화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.21, No.2, 161-168, February, 2013
DOI10.1007/s13233-013-1015-8  Export Citation
Development of creatine and arginine-6-oligomer for the ring-opening polymerization of cyclic esters
Ewa Oledzka†, Marcin Sobczak, Mateusz Kolakowski, Bartlomiej Kraska1, Wojciech Kamysz1, and Waclaw Kolodziejski
  • Department of Inorganic and Analytical Chemistry, Medical University of Warsaw, Faculty of Pharmacy, Banacha 1, Warsaw, 02-097, Poland
  • 1Department of Inorganic Chemistry, Medical University of Gdansk, Al. Gen. J. Hallera 107, Gdansk, 80-416, Poland
E-mail:
Natural creatine and arginine-6-oligomer have been effectively engaged as ring-opening polymerization initiators of poly(L-lactide) (PLLA) and poly(?-caprolactone) (PCL) in bulk. The nonlinear structure and thermal properties of the resulted polymers were further elucidated by 1H, 13C nuclear magnetic resonance, and a modulated differencial scanning calorimetry (MDSC). Thermal analysis indicated that the synthesized polymers had lower melting points, glass-transition temperatures, fusion enthalpy, and crystallization temperature than those of linear PCL or PLLA due to the presence of the arginine-6-oligomer in the macromolecule and crystalline imperfections caused by the branched structure. This study provides an efficient and metal-free method for the synthesis of branched biodegradable polymers with incorporated compounds, which exhibit therapeutic properties, adequate for the drug carrier applications.
Keywords:creatine;arginine oligomer;polyesters;ring-opening polymerization;natural initiator
  1. Agrawal CM, Ray RB, J. Biomed. Mater. Res., 55, 141 (2001)
  2. Li SM, Liu LJ, Garreau H, Vert M, Biomacromolecules, 4(2), 372 (2003)
  3. Sinha VR, Bansal K, Kausshik R, Kumria R, Trehan A, Int. J. Pharm., 278, 1 (2004)
  4. Ignatius AA, Claes LE, Biomaterials., 17, 831 (1996)
  5. Chamberlain BM, Jazdzewski BA, Pink M, Hillmyer MA, Tolman WB, Macromolecules, 33(11), 3970 (2000)
  6. Ryner M, Albertsson AC, Biomacromolecules, 3(3), 601 (2002)
  7. Stridsberg K, Albertsson AC, Polymer, 41(20), 7321 (2000)
  8. Leong JC, Lee J, Cho K, J. Control. Release., 92, 249 (2003)
  9. Kricheldorf HR, Kreisersaunders I, Polymer, 35(19), 4175 (1994)
  10. Klok HA, Hwang JJ, Hartgerink JD, Stupp SI, Macromolecules, 35(16), 6101 (2002)
  11. Cho H, Chung D, Jeongho A, Biomaterials., 25, 3733 (2004)
  12. Waite JH, Polym. Prepr., 31, 181 (1990)
  13. Viney C, Case ST, Waite JH, Mater. Res. Soc. Proc., 292 (1992)
  14. Lutz JF, Borner HG, Prog. Polym. Sci., 33, 1 (2008)
  15. Jiang GH, Wang L, Chen T, Yu HJ, Wang CL, Chen C, Polymer, 46(14), 5351 (2005)
  16. Rong GZ, Deng MX, Deng C, Tang ZH, Piao LH, Chen XS, Jing XB, Biomacromolecules, 4(6), 1800 (2003)
  17. Biagini SCG, Parry AL, J. Polym. Sci. A: Polym. Chem., 45(15), 3178 (2007)
  18. Liu JY, Liu LJ, Macromolecules, 37(8), 2674 (2004)
  19. Sobczak M, Oledzka E, Kolodziejski WL, J. Macromol. Sci. Part A: Pure Appl. Chem., 45, 872 (2008)
  20. Juhn MS, Tarnopolsky M, Clin. J. Sport Med., 8, 286 (1998)
  21. Adhihetty PJ, Beal MF, Neuromol. Med., 10, 275 (2008)
  22. Trabulo S, Cardoso AL, Mano M, de Lima MCP, Pharmaceuticals., 3, 961 (2010)
  23. Kerkis A, Hayashi M, Yamane T, Kerkis I, IUBMB Life., 58, 7 (2006)
  24. Wang C, Li H, Zhao X, Biomaterials., 25, 5797 (2004)
  25. Lohmeijer BGG, Pratt RC, Leibfarth F, Logan JW, Long DA, Dove AP, Nederberg F, Choi J, Wade C, Waymouth RM, Hedrick JL, Macromolecules, 39(25), 8574 (2006)
  26. Zhang L, Pratt RC, Nederberg F, Horn HW, Rice JE, Waymouth RM, Wade CG, Hedrick JL, Macromolecules, 43(3), 1660 (2010)
  27. Li H, Wang CH, Yue J, Zhao XN, Bai F, J. Polym. Sci. A: Polym. Chem., 42(15), 3775 (2004)
  28. Oledzka E, Sokolowski K, Sobczak M, Kolodziejski W, Polym. Int., 60, 787 (2011)
  29. Fields GB, Noble RL, Int. J. Pept. Protein Res., 35, 161 (1990)
  30. Christensen T, Acta Chem. Scand. B: Org. Chem. Biochem., 33b, 763 (1979)
  31. Meaurio E, Zuza E, Sarasua JR, Macromolecules, 38(4), 1207 (2005)
  32. Schindler A, Harper D, J. Polym. Sci. Part A: Polym.Chem. Ed., 17, 2593 (1979)
  33. Dell'Erba R, Groeninckx G, Maglio G, Malinconico M, Migliozzi A, Polymer, 42(18), 7831 (2001)
  34. Duda A, Biela T, Kowalski A, Libiszowski J, Polimery (Polymers)., 50, 7 (2003)
  35. Cai Q, Zhao YL, Bei JZ, Xi F, Wang SG, Biomacromolecules, 4(3), 828 (2003)
  36. Brode GL, Koleske JV, J. Macromol. Sci. Chem., A6, 1109 (1972)
  37. Persson PV, Casas J, Iversen T, Cordova A, Macromolecules, 39(8), 2819 (2006)
  38. Bordwell FG, Acc. Chem. Res., 21, 456 (1988)
  39. Liu JY, Liu LJ, Macromolecules, 37(8), 2674 (2004)
  40. Sobczak M, Oledzka E, Kolodziejski WL, J. Macromol. Sci. Part A: Pure Appl. Chem., 45, 872 (2008)
  41. Qiu LY, Bae YH, Pharm. Res., 23, 1 (2006)
  42. Wang L, Diong CM, J. Polym. Sci. Part A: Polym. Chem., 44, 2226 (2003)
  43. Choi YR, Bae YH, Kim SW, Macromolecules, 31(25), 8766 (1998)
  44. Zhao YL, Qing C, Jing J, Shuai XT, Bei JZ, Chen CF, Fu X, Polymer, 43(22), 5819 (2002)
  45. Wang JL, Dong CM, Polymer, 47(9), 3218 (2006)
  46. Deng C, Chen XS, Yu HJ, Sun J, Lu TC, Jing XB, Polymer, 48(1), 139 (2007)