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Hydrolytic Degradation and Drug Release of Ricinoleic Acid–Lactic Acid Copolyesters

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Abstract

A systematic study on the degradation and drug release from l-lactic acid and ricinoleic-acid-based copolyesters is reported. These copolyesters were synthesized by ring opening polymerization (ROP), melt condensation (COND) and transesterification (TRANS) of high molecular weight poly(lactic acid) (PLA) with ricinoleic acid (PLA-RA), and repolymerization by condensation to yield random and block copolymers of weight average molecular weights (Mw) between 3000 and 13,000. All polymers showed an almost zero-order weight loss, with a 20–40% loss after 60 days of incubation. Lactic acid release to the degradation solution is proportional to weight loss of the polymer samples. The main decrease in molecular weight was observed during the first 20 days, followed by a slow degradation phase, which kept the number average molecular weight (Mn) at 4000–2000 for another 40 days. Water-soluble 5FU was released from ricinoleic-acid-based polymers faster than slightly water-soluble triamcinolone. Drug release into phosphate-buffered saline (pH 7.4, 0.1 M) at 37°C from P(LA-RA) 60:40 prepared by condensation of the acids was faster than from pasty P(PLA-RA) 60:40 synthesized by transesterification for both drugs.

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References

  1. A. J. Domb M. Maniar (1993) ArticleTitleAbsorbable biopolymers derived from dimer fatty acids J. Polym. Sci. A Polym. Chem. 31 1275 Occurrence Handle1:CAS:528:DyaK3sXltVeju7k%3D Occurrence Handle10.1002/pola.1993.080310523

    Article  CAS  Google Scholar 

  2. A. Sodergard M. Stolt (2002) ArticleTitleProperties of lactic acid based polymers and their correlation with composition Prog. Polym. Sci. 27 1123–1163 Occurrence Handle1:CAS:528:DC%2BD38XjvF2qsbs%3D Occurrence Handle10.1016/S0079-6700(02)00012-6

    Article  CAS  Google Scholar 

  3. K. Hiltunen M. Harkonen J. V. Seppala T. Vaananen (1996) ArticleTitleSynthesis and characterization of lactic acid based telechelic prepolymers Macromolecules 29 8677–8682 Occurrence Handle1:CAS:528:DyaK28XntlWkt78%3D Occurrence Handle10.1021/ma960402k

    Article  CAS  Google Scholar 

  4. K. Hiltunen J. V. Seppala M. Harkonen (1997) ArticleTitleLactic acid based poly(ester-urethane)s: the effects of different polymerization conditions on the polymer structure and properties J. Appl. Polym. Sci. 64 865–873 Occurrence Handle1:CAS:528:DyaK2sXislOls74%3D Occurrence Handle10.1002/(SICI)1097-4628(19970502)64:5<865::AID-APP6>3.0.CO;2-N

    Article  CAS  Google Scholar 

  5. J. Tuominen J. V. Seppala (2000) ArticleTitleSynthesis and characterization of lactic acid based poly(ester-amide) Macromolecules 33 3530–3535 Occurrence Handle1:CAS:528:DC%2BD3cXislygtbs%3D Occurrence Handle10.1021/ma991676l

    Article  CAS  Google Scholar 

  6. D. W. Grijma A. J. Nijenhuis A. J. Pennings (1990) ArticleTitleSynthesis and hydrolytic degradation behaviour of high-molecular-weight l-lactide and glycolide copolymers Polymer 31 2201–2206 Occurrence Handle10.1016/0032-3861(90)90096-H

    Article  Google Scholar 

  7. D. W. Grijma A. J. Pennings (1991) ArticleTitlePolymerization temperature effects on the properties of l-lactide and e-caprolactone copolymers Polym. Bull. 25 335–341 Occurrence Handle10.1007/BF00316903

    Article  Google Scholar 

  8. D. W. Grijma A. J. Pennings (1994) ArticleTitle(Co)polymers of l-lactide. 1: synthesis, thermal properties and hydrolytic degradation Macromol. Chem. Phys. 195 1633–1647 Occurrence Handle10.1002/macp.1994.021950515

    Article  Google Scholar 

  9. B. Buchholz (1993) ArticleTitleAnalysis and characterization of resorbable dl-lactide-trimethylene carbonate copolyesters J. Mater. Sci. 4 381–388 Occurrence Handle1:CAS:528:DyaK2cXhtlGgs74%3D Occurrence Handle10.1007/BF00122196

    Article  CAS  Google Scholar 

  10. D. Teomim A. J. Domb (2001) ArticleTitleNonlinear fatty acid terminated polyanhydrides Biomacromolecules 2 37–44 Occurrence Handle11749153 Occurrence Handle1:CAS:528:DC%2BD3cXoslGqtrw%3D Occurrence Handle10.1021/bm000081r

    Article  PubMed  CAS  Google Scholar 

  11. D. Teomim A. Nyska A. J. Domb (1999) ArticleTitleRicinoleic acid-based biopolymers J. Biomed. Mater. Res. 45 258–267 Occurrence Handle10397984 Occurrence Handle1:CAS:528:DyaK1MXisVequr8%3D Occurrence Handle10.1002/(SICI)1097-4636(19990605)45:3<258::AID-JBM14>3.0.CO;2-W

    Article  PubMed  CAS  Google Scholar 

  12. A. J. Domb R. Nudelman (1995) ArticleTitleBiodegradable polymers derived from natural fatty-acids J. Polym. Sci. A Polym. Chem. 33 717–725 Occurrence Handle1:CAS:528:DyaK2MXktVGqtrc%3D Occurrence Handle10.1002/pola.1995.080330413

    Article  CAS  Google Scholar 

  13. D. Teomim A. J. Domb (1999) ArticleTitleFatty acid terminated polyanhydrides J. Polym. Sci. A Polym. Chem. 37 3337–3344 Occurrence Handle1:CAS:528:DyaK1MXltFCmtrY%3D Occurrence Handle10.1002/(SICI)1099-0518(19990815)37:16<3337::AID-POLA32>3.0.CO;2-S

    Article  CAS  Google Scholar 

  14. G. Borsotti G. Guglielmetti S. Spera E. Battistel (2001) ArticleTitleSynthesis of phosphatidylcholines containing ricinoleic acid Tetrahedron 57 10219–10227 Occurrence Handle1:CAS:528:DC%2BD3MXptVSiu78%3D Occurrence Handle10.1016/S0040-4020(01)01057-2

    Article  CAS  Google Scholar 

  15. R. Slivniak A. J. Domb (2004) ArticleTitleLactic acid and ricinoleic acid based co-polyesters Macromolecules 38 5545–5553 Occurrence Handle10.1021/ma0503918

    Article  Google Scholar 

  16. M. Y. Krasko A. Shikanov A. Ezra A. J. Domb (2003) ArticleTitlePoly(ester anhydride)s prepared by the insertion of ricinoleic acid into poly(sebacic acid) J. Polym. Sci. A Polym. Chem. 41 1059–1069 Occurrence Handle1:CAS:528:DC%2BD3sXisVKrt70%3D Occurrence Handle10.1002/pola.10651

    Article  CAS  Google Scholar 

  17. R. Slivniak R. Langer A. J. Domb (2005) ArticleTitleLactic and ricinoleic acid based copolyesters stereocomplexation Macromolecules 38 5634–5639 Occurrence Handle1:CAS:528:DC%2BD2MXktlWnu7s%3D Occurrence Handle10.1021/ma050157h

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Medicinal Chemistry and Natural Products, School of Pharmacy–Faculty of Medicine, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel

    Raia Slivniak, Aviva Ezra & Abraham J. Domb

  2. David R. Bloom Center for Pharmacy, The Hebrew University of Jerusalem, Jerusalem, Israel

    Abraham J. Domb

  3. Alex Grass Center for Synthesis and Drug Design, The Hebrew University of Jerusalem, Jerusalem, Israel

    Abraham J. Domb

Authors
  1. Raia Slivniak
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  2. Aviva Ezra
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  3. Abraham J. Domb
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Correspondence to Abraham J. Domb.

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Slivniak, R., Ezra, A. & Domb, A.J. Hydrolytic Degradation and Drug Release of Ricinoleic Acid–Lactic Acid Copolyesters. Pharm Res 23, 1306–1312 (2006). https://doi.org/10.1007/s11095-006-0140-x

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