Abstract
The ability of polymers to be degraded in physiological environments makes them interesting candidates for various medical applications. Degradation and metabolisation or excretion of polymeric implants can avoid a second surgery for the removal of an implant. They follow a distinct pathway for degradation, depending on their structure. Biodegradable materials can serve as a temporary substitute of the extracellular matrix or as matrix in controlled drug release systems, which both can be utilized in Regenerative Therapies.
This chapter gives an overview about polymeric materials established in clinical use such as polyesters, polyurethanes, polyanhydrides, or carbohydrates. It describes further their synthesis and exemplary applications such as surgical sutures. Finally the importance of a continuing development of novel materials for future applications is pointed out, since the number of potential applications in the medical field is expanding rapidly.
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References
Ahmed FE, Lalia BS, Hashaikeh R (2015) A review on electrospinning for membrane fabrication: challenges and applications. Desalination 356:15–30. doi:10.1016/j.desal.2014.09.033
Ajioka M, Enomoto K, Suzuki K, Yamaguchi A (1995) Basic properties of polylactic acid produced by the direct condensation polymerization of lactic-acid. Bull Chem Soc Jpn 68(8):2125–2131. doi:10.1246/bcsj.68.2125
Allen CW (1981) Organofluorophosphazenes – a short review. Ind Eng Chem Prod Rd 20(1):77–79. doi:10.1021/i300001a006
Andrianov AK (2009) Polyphosphazenes for biomedical applications. Wiley-Blackwell, Hoboken doi:10.1002/9780470478882
Bao RY, Yang W, Jiang WR, Liu ZY, Xie BH, Yang MB, Fu Q (2012) Stereocomplex formation of high-molecular-weight polylactide: a low temperature approach. Polymer 53(24):5449–5454. doi:10.1016/j.polymer.2012.09.043
Barker SA, Young NM (1966) Isolation of hyaluronic acid by gel filtration on agarose. Carbohydr Res 2:363–370
Behl M, Lendlein A (2007) Actively moving polymers. Soft Matter 3:58–67
Bera S, Jedlinski Z (1993) Block segmented polymers – a new method of synthesis of copoly(amide-ester) ester polymer. J Polym Sci Polym Chem 31(3):731–739. doi:10.1002/pola.1993.080310318
Boas NF (1949) Isolation of hyaluronic acid from the cocks comb. J Biol Chem 181(2):573–575
Brannon-Peppas L (1997) Polymers in controlled drug delivery. Med Plast Biomater:34
Bucher JE, Slade WC (1909) The anhydrides of isophthalic and terephthalic acids. J Am Chem Soc 31:1319–1321
Cardy RH (1979) Carcinogenicity and chronic toxicity of 2,4-toluenediamine in F344 rats. J Natl Cancer Inst 62:1107–1116
Carothers WH, Hill JW (1932) Studies of polymerization and ring formation. XIII. Polyamides and mixed polyester—polyamides. J Am Chem Soc 54(4):1566–1569. doi:10.1021/ja01343a049
Chabot F, Vert M, Chapelle S, Granger P (1983) Configurational structures of lactic-acid stereocopolymers as determined by C-13-labeled (H-1)-NMR. Polymer 24(1):53–59. doi:10.1016/0032-3861(83)90080-0
Commandeur S, van Beusekom HM, van der Giessen WJ (2006) Polymers, drug release, and drug-eluting stents. J Interv Cardiol 19(6):500–506. doi:10.1111/j.1540-8183.2006.00198.x
Crivello JV, Malik R, Lai YL (1996) Ketene acetal monomers: synthesis and characterization. J Polym Sci Polym Chem 34(15):3091–3102
Deasy PB, Finan MP, Meegan MJ (1989) Preparation and characterization of lactic/glycolic acid polymers and copolymers. J Microencapsul 6(3):369–378. doi:10.3109/02652048909019919
Deng M, Nair LS, Nukavarapu SP, Kumbar SG, Jiang T, Weikel AL, Krogman NR, Allcock HR, Laurencin CT (2010) In situ porous structures: a unique polymer erosion mechanism in biodegradable dipeptide-based polyphosphazene and polyester blends producing matrices for regenerative engineering. Adv Funct Mater 20(17):2794–2806. doi:10.1002/adfm.201000968
Di Lullo GA, Sweeney SM, Körkkö J, Ala-Kokko L, San Antonio JD (2002) Mapping the ligand-binding sites and disease-associated mutations on the most abundant protein in the human, type I collagen. J Biol Chem 277(6):4223–4231
Domb AJ, Amselem S, Langer RS, Maniar M (1994) In: Shalaby SW (ed) Biomedical polymers. Hanser Publishers, Munich, pp 17–32
Ero-Phillips O, Jenkins M, Stamboulis A (2012) Tailoring crystallinity of electrospun plla fibres by control of electrospinning parameters. Polymers-Basel 4(3):1331–1348. doi:10.3390/polym4031331
Feng YK, Guo JT (2009) Biodegradable polydepsipeptides. Int J Mol Sci 10(2):589–615. doi:10.3390/ijms10020589
Fine NA, Lehfeldt M, Gross JE, Downey S, Kind GM, Duda G, Kulber D, Horan R, Ippolito J, Jewell M (2015) SERI surgical scaffold, prospective clinical trial of a silk-derived biological scaffold in two-stage breast reconstruction: 1-year data. Plast Reconstr Surg 135(2):339–351. doi:10.1097/Prs.0000000000000987
Friedlaender GE, Perry CR, Cole JD, Cook SD, Cierny G, Muschler GF, Zych GA, Calhoun JH, LaForte AJ, Yin S (2001) Osteogenic protein-1 (Bone morphogenetic protein-7) in the treatment of tibial nonunions: a prospective, randomized clinical trial comparing rhOP-1 with fresh bone autograft. J Bone Joint Surg-Am 83(1_suppl_2):S151
Govender S, Csimma C, Genant HK, Valentin-Opran A (2002) Recombinant human bone morphogenetic protein-2 for treatment of open tibial fractures – a prospective, controlled, randomized study of four hundred and fifty patients. J Bone Joint Surg-Am 84A(12):2123–2134
Greenstein G, Caton JG (1993) Biodegradable barriers and guided tissue regeneration. Periodontol 2000 1:36–45
Grigat E, Koch R, Timmermann R (1998) BAK 1095 and BAK 2195: completely biodegradable synthetic thermoplastics. Polym Degrad Stab 59(1–3):223–226
Gunatillake P, Mayadunne R, Adhikari R (2006) Recent developments in biodegradable synthetic polymers. Biotechnol Annu Rev 12:301–347. doi:10.1016/S1387-2656(06)12009-8
Guo K, Chu CC (2007) Synthesis, characterization, and biodegradation of copolymers of unsaturated and saturated poly(ester amide)s. J Polym Sci Polym Chem 45(9):1595–1606. doi:10.1002/pola.21926
Han MG, Kim S, Liu SX (2008) Synthesis and degradation behavior of poly(ethyl cyanoacrylate). Polym Degrad Stab 93(7):1243–1251. doi:10.1016/j.polymdegradstab.2008.04.012
Heller J, Penhale DWH, Fritzinger BK, Rose JE, Helwing RF (1983) Controlled release of contraceptive steroids from biodegradable poly (ortho esters). Contracept Deliv Syst 4(1):43–53
Heller J, Ng SY, Fritzinger BK (1992) Synthesis and characterization of a new family of poly(Ortho ester)S. Macromolecules 25(13):3362–3364. doi:10.1021/ma00039a007
Heller J, Rime AF, Rao SS, Fritzinger BK, Ng SY (1995) Poly(ortho esters) for the pulsed and continuous delivery of peptides and proteins. In: Lee VHL, Hashida M, Mizushima Y (eds) Trends and future perspectives in peptide and protein drug delivery, vol 4, Drug targeting and delivery. Harwood Academic Publishers Gmbh, Chur, pp 39–56
Heller J, Barr J, Ng SY, Abdellauoi KS, Gurny R (2002) Poly(ortho esters): synthesis, characterization, properties and uses. Adv Drug Deliv Rev 54(7):1015–1039
Hodde J (2006) Extracellular matrix as a bioactive material for soft tissue reconstruction. ANZ J Surg 76(12):1096–1100. doi:10.1111/j.1445-2197.2006.03948.x
Hoffman AS (2002) Hydrogels for biomedical applications. Adv Drug Deliv Rev 54(1):3–12
Horton VL, Blegen PE, Barrows TH (1988) Comparison of bioabsorbable poly(ester-amide) monomers and polymers in vivo using radiolabeled homologs. In: Gebelijn CG, Dunn RL (eds) Progress in biomedical polymers. Plenum Press, New York, pp 263–282
Hughes CS, Postovit LM, Lajoie GA (2010) Matrigel: a complex protein mixture required for optimal growth of cell culture. Proteomics 10(9):1886–1890. doi:10.1002/pmic.200900758
Ikada Y, Jamshidi K, Tsuji H, Hyon SH (1987) Stereocomplex formation between enantiomeric poly(lactides). Macromolecules 20(4):904–906. doi:10.1021/ma00170a034
Jain JP, Modi S, Domb AJ, Kumar N (2005) Role of polyanhydrides as localized drug carriers. J Control Release 103(3):541–563. doi:10.1016/j.jconrel.2004.12.021
Kaidar-Person O, Rosenthal RJ, Wexner SD, Szomstein S, Person B (2008) Compression anastomosis: history and clinical considerations. Am J Surg 195(6):818–826. doi:10.1016/j.amjsurg.2007.10.006
Konan S, Haddad FS (2009) A clinical review of bioabsorbable interference screws and their adverse effects in anterior cruciate ligament reconstruction surgery. Knee 16(1):6–13. doi:10.1016/j.knee.2008.06.001
Kricheldorf HR, Serra A (1985) Polylactones.6. Influence of various metal-salts on the optical purity of poly(L-lactide). Polym Bull 14(6):497–502
Kricheldorf HR, Stricker A (2000) Macrocycles. 13. Stannylenated glucose glycosides as cyclic initiators of epsilon-caprolactone and the synthesis of biodegradable networks. Macromolecules 33(3):696–701
Kroehne V, Heschel I, Schugner F, Lasrich D, Bartsch JW, Jockusch H (2008) Use of a novel collagen matrix with oriented pore structure for muscle cell differentiation in cell culture and in grafts. J Cell Mol Med 12(5a):1640–1648. doi:10.1111/j.1582-4934.2008.00238.x
Krogman NR, Singh A, Nair LS, Laurencin CT, Allcock HR (2007) Miscibility of bioerodible polyphosphazene/poly(lactide-co-glycolide) blends. Biomacromolecules 8(4):1306–1312. doi:10.1021/bm061064q
Kulkarni A, Reiche J, Lendlein A (2007) Hydrolytic degradation of poly(rac-lactide) and poly[(rac-lactide)-co-glycolide] at the air-water interface. Surf Interface Anal 39(9):740–746
Kuppermann BD, Blumenkranz MS, Haller JA, Williams GA, Weinberg DV, Chou C, Whitcup SM, DDPIS G (2007) Randomized controlled study of an intravitreous dexamethasone drug delivery system in patients with persistent macular edema. Arch Ophthalmol-Chic 125(3):309–317. doi:10.1001/archopht.125.3.309
Lakshmi S, Katti DS, Laurencin CT (2003) Biodegradable polyphosphazenes for drug delivery applications. Adv Drug Deliv Rev 55(4):467–482. doi:10.1016/S0169-409x(03)00039-5
Laurencin C, Sobrasua I, Langer R (1995) In: Hollinger J (ed) Biomedical applications of synthetic biodegradable polymers. CRC Press, Boca Raton, pp 59–101
Leaper D, Assadian O, Hubner NO, McBain A, Barbolt T, Rothenburger S, Wilson P (2011) Antimicrobial sutures and prevention of surgical site infection: assessment of the safety of the antiseptic triclosan. Int Wound J 8(6):556–566. doi:10.1111/j.1742-481X.2011.00841.x
Leenslag JW, Pennings AJ (1987) Synthesis of high-molecular-weight poly(L-lactide) initiated with Tin 2-ethylhexanoate. Makromolekulare Chemie-Macromol Chem Phys 188(8):1809–1814
Leenslag JW, Gogolewski S, Pennings AJ (1984) Resorbable materials of poly(L-lactide).5. Influence of secondary structure on the mechanical-properties and hydrolyzability of poly(L-lactide) fibers produced by a dry-spinning method. J Appl Polym Sci 29(9):2829–2842. doi:10.1002/app.1984.070290913
Lendlein A (1999) Polymere als Implantatwerkstoffe. Chemie in unserer Zeit 33:279–295
Lendlein A, Kelch S (2002) Shape-memory polymers. Angew Chem Int Ed 41(12):2034–2057
Lendlein A, Langer R (2002) Biodegradable, elastic shape-memory polymers for potential biomedical applications. Science 296(5573):1673–1676
Lendlein A, Neuenschwander P, Suter UW (1998) Tissue-compatible multiblock copolymers for medical applications, controllable in degradation rate and mechanical properties. Macromol Chem Phys 199(12):2785–2796
Li X, Jastri BR (2006) Biodegradable polymeric delivery systems. In: Design of controlled release drug delivery systems. McGraw-Hill, New York, pp 271–304
Li LC, Deng J, Stephens D (2002) Polyanhydride implant for antibiotic delivery – from the bench to the clinic. Adv Drug Deliv Rev 54(7):963–986
Little U, Buchanan F, Harkin-Jones E, McCaigue M, Farrar D, Dickson G (2009) Accelerated degradation behaviour of poly(epsilon-caprolactone) via melt blending with poly(aspartic acid-co-lactide) (PAL). Polym Degrad Stab 94(2):213–220. doi:10.1016/j.polymdegradstab.2008.11.001
Martinez MB, Pinilla IM, Mata FZ, Perez JAG (1997) Hydrolytic degradation of poly(ester amides) derived from carbohydrates. Macromolecules 30(11):3197–3203
Masutani K, Kimura Y (2015) Chapter 1: PLA synthesis. From the monomer to the polymer. In: Poly(lactic acid) science and technology: processing, properties, additives and applications. The Royal Society of Chemistry, Cambridge, pp 1–36. doi:10.1039/9781782624806-00001
Meek MF, Coert JH (2008) US food and drug administration/conformit Europe- approved absorbable nerve conduits for clinical repair of peripheral and cranial nerves. Ann Plast Surg 60(4):466–472
Nair LS, Laurencin CT (2007) Biodegradable polymers as biomaterials. Prog Polym Sci 32(8–9):762–798. doi:10.1016/j.progpolymsci.2007.05.017
Ng SY, Vandamme T, Taylor MS, Heller J (1997) Synthesis and erosion studies of self-catalyzed poly(ortho ester)s. Macromolecules 30(4):770–772
Nieuwenhuis J (1992) Synthesis of polylactides, polyglycolides and their copolymers. Clin Mater 10(1–2):59–67
Ormiston JA, Serruys PWS (2009) Bioabsorbable coronary stents. Circ-Cardiovasc Interv 2(3):255–260. doi:10.1161/Circinterventions.109.859173
Paredes N, Rodriguez-Galan A, Puiggali J (1998) Synthesis and characterization of a family of biodegradable poly(ester amide)s derived from glycine. J Polym Sci Polym Chem 36(8):1271–1282
Pasternak B, Rehn M, Andersen L, Agren MS, Heegaard AM, Tengvall P, Aspenberg P (2008) Doxycycline-coated sutures improve mechanical strength of intestinal anastomoses. Int J Colorectal Dis 23(3):271–276. doi:10.1007/s00384-007-0401-0
Peltoniemi H, Ashammakhi N, Kontio R, Waris T, Salo A, Lindqvist C, Gratz K, Suuronen R (2002) The use of bioabsorbable osteofixation devices in craniomaxillofacial surgery. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 94(1):5–14. doi:10.1067/moe.2002.122160
Peppas NA (ed) (1987) Hydrogels in medicine and pharmacy. CRC-Press, Boca Raton
Pham QP, Sharma U, Mikos AG (2006) Electrospinning of polymeric nanofibers for tissue engineering applications: a review. Tissue Eng 12(5):1197–1211. doi:10.1089/ten.2006.12.1197
Pietrzak WS, Eppley BL (2000) Resorbable polymer fixation for craniomaxillofacial surgery: development and engineering paradigms. J Craniofac Surg 11(6):575–585. doi:10.1097/00001665-200011060-00011
Pillai CKS, Sharma CP (2010) Review paper: absorbable polymeric surgical sutures: chemistry, production, properties, biodegradability, and performance. J Biomater Appl 25(4):291–366. doi:10.1177/0885328210384890
Piskin E (1995) Biodegradable polymers as biomaterials. J Biomater Sci Polym Ed 6(9):775–795
Purcell DB, Rudzki JR, Wright RW (2004) Bioabsorbable interference screws in ACL reconstruction. Oper Tech Sports Med 12(3):180–187. doi:10.1053/j.otsm.2004.07.014
Qiu Y, Park K (2001) Environment-sensitive hydrogels for drug delivery. Adv Drug Deliv Rev 53(3):321–339
Schmidmaier G, Lucke M, Wildemann B, Haas NP, Raschke M (2006) Prophylaxis and treatment of implant-related infections by antibiotic-coated implants: a review. Injury 37(Suppl 2):S105–S112. doi:10.1016/j.injury.2006.04.016
Serra T, Planell JA, Navarro M (2013) High-resolution PLA-based composite scaffolds via 3-D printing technology. Acta Biomater 9(3):5521–5530. doi:10.1016/j.actbio.2012.10.041
Sethuraman S, Nair LS, El-Amin S, Nguyen MT, Singh A, Greish YE, Allcock HR, Brown PW, Laurencin CT (2011) Development and characterization of biodegradable nanocomposite injectables for orthopaedic applications based on polyphosphazenes. J Biomater Sci-Polym E 22(4–6):733–752. doi:10.1163/092050610x491670
Shalaby SW, Johnson A (1994) Biomedical polymers. Designed-to-degrade systems. Hanser Publishers, Munich
Shih C, Fix J, Seward RL (1993) Invivo and invitro release of ivermectin from poly(ortho ester) matrices.1. Cross-linked matrix prepared from ketene acetal end-capped prepolymer. J Control Release 25(1–2):155–162. doi:10.1016/0168-3659(93)90104-D
Shrivastav A, Kim H-Y, Kim Y-R (2013) Advances in the applications of polyhydroxyalkanoate nanoparticles for novel drug delivery system. BioMed Res Int 2013:12. doi:10.1155/2013/581684
Sinha VR, Trehan A (2003) Biodegradable microspheres for protein delivery. J Control Release 90(3):261–280
Södergård A, Stolt M (2010) Industrial production of high molecular weight poly(lactic acid). In: Poly(lactic acid). Wiley, Hoboken, pp 27–41. doi:10.1002/9780470649848.ch3
Spaans CJ, de Groot JH, Dekens FG, Pennings AJ (1998) High molecular weight polyurethanes and a polyurethane urea based on 1,4-butanediisocyanate. Polym Bull 41(2):131–138
Spotnitz WD, Burks S (2008) Hemostats, sealants, and adhesives: components of the surgical toolbox. Transfusion 48(7):1502–1516. doi:10.1111/j.1537-2995.2008.01703.x
Sun DM, Zheng YM, Yin TY, Tang CJ, Yu QS, Wang GX (2014) Coronary drug-eluting stents: from design optimization to newer strategies. J Biomed Mater Res A 102(5):1625–1640. doi:10.1002/jbm.a.34806
Syzcher M (ed) (1999) Syzcher’s handbook of polyurethanes. CRC-Press, Boca Raton
Tang RP, Palumbo RN, Ji WH, Wang C (2009) Poly(Ortho ester amides): acid-labile temperature-responsive copolymers for potential biomedical applications. Biomacromolecules 10(4):722–727. doi:10.1021/bm9000475
The European Society for Biomaterials (1991) 2nd consensus conference on definitions in biomaterials 7–8th September. J Mater Sci Mater Med 2(1):62. doi:10.1007/BF00701689
Toxicology Subgroup – Tripartite Subcommittee on Medical Devices (1986) Tripartite biocompatibility guidance for medical devices. FDA, Center for Devices and Radiological Health (CDRH), Rockville
Tsuji H (2003) In vitro hydrolysis of blends from enantiomeric poly(lactide)s. Part 4: well-homo-crystallized blend and nonblended films. Biomaterials 24(4):537–547. doi:10.1016/S0142-9612(02)00365-4
Tsuji H, Ishida T, Fukuda N (2003) Surface hydrophilicity and enzymatic hydrolyzability of biodegradable polyesters: 1. Effects of alkaline treatment. Polym Int 52(5):843–852. doi:10.1002/pi.1199
Tsuji H, Deguchi F, Sakamoto Y, Shimizu S (2012) Heterostereocomplex crystallization and homocrystallization from the melt in blends of substituted and unsubstituted poly(lactide)s. Macromol Chem Phys 213(24):2573–2581. doi:10.1002/macp.201200395
Ueda H, Tabata Y (2003) Polyhydroxyalkanonate derivatives in current clinical applications and trials. Adv Drug Deliv Rev 55(4):501–518
Vaccaro AR, Chiba K, Heller JG, Patel TC, Thalgott JS, Truumees E, Fischgrund JS, Craig MR, Berta SC, Wang JC (2002) Bone grafting alternatives in spinal surgery. Spine J 2(3):206–215
van Bakelen NB, Buijs GJ, Jansma J, de Visscher JG, Hoppenreijs TJ, Bergsma JE, Stegenga B, Bos RR (2013) Comparison of biodegradable and titanium fixation systems in maxillofacial surgery: a two-year multi-center randomized controlled trial. J Dent Res 92(12):1100–1105. doi:10.1177/0022034513508953
Vera M, Puiggali J, Coudane J (2006) Microspheres from new biodegradable poly(ester amide)s with different ratios of L- and D-alanine for controlled drug delivery. J Microencapsul 23(6):686–697. doi:10.1080/02652040600787942
Vert M (1986) Biomedical polymers from chiral lactides and functional lactones – properties and applications. Makromolekulare Chemie-Macromol Symp 6:109–122. doi:10.1002/masy.19860060113
Vert M (1989) Bioresorbable polymers for temporary therapeutic applications. Angew Makromol Chem 166:155–168. doi:10.1002/apmc.1989.051660111
Wang YQ, Liu SJ, Luo YL, Wang FJ, Liu HY, Li LF, Zhao XH, Huang L (2014) Safety and efficacy of degradable vs. permanent polymer drug-eluting stents: a meta-analysis of 18,395 patients from randomized trials. Int J Cardiol 173(1):100–109. doi:10.1016/j.ijcard.2014.02.023
Weigel T, Schinkel G, Lendlein A (2006) Design and preparation of polymeric scaffolds for tissue engineering. Expert Rev Med Devices 3(6):835–851. doi:10.1586/17434440.3.6.835
Wolff LF, Mullally B (2000) New clinical materials and techniques in guided tissue regeneration. Int Dent J 50(5):235–244
Wu XS (1995) Synthesis and properties of biodegradable lactic/glycolic acid polymers. In: Wise DJT DL, Altobelli DE, Yaszemski MJ, Gresser DJ, Schwartz ER (eds) Encyclopaedic handbook of biomaterials and bioengineering, vol 2. Marcel Decker, New York, pp 1015–1054
Xiong X, Mertsching H, Rupp S, Brunner H (2007) Isolated nature-identical collagen. Germany Patent
Ye T, Zhou CR, Zeng QH, Yang JL, Han FX, Tian JH (2008) Enhanced cell affinity of poly(L-lactide) film by immobilizing phosphonized chitosan. Appl Surf Sci 255(2):446–448. doi:10.1016/j.apsusc.2008.06.073
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We would like to thank the Deutsche Forschungsgemeinschaft (DFG, SFB 760) and the Bundesministerium für Bildung und Forschung (BMBF, FKZ1315848A) for supporting the interdisciplinary research in the field of tissue regeneration.
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Schroeter, M., Wildemann, B., Lendlein, A. (2016). Biodegradable Polymeric Materials. In: Steinhoff, G. (eds) Regenerative Medicine - from Protocol to Patient. Springer, Cham. https://doi.org/10.1007/978-3-319-28274-9_4
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