Biosynthetic polyhydroxyalkanoates and their potential in drug delivery

Advanced Drug Delivery Reviews

Volumn 18, Issue 2, 1996, Pages 133-162

  Pouton, Colin W ^a   Akhtar, Saghir ^b  

^a University of Bath   (United Kingdom)

^b ASTON UNIVERSITY   (United Kingdom)

Author keywords

Bacterial energy storage; Biodegradable polymer; Bioerodible polymer; Controlled release; Implant; Polyester; Polyhydroxybutyrate; Polyhydroxyvalerate; Polymer crystallinity

Indexed keywords

BIOCOMPATIBILITY; BIODEGRADATION; BIOPOLYMERS; CONTROLLED DRUG DELIVERY; COPOLYMERS; ENERGY STORAGE; FERMENTATION; IMPLANTS (SURGICAL); POLYESTERS; POLYMER BLENDS; POROSITY;

BACTERIAL ENERGY STORAGE; BACTERIAL STRAIN; BIODEGRADABLE POLYMERS; CRYSTALLINITY; HOMOPOLYMERS; HYDROLYTIC DEGRADATION; PHYSICOMECHANICAL PROPERTIES; POLYHYDROXBUTYRATE; POLYHYDROXY VALERATE; POLYHYDROXYALKANOATES;

DRUG THERAPY;

ACLARUBICIN; ANTINEOPLASTIC AGENT; BLEOMYCIN; COPOLYMER; DOXORUBICIN; ETOFYLLINE; FLUOROURACIL; GONADORELIN; LOMUSTINE; POLY(3 HYDROXYBUTYRATE CO 3 HYDROXYVALERATE); POLY(3 HYDROXYBUTYRIC ACID); POLYESTER; POLYGLACTIN; POLYHYDROXYALKANOIC ACID; POLYMER; SOLVENT; UNCLASSIFIED DRUG;

BACTERIUM; BIOCOMPATIBILITY; BIODEGRADATION; BIOENGINEERING; BIOSYNTHESIS; CRYSTALLIZATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; ENERGY METABOLISM; FERMENTATION; HUMAN; HYDROLYSIS; IMPLANT; MORPHOLOGY; NONHUMAN; PHARMACEUTICS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; SUSTAINED RELEASE PREPARATION;

EID: 0029671369     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0169-409X(95)00092-L     Document Type: Review

References (202)

1. Kitchell, J.P. and Wise, D.L. (1985) Poly(lactic glycolic acid) biodegradable drug polymer matrix systems. Methods Enzymol. 112, 436-448.
2. Eppstein, D.A. and Longenecker, J.P. (1988) Alternative delivery systems for peptides and proteins as drugs. CRC Crit. Rev. Ther. Drug Carrier Systems 5, 99-139.
3. Juni, K. and Nakano, M. (1987) Poly(lactic acid) microspheres as drug carrier systems. In: L. Ilium and S.S. Davis (Eds), Polymers in Controlled Drug Delivery, Wright Publishers, Bristol, pp. 49-59.
4. Tice, T.R., Mason, D.W. and Gilley, R.M. (1989) Poly(lactide-co-glycolide) drug delivery systems. In: L.F. Prescott and W.S. Nimmo (Eds), Novel Drug Delivery and its Therapeutic Application, John Wiley and Sons, Chichester, pp. 223-235
5. Fildes, F.J.T., Hutchinson, F.G. and Furr, B.J.A. (1991) The development of 'Zoladex'-a case history. In: R.C. Hider and D. Barlow (Eds), Polypeptide and Protein Drugs: Production, Characterization and Formulation, Ellis Horwood, Chichester, pp. 228-250
6. Heller, J. (1993) Poly(ortho esters). Adv. Polym. Sci. 107, 41-92
7. Heller, J. (1994) Use of poly(ortho esters) and polyanhydrides in the development of peptide and protein delivery systems. Am. Chem. Soc. Symp. Ser. 567, 292-305.
8. Shieh, L., Tamada, J., Tabata, Y., Domb, A. and Langer, R. (1994) Drug release from a new family of biodegradable polyanhydrides. J. Controlled Release 29, 73-82.
9. Wu, M.P. Tamada, J.A., Brein, H. and Langer, R. (1994) In vivo versus in vitro degradation of controlled release polymers for intracranial surgical therapy. J. Biomed. Mater. Res. 28, 387-395.
10. Anderson, A.J. and Dawes, E.A. (1990) Occurrence, metabolism, metabolic role, and industrial uses of polyhydroxyalkanoates. Microbiol. Rev. 54, 450-472.
11. Brandl, H., Bachofen, R., Mayer, J. and Wintermantel, E. (1995) Degradation and applications of polyhydroxyalkanoates. Can. J. Microbiol. 41, 143-153.
12. Lemoigne, M. (1925) Etudes sur l'autolyse microbienne acidification par formation d'ucide β-oxybutyrique. Ann. Inst. Pasteur 39, 144-173.
13. Dawes, E.A and Senior, P.J. (1973) The role and regulation of energy reserve polymers in microorganisms. In: A.H. Rose and D.W. Tempest (Eds), Advances in Microbial Physiology, Academic Press, Vol. 10, pp. 136-267.
14. Herron, J.S., King, J.D. and White, D.C. (1978) Recovery of poly-β-hydroxybutyrate from estuarine microflora. Appl. Environ. Microbiol. 35, 251-257.
15. Carr, N.G. (1966) The occurrence of poly-β-hydroxybutyrate in the blue-green alga, Chlorogloea fritschii. Biochim. Biophys. Acta 120, 308-310.
16. Ward, A.C., Rowley, B.I. and Dawes, E.A. (1977) Effect of oxygen and nitrogen limitation on poly-β-hydroxybutyrate biosynthesis in ammonium-grown Azotobacter beijerinckii. J. Gen. Microbiol. 102, 61-68.
17. Williamson, D.H. and Wilkinson, J.F. (1958) The isolation and estimation of the poly-β-hydroxybutyrate inclusions of Bacillus species. J. Gen. Microbiol. 19, 198-209.
18. Merrick, J.M. and Doudoroff, M. (1961) Enzymatic sythesis of poly-β-hydroxybutyrate in bacteria. Nature 189, 890-892.
19. Lundgren, D.G., Alper, R., Schnaitman, C. and Marchessault, R.H. (1965) Characterization of poly-β-hydroxybutyrate extracted from different bacteria. J. Bacteriol. 89, 245-251.
20. Laffferty, R.M., Korsatko, B. and Korsatko, W. (1988) Microbial production of poly-3-hydroxybutyric acid. In: H.J. Rehm and G. Reed (Eds), Biotechnology: A Comprehensive Treatise, Special Microbial Processes, VCH Verlagsgesellschaft, Weinhheim, Vol. 6b, pp.135-176.
21. Holmes, P.A. (1985) Applications of PHB-a microbially produced biodegradable thermoplastic. Phys. Technol. 16, 32-36.
22. Howells, E.R. (1982) Single-cell protein and related technology. Chem. Ind. 7, 508-511.
23. Senior, P.J. and Dawes, E.A. (1973) Poly-β-hydroxybutyrate biosynthesis and the regulation of glucose metabolism in grown Azotobacter beijerinckii. Biochem. J. 134, 225-238.
24. Oeding, V. and Schlegel, H.G. (1973) β-ketothiolase from Hydrogenomonus eutrophus H16 and its significance in regulation of poly-β-hydroxybutyrate metabolism. Biochem. J. 134, 239-248.
25. Dawes, E.A. (1988) polyhydroxybutyrate-an intriguing bio-polymer. Biosci. Rep. 8, 537-547.
26. Griebel, R. and Merrick, J.M. (1971) PHB synthase activity in Alcaligenes eutrophus. J. Bacteriol. 108, 782-789
27. Haywood, G.W., Anderson, A.J. and Dawes, E.A. (1989) The importance of PHB-synthase substrate specificity in polyhydroxyalkanoate synthesis by Alcaligenes eutrophus. FEMS Microbiol. Lett. 57, 1-6.
28. Suzuki, T., Yamane, T. and Shimizu, S. (1986) Mass production of poly-β-hydroxybutyric acid by fully automatic fed-culture methylotroph. Appl. Microbiol. Biotechnol. 23, 322-329.
29. Doi, Y. (1988) European Patent No. 0 288 908.
30. 13C-labeled acetate and propionate. J. Chem. Soc. Chem. Commun. 23, 1696-1697.
31. 13C NMR analysis of poly(β-hydroxybutyrate) isolated from Bacillus megaterium. Macromolecules 19, 1274-1276.
32. 13C-labeled acetate and propionate. Macromolecules 20, 2988-2991.
33. Kunioka, M., Nakamura, Y. and Doi, Y. (1988) New bacterial copolyesters produced in Alcaligenes eutrophus from organic acids. Polym. Commun. 29, 174-176.
34. Doi, Y., Tamaki, A., Kunioka, M. and Soga, K. (1988) Production of copolyesters of 3-hydroxybutyrate and 3-hydroxyvalerate by Alcaligenes eutrophus from butyric and pentanoic acids. Appl. Microbiol. Biotechnol. 28, 330-334.
35. Doi, Y., Kunioka, M., Nakamura, Y. and Soga, Y. (1988) Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate. Macromolecules 21, 2722-2727.
36. 13C NMR spectroscopy. Makromol. Chem. Rapid. Commun. 7, 661-664.
37. Doi, Y., Kunioka, M., Tamaki, A., Nakamura, Y. and Soga, Y. (1988)) Nuclear magnetic resonance studies on bacterial copolyesters of 3-hydroxybutyric acid and 3-hydroxyvaleric acid. Makromol. Chem. 189, 1077-1086.
38. Kamiya, N., Yamamoto, Y., Inoue, Y., Chujo, R. and Doi, Y. (1989) Microstructure of bacterially synthesized poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 22, 1676-1682.
39. Lee, E.Y., Kang, S.H. and Choi, C.Y. (1995) Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by newly isolated Agrobacterium sp. SH-1 and GW-014 from structurally unrelated single carbon substrates. J. Ferment. Bioeng. 79, 328-334.
40. Martineztoledo, M.V., Gonzalezlopez, J., Rodelas, B., Pozo, C. and Salmeron, V. (1995) Production of poly(β-hydroxybutyrate) by Azotobacter chroococcum H23 in chemically-defined medium and alpechin medium. J. Appl. Bacteriol. 78, 413-418.
41. Takeda, M., Matsuoka, H., Hamana, H. and Hikuma, M. (1995) Biosynthesis of poly-3-hydroxybutyrate by Sphaerotilus natans. Appl. Microbiol. Biotechnol. 43, 31-34
42. Page, W.J. and Cornish, A. (1993) Growth of Azotobacter vinelandii UWD in fish peptone medium and simplified extraction of poly-β-hydroxybutyrate. Appl. Environ. Microbiol. 59, 4236-4244.
43. Ballisteri, A., Garazzo, D., Giuffrida, M., Impallomeni, G., Montaudo G. (1989) Sequencing bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate) by partial methanolysis, high performance liquid chromatography, fractionation, and fast atom bombardment mass spectrometry analysis. Macromolecules 22, 2107-2111.
44. Doi, Y., Kunioka, M., Nakamura, Y. and Soga, Y. (1986) Nuclear magnetic resonance studies on poly(β-hydroxybutyrate) and a copolyester of β-hydroxybutyrate and β-hydroxyvalerate isolated from Alcaligenes eutrophus H16. Macromolecules 19, 2860-2864.
45. Bluhm, T.L., Hamer, G.K., Marchessault, R.H., Fyfe, C.A. and Veregin, R.P. (1986) Isodimorphism in bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 19, 2871-2876.
46. Wallen, L.L. and Rohwedder, W.K. (1974) poly-β-hydroxyalkanoate from activated sludge. Environ. Sci. Technol. 8, 576-579.
47. Findlay, R.H. and White, D.C. (1983) Polymeric β-hydroxyalkanoates from environmental samples and Bacillus megaterium. Appl. Environ. Microbiol. 45, 71-78.
48. De Smet, M., Eggink, G., Witholt, B., Kingma, J. and Wynberg, H. (1983) Characterisation of intracellular inclusions formed by Pseudomonas oleovorans during growth on octane. J. Bacteriol. 154, 870-878.
49. Brandl, H., Gross, R.A., Lenz, R.W. and Fuller, C.W. (1988) Pseudomonas oleovorans as a source of poly(β-hydroxyalkanoates) for potential applications as biodegradable polyesters. Appl. Environ. Microbiol. 54, 1977-1982.
50. Gross, R.A., DeMello, C., Lenz, R.W., Brandl, H. and Fuller, C.W. (1989) Biosythesis and characterization of poly(β-hydroxyalkanoates) produced by Pseudomonas oleovorans. Macromolecules 22, 1106-1115.
51. Anderson, A.J. and Dawes, E.A. (1990) Occurrence, metabolism,metabolic role, and industrial uses of polyhydroxyalkanoates. Microbiol. Rev. 54, 450-472.
52. Brandl, H., Bachofen, R., Mayer, J. and Wintermantel, E. (1995) Degradation and applications of polyhydroxyalkanoates. Can. J. Microbiol. 41, 143-153.
53. Lee, E.Y., Jendrossek, D., Schirmer, A., Choi, C.Y. and Steinbuchel, A. (1995) Biosynthesis of copolyesters consisting of 3-hydroxybutyric acid and medium-chain length 3-hydroxyalkanoic acids from 1,3-butanediol or from 3-hydroxybutyrate by Psuedomonas sp. A33. Appl. Microbiol. Technol. 42, 901-909.
54. Scholz, C., Fuller, R.C. and Lenz, R.W. (1995) Growth behavior of Bacillus thuringiensis and production of poly(3-hydroxyalkanoates) on different organic substrates. Polym. Bull. 34, 577-584.
55. Peoples, O.P. and Sinskey, A.J. (1987) Polyhydroxybutyrate (PHB): a model system for biopolymer engineering. In: M. Yalpni (Ed.), Progress in Biotechnology: Industrial Polysaccharides, Elsevier, Vol. 3, pp. 51-56.
56. Masamune, S., Walsh, C.T., Sinskey, A.J. and Peoples, O.P. (1989) Poly-(R)-3-polyhydroxybutyrate (PHB) biosynthesis -mechanistic studies of the biological claisen condensation catalysed by β-ketoacyl thiolase. Pure Appl. Chem. 61, 303-312.
57. Page, W.J. and Knosp, O. (1989) Hyperproduction of poly-β-hydroxybutyrate during exponential growth of Azotobacter vinelandii UWD. Appl. Environ. Microbiol. 55, 1334-1339.
58. Fries, K. and Lafferty, R.M. (1989) Cloning and expression of the levanase gene in Alcaligenes eutrophus H16 enables the strain to hydrolyse sucrose. J. Biotechnol. 10, 285-292.
59. Slater, S.C., Voige, W.H. and Dennis, D.E. (1988) Cloning and expression in Escherichia coli of the Alcaligenes eutrophus H16 poly-β-hydroxybutyrate biosynthetic pathway. J. Bacteriol. 170, 4431-4436.
60. Schubert, P., Steinbuchel, A. and Schlegel, H.G. (1988) Cloning of the Alcaligenes eutrophus genes for synthesis of poly-β-hydroxybutyrate (PHB) and synthesis of PHB in Escherichia coli. J. Bacteriol. 170, 5837-5847.
61. Kidwell, J., Valentin, H.E. and Dennis, D. (1995) Regulated expression of the Alcaligenes eutrophus PHA biosynthesis genes in Escherichia coli. Appl. Environ. Microbiol. 61, 1391-1398.
62. Zhang, H., Obias, V., Gonyer, K. and Dennis, D. (1994) Production of polyhydroxyalkanoates in sucrose-utilizing recombinant Escherichia coli and Klebsiella strains. Appl. Environ. Microbiol. 60, 1198-1205.
63. Pool, R. (1989) In search of the plastic potato. Science 245, 1187-1189.
64. Poirier, Y., Somerville, C., Schechtman, L.A., Satkowski, M.M. and Noda, I. (1995) Synthesis of high molecular weight poly( [R]-(-)-3-hydroxybutyrate) in transgenic Arabidopsis thaliana plant cells. Int. J. Biol. Macromol. 17, 7-12
65. Nawrath, C., Poirier, Y. and Somerville, C. (1994) Targeting of the polyhydroxybutyrate biosythetic pathway to the plastids of Arabidopsis thaliana results in high levels of polymer accumulation. Proc. Natl. Acad. Sci. USA 91, 12760-12764.
66. 2 by a novel photosynthetic bacterium. Appl. Biochem. Biotechnol. 45/46, 395-406.
67. Ellar, D., Lundgren, D.G., Okamura, K. and Marchessault, R.H. (1968) Morphology of poly-β-hydroxybutyrate granules. J. Mol. Biol. 35, 489-502.
68. Barnard, G.N. and Sanders, J.K.M. (1989) The poly-β-hydroxybutyrate granule in vivo. A new insight based on NMR spectroscopy of whole cells. J. Biol. Chem. 264, 3286-3291.
69. Bonthrone, K.M., Clauss, J., Horowitz, D.M., Hunter, B.K. and Sanders, J.K.M. (1992) The biological and physical chemistry of polyhydroxyalkanoates as seen by NMR spectroscopy. FEMS Microbiol. Rev. 103, 311-316.
70. Fuller, R.C., O'Donnell, J.P., Saulnier, J., Redlinger, T.E., Foster, J. and Lenz, R.W. (1992) The supramolecular architecture of the polyhydroxyalkanoate inclusions in Pseudomonas oleovorans. FEMS Microbiol. Rev. 103, 279-288.
71. Horowitz, D.M. and Sanders, J.K.M. (1994) Amorphous, biomimetic granules of polyhydroxybutyrate-prparation, characterization, and biological implications. J. Am. Chem. Soc. 116, 2695-2702.
72. Sillerud, L.O. and Schulman, R.G. (1983) Structure and metabolism of mammalian liver glycogen monitored by C-13 nuclear magnetic resonance. Biochemistry 22, 1087-1094.
73. Kung, F.E. (1950) US Patent 2 361 036.
74. Gresham, T.L., Jansen, J.E. and Shaver, F.W. (1948) β-propiolactone 1. Polymerization reactions. J. Am. Chem. Soc. 70, 998-999.
75. Shiota, T., Goto, Y. and Hayaski, K. (1967) Polymerization of racemic β-butyrolactone. J. Appl. Polym. Sci. 11, 753-756
76. Agostini, D.E., Lando, J.B. and Shelton, J.R. (1971) Synthesis and characterization of poly-β-hydroxybutyrate. I. Synthesis of crystalline DL-poly-β-hydroxybutyrate from DL-β-butyrolactone. J. Polym. Sci. A-1, 9, 2775-2787.
77. Shelton, J.R., Agostini, D.E. and Lando, J.B. (1971) Synthesis and characterization of poly-β-hydroxybutyrate. II. Synthesis of D-poly-β-hydroxybutyrate and the mechanism of rin-opening polymerization of β-butyrolactone. J. Polym. Sci. A-1, 9, 2789-2799.
78. Shelton, J.R., Lando, J.B. and Agostini, D.E. (1971) Synthesis and characterization of poly-β-hydroxybutyrate. J. Polym. Sci. Polym. Lett. B 9, 173-178.
79. Tani, H., Yamashita, S. and Teranishi, K. (1972) Polymerization of β-alkyl-β-propiolactone. Polym. J. 3, 417-421
80. Teranishi, K., Iida, M., Araki, T., Yamshita, S. and Tani, H. (1974) Stereospecific polymerization of β-alkyl-β-propiolactone. Macromolecules 7, 421-427.
81. Yokouchi, M., Chatani, Y., Tadokora, H. and Tani, H. (1974) Structural studies of polyesters. VII. Molecular and crystal structures of racemic poly(β-ethyl-β-propiolactone). Polym. J. 6, 248-255.
82. Bloembergen, S., Holden, D.A., Bluhm, T.L., Hamer, G.K. and Marchessault, R.H. (1989) Stereoregularity in synthetic β-hydroxybutyrate and β-hydroxyvalerate homopolyesters. Macromolecules 22, 1656-1663.
83. Bloembergen, S., Holden, D.A, Bluhm, T.L., Hamer, G.K. and Marchessault, R.H. (1987) Synthesis of crystalline β-hydroxybutyrate/β-hydroxyvalerate coployesters by co-ordination polymerization of β-lactone. Macromolecules 20, 3086-3089.
84. Bloembergen, S., Holden, D.A., Bluhm, T.L., Hamer, G.K. and Marchessault, R.H. (1989) Isodimorphism in synthetic poly(β-hydroxybutyrate-co-β-hydroxyvalerate)-stereoregular copolyesters from racemic β-lactones. Macromolecules 22, 1663-1669.
85. Yokouchi, M., Chatani, Y., Tadokora, H., Teranishi, K. and Tani, H. (1973) Structural studies of polyesters. 5. Molecular and crystal structures of optically active and racemic poly(β-hydroxybutyrate). Polymer 14, 267-272.
86. Bloembergen, S., Holden, D.A., Hamer, G.K., Bluhm, T.L. and Marchessault, R.H. (1986) Studies of composition and crystalliity of bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 19, 2865-2871.
87. Barham, P.J., Keller, A., Otun, E.L. and Holmes, P.A. (1984) Crystallisation and morphology of a bacterial thermoplastic: poly-3-hydroxybutyrate. J. Mater. Sci. 19, 2781-2794.
88. Barham, P.J. (1984) Nucleation behaviour of poly-3-hydroxybutyrate. J. Mater. Sci. 19, 3826-3834.
89. Barham, P.J. and Keller, A. (1986) The relationship between microstructure and mode of fracture in polyhydroxybutyrate. J. Polym. Sci. Polym. Phys. Ed. 24, 69-77.
90. Avella, M. and Martuscelli, E. (1988) Poly-D-(-)-(3-hydroxybutyrate) poly(ethylene oxide) blends -phase diagram, thermal and crystallisation behaviour. Polymer 29, 1731-1737.
91. Greco, P. and Martuscelli, E. (1989) Crystallization and thermal behaviour of poly-D-(-)-(3-hydroxybutyrate)-based blends. Polymer 30, 1475-1483.
92. Alper, R., Lundgren, D.G., Marchessault, R.H. and Cote, W.A. (1963) Properties of poly-β-hydroxybutyrate. 1. General considerations concerning the naturally occuring polymer. Biopolymers 1, 545-556.
93. Okamura, K. and Marchessault, R.H. (1967) Physical properties of poly(β-hydroxybutyrate). II. Conformational aspects in solution. In: G.N. Ramachandran (Ed.), Conformation of Biopolymers, Academic Press, London, Vol. 2, pp. 709-720.
94. Cornibert, J. and Marchessault, R.H. (1972) Physical properties of of poly(β-hydroxybutyrate. IV. Conformational analysis and crystalline structure. J. Mol. Biol. 71, 735-756.
95. Marchessault, R.H., Coulombe, S., Morikawa, H., Okamura, K. and Revol, J.F. (1981) Solid state properties of poly(β-hydroxybutyrate) and its oligomers. Can. J. Chem. 59, 38-44.
96. Bruckner, S., Meille, S.V., Malpezzi, L., Cesaro, A., Navarini, L. and Tombolini, R. (1988) The structure of poly(D-(-)-β-hydroxybutyrate). A refinement based on the Rietveld method. Macromolecules 21, 967-972.
97. Pundsack, A.L. and Bluhm, T.L. (1981) Technique for determining unit-cell constants of polyhydroxyvalerate using electron diffraction. J. Mater. Sci. 16, 545-547.
98. Marchessault, R.H., Morikawa, H., Revol, J.F. and Bluhm, T.L. (1984) Physical properties of a naturally occurring polyester: poly(β-hydroxyvalerate)/poly(β-hydroxybutyrate). Macromolecules 17, 1882-1884.
99. Mitomo, H., Barham, P.J. and Keller, A. (1986) Lamellar thickening behaviour of poly(β-hydroxybutyrate) and its copolymer on annealing. Sen-i-Gakkaishi 42, T-589-T-596.
100. Mitomo, H., Barham, P.J. and Keller, A. (1987) Crystallisation and morphology of poly(β-hydroxybutyrate) and its copolymer. Polym. J. 19, 1241-1253.
101. Cuesta, M.S., Martinezsalazar, J., Barker, P.A. and Barham, P.J. (1992) Cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). J. Mater. Sci. 27, 5335-5338.
102. Calos, N.J. and Kennard, C.H.L. (1994) Crystallinity of poly(β-hydroxybutyrate) using the Rietveld technique. Polymer 35, 4595-4597.
103. Billingham, N.C., Henman, T.J. and Holmes, P.A. (1987) Degradation and stabilisation of polyesters of biological and synthetic origin. In: N. Grassie (Ed.), Developments in Polymer Degradation, Elsevier, Vol. 7, pp. 81-121.
104. Owen, A.J. (1985) Some dynamic mechanical properties of microbially produced poly(β-hydroxybutyrate/β-hydroxyvalerate) copolymers. Colloid Polym. Sci. 263, 799-803.
105. Barker, P.A., Mason, F. and Barham, P.J. (1990) Density and crystallinity of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) copolymers. J. Mater. Sci. 25, 1952-1956.
106. Akhtar, S., Pouton, C.W. and Notarianni, L.J. (1992) Crystallization behaviour and drug release from bacterial polyhydroxyalkanoates. Polymer 33, 117-126.
107. Marchessault, R.H., Okamura, K. and Su, C.J. (1970) Physical properties of poly(β-hydroxybutyrate). II. Conformational aspects in solution. Macromolecules 3, 735-740.
108. Cornibert, J., Marchessault, R.H., Benoit, H. and Weill, G. (1970) Physical properties of poly(β-hydroxybutyrate). III. Folding of helical segments in 2,2,-trifluoroethanol. Macromolecules 3, 741-746.
109. Akita, S., Einaga, Y., Miyaki, Y. and Fujita, H. (1976) Solution properties of poly(D-β-hydroxybutyrate). 1. Biosynthesis and characterization. Macromolecules 9, 774-780.
110. Miyaki, Y., Einaga, Y., Hirosye, T. and Fujita, H. (1977) Solution properties of poly(D-β-hydroxybutyrate). 2. Light scattering and viscosity in trifluoroethanol and behavior of highly expanded polymer coils. Macromolecules 10, 1356-1364.
111. Miyaki, Y., Einaga, Y. and Fujita, H. (1978) Excluded volume effects in dilute polymer solutions. 7. Very high molecular weight polystyrene in benzene and cyclohexane. Macromolecules 11, 1180-1186.
112. Hiroyse, T., Einaga, Y. and Fujiata, H. (1979) Excluded volume effects in dilute polymer solutions. VIII. Poly(DL-β-methyl-propiolactone) in several solvents and reanalysis of data on poly(D-β-hydroxybutyrate). Polym. J. 11, 819-826.
113. Scandola, M., Pizzolli, M., Cerrocorulli, G., Cesaro, A., Paoletti, S. and Navarini, L. (1989) Viscoelastic and thermal properties of bacterial poly(D-(-)-β-hydroxybutyrate). Int. J. Biol. Macromol. 10, 373-377.
114. Akhtar, S. and Pouton, C.W. (1989) Biodegradable polymers in drug delivery. Drug News Perspect. 2, 89-93.
115. Akhtar, S., Pouton, C.W., Notarianni, L.J. and Gould, PL. (1987) Mechanical properties of Biopol polyester films and the effect of inclusion of a solid crystalline drug. J. Pharm. Pharmacol. 39, 43P.
116. Knowles, J.C. and Hastings, G.W. (1989) Physical characteristics of 'PHB' a degradable polymer. Abstracts of the 8th European Conference on Biomaterials, 7-9th Sept., Heidelberg, B4-4, p. 87.
117. Tanner, K.E., Doyle, C. and Bonfield, W. (1989) The strength of the interface developed between biomaterials and bone. Abstracts of the 8th European Conference on Biomaterials, 7-9th Sept., Heidelberg, D5-5, p. 163.
118. Doyle, C., Luklinska, Z.B., Tanner, K.E. and Bonfield, W. (1989) A structural and ultrastructural study of the interface between a hydroxyapatite/polymer composite and bone. Abstracts of the 8th European Conference on Biomaterials, 7-9th Sept., Heidelberg, D6-5, p. 169.
119. Doyle, C. and Bonfield, W. (1988) Biodegradable composites. In: S.A. Paipetis and G.C. Papanicolaou (Eds), Engineering Applications of New Composites, Omega Scientific, Wallingford, pp. 114-118.
120. Akhtar, S. (1990) Physicomechanical properties of P(HB-HV) polyesters and their uses in drug delivery. PhD Thesis, University of Bath, UK.
121. McRae, R.M. and Wilkinson, J.F. (1958) Poly-β-hydroxybutyrate metabolism in washed suspensions of Bacillus cereus and Bacillus megaterium. J. Gen. Microbiol. 19, 210-222.
122. Grassie, N., Murray, E.J. and Holmes, P.A. (1984) The thermal degradation of poly(D-β-hydroxybutyric acid). I. Identification and qualitative analysis of products. II. Changes in molecular weight. III. The reaction mechanism. Polym. Degradation Stability 6, 47-134.
123. Fukada, E. (1984) Piezoelectricity of natural biomaterials. Ferroelectrics 60, 285-296.
124. Fukada, E. and Ando, Y. (1986) Piezoelectric properties of poly-β-hydroxybutyrate and copolymers of β-hydroxybutyrate and β-hydroxyvalerate. Int. J. Biol. Macromol. 8, 361 -366.
125. Fukada, E. and Ando, Y. (1988) Bending piezoelectricity in amicrobially produced polyβ-hydroxybutyrate. Biorheology 25, 297-302.
126. Black, J. (1987) Electrical Stimulation. Its Role in Growth, Repair, and Remodeling of the Musculoskeletal System, Praeger Publishers, New York.
127. Chowdhury, A.A. (1963) Bacteria and exoenzymes capable of degrading poly(β-hydroxybutyric acid). Arch. Mikrobiol. 47, 167-200.
128. Yakabe, Y., Nohara, K., Hara, T. and Fujino, Y. (1992) Factors affecting the biodegradability of biodegradable polyester in soil. Chemosphere 25, 1879-1888.
129. Mergaert, J., Webb, A., Anderson, C., Wouters, A. and Swings, J. (1993) Microbial degradation of poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in soils. Appl. Environ. Microbiol. 59, 3233-3238.
130. Merrick, J.M., Delafield, F.P. and Doudoroff, M. (1962) Hydrolysis of poly-ß-hydroxybutyrate by intracellular and extracellular enzymes. Fed. Proc. 21, 228
131. Merrick, J.M. and Doudoroff, M. (1964) Depolymerization of poly-β-hydroxybutyrate by an intracellular enzyme system. J. Bacteriol. 88, 60-71.
132. Delafield, F.P., Cooksey, K.E. and Doudoroff, M. (1965) β-hydroxybutyric dehydrogenase and dimer hydrolase of Pseudomanas lemoignei. J. Biol. Chem. 240, 4023-4028.
133. Lusty, C.J. and Doudoroff, M. (1966) Poly-β-hydroxybutyrate depolymerase of Pseudomanas lemoignei. Biochemistry 56, 960-965.
134. Jendrossek, D., Muller, B. and Schlegel, H.G. (1993) Cloning and characterisation of the poly(hydroxyalkanoic acid)-depolymerase gene locus, Phaz1, of Pseudomanas lemoignei and its gene product. Eur. J. Biochem. 218, 701-710.
135. Tanio, T., Fukui, T., Shirakura, Y., Saito, T., Tomita, K., Kaiho, T. and Masamune, K. (1982) An extracellular poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis. Eur. J. Biochem. 124, 71-77.
136. Shirakura, Y., Fukui, T., Saito, T., Okamoto, Y., Narikawa, T., Koide, K., Tomita, K., Takemasa, T. and Masamune, S. (1986) Degradation of poly(3-hydroxybutyrate) by poly(3-hydroxybutyrate) depolymerase from from Alcaligenes faecalis T-1. Biochim. Biophys. Acta 880, 46-53.
137. Fukui, T., Narikawa, T., Miwa, K., Shirakura, Y., Saito, T. and Tomita, K. (1988) Effect of tryptic modification of a bacterial poly(3-hydroxybutyrate) depolymerase on its catalytic activity. Biochem. Biophys. Acta 952, 164-171.
138. Briese, B.H., Jendrossek, D. and Schlegel, H.G. (1994) Degradation of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by aerobic sewage sludge. FEMS Microbiol. Lett. 16, 155-160.
139. Doi, Y., Segawa, A. and Kunioka, M. (1989) Biodegradable of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) produced from γ-butyrolactone and butyric acid by Alcaligenes eutrophus. Polym. Commun. 30, 169-171.
140. Kemnitzer, J.E., McCarthy, S.P. and Gross, R.A. (1992) Poly(γ-hydroxybutyrate) stereoisomers-a model study of the effects of stereochemical and morphological variables on polymer biological degradability. Macromolecules 25, 5927-5934.
141. Majid, M.I.A. (1988) The degradation of PHB and P(HB-HV) copolymers and their uses in drug delivery. PhD Thesis, University of Bath, UK.
142. Pouton, C.W., Majid, M.I.A. and Notarianni, L.J. (1988) Degradation of polyhydroxybutyrate and related copolymers. Proc. Int. Symp. Controlled Release Bioact. Mater. 15, 181-183.
143. Gilding, D.K. (1981) Biodegradable Polymers. In: D.F. Williams (Ed.), Biocomaptibility of Clinical Implant Materials, CRC Press, Boca Raton, FL, Vol. 2, pp. 209-232.
144. Holland, S.J., Jolly, A.M., Yasin, M. and Tighe, B.J. (1987) Polymers for biodegradable medical devices. II. Hydroxybutyrate-hydroxyvalerate copolymers: hydrolytic degradation studies. Biomaterials 8, 289-295.
145. Yasin, M., Holland, S.J., Jolly, A.M. and Tighe, B.J. (1989) Polymers for biodegradable medical devices. VI. Hydroxybutyrate-hydroxyvalerate copolymers: accelerated degradation of blends with polysaccharides. Biomaterials 10, 400-412.
146. Yasin, M. and Tighe, B.J. (1993) Strategies for the design of biodegradable polymer systems-manipulation of polyhydroxybutyrate-based materials. Plastics Rubber Composites Processing Appl. 19, 15-27.
147. Miller, N.D. and Williams, D.F. (1987) On the biodegradation of poly-β-hydroxybutyrate (PHB) homopolymer and poly-β-hydroxybutyrate-hydroxyvalerate copolymers. Biomaterials 8, 129-137.
148. Williams, D.F. and Miller, N.D. (1987) The degradation of polyhydroxybutyrate (PHB). Advances in Biomaterials: Biomaterials Clin. Appl. 7, 471-476.
149. Gerlach, K.L. and Pesch, H.J. (1989) In vivo evaluation of a copolymer of polyhydroxybutyrate and polyhydroxyvalerate. Abstracts of the 8th European Conference on Biomaterials, 7-9th Sept., Heidelberg, B3-1, p. 79.
150. Kronenthal, R.L. (1974) Biodegradable polymers in medicine and surgery. In: R.L. Kronenthal, Z. User and E. Martin (Eds), Polymers in Medicine and Surgery, Plenum Press, New York, pp. 126-136.
151. Kennedy, J.E. (1990) Assessment of the biocompatibility of PHB and P(HB-HV). PhD Thesis, University of Bath, UK.
152. Gogolewski, S., Jovanovic, M., Perren, S.M., Dillon, J.G. and Hughes, M.K. (1993) Tissue response and in vivo degradation of selected polyhydroxyacids -polylactides (PLA), poly(3-hydroxybutyrate) (PHB), and of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHB/ VA). J. Biomed. Mater. Res. 27, 1135-1148.
153. Ali, S.A.M., Doherty, P.J. and Williams, D.F. (1994) The mechanism of oxidative degradation of biomedical polymers by free-radicals. J. Appl. Polym. Sci. 51, 1389-1398.
154. Ali, S.A.M., Doherty, P.J. and Williams, D.F. (1994) Molecular biointeractions of biomedical polymers with extracellular exudate and inflammatory cells and their effects on biocompatibility in vivo. Biomaterials 15, 779-785.
155. Verhoogt, H., Ramsay, B.A. and Favis, B.D. (1994) Polymer blends containing poly(3-hydroxyalkanoate)s. Polymer 35, 5155-5169.
156. Embleton, J.K. and Tighe, B.J. (1993) Polymers for biodegradable medical devices. 10. Microencapsulation studies-control of poly-hydroxybutyrate-hydroxyvalerate microcapsules porosity via polycaprolactone blending. J. Microencapsul. 10, 341-352.
157. Ramsay, B.A., Langlade, V., Carreau, P.J. and Ramsay, J.A. (1993) Biodegradability and mechanical properties of poly(β-hydroxybutyrate-co-β-hydroxyvalerate) starch blends. Appl. Environ. Microbiol. 59, 1242-1246.
158. Domb, A.J. (1993) Degradable polymer blends. 1. Screening of miscible polymers. J. Polym. Sci. A: Polym. Chem. 31, 1973-1981.
159. Lotti, N., Pizzoli, M., Ceccorulli, G. and Scandola, M. (1993) Binary blends of microbial poly(3-hydroxybutyrate) with polymethacrylates. Polymer 34, 4935-4940.
160. Abe, H., Matsubara, I. and Doi, Y. (1995) Physical properties and enzymatic degradability of polymer blends of bacterial poly[(R)-3-hydroxybutyrate] and poly[(R,S)-3-hydroxybutyrate) stereoisomers. Macromolecules 28, 844-853.
161. Yoshie, N., Azuma, Y., Sakurai, M. and Inoue, Y. (1995) Crystallization and compatibility of poly(vinyl alcohol) poly(3-hydroxybutyrate) blends-influence of blend composition and tacticity of poly(vinyl alcohol). J. Appl. Polym. Sci. 56, 17-24.
162. Zhang, L.L., Xiong, C.D. and Deng, X.M. (1995) Biodegradable polyester blends for biomedical application. J. Appl. Polym. Sci. 56, 103-112.
163. Iannace, S., Ambrosio, L., Huang, S.J. and Nicolais, L. (1995) Effect of degradation on the mechanical properties of multiphase polymer blends PHBV/PLLA. J. Macromol. Sci. Pure Appl. Chem. A32, 881-888.
164. Williams, D.F. (1986) Techniques of Biocompatibility Testing, CRC Press, Boca Raton, FL, Vol. 2.
165. Korsatko, W., Wabnegg, B., Tillian, H.M., Egger, G., Pfragner, R. and Walser, V. (1984) Poly-D-(-)-3-hydroxybutyric acid (polyHBA) a biodegradable carrier for long term medication dosage. III. Studies on biocompatibility of polyHBA implantation tablets in tissue culture and animals. Pharm. Ind. 46, 952-954.
166. Kennedy, J.E., Notarianni, L.J. and Pouton, C.W. (1987) Biocompatibility of a biodegradable polyester in rats. J. Pharm. Pharmacol. 39, 58P.
167. Pouton, C.W., Kennedy, J.E., Notarianni, L.J. and Gould, P.L. (1988) Biocompatibility of polyhydroxybutyrate and related copolymers. Proc. Int. Symp. Controlled Release Bioact. Mater. 15, 179-180.
168. Kennedy, J.E., Notarianni, L.J. and Pouton, C.W. (1988) Assessment of the cellular toxicity of a biodegradable polyester. J. Pharm. Pharmacol. 40, 33P.
169. Juni, K. and Nakano, M. (1987) Poly(hydroxy acids) in drug delivery. CRC Crit. Rev. Ther. Drug Carrier Systems. 3, 209-232.
170. Koosha, F., Muller, R.H. and Davis, S.S. (1989) Polyhydroxybutyrate as a drug carrier. CRC Crit. Rev. Ther. Drug Carrier Systems. 6, 117-130.
171. Korasatko, W., Wabnegg, B., Braunegg, G., Lafferty, R.M. and Strempfl F. (1983) Poly-D-(-)-3-hydroxybutyric acid (polyHBA) a biodegradable carrier for long term medication dosage. I. Development of parenteral matrix tablets for long-term administration of pharmaceuticals. Pharm. Ind. 45, 525-527.
172. Korasatko, W., Wabnegg, B., Braunegg, G. and Lafferty, R.M. (1983) Poly-D-(-)-3-hydroxybutyric acid (polyHBA) a biodegradable carrier for long term medication dosage. II. The biodegradation in animals and in vitro-in vivo correlation with the liberation of pharmaceuticals from parenteral matrix tablets. Pharm. Ind. 45, 1004-1007.
173. Gould, P.L., Holland, S.J. and Tighe, B.J. (1987) Polymers for biodegradable medical devices IV. Hydroxybutyrate-hydroxyvalerate copolymers as non-disintegrating matrices for controlled release oral dosage forms. Int. J. Pharm. 38, 231-237.
174. Gangrade, N., Price, J.C. (1992) Properties of implantable pellets prepared from a biodegradable polyester. Drug Dev. Ind. Pharm. 18, 1633-1648.
175. Jones, R.D., Price, J.C., Stuedemann, J.A. and Bowen, J.M. (1994) In vitro and in vivo release of metoclopramide from a subdermal diffusion matrix with potential in preventing fescue toxicosis in cattle. J. Controlled Release 30, 35-44
176. Brophy, M.R. and Deasy, P.B. (1986) In vitro and in vivo studies on biodegradable polyester microparticles containing sulphamethiazole. Int. J. Pharm. 29, 223-231.
177. Bissery, M.C., Valeriote, F. and Thies, C. (1984) In vitro and in vivo evaluation of CCNU-loaded microspheres prepared from polylactide and poly(β-hydroxybutyrate). In: S.S. Davis, L. Illum, J.G. McVie and E. Tomlinson (Eds), Microspheres and Drug Therapy, Pharmaceutical, Immunological and Medical Aspects, Elsevier, Amsterdam, pp. 217-227.
178. Bissery, M.C., Valeriote, F. and Thies, C. (1984) In vitro lomustine release from small poly(β-hydroxybutyrate) and poly(DL-lactide) microspheres. Proc. Int. Symp. Controlled Release Bioact. Mater. 11, 25-26.
179. Bissery, M.C., Valeriote, F. and Thies, C. (1985) Fate and effect of CCNU-loaded microspheres made of poly(DL-lactide) or poly(β-hydroxybutyrate) in mice. Proc. Int. Symp. Controlled Release Bioact. Mater. 12, 69-70.
180. Embleton, J.K. and Tighe, B.J. (1992) Polymers for biodegradable medical devices. 9. Microencapsulation studies-effects of polymer composition and process parameters on poly-hydroxybutyrate-hydroxyvalerate microcapsule morphology. J. Microencapsul. 9, 73-87.
181. Juni, K., Nakano, M. and Kubota, M. (1986) Controlled release of aclarubicin, an anticancer antibiotic from poly(β-hydroxybutyrate) microspheres. J. Controlled Release 4, 25-32.
182. Kubota, M., Nakano, M. and Juni, K. (1988) Mechanism of enhancement of the release rate of aclarubicin from poly(3-hydroxybutyrate) microspheres by fatty acid esters. Chem. Pharm. Bull. 36, 333-337.
183. Kawaguchi, T., Tsugane, A., Higashide, K., Endoh, H., Hasegawa, T., Kanno, H., Seki, T., Juni, K., Fukushima, S. and Nakano, M. (1992) Control of drug release with a combination of prodrug and polymer matrix-antitumour activity and release profiles of 2,3,-diacyl-5-fluoro-2-deoxyuridine from poly(3-hydroxybutyrate) microspheres. J. Pharm. Sci. 81, 508-512.
184. Gursel, I. and Hasirci, V. (1995) Properties and drug-release behavior of poly(3-hydroxybutyric acid) and various poly(3-hydroxybutyrate-hydroxyvalerate) copolymer microcapsules. J. Microencapsul. 12, 185-193.
185. Akhtar, S., Pouton, C.W. and Notarianni, L.J. (1991) Influence of crystalline morphology and copolymer composition on drug release from solution cast and melt processed P(HB-HV). J. Controlled Release 17, 225-234.
186. Koosham F., Muller, R.H. and Washington, C.W. (1987) Production of polyhydroxybutyrate (PHB) nanoparticles for drug targeting. J. Pharm. Pharmacol 39, 136P.
187. Koosha, F., Muller, R.H. and Davis, S.S. (1988) A continuous flow system for in vitro evaluation of drug-loaded biodegradable colloid carriers. J. Pharm. Pharmacol. 40, 131P.
188. Akhtar, S., Pouton, C.W., Notarianni, L.J. and Gould, P.L. (1989) A study of the mechanism of drug release from solvent evaporated carrier systems of biodegradable P(HB-HV) polymers. J. Pharm. Pharmacol. 41, 5P.
189. Collins, A.E.M., Deasy, P.B., MacCarthy, D.J. and Shanley, D.B. (1989) Evaluation of a controlled release compact containing tetracycline hydrochloride bonded to tooth for the treatment of peridontal disease. Int. J. Pharm. 51, 103-114.
190. Deasy, P.B., Collins, A.E.M., MacCarthy, D.J. and Russell, R.J. (1989) Use of strips containing tetracycline hydrochloride for the treatment of advanced peridontal disease. J. Pharm. Pharmacol. 41, 694-699.
191. Konig, W., Seidel, H.R. and Sandow, J.K. (1984) European Patent No. 0 133 988.
192. Sandow, J., Seidel, H.R. (1986) German Patent A 61 K 9/52.
193. McLeod, B.J., Haresign, W., Peters, A.R., Humke, R. and Lamming, G.E. (1988) The development of subcutaneous delivery preparations of GnRH for the induction of ovulation in acyclic sheep and cattle. Animal Reprod. Sci. 17, 33-50.
194. Morikawa, H. and Marchessault, R.H. (1981) Pyrolysis of bacterial polyalkanoates. Can. J. Chem. 59, 2306-2313.
195. Seebach, D. and Zueger, M. (1982) On the depolymerization of poly-(R)-3-hydroxybutyrate (PHB). Helv. Chim. Acta 65, 495-503.
196. Seebach, D. and Zueger, M. (1985) On the preparation of methyl and ethyl (R)-(-)-3-hydroxyvalerate by depolymerization of a mixed PHB-PHV bio-polymer. Tetrahedron Lett. 25, 2747-2750.
197. Webb, A. and Adsetts, J.R (1986) UK Patent Appl. GB 2 166 354 A.
198. Holmes, P.A. (1985) UK Patent Appl. GB 2 160 208 A.
199. Francesco, M., Luigi, P. and Paolo, V. (1987) European Patent No. 0 226 439.
200. Japan Kokai Tokyo Koho (1988) Japanese Patent 63/ 302845 A2.
201. Boeree, N.R., Dove, J., Cooper, J.J., Knowles, J. and Hastings, G.W. (1993) Development of a degradable composite for orthopedic use-mechanical evaluation of an hydroxyapatite polyhydroxybutyrate composite material. Biomaterials 14, 793-796.
202. Knowles, J.C. (1993) Development of a natural degradable polymer for orthopedic use. J. Med. Eng. Technol. 17, 129-137.