Thermosensitive Block Copolymers PEG-b-PBEMAGG Containing Functional Pendant Amino Groups

Zhenke Wei; Qingsong Yu; Zhihua Gan

Macromolecular Research, Vol.20, No.3, 313-318, March, 2012

DOI10.1007/s13233-012-0060-z Export Citation

Thermosensitive Block Copolymers PEG-b-PBEMAGG Containing Functional Pendant Amino Groups

Zhenke Wei^{1, 2}, Qingsong Yu^{1, 2}, and Zhihua Gan^{1, 3, †}

¹The CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China
²Graduate School of Chinese Academy of Sciences, Beijing, 100043, P. R. China
³, China

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A novel thermosensitive block copolymer composed of poly(ethylene glycol) (PEG) and poly(N-(NBoc-ethylenediamine)methacryloylglycylglycylamide) (PBEMAGG) with pendant amino groups was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. The thermosensitivity of these copolymers was studied with varying temperatures and block lengths of copolymers. The results indicated that the lowest critical solution temperatures (LCST) of this thermosensitive copolymer cover the range from 20 ℃ up to near 45 ℃, and can be easily and precisely regulated by changing the block length or the amount of pendant amino groups. This copolymer with well-controlled LCST and pendant functional groups shows great potential for use as a smart drug-delivery system.

Keywords:thermosensitive;block copolymers;amino functional groups;poly(ethylene glycol) (PEG).

[References]

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[Referenced By]

[1] Kopecek J, Kopeckova P, Europ T, J. Pharm. Biopharm., 50, 61 (2000)

[2] Chytil P, Etrych T, Konak C, J. Control. Release., 127, 121 (2008)

[3] Rihova B, Strohalm BJ, Hovorka O, J. Control.Release., 127, 110 (2008)

[4] Wester HJ, Kessler H, J. Nucl. Med., 46, 1940 (2005)

[5] Mitra A, Mulholland J, Nan A, J. Control. Release., 102, 191 (2005)

[6] Mitra A, Nan A, Ghandehari H, Pharm. Res., 21, 1153 (2004)

[7] Harris JM, Zalipsky S, ACS Symp. Ser., 680, 1 (1997)

[8] Uhrich KE, Cannizzaro SM, Langer RS, Shakesheff KM, Chem. Rev., 99(11), 3181 (1999)

[9] Bromberg LE, Ron ES, Adv. Drug Deliv. Rev., 31, 197 (1998)

[10] Dimitrov I, Trzebicka B, Prog. Polym. Sci., 32, 1275 (2007)

[11] Schild HG, Prog. Polym. Sci., 17, 163 (1992)

[12] Pelton R, Adv. Colloid Interface Sci., 85, 1 (2000)

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

[14] Kawasaki H, Sasaki S, Maeda H, J. Phys. Chem. B, 101(26), 5089 (1997)

[15] Shibayama M, Tanaka T, Adv. Polym. Sci., 109, 1 (1993)

[16] Feil H, Bae YH, Feien J, Macromolecules., 26, 2496 (1993)

[17] Chen GH, Hoffman AS, Nature, 373(6509), 49 (1995)

[18] Weng YM, Ding YW, Zhang GZ, J. Phys. Chem., 110, 11813 (2006)

[19] Huang HY, Remsen EE, Kowalewski T, Wooley KL, J. Am. Chem. Soc., 121(15), 3805 (1999)

[20] Liu SY, Weaver JVM, Tang YQ, Billingham NC, Armes SP, Tribe K, Macromolecules, 35(16), 6121 (2002)

[21] Yuan JJ, Mykhaylyk OO, Ryan AJ, Armes SP, J. Am. Chem. Soc., 129(6), 1717 (2007)

[22] Wei H, Cheng C, Chang C, Chen WQ, Cheng S, Zhang XZ, Zhuo RX, Langmuir, 24(9), 4564 (2008)

[23] Chytil P, Etrych T, Konak C, J. Control. Release., 115, 26 (2006)

[24] Line BR, Mitra A, Nan AH, J. Nucl. Med., 46, 1552 (2005)

[25] Butun V, Wang XS, Banez MVD, Robinson KL, Billingham NC, Armes SP, Tuzar Z, Macromolecules, 33(1), 1 (2000)

[26] Sanji T, Nakatsuka Y, Sakurai H, Chem. Commun., 21, 2201 (1999)

[27] Wooley KL, J. Polym. Sci. A: Polym. Chem., 38(9), 1397 (2000)

[28] O'Reilly RK, Joralemon MJ, Hawker CJ, Wooley KL, J. Polym. Sci. A: Polym. Chem., 44(17), 5203 (2006)

[29] O’Reilly RK, Joralemon MJ, Wooley KL, Chem.Eur. J., 12, 6776 (2006)

[30] Urry DW, J. Phys. Chem. B, 101(51), 11007 (1997)

[31] Betre H, Setton LA, Meyer DE, Chilkoti A, Biomacromolecules, 3(5), 910 (2002)

[32] Mitsukami Y, Donovan MS, Lowe AB, McCormick CL, Macromolecules, 34(7), 2248 (2001)

[33] Drobnik J, Kopecek J, Labsky J, Makromol. Chem., 177, 2833 (1976)

[34] Shi LJ, Chapman TM, Beckman EJ, Macromolecules, 36(7), 2563 (2003)

[35] Luo SZ, Xu J, Zhang YF, Liu SY, Wu C, J. Phys. Chem. B, 109(47), 22159 (2005)

[36] An ZS, Shi QH, Tang W, Tsung CK, Hawker CJ, Stucky GD, J. Am. Chem. Soc., 129(46), 14493 (2007)

[37] Wang H, Wang JL, Tetrahedron., 61, 8465 (2005)

[38] Favier A, Charreyre MT, Macromol. Rapid Commun., 27(9), 653 (2006)

[39] Zhang GZ, Wu C, Adv. Polym. Sci., 195, 101 (2006)

[40] Okhapkin IM, Makhaeva EE, Adv. Polym. Sci., 195, 177 (2006)

[41] You YZ, Oupicky D, Biomacromolecules, 8(1), 98 (2007)