Stereocomplexes of enantiomeric lactic acid and sebacic acid ester-anhydride triblock copolymers.
A systematic study on the synthesis, characterization, degradation, and drug release of d-, l-, and dl-poly(lactic acid) (PLA)-terminated poly(sebacic acid) (PSA) and their stereocomplexes is reported. PLA-terminated sebacic acid polymers were synthesized by melt condensation of the acetate anhydride derivatives of PLA oligomers and sebacic anhydride oligomers to yield ABA triblock copolymers of molecular weights between 3000 and 9000 that melt at temperatures between 35 and 80 degrees C. Pairs of the corresponding enantiomeric ABA copolymers composed of l-PLA-PSA-l-PLA and d-PLA-PSA-d-PLA were solvent mixed to form stereocomplexes. The formed stereocomplexes exhibited higher crystalline melting temperature than the enantiomeric polymers, which indicate stereocomplex formulation. The PLA terminals had a significant effect on the polymer degradation and drug release rate. PSA with up to 20% w/w of PLA terminals degraded and released the incorporated drug for more than 3 weeks as compared with 10 days for PSA homopolymer.
Slivniak
Raia
R
Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem 91120, Israel.
Domb
Abraham J
AJ
D000893:Anti-Inflammatory Agents / Q000008:administration & dosage / Q000493:pharmacokinetics; D001673:Biodegradation, Environmental; D003652:Decanoic Acids / Q000737:chemistry; D003692:Delayed-Action Preparations / Q000138:chemical synthesis*; D003998:Dicarboxylic Acids; D004339:Drug Compounding / Q000379:methods; D006868:Hydrolysis; D007700:Kinetics; D019344:Lactic Acid / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014221:Triamcinolone / Q000008:administration & dosage / Q000493:pharmacokinetics
D000893:Anti-Inflammatory Agents; D003652:Decanoic Acids; D003692:Delayed-Action Preparations; D003998:Dicarboxylic Acids; D011108:Polymers; D014221:Triamcinolone; D019344:Lactic Acid; C011107:sebacic acid