic of Korea
¹TKM Converging Research Division, Korea Institute of Oriental Medicine, Daejeon 305-811, Republic of Korea

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Photo-responsive liposome was developed by modifying the surface of egg yolk phosphatidylcholine (egg PC) liposomes with hydrophobically modified poly (vinyl alcohol)-epoxypropoxy coumarin conjugate (HmPVA-EPC). Decanoyl chloride (DC) was used as a hydrophobic pendant for the hydrophobic modification of PVA. The fluorescence quenching of liposomes was more than 65% when the ratio of lipid/HmPVA-EPC was 1:0.01-1:0.1, but the value was less than 35% in the ratio range of 1:0.2-1:1. Under UV irradiation (l = 254 nm), egg PC liposomes of which lipid/HmPVA-EPC ratio was 1:0.1 readily release their content for 60 min possibly due to the photo-dimerization of EPC residues.

Keywords:Egg yolk phosphatidylcholine;Liposomes;HmPVA-EPC;Surface modification;Photo-responsive release

[References]

Peek BM, Callahan JH, Namboodiri K, Singh A, Gaber BP, Macromolecules, 27(1), 292 (1994)
Morgan CG, Thomas EW, Sandhu SS, Yianni YP, Mitchell AC, Biochimica et Biophysica Acta., 903, 504 (1987)
Bisby RH, Mead C, Morgan CG, Photochemistry and Photobiology., 72, 57 (2000)
Morgan CG, Sandhu SS, Yianni YP, Dodd NJF, Biochimica et Biophysica Acta., 903, 495 (1987)
Chandra B, Subramaniam R, Mallik S, Srivastava DK, Organic and Biomolecular Chemistry., 4, 1730 (2006)
Katz JS, Burdick JA, Macromolecular Biosciences., 10, 339 (2010)
Yavlovich A, Smith B, Gupta K, Blumenthal R, Puri A, Molecular Membrane Biology., 27, 364 (2010)
Seo HJ, Kim JC, Journal of Nanoscience and Nanotechnology., 11, 10262 (2011)
Chen Y, Chen KH, J. Polym. Sci. A: Polym. Chem., 35(4), 613 (1997)
Mal NK, Fujiwara M, Tanaka Y, Taguchi T, Matsukat M, Chemistry of Materials., 15, 3385 (2003)
Kim HC, Kreiling S, Greiner A, Hampp N, Chem. Phys. Lett., 372(5-6), 899 (2003)
He J, Zhao Y, Dyes and Pigments., 89, 278 (2011)
Yahya GO, Ali SK, Hamad EZ, Polymer, 37(7), 1183 (1996)
Chen YL, Wang TC, Lee KH, Tzeng CC, Chang YL, Teng CM, Helvetica Chimica Acta., 79, 651 (1994)
Agag T, Takeichi T, Polymer, 40(23), 6557 (1999)
Chen BK, Chiu TM, Tsay SY, J. Appl. Polym. Sci., 94(1), 382 (2004)
Chen WQ, Wei H, Li SL, Feng J, Nie J, Zhang XZ, Zhuo RX, Polymer, 49(18), 3965 (2008)
Cammas S, Suzuki K, Sone C, Sakurai Y, Kataoka K, Okanoa T, Journal of Controlled Release., 48, 157 (1997)
Nakayama M, Okano T, Biomacromolecules, 6(4), 2320 (2005)
Takeuchi H, Kojima H, Yamamoto H, Kawashima Y, Journal of Controlled Release., 68, 195 (2000)
Mu X, Zhong Z, International Journal of Pharmaceutics., 318, 55 (2006)
Jo SM, Xia Y, Lee HY, Kim YC, Kim JC, Korean J. Chem. Eng., 25(5), 1221 (2008)
Hong YJ, Kim JC, Journal of Nanoscience and Nanotechnology., 10, 8380 (2010)
Dayan N, Touitou E, Biomaterials., 21, 1879 (2000)
Lee MS, Kim JC, Polymer Engineering and Science, submitted for publication.
Jo SM, Kim JC, Colloid and Polymer Science., 287, 379 (2009)
Lei L, Ma Y, Kodali DR, Liang J, Davis HT, Journal of the American Oil Chemists Society., 80, 383 (2003)
Schroeder A, Kost J, Barenholz Y, Chemistry and Physics of Lipids., 162, 1 (2009)
Szoka F, Olson F, Heath T, Vail W, Mayhew E, Biochimica et Biophysica Acta - Biomembranes., 601, 559 (1980)
Gad SC, JinF Y., Pharmaceutical Manufacturing Handbook: Production and Processes, John Wiley & Sons, Inc., New Jersey, 1258 (2008)
Hong YJ, Seo HJ, Kim JD, Shin WC, Kim JC, European Journal of Lipid Science and Technology., 113, 146 (2011)

[Referenced By]

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[1] Peek BM, Callahan JH, Namboodiri K, Singh A, Gaber BP, Macromolecules, 27(1), 292 (1994)

[2] Morgan CG, Thomas EW, Sandhu SS, Yianni YP, Mitchell AC, Biochimica et Biophysica Acta., 903, 504 (1987)

[3] Bisby RH, Mead C, Morgan CG, Photochemistry and Photobiology., 72, 57 (2000)

[4] Morgan CG, Sandhu SS, Yianni YP, Dodd NJF, Biochimica et Biophysica Acta., 903, 495 (1987)

[5] Chandra B, Subramaniam R, Mallik S, Srivastava DK, Organic and Biomolecular Chemistry., 4, 1730 (2006)

[6] Katz JS, Burdick JA, Macromolecular Biosciences., 10, 339 (2010)

[7] Yavlovich A, Smith B, Gupta K, Blumenthal R, Puri A, Molecular Membrane Biology., 27, 364 (2010)

[8] Seo HJ, Kim JC, Journal of Nanoscience and Nanotechnology., 11, 10262 (2011)

[9] Chen Y, Chen KH, J. Polym. Sci. A: Polym. Chem., 35(4), 613 (1997)

[10] Mal NK, Fujiwara M, Tanaka Y, Taguchi T, Matsukat M, Chemistry of Materials., 15, 3385 (2003)

[11] Kim HC, Kreiling S, Greiner A, Hampp N, Chem. Phys. Lett., 372(5-6), 899 (2003)

[12] He J, Zhao Y, Dyes and Pigments., 89, 278 (2011)

[13] Yahya GO, Ali SK, Hamad EZ, Polymer, 37(7), 1183 (1996)

[14] Chen YL, Wang TC, Lee KH, Tzeng CC, Chang YL, Teng CM, Helvetica Chimica Acta., 79, 651 (1994)

[15] Agag T, Takeichi T, Polymer, 40(23), 6557 (1999)

[16] Chen BK, Chiu TM, Tsay SY, J. Appl. Polym. Sci., 94(1), 382 (2004)

[17] Chen WQ, Wei H, Li SL, Feng J, Nie J, Zhang XZ, Zhuo RX, Polymer, 49(18), 3965 (2008)

[18] Cammas S, Suzuki K, Sone C, Sakurai Y, Kataoka K, Okanoa T, Journal of Controlled Release., 48, 157 (1997)

[19] Nakayama M, Okano T, Biomacromolecules, 6(4), 2320 (2005)

[20] Takeuchi H, Kojima H, Yamamoto H, Kawashima Y, Journal of Controlled Release., 68, 195 (2000)

[21] Mu X, Zhong Z, International Journal of Pharmaceutics., 318, 55 (2006)

[22] Jo SM, Xia Y, Lee HY, Kim YC, Kim JC, Korean J. Chem. Eng., 25(5), 1221 (2008)

[23] Hong YJ, Kim JC, Journal of Nanoscience and Nanotechnology., 10, 8380 (2010)

[24] Dayan N, Touitou E, Biomaterials., 21, 1879 (2000)

[25] Lee MS, Kim JC, Polymer Engineering and Science, submitted for publication.

[26] Jo SM, Kim JC, Colloid and Polymer Science., 287, 379 (2009)

[27] Lei L, Ma Y, Kodali DR, Liang J, Davis HT, Journal of the American Oil Chemists Society., 80, 383 (2003)

[28] Schroeder A, Kost J, Barenholz Y, Chemistry and Physics of Lipids., 162, 1 (2009)

[29] Szoka F, Olson F, Heath T, Vail W, Mayhew E, Biochimica et Biophysica Acta - Biomembranes., 601, 559 (1980)

[30] Gad SC, JinF Y., Pharmaceutical Manufacturing Handbook: Production and Processes, John Wiley & Sons, Inc., New Jersey, 1258 (2008)

[31] Hong YJ, Seo HJ, Kim JD, Shin WC, Kim JC, European Journal of Lipid Science and Technology., 113, 146 (2011)