Polyanhydrides
Part 4. Polyesters
Dr. Neeraj Kumar,
Prof. Ann-Christine Albertsson,
Dr. Ulrica Edlund,
Dr. Doron Teomim,
Aliza Rasiel,
Prof. Abraham J. Domb,
Dr. Neeraj Kumar
- [email protected]
- +972-2-6757573 | Fax: +972-2-6757629
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorProf. Ann-Christine Albertsson
- [email protected]
- +46-8-7908274 | Fax: +46-8-100775
Royal Institute of Technology, Department of Polymer Technology, Stockholm, Sweden, S-100 44
Search for more papers by this authorDr. Ulrica Edlund
- [email protected]
- +46-8-7908274 | Fax: +46-8-100775
Royal Institute of Technology, Department of Polymer Technology, Stockholm, Sweden, S-100 44
Search for more papers by this authorDr. Doron Teomim
- [email protected]
- +972-2-6757573 | Fax: +972-2-6757629
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorAliza Rasiel
- [email protected]
- +972-2-6757573 | Fax: +972-2-6758959
Police Headquarters, Forensic Department, Jerusalem
Search for more papers by this authorProf. Abraham J. Domb
- [email protected]
- +972-2-6757573 | Fax: +972-2-6758959
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorDr. Neeraj Kumar,
Prof. Ann-Christine Albertsson,
Dr. Ulrica Edlund,
Dr. Doron Teomim,
Aliza Rasiel,
Prof. Abraham J. Domb,
Dr. Neeraj Kumar
- [email protected]
- +972-2-6757573 | Fax: +972-2-6757629
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorProf. Ann-Christine Albertsson
- [email protected]
- +46-8-7908274 | Fax: +46-8-100775
Royal Institute of Technology, Department of Polymer Technology, Stockholm, Sweden, S-100 44
Search for more papers by this authorDr. Ulrica Edlund
- [email protected]
- +46-8-7908274 | Fax: +46-8-100775
Royal Institute of Technology, Department of Polymer Technology, Stockholm, Sweden, S-100 44
Search for more papers by this authorDr. Doron Teomim
- [email protected]
- +972-2-6757573 | Fax: +972-2-6757629
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorAliza Rasiel
- [email protected]
- +972-2-6757573 | Fax: +972-2-6758959
Police Headquarters, Forensic Department, Jerusalem
Search for more papers by this authorProf. Abraham J. Domb
- [email protected]
- +972-2-6757573 | Fax: +972-2-6758959
The Hebrew University of Jerusalem, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel, 91120
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Synthesis
- Polyanhydride Structures
- Unsaturated Polymers
- Aliphatic-aromatic Homopolymers
- Soluble Aromatic Copolymers
- Poly(ester-anhydrides)
- Fatty Acid-based Polyanhydrides
- Amino Acid-based Polymers
- Modified Polyanhydrides and Blends
- Characterization
- Composition by 1H-NMR
- Molecular Weight
- Crystallinity
- Infra-red and Raman Analysis
- Surface and Bulk Analysis
- Stability
- Fabrication of Delivery Systems
- In vitro Degradation and Drug Release
- Biocompatibility and Elimination
- Applications
- Outlook and Perspectives
- Patents
References
- Abuganima, E. (1996) Synthesis and characterization of copolymers and blends of polyanhydrides and polyesters, M.Sc. Thesis, The Hebrew University of Jerusalem.
- Albertsson, A.-C., Lundmark, S. (1988) Synthesis of poly(adipic anhydride) by use of ketenes, J. Macromol. Sci.- Chem. A 25, 247–258.
- Albertsson, A.-C., Lundmark, S. (1990) Synthesis of poly(adipic) anhydride by use of ketene, J. Macromol. Sci.- Chem. A 27, 397–412.
- Albertsson, A.-C., Carlfors, J., Sturesson, C. (1996) Preparation and characterization of poly(adipic anhydride) microspheres for ocular drug delivery, J. Appl. Polym. Sci. 62, 695–705.
- Bindschaedler, C., Leong, K., Mathiowitz, E., Langer, R. (1988) Poly(anhydride) microspheres formulation by solvent extraction, J. Pharm. Sci. 77, 696–698.
- Braun, A. G., Buckner, C. A., Emerson, D. J., Nichinson, B. B. (1982) Quantitative correspondence between the in vivo and in vitro activity of teratogenic agents, Proc. Natl. Acad. Sci. USA 79, 2056.
-
Brem, H.,
Lawson, H. C.
(1999)
The development of new brain tumor therapy utilizing the local and sustained delivery of chemotherapeutic agents from biodegradable polymers,
Cancer 86,
197–199.
10.1002/(SICI)1097-0142(19990715)86:2<197::AID-CNCR2>3.0.CO;2-6 CAS PubMed Web of Science® Google Scholar
- Brem, H., Tamargo, R. J., Pinn, M., Chasin, M. (1988) Biocompatibility of a BCNU-loaded biodegradable polymer: a toxicity study in primates, Am. Assoc. Neurol. Surg. 24, 381.
- Brem, H., Kader, A., Epstein, J. I., Tamargo, R. J., Domb, A. J., Langer, R., Leong, K. W. (1989) Biocompatibility of bioerodible controlled release polymer in the rabbit brain, Sel. Cancer Ther. 5, 55–65.
- Brem, H., Mahley, M. S., Vick, N. A. et al. (1991) Interstitial chemotherapy with drug polymer implants for the treatment of recurrent gliomas, J. Neurosurg. 74, 441–446.
- Brem, H., Walter, K. A., Tamargo, R. J., Olivi, A., Langer, R. (1994) Drug delivery to the brain, in: Polymeric Site-Specific Pharmacotherapy ( A. Domb, Ed.), Chichester: John Wiley & Sons, 117–140.
- Brem, H., Piantadosi, S., Burger, P. C. et al. (1995) Placebo-controlled trial of safety and efficacy of intraoperative controlled delivery by biodegradable polymers of chemotherapy for recurrent gliomas. The Polymer-brain Tumor Treatment Group, Lancet 345, 1008–1012.
- Bucher, J. E., Slade, W. C. (1909) The anhydrides of isophthalic and terephthalic acids, J. Am. Chem. Soc. 31, 1319–1321.
- Chasin, M., Domb, A., Ron, E., Mathiowitz, E., Leong, K., Laurencin, C., Brem, H., Grossman, S., Langer, R. (1990) Polyanhydrides as drug delivery systems, in: Biodegradable Polymers as Drug Delivery Systems ( M. Chsin, R. Langer, Eds.), New York: Marcel Dekker, 43–70.
- Chickering, D., Jacob, J., Mathiowitz, E. (1996) Poly(fumaric-co-sebacic) microspheres as oral drug delivery systems, Biotechnol. Bioenerg. 52, 96–101.
- Conix, A. (1958) Aromatic poly(anhydrides): a new class of high melting fiber-forming polymers, J. Polym. Sci. 29, 343–353.
- Dang, W. B., Daviau, T., Nowotnik, D. (1996) In vitro erosion kinetics of implantable polyanhydride GliadelTM, Proc. Int. Symp. Control. Rel. Bioact. Mater. 23, 731–732.
- Davies, M. C., Khan, M. A., Domb, A. J., Langer, R., Watts, J. F., Paul, A. (1991) The analysis of the surface chemical structure of biomedical aliphatic poly(anhydrides) using XPS and ToF-SIMS, J. Appl. Polym. Sci. 42, 1597–1605.
- Davies, M. C., Shakesheff, K. M., Shard, K. M., Domb, A. J., Roberts, C. J., Tendler, S. J. B., Williams, P. M., Tendler, S. J. B. and Williams, P. M. (1996) Surface analysis of biodegradable polymer blends of poly(sebacic anhydride) and poly(DL-lactic acid), Macromolecules 29, 2205–2212.
- D'Emanuele, A., Hill, J., Tamada, J. A., Domb, A. J., Langer, R. (1994) Molecular weight changes in polymer erosion, Pharmaceut. Res. 9, 1279–1283.
- Domb, A. J. (1990) Biodegradable polymers derived from amino acids, Biomaterials 11, 686–689.
- Domb, A. J. (1992) Synthesis and characterization of bioerodible aromatic anhydride copolymers, Macromolecules 25, 12–17.
- Domb, A. J. (1993) Biodegradable polymer blends: screening for miscible polymers, J. Polym. Sci.: Polym. Chem. 31, 1973–1981.
- Domb, A. J., Amselem, S. (1994) Antibiotic delivery systems for the treatment of bone infections, in: Polymeric Site-Specific Pharmacotherapy (Domb, A.J., Ed.), Chichester: John Wiley & Sons, 242–265.
- Domb, A. J., Langer, R. (1987) Poly(anhydrides). I. Preparation of high molecular weight polyanhydrides, J. Polym. Sci. Polym. Chem. 25, 3373–3386.
- Domb, A. J., Langer, R. (1989) Solid-state and solution stability of poly(anhydrides) and poly(esters), Macromolecules 22, 2117–2122.
- Domb, A. J., Maniar, M. (1993a) Absorbable biopolymers derived from dimers fatty acids, J. Poly. Sci.: Polym. Chem. 31, 1275–1285.
- Domb, A. J., Maniar, M. (1993b) Fatty acid terminated polyanhydrides, US Patent 5,179,189.
- Domb, A. J., Nudelman, R. (1995a) Biodegradable polymers derived from natural fatty acids, J. Polym. Sci. 33, 717–725.
- Domb, A. J., Nudelman, R. (1995b) In vivo and in vitro elimination of aliphatic polyanhydrides, Biomaterials 16, 319–323.
-
Domb, A. J.,
Ringel, I.
(1994)
Polymeric Drug Carrier Systems in the Brain, in: Providing Pharmaceutical Access to the Brain, Methods in Neuroscience ( T. R. Flanaga, D. F. Emerich, S. R. Winn Eds.) Boca Raton, FL: CRC Press,
169–183, Vol. 21.
10.1016/B978-0-12-185291-7.50016-3 Google Scholar
- Domb, A. J., Ron, E., Langer, R. (1988) Poly(anhydrides). II. One step polymerization using phosgene or diphosgene as coupling agents, Macromolecules 21, 1925–1929.
- Domb, A. J., Gallardo, C. F., Langer, R. (1989) Poly(anhydrides). 3. Poly(anhydrides) based on aliphatic-aromatic diacids, Macromolecules 22, 3200–3204.
- Domb, A. J., Mathiowitz, E., Ron, E., Giannos, S., Langer, R. (1991) Polyanhydrides IV. Unsaturated and cross-linked poly(anhydrides), J. Polym. Sci. Part A: Polym. Chem. 29, 571–579.
- Domb, A. J., Amselem, S., Shah, J., Maniar, M. (1993) Polyanhydrides: Synthesis and characterization, in: Advances in Polymer Sciences ( N. A. Peppas, R. Langer, Eds.), Heidelberg: Springer-Verlag, 93–141.
- Domb, A. J., Amselem, S., Langer, R., Maniar, M. (1994a) Polyanhydrides as carriers of drugs, in: Designed to Degrade Biomedical Polymers ( S. Shalaby, Ed.), Munich: Carl Hanser Verlag, 69–96.
- Domb, A. J., Rock, M., Perkin, C., Proxap, B., Villemure, J. G. (1994b) Metabolic disposition and elimination studies of a radiolabelled biodegradable polymeric implant in the rat brain, Biomaterials 15, 681–688.
- Domb, A. J., Rock, M., Perkin, C., Proxap, B., Villemure, J. G. (1995) Excretion of a radiolabelled biodegradable polymeric implant in the rabbit brain, Biomaterials 16, 1069–1072.
- Domb, A. J., Elmalak, O., Shastri, V. R., Ta-Shma, Z., Masters, D. M., Ringel, I., Teomim, D., Langer, R. (1997) Polyanhydrides, in: Handbook of Biodegradable Polymers ( A. J. Domb, J. Kost, D. M. Weiseman, Eds.), Amsterdam: Harwood Academic Publishers, 135–159.
- Domb, A. J., Israel, J. H., Elmalak, O., Teomim, D., Bentolila, A. (1999) Preparation and characterization of Carmustine loaded biodegradable disc for treating brain tumors, Pharm. Res. 16, 762–765.
- Edlund, U., Albertsson, A.-C. (1999) Copolymerization and polymer blending of trimethylene carbonate and adipic anhydride for tailored drug delivery, J. Appl. Polym. Sci. 72, 227–239.
- Edlund, U., Albertsson, A.-C., Singh, S. K., Fogelberg, I. (2000) Sterilization, storage, stability and in vivo biocompatibility of poly(trimethylene carbonate)/poly(adipic anhydride) blends, Biomaterials 21, 945–955.
- Fung, L. K., Ewend, M., Sills, A. et al. (1998) Pharmacokinetics of interstitial delivery of carmustine, 4-hydroperoxycyclophosphamide and paclitaxel from a biodegradable polymer implant in the monkey brain, Cancer Res. 58, 672–684.
- Gopferich, A., Langer, R. (1993) The influence of microstructure and monomer properties on the erosion mechanism of a class of polyanhydrides, J. Polym. Sci. 31, 1445–1458.
- Gopferich, A., Langer, R. (1995a) Modeling of polymer erosion in three dimensions: rotationally symmetric devices, AIChE J. 41, 2292–2299.
- Gopferich, A., Langer, R. J (1995b) Modeling monomer release from bioerodible polymers, J. Control. Rel. 33, 55–69.
- Gopferich, A., Karydas, D., Langer, R. (1995) Predicting drug release from cylindrical polyanhydride matrix discs, Eur. J. Pharm. Biopharm. 41, 81–87.
- Gref, R., Minamitake, Y., Peracchia, M. T., Domb, A. J., Trubetskoy, V., Torchilin, V., Langer, R. (1995) Poly(ethylene glycol) coated nanospheres, Adv. Drug Deliv. Rev. 16, 215–233.
- Gupta, B. (1988) Polyanhydride process from bis(trimethylsilyl) ester of dicarboxylic acid, US Patent 4,868,265.
- Hamilton-Byrd, E. L., Sokoloff, A. J., Domb, A. J., Terr, L., Byrd, K. E. (1992) L-Glutamate microsphere stimulation of the trigeminal motor nucleus in growing rats, Polym. Adv. Technol. 3, 337–344.
- Hartmann, M., Schultz, V. (1989) Synthesis of poly(anhydride) containing amido groups, Macromol. Chem. 190, 2133.
- Hill, J. W. (1930) Studies on polymerization and ring formation. VI. Adipic anhydride, J. Am. Chem. Soc. 52, 4110–4114.
-
Hill, J. W.,
Carothers, H. W.
(1932)
Studies on polymerization and ring formation. XIV. A linear superpolyanhydride and a cyclic dimeric anhydride from sebacic acid,
J. Am. Chem. Soc. 54,
5169.
10.1021/ja01343a050 Google Scholar
- Jiang, H. L., Zhu, K. J. (2000) Pulsatile protein release from a laminated device comprising of polyanhydrides and pH-sensitive complexes, Int. J. Pharm. 194, 51–60.
- Judy, K. D., Olivi, A., Buahin, K. G., Domb, A. J., Epstein, J. I., Colvin, O. M., Brem, H. (1995) Effectiveness of controlled release of a cyclophosphamide derivative with polymers against rat gliomas, J. Neurosurg. 82 481–486.
-
Kim, B. S.,
Hrkach, J. S.,
Langer, R.
(2000)
Synthesis and characterization of novel degradable photocrosslinked poly(ester-anhydride) networks,
J. Polym. Sci. A: Polym. Chem. 38,
1277–1282.
10.1002/(SICI)1099-0518(20000415)38:8<1277::AID-POLA11>3.0.CO;2-S CAS Web of Science® Google Scholar
- Knobloch, J. O., Ramirez, F. (1975) J. Org. Chem. 40, 1101–1106.
- Kubek, M. J., Liang, D., Byrd, K. E., Domb, A. J. (1998) Prolonged seizure suppression by a single implantable polymeric TRH microdisk preparation, Brain. Res. 809, 189–197.
- Laurencin, C. T., Domb, A. J., Morris, C., Brown, V., Chasin, M., McConnell, R., Lange, N., Langer, R. (1990) Poly(anhydrides) administration in high doses in vivo: studies of biocompatibility and toxicology, J. Biomed. Mater. Res. 24, 1463–1481.
- Laurencin, C., Gerhart, T., Witschger, P., Satcher, R., Domb, A. J., Hanff, P., Edsberg, L., Hayes, W., Langer, R. (1993) Biodegradable polyanhydrides for antibiotic drug delivery, J. Orthop. Res. 11, 256–262.
- Laurencin, C. T., Ibim, S. E. M., Langer, R. (1995) Poly(anhydrides) in: Biomedical Applications of Synthetic Biodegradable Polymers ( J. O. Hollinger, Ed.), Boca Raton, FL: CRC Press, 59–102.
- Leong, K. W., D'Amore, P., Langer, R. (1986a) Bioerodible poly(anhydrides) as drug carrier matrices. II. Biocompatibility and chemical reactivity, J. Biomed. Mater. Res. 20, 51–64.
- Leong, K.W., Kost, J., Mathiowitz, E., Langer, R. (1986b) Poly(anhydrides) for controlled release of bioactive agents, Biomaterials 7, 364.
- Leong, K. W., Simonte, V., Langer, R. (1987) Synthesis of poly(anhydrides): melt-polycondensation, dehydrochlorination, and dehydrative coupling, Macromolecules 20, 705–712.
- Leong, K. W., Domb, A., Langer, R. (1989) Poly(anhydrides), in: Encyclopedia of Polymer Science and Engineering, 2nd Ed., New York: John Wiley & Sons.
- Lundmark, S., Sjoling, M., Albertsson, A.-C. (1991) Polymerization of oxipane-2,7-dione in solution and synthesis of block copolymer of oxipane-2,7-dione and 2-oxipanone, J. Macromol. Sci.- Chem. A 28, 15–29.
- Mader, K., Domb, A. J., Swartz, H. M. (1996) Gamma sterilization induced radicals in biodegradable drug delivery systems, J. Appl. Rad. Isotop. 47, 1669–1674.
- Mader, K., Bacic, G., Domb, A. J., Elmalak, O., Langer, R., Swartz, H. M. (1997a) Noninvasive in vivo monitoring of drug release and polymer erosion from biodegradable polymers by EPR spectroscopy and NMR imaging, J. Pharm. Sci. 86, 126–134.
- Mader, K., Cremmilleleux, Y., Domb, A. J., Dunn, J. F., Swartz, H. M. (1997b) In vitro/in vivo comparison of drug release and polymer erosion from biodegradable P(FAD-SA) polyanhydrides – a noninvasive approach by the combined use of Electron Paramagnetic Resonance Spectroscopy and Nuclear Magnetic Resonance Imaging, Pharm. Res. 14, 820–826.
- Maniar, M., Xie, X., Domb, A. J. (1990) Poly(anhydrides). V. Branched poly(anhydrides), Biomaterials 11, 690–694.
- Maniar, M., Domb, A., Haffer, A., Shah, J. (1994) Controlled release of local anesthetics from fatty acid dimer based polyanhydrides, J. Control. Rel. 30, 233–239.
- Mark, H.E., et al. (Eds.) (1969) Poly(anhydrides), in: Encyclopedia of Polymer Science and Technology New York: John Wiley & Sons, 630, Vol. 10.
- Masters, D. B., Berde, C. B., Dutta, S. K., Griggs, C. T., Hu, D., Kupsky, W., Langer, R. (1993a) Prolonged regional nerve blockade by controlled release of local anesthetic from a biodegradable polymer matrix, Anesthesiology 79, 340–346.
- Masters, D. B., Berde, C. B., Dutta, S., Turek, T., Langer, R. (1993b) Sustained local anesthetic release from bioerodible polymer matrices: a potential method for prolonged regional anesthesia, Pharm. Res. 10, 1527–1532.
- Mathiowitz, E., Langer, R. (1987) Poly(anhydride) microspheres as drug carriers. I. Hot-melt microencapsulation, J. Control. Rel. 5, 13–22.
- Mathiowitz, E., Kline, D., Langer, R. (1990) Morphology of poly(anhydride) microspheres delivery systems, J. Scan. Microsc. 4, 329.
- Mathiowitz, E., Jacob, J. S., Jong, Y. S., Carino, G. P., Chickering, D. E., Chaturvedi, P., Santos, C. A., Vijyaraghavan, K., Montgomery, S., Basset, M., Morrell, C. (1997) Biologically erodible microspheres as potential oral drug delivery systems, Nature 386, 410–414.
- McIntyre, J. E. (1994) British Patent 978,669.
-
Muggli, D. S.,
Burkoth, A. K.,
Anseth, K. S.
(1999)
Crosslinked polyanhydrides for use in orthopedic applications: degradation behavior and mechanics,
J. Biomed. Mater. Res. 46,
271–278.
10.1002/(SICI)1097-4636(199908)46:2<271::AID-JBM17>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- Olivi, A., Awend, M.G., Utsuki, T., Tyler, B., Domb, A. J., Brat, D. J., Brem, H. (1996) Interstitial delivery of carboplatin via biodegradable polymers is effective against experimental glioma in the rat, Cancer, Chemother. Pharmacol. 39, 90–96.
- Pekarek, K. J., Jacob, J. S., Mathiowitz, E. (1994) One-step preparation of double-walled microspheres Nature 357, 258–260.
- Rock, M., Green, M., Fait, C., Gell, R., Myer, J., Maniar, M., Domb, A. (1991) Evaluation and comparison of biocompatibility of various classes of polyanhydrides, Polym. Preprints 32, 221.
- Ron, E., Mathiowitz, E., Mathiowitz, G., Domb, A., Langer, R. (1991) NMR characterization of erodible copolymers, Macromolecules 24, 2278–2282.
- Rosen, H. B., Chang, J., Wnek, G. E., Lindhardt, R. J., Langer, R. (1983) Biodegradable poly(anhydrides) for controlled drug delivery, Biomaterials 4, 131–133.
- Santos, S. A., Freedman, B. D., Leach, K. J., Press, D. L., Scarpulla, M., Mathiowitz, E. (1999) Poly(fumaric-co-sebasis anhydride) – A degradation study as evaluated by FTIR, DSC, GPC and X-ray diffraction, J. Control. Rel. 60, 11–22.
- Shakesheff, K. M., Davies, M. C., Roberts, C. J., Tendler, S. J. B., Shard, K. M., Domb, A. J. (1994) In situ AFM imaging of polymer degradation in an aqueous environment, Langmuir 10, 4417–4419.
- Shakesheff, K. M., Chen, X., Davies, M. C., Domb, A. J., Roberts, M. C., Tendler, S. J. B., Williams, P. M. (1995) Relating the phase morphology of a biodegradable polymer blend to erosion kinetics using simultaneous in situ atomic force microscopy and surface plasmon resonance analysis, Langmuir 11, 3921–3927.
- Staubli, A., Ron, E., Langer, R. (1990) Hydrolytically degradable amino acid containing polymers, J. Am. Chem. Soc. 112, 4419–4424.
- Staubli, A., Mathiowitz, E., Lucarelli, M., Langer, R. (1991a) Characterization of hydrolytically degradable amino acid containing poly(anhydride-co-imides), Macromolecules 24, 2283–2290.
- Staubli, A., Mathiowitz, E., Langer, R. (1991b) Sequence distribution and its effects on glass transition temperatures of poly(anhydrides-co-imides) containing asymmetric monomers, Macromolecules 24, 2291–2298.
- Stephens, D., Li, L., Robinson, D., Chen, S., Chang, H. C., Liu, R. M., Tian, Y. Q., Ginsberg, E. J., Gao, X. Y., Stultz, T. (2000) Investigation of the in vitro release of gentamicin from a polyanhydride matrix, J. Control. Rel. 63, 305–317.
- Subramanyam, R., Pinkus, A. G. (1985) Synthesis of poly(terephthalic anhydride) by hydrolysis of terephthaloyl chloride triethylamine intermediate adduct: characterization of intermediate adduct, J. Macromol. Sci. Chem. A22, 23.
- Tabata, Y., Domb, A. J., Langer, R. (1994) Polyanhydride granules provide controlled release of water-soluble drugs with reduced initial burst, J. Pharm. Sci. 83, 5–11.
- Tamargo, R. J., Epstein, J. I., Reinhard, C. S., Chasin, M., Brem, H. (1989) Brain biocompatibility of a biodegradable controlled-release polymer in rats, J. Biomed. Mater. Res. 23, 253–266.
- Tamargo, R. J., Myseros, J. S., Epstein, J. I., Yang, M. B., Chasin, M., Brem, H. (1993) Interstitial chemotherapy of the 9L-glyosarcoma – Controlled release polymers for drug delivery in the brain, Cancer Res. 53, 329–333.
-
Teomim, D.,
Domb, A. J.
(1999)
Fatty acid terminated polyanhydrides,
J. Polym. Sci. A: Polym. Chem. 37,
3337–3344.
10.1002/(SICI)1099-0518(19990815)37:16<3337::AID-POLA32>3.0.CO;2-S CAS Web of Science® Google Scholar
- Teomim, D., Fishbien, I., Golomb, G., Orloff, L., Mayberg, M., Domb, A. J. (1999a) Perivascular delivery of heparin for the reduction of smooth muscle cell proliferation after endothelial injury, J. Control. Rel. 60, 129–142.
-
Teomim, D.,
Nyska, A.,
Domb, A. J.
(1999b)
Ricinoleic acid based biopolymers,
J. Biomed. Mater. Res. 45,
258–267.
10.1002/(SICI)1097-4636(19990605)45:3<258::AID-JBM14>3.0.CO;2-W CAS PubMed Web of Science® Google Scholar
- Teomim, D., Mader, K., Bentolila, A., Magora, A., Domb, A. J. (2001) Macromolecules (in press).
- Tudor, A. M., Melia, C. D., Davies, M. C., Hendra, P. J., Church, S., Domb, A. J., Langer, R. (1991) The application of the Fourier-Transform Raman spectroscopy to the analysis of poly(anhydride) home and copolymers, Spectrochim. Acta 47A, 1335–1343.
- Uhrich, K. E., Gupta, A., Thomas, T. T., Laurencin, C. T., Langer, R. (1995) Synthesis and characterization of degradable poly(anhydride-co-imides), Macromolecules 28, 2184–2193.
- Uhrich, K. E., Thomas, T. T., Laurencin, C. T., Langer, R. (1997) In vitro degradation characteristics of poly(anhydride-co-imides) containing trimellityimidoglycine, J. Appl. Polym. Sci. 63, 1401–1411.
- Wu, M. P., Tamada, J. A., Brem, H., Langer, R. (1994) In vivo versus in vitro degradation of controlled release polymers for intercranial surgery therapy, J. Biomed. Mater. Res. 28, 387–395.
- Yoda, N. (1962) Synthesis of poly(anhydrides). Poly(anhydrides) of five-membered heterocyclic dibasic acids, Makromol. Chem. 55, 174–190.
- Yoda, N. (1963) Synthesis of poly(anhydrides). Crystalline and high melting poly(amide) poly(anhydrides) of methylene bis(p-carboxyphenyl) amide, J. Polym. Sci., Part A 1, 1323–1338.
- Young, J. S., Gonzales, K. D., Anseth, K. S. (2000) Photopolymers in orthopedics: Characterization of novel crosslinked polyanhydrides, Biomaterials 110, 1181–1188.
Citing Literature
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work:
