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An In Situ Gel-Forming Heparin-Conjugated PLGA-PEG-PLGA Copolymer

Department of Molecular Science and Technology, Ajou University San 5 Wonchun, Yeongtong, Suwon, Republic of Korea, 443-749

Yoon Ki Joung

Department of Molecular Science and Technology, Ajou University San 5 Wonchun, Yeongtong, Suwon, Republic of Korea, 443-749

Jin Woo Bae

Department of Molecular Science and Technology, Ajou University San 5 Wonchun, Yeongtong, Suwon, Republic of Korea, 443-749

Ki Dong Park

Department of Molecular Science and Technology, Ajou University San 5 Wonchun, Yeongtong, Suwon, Republic of Korea, 443-749, kdp{at}ajou.ac.kr

Novel heparin-conjugated PLGA-PEG-PLGA hydrogels were prepared via Michael-type addition between thiolated heparin and PLGA-PEG-PLGA diacrylate. The thiolated heparin (HP-SH) was conjugated with thiolacid dihydrazide followed by reduction. The structure and the thiol determination of obtained HP-SH were characterized by ¹H NMR and the Ellman method. Anticoagulant activity and pK _a of the HP-SH were determined by aPTT test and UV absorbance measurement which were 79.3% and 10.5, respectively. The PLGA-PEG-PLGA diacrylate was synthesized by bulk ring-opening polymerization of D,L-lactide (DLLA) and glycolide (GA) with PEG and stannous 2-ethylhexanoate, followed by the acrylation of the terminal groups. HP—SH was then conjugated to PLGA-PEG-PLGA diacrylate by Michael addition. Phase diagrams of the hydrogels were obtained by vial tilting; the release of heparin from the hydrogels exhibited temperature dependent sol—gel transition behavior. These in situ-forming heparin-conjugated hydrogels are novel as injectable and tissue-compatible scaffold formation, thermo-sensitivity, and growth factor binding.

Key Words: in situ-forming hydrogel • heparin • Michael-type addition • PLGA-PEG-PLGA • tissue engineering.

Journal of Bioactive and Compatible Polymers, Vol. 23, No. 5, 444-457 (2008)
DOI: 10.1177/0883911508095245


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