Abstract
The fabrication of novel scaffolds was represented on the basis of conductive and biodegradable copolymers. The star-like polycaprolactone (S-PCL) was synthesized from dipentaerythritol as a core by a catalyst of Sn(oct)8 through ring-opening technique. After functionalization of S-PCL by thiophene, thiophene monomer was polymerized from polycaprolactone ends via chemical oxidation polymerization to reach star-like polycaprolactone–polythiophene (S-PCL–PTh). The scaffolds demonstrated a porous configuration (160–190 nm) having the great surface area as well as conductivity of 0.011 S cm−1. The cytocompatibility measurements exhibited that the nanofibers were not toxic to the MG63 cells.
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References
Heegar AJ (1986) In: Skotheim TA (ed) Handbook of conducting polymers, vol 2. Marcel Dekker, New York, pp 729–756
Heeger AJ (2001) Semiconducting and metallic polymers: the fourth generation of polymeric materials (Nobel lecture). Angew Chem Int Ed 40(14):2591–2611
Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ (1977) Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH) x. J Chem Soc Chem Commun 16:578–580
Street GB, Clarke TC (1981) Conducting polymers: a review of recent work. IBM J Res Dev 25(1):51–57
Abidian MR, Kim DH, Martin DC (2006) Conducting-polymer nanotubes for controlled drug release. Adv Mater 18(4):405–409
Abidian MR, Martin DC (2008) Experimental and theoretical characterization of implantable neural microelectrodes modified with conducting polymer nanotubes. Biomaterials 29(9):1273–1283
Guimard NK, Gomez N, Schmidt CE (2007) Conducting polymers in biomedical engineering. Prog Polym Sci 32(8–9):876–921
George PM, LaVan DA, Burdick JA, Chen CY, Liang E, Langer R (2006) Electrically controlled drug delivery from biotin-doped conductive polypyrrole. Adv Mater 18(5):577–581
George PM, Lyckman AW, LaVan DA, Hegde A, Leung Y, Avasare R, Testa C, Alexander PM, Langer R, Sur M (2005) Fabrication and biocompatibility of polypyrrole implants suitable for neural prosthetics. Biomaterials 26(17):3511–3519
Smela E (2003) Conjugated polymer actuators for biomedical applications. Adv Mater 15(6):481–494
Richardson-Burns SM, Hendricks JL, Foster B, Povlich LK, Kim DH, Martin DC (2007) Polymerization of the conducting polymer poly(3,4-ethylenedioxythiophene)(PEDOT) around living neural cells. Biomaterials 28(8):1539–1552
Guimard NK, Sessler JL, Schmidt CE (2008) Toward a biocompatible and biodegradable copolymer incorporating electroactive oligothiophene units. Macromolecules 42(2):502–511
O’brien FJ (2011) Biomaterials and scaffolds for tissue engineering. Mater Today 14(3):88–95
Baino F, Marshall M, Kirk N, Vitale-Brovarone C (2016) Design, selection and characterization of novel glasses and glass-ceramics for use in prosthetic applications. Ceram Int 42(1):1482–1491
Lakard B, Ploux L, Anselme K, Lallemand F, Lakard S, Nardin M, Hihn JY (2009) Effect of ultrasounds on the electrochemical synthesis of polypyrrole, application to the adhesion and growth of biological cells. Bioelectrochemistry 75(2):148–157
Kotwal A, Schmidt CE (2001) Electrical stimulation alters protein adsorption and nerve cell interactions with electrically conducting biomaterials. Biomaterials 22(10):1055–1064
Lee JY, Bashur CA, Goldstein AS, Schmidt CE (2009) Polypyrrole-coated electrospun PLGA nanofibers for neural tissue applications. Biomaterials 30(26):4325–4335
Wallace GG, Smyth M, Zhao H (1999) Conducting electroactive polymer-based biosensors. TrAC Trends Anal Chem 18(4):245–251
Rivers TJ, Hudson TW, Schmidt CE (2002) Synthesis of a novel, biodegradable electrically conducting polymer for biomedical applications. Adv Func Mater 12(1):33–37
Kim DH, Richardson-Burns SM, Hendricks JL, Sequera C, Martin DC (2007) Effect of immobilized nerve growth factor on conductive polymers: electrical properties and cellular response. Adv Func Mater 17(1):79–86
Huang L, Zhuang X, Hu J, Lang L, Zhang P, Wang Y, Chen X, Wei Y, Jing X (2008) Synthesis of biodegradable and electroactive multiblock polylactide and aniline pentamer copolymer for tissue engineering applications. Biomacromolecules 9(3):850–858
Garner B, Georgevich A, Hodgson AJ, Liu L, Wallace GG (1999) Polypyrrole–heparin composites as stimulus-responsive substrates for endothelial cell growth. J Biomed Mater Res Part A 44(2):121–129
Aoki T, Tanino M, Sanui K, Ogata N, Kumakura K (1996) Secretory function of adrenal chromaffin cells cultured on polypyrrole films. Biomaterials 17(20):1971–1974
Guiseppi-Elie A (2010) Electroconductive hydrogels: synthesis, characterization and biomedical applications. Biomaterials 31(10):2701–2716
Balint R, Cassidy NJ, Cartmell SH (2014) Conductive polymers: towards a smart biomaterial for tissue engineering. Acta Biomater 10(6):2341–2353
Cui X, Wiler J, Dzaman M, Altschuler RA, Martin DC (2003) In vivo studies of polypyrrole/peptide coated neural probes. Biomaterials 24(5):777–787
Li M, Guo Y, Wei Y, MacDiarmid AG, Lelkes PI (2006) Electrospinning polyaniline-contained gelatin nanofibers for tissue engineering applications. Biomaterials 27(13):2705–2715
Zhang Z, Rouabhia M, Wang Z, Roberge C, Shi G, Roche P, Li J, Dao LH (2007) Electrically conductive biodegradable polymer composite for nerve regeneration: electricity-stimulated neurite outgrowth and axon regeneration. Artif Organs 31(1):13–22
Patel N, Poo MM (1982) Orientation of neurite growth by extracellular electric fields. J Neurosci 2(4):483–496
Collier JH, Camp JP, Hudson TW, Schmidt CE (2000) Synthesis and characterization of polypyrrole–hyaluronic acid composite biomaterials for tissue engineering applications. J Biomed Mater Res Part A 50(4):574–584
Lee JW, Serna F, Nickels J, Schmidt CE (2006) Carboxylic acid-functionalized conductive polypyrrole as a bioactive platform for cell adhesion. Biomacromolecules 7(6):1692–1695
Subramanian A, Krishnan UM, Sethuraman S (2012) Axially aligned electrically conducting biodegradable nanofibers for neural regeneration. J Mater Sci Mater Med 23(7):1797–1809
Roncali J (1992) Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chem Rev 92(4):711–738
Cardoso GB, Perea GN, D’Avila MA, Dias CG, Zavaglia CA, Arruda AC (2011) Initial study of electrospinning PCL/PLLA blends. Adv Mater Phys Chem 1(03):94
Salehi M, Bastami F (2016) Characterization of wet-electrospun poly(ε-caprolactone)/poly(l-lactic) acid with calcium phosphates coated with chitosan for bone engineering. Regener Reconstr Restor 1(2):69–74
Miculescu F, Maidaniuc A, Voicu SI, Thakur VK, Stan GE, Ciocan LT (2017) Progress in hydroxyapatite–starch based sustainable biomaterials for biomedical bone substitution applications. ACS Sustain Chem Eng 5(10):8491–8512
Wróblewska-Krepsztul J, Rydzkowski T, Borowski G, Szczypiński M, Klepka T, Thakur VK (2018) Recent progress in biodegradable polymers and nanocomposite-based packaging materials for sustainable environment. Int J Polym Anal Charact 23(4):383–395
Nasajpour A, Mandla S, Shree S, Mostafavi E, Sharifi R, Khalilpour A, Saghazadeh S, Hassan S, Mitchell MJ, Leijten J, Hou X (2017) Nanostructured fibrous membranes with rose spike-like architecture. Nano Lett 17(10):6235–6240
Nasajpour A, Ansari S, Rinoldi C, Rad AS, Aghaloo T, Shin SR, Mishra YK, Adelung R, Swieszkowski W, Annabi N, Khademhosseini A (2018) A multifunctional polymeric periodontal membrane with osteogenic and antibacterial characteristics. Adv Func Mater 28(3):1703437
Uhrich KE, Cannizzaro SM, Langer RS, Shakesheff KM (1999) Polymeric systems for controlled drug release. Chem Rev 99(11):3181–3198
Kricheldorf HR, Fechner B (2001) Polylactones. 51. Resorbable networks by combined ring-expansion polymerization and ring-opening polycondensation of ε-caprolactone or dl-lactide. Macromolecules 34(11):3517–3521
Nabid MR, Rezaei SJT, Sedghi R, Niknejad H, Entezami AA, Oskooie HA, Heravi MM (2011) Self-assembled micelles of well-defined pentaerythritol-centered amphiphilic A4B8 star-block copolymers based on PCL and PEG for hydrophobic drug delivery. Polymer 52(13):2799–2809
Guo B, Finne-Wistrand A, Albertsson AC (2010) Enhanced electrical conductivity by macromolecular architecture: hyperbranched electroactive and degradable block copolymers based on poly(ε-caprolactone) and aniline pentamer. Macromolecules 43(10):4472–4480
Miao Y, Phuphuak Y, Rousseau C, Bousquet T, Mortreux A, Chirachanchai S, Zinck P (2013) Ring-opening polymerization of lactones using binaphthyl-diyl hydrogen phosphate as organocatalyst and resulting monosaccharide functionalization of polylactones. J Polym Sci Part A Polym Chem 51(10):2279–2287
Lanao RPF, Jonker AM, Wolke JG, Jansen JA, van Hest JC, Leeuwenburgh SC (2013) Physicochemical properties and applications of poly(lactic-co-glycolic acid) for use in bone regeneration. Tissue Eng Part B Rev 19(4):380–390
Okada M (2002) Chemical syntheses of biodegradable polymers. Prog Polym Sci 27(1):87–133
Nair LS, Laurencin CT (2007) Biodegradable polymers as biomaterials. Prog Polym Sci 32(8–9):762–798
Stavridi M, Katsikogianni M, Missirlis YF (2003) The influence of surface patterning and/or sterilization on the haemocompatibility of polycaprolactones. Mater Sci Eng C 23(3):359–365
Ng KW, Hutmacher DW, Schantz JT, Ng CS, Too HP, Lim TC, Phan TT, Teoh SH (2001) Evaluation of ultra-thin poly(ε-caprolactone) films for tissue-engineered skin. Tissue Eng 7(4):441–455
Engelberg I, Kohn J (1991) Physico-mechanical properties of degradable polymers used in medical applications: a comparative study. Biomaterials 12(3):292–304
Woodruff MA, Hutmacher DW (2010) The return of a forgotten polymer—polycaprolactone in the 21st century. Prog Polym Sci 35(10):1217–1256
Musyanovych A, Landfester K (2012) Biodegradable polyester-based nanoparticle formation by miniemulsion technique. Mater Matters 7(3):30–34
Baek KY, Kamigaito M, Sawamoto M (2001) Star-shaped polymers by metal-catalyzed living radical polymerization. 1. Design of Ru (II)-based systems and divinyl linking agents. Macromolecules 34(2):215–221
Li C, Wang B, Liu Y, Cao J, Feng T, Chen Y, Luo X (2013) Synthesis and evaluation of star-shaped poly(ε-caprolactone)–poly(2-hydroxyethyl methacrylate) as potential anticancer drug delivery carriers. J Biomater Sci Polym Ed 24(6):741–757
Dong CM, Qiu KY, Gu ZW, Feng XD (2001) Synthesis of star-shaped poly(ε-caprolactone)-b-poly(dl-lactic acid-alt-glycolic acid) with multifunctional initiator and stannous octoate catalyst. Macromolecules 34(14):4691–4696
Choi YK, Bae YH, Kim SW (1998) Star-shaped poly(ether–ester) block copolymers: synthesis, characterization, and their physical properties. Macromolecules 31(25):8766–8774
Higashi N, Koga T, Niwa M (2000) Dendrimers with attached helical peptides. Adv Mater 12(18):1373–1375
Heise A, Diamanti S, Hedrick JL, Frank CW, Miller RD (2001) Investigation of the initiation behavior of a dendritic 12-arm initiator in atom transfer radical polymerization. Macromolecules 34(11):3798–3801
Guo B, Finne-Wistrand A, Albertsson AC (2010) Molecular architecture of electroactive and biodegradable copolymers composed of polylactide and carboxyl-capped aniline trimer. Biomacromolecules 11(4):855–863
Shadi L, Karimi M, Ramazani S, Entezami AA (2014) Preparation of electrospun nanofibers of star-shaped polycaprolactone and its blends with polyaniline. J Mater Sci 49(14):4844–4854
Li X, Kolega J (2002) Effects of direct current electric fields on cell migration and actin filament distribution in bovine vascular endothelial cells. J Vasc Res 39(5):391–404
Pullar CE, Isseroff RR, Nuccitelli R (2001) Cyclic AMP-dependent protein kinase A plays a role in the directed migration of human keratinocytes in a DC electric field. Cytoskeleton 50(4):207–217
Brown MJ, Loew LM (1994) Electric field-directed fibroblast locomotion involves cell surface molecular reorganization and is calcium independent. J Cell Biol 127(1):117–128
Ozawa H, Abe E, Shibasaki Y, Fukuhara T, Suda T (1989) Electric fields stimulate DNA synthesis of mouse osteoblast-like cells (MC3T3-E1) by a mechanism involving calcium ions. J Cell Physiol 138(3):477–483
McBain VA, Forrester JV, McCaig CD (2003) HGF, MAPK, and a small physiological electric field interact during corneal epithelial cell migration. Invest Ophthalmol Vis Sci 44(2):540–547
Zhao Y, Shuai X, Chen C, Xi F (2003) Synthesis and characterization of star-shaped poly(l-lactide) s initiated with hydroxyl-terminated poly(amidoamine)(PAMAM-OH) dendrimers. Chem Mater 15(14):2836–2843
Kim DH, Kim P, Song I, Cha JM, Lee SH, Kim B, Suh KY (2006) Guided three-dimensional growth of functional cardiomyocytes on polyethylene glycol nanostructures. Langmuir 22(12):5419–5426
Kai D, Prabhakaran MP, Jin G, Ramakrishna S (2011) Polypyrrole-contained electrospun conductive nanofibrous membranes for cardiac tissue engineering. J Biomed Mater Res Part A 99(3):376–385
Jaymand M, Sarvari R, Abbaszadeh P, Massoumi B, Eskandani M, Beygi-Khosrowshahi Y (2016) Development of novel electrically conductive scaffold based on hyperbranched polyester and polythiophene for tissue engineering applications. J Biomed Mater Res Part A 104(11):2673–2684
Liu Y, Hu J, Zhuang X, Zhang P, Chen X, Wei Y, Wang X (2011) Preparation and characterization of biodegradable and electroactive polymer blend materials based on mPEG/tetraaniline and PLLA. Macromol Biosci 11(6):806–813
Sarvari R, Massoumi B, Jaymand M, Beygi-Khosrowshahi Y, Abdollahi M (2016) Novel three-dimensional, conducting, biocompatible, porous, and elastic polyaniline-based scaffolds for regenerative therapies. RSC Adv 6(23):19437–19451
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Sarvari, R., Massoumi, B., Zareh, A. et al. Porous conductive and biocompatible scaffolds on the basis of polycaprolactone and polythiophene for scaffolding. Polym. Bull. 77, 1829–1846 (2020). https://doi.org/10.1007/s00289-019-02732-z
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DOI: https://doi.org/10.1007/s00289-019-02732-z