This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Albes JM, Krettek C, Hausen B, Rohde R, Haverich A, Borst HG (1993) Biophysical properties of the gelatin-resorcin-formaldehyde/glutaraldehyde adhesive. Ann Thorac Surg 56:910–915.
Alexandridis P (1997) Poly(ethylene oxide) poly(propylene oxide) block copolymer surfactants. Curr Opin Colloid Interface Sci 2:478.
Andersen SO, Jacobsen JP, Bojesen G, Roepstorff P (1992) Phenoloxidase catalyzed coupling of catechols. Identification of novel coupling products. Biochim Biophys Acta 1118:134–138.
Arnoult C, Cardullo RA, Lemos JR, Florman HM (1996) Activation of mouse sperm T-type Ca2+ channels by adhesion to the egg zona pellucida. Proc Natl Acad Sci USA 93:13004–13009.
Autumn K, Liang YA, Hsieh ST, Wzesch W, Chan WP, Kenny TW, Fearing R, Full RJ (2000) Adhesive force of a single gecko foot-hair. Nature 405:681–685.
Baty AM, Leavitt PK, Siedlecki CA, Tyler BJ, Suci PA, Marchant RE, Geesey GG (1997) Adsorption of adhesive proteins from the marine mussel, Mytilus edulis, on polymer films in the hydrated state using angle dependent X-ray photoelectron spectroscopy and atomic force microscopy. Langmuir 13:5702–5710.
Brothers MF, Kaufmann JC, Fox AJ, Deveikis JP (1989) n-Butyl 2-cyanoacrylate—substitute for IBCA in interventional neuroradiology: histopathologic and polymerization time studies. AJNR Am J Neuroradiol 10:777–786.
Brunette DM, Tengvall P, Textor M, Thomsen P (2001) Titanium in medicine. Springer, Berlin Heidelberg New York.
Burzio LA, Waite JH (2000) Cross-linking in adhesive quinoproteins: studies with model decapeptides. Biochemistry 39:11147–11153.
Burzio LO, Burzio VA, Silva T, Burzio LA, Pardo J (1997) Environmental bioadhesion: themes and applications. Curr Opin Biotechnol 8:309–312.
Celik H, Caner H, Tahta K, Ozcan OE, Erbengi A, Onol B (1991) Nonsuture closure of arterial defect by vein graft using isobutyl-2-cyanoacrylate as a tissue adhesive. J Neurosurg Sci 35:83–87.
Characklis KC (1990) Biofilm processes. In: Characklis WG, Marshall KC (eds) Biofilms. Wiley, New York, pp 195–231.
Chen LX, Liu T, Thurnauer MC, Csencsits R, Rajh T (2002) Fe2O3 nanoparticle structures investigated by X-ray absorption near-edge structure, surface modifications, and model calculations. J Phys Chem B 106:8539–8546.
Chirdon WM, O’Brien WJ, Robertson RE (2003) Adsorption of catechol and comparative solutes on hydroxyapatite. J Biomed Mat Res 66B:532–538.
Chivers RA, Wolowacz RG (1997) The strength of adhesive-bonded tissue joints. Int J Adh Adhesives 17:127–132.
Connor PA, Dobson KD, Mcquillan AJ (1995) New Sol-Gel attenuated total-reflection infrared spectroscopic method for analysis of adsorption at metal-oxide surfaces in aqueous-solutions -chelation of Tio2, Zro2, and Al2o3 surfaces by Catechol, 8-Quinolinol, and Acetylacetone. Langmuir 11:4193–4195.
Coombs TL, Keller PJ (1981) Mytilus byssal threads as an environmental marker for metals. Aquat Toxicol 1:291–300.
Cooper CW, Falb RD (1968) Surgical adhesives. Ann NY Acad Sci 146:214–224.
Crisp DJ, Walker G, Young GA, Yule AB (1985) Adhesion and substrate choice in Mussels and Barnacles. J Colloid Interface Sci 104:40–50.
Dalsin JL, Messersmith PB (2003) Surface modification for protein resistance using a biomimetic approach. In: Thomas JL, Gower LA (eds) Materials inspired by biology, vol 774. Materials Research Society, Warrendale PA, USA, pp 75–80.
Dalsin JL, Messersmith PB (2005) Bioinspired antifouling polymers. Materials Today 8:38–46.
Dalsin JL, Hu B-H, Lee BP, Messersmith PB (2003) Mussel adhesive protein mimetic polymers for the preparation of nonfouling surfaces. J Am Chem Soc 125:4253–4258.
Dalsin JL, Tosatti S, Vörös J, Textor M, Messersmith PB (2005) Protein resistance of titanium oxide surfaces modified by biologically inspired mPEG-DOPA. Langmuir 21:640–646.
Deacon MP, Davis SS, Waite JH, Harding SE (1998) Structure and mucoadhesion of mussel glue protein in dilute solution. Biochemistry 37:14108–14112.
Dossot M, Sylla M, Allonas X, Merlin A, Jacques P, Fouassier J-P (2000) Role of phenolic derivatives in photopolymerization of an acrylate coating. J Appl Poly Sci 78:2061–2074.
Ennker J, Ennker IC, Schoon D, Schoon HA, Dorge S, Meissler J, Rimpler M, Helzer R (1994) The Impact of gelatin-resorcinol glue on aortic tissue: ahistomophologic evaluation. J Vasc Surg 20(1):34–43.
Fan X, Lin L, Dalsin JL, Messersmith PB (2005) Biomimetic anchor for surface-initiated polymerization from metal substrates. J Am Chem Soc 127 (45):15843–15847.
Filpula DR, Lee SM, Link RP, Strausberg SL, Strausberg RL (1990) Structural and functional repetition in a marine mussel adhesive protein. Biotechnol Prog 6:171–177.
Geim AK, Dubonos SV, Grigorieva IV, Novoselov KS, Zhukov AA, Shapoval SY (2003) Microfabricated adhesive mimicking gecko foot-hair. Nature Materials 2:461–463.
Gilbert CE, Grierson I, McLeod D (1989) Retinal patching: a new approach to the management of selected retinal breaks. Eye 3:19–26.
Goldin AR (1976) Control of duodenal haemorrhage with cyanoacrylate. Br J Radiol 49:583–588.
Grande DA, Pitman MI (1988) The use of adhesives in chondrocyte transplantation surgery. Preliminary studies. Bull Hosp Jt Dis Orthop Inst 48:140–148.
Green K, Berdecia R, Cheeks L (1987) Mussel adhesive protein: permeability characteristics when used as a basement membrane. Curr Eye Res 6:835–837.
Hansen DC, Dexter SC, Waite JH (1995) The inhibition of corrosion of S30403 stainless steel by a naturally occurring catecholic polymer. Corrosion Science 37:1423–1441.
Harris JM (1992) Introduction to biotechnical and biomedical applications of poly(ethylene glycol). In: Harris JM (ed) Poly(ethylene glycol) chemistry: biotechnical and biomedical applications. Plenum Press, New York, pp 1–14.
Hartnett ME, Hirose T (1998) Cyanoacrylate glue in the repair of retinal detachment associated with posterior retinal breaks in infants and children. Retina 18:125–129.
Huang K, Lee B, Ingram D, Messersmith P (2002) Synthesis and characterization of self-assembling block copolymers containing adhesive moieties. Biomacromolecules 3:397–406.
Hwang DS, Yoo HJ, Jun JH, Moon WK, Cha HJ (2004) Expression of functional recombinant mussel adhesive protein Mgfp-5 in Escherichia coli. Appl Environ Microbiol 70:3352–9.
Hwang DS, Gim Y, Cha HJ (2005) Expression of functional recombinant mussel adhesive protein type 3A in Eschereschia coli. Biotechnology Progress 21:965–70.
Ikada Y (1997) Tissue adhesives. In: Chu CC, von Fraunhofer JA, Greisler HP (eds) Wound closure biomaterials and devices. CRC Press, Boca Raton, Florida, pp 317–346.
Kakio T, Ito T, Sue K, Sakaguchi K, Shiota T, Oka T, Kobashi H, Sakai N, Omoto M, Mikami M et al (1993) Hemostasis of gastric variceal hemorrhage by transileocoecal and transhepatic obliteration. Acta Med Okayama 47:39–43.
Kamino K (2001) Novel barnacle underwater adhesive protein is a charged amino acid-rich protein constituted by a Cys-rich repetitive sequence. Biochem J 356:503–507.
Kamino K, Inoue K, Maruyama T, Takamatsu N, Harayama S, Shizuri Y (2000) Barnacle cement proteins. Importance of disulfide bonds in their insolubility. J Biol Chem 273:27360–27365.
Kenausis GL, Voros J, Elbert DL, Huang N, Hofer R, Ruiz-Taylor L, Textor M, Hubbell JA, Spencer ND (2000) Poly(L-lysine)-g-Poly(ethylene glycol) layers on metal oxide surfaces: attachment mechanism and effects of polymer architecture on resistance to protein adsorption. J Phys Chem B 104:3298–3309.
Khowassah MA, Shippy RL (1971) In vitro investigation of the adhesive strength of cyanoacrylate bonds to human hard tooth structures. J Biomed Mat Res 5:159–68.
Kramer KJ, Morgan TD, Hopkins TL, Christensen A, Schaefer J (1991) Insect cuticle tanning: enzymes and cross-link structure. Nat Occur Pest Bioreg 449:87–105.
Kummert R, Stumm W (1980) The surface complexation of organic acids on hydrous g-alumina. J Colloid Interface Sc 75:373–385.
Lee BP, Dalsin JL, Messersmith PB (2002) Synthesis and gelation of DOPA-modified poly(ethylene glycol) hydrogels. Biomacromolecules 3:1038–1047.
Lee BP, Huang K, Nunalee N, Shull K, Messersmith PB (2004) Synthesis of 3, 4-dihydroxyphenylalanine (DOPA) containing monomers and their copolymerization with PEG-diacrylate to form hydrogels. J Biomat Sci, Polym Ed 15:449–464.
Long JR, Dindot JL, Zebroski HK, Suzanne, Clark RH, Campbell AA, Stayton PS, Drobny GP (1998) A peptide that inhibits hydroxyapatite growth is in an extended conformation on the crystal surface. Proc Natl Acad Sci USA 95:12083–12087.
Ma H, Hyun J, Stiller P, Chilkoti A (2004) “Non-fouling” oligo(ethylene glycol)-functionalized polymer brushes synthesized by surface-initiated atom transfer radical polymerization. Adv Mater 16:338–341.
Malmsten M, Emoto K, Van Alstine JM (1998) Effect of chain density on inhibition of protein adsorption by poly(ethylene glycol) based coatings. J Colloid Interface Sci 202:507–517.
Marumo K, Waite JH (1986) Optimization of hydroxylation of tyrosine and tyrosine-containing peptides by mushroom tyrosinase. Biochim Biophys Acta 872:98–103.
Maugh KJ, Anderson DM, Strausberg R, Strausberg SL, Mccandliss R, Wei T, Filpula D (1988) Recombinant bioadhesive proteins of marine animals and their use in adhesive compositions. USA patent no 87–US3048.
McDowell LM, Burzio LA, Waite JH, Schaefer J (1999) Rotational echo double resonance detection of cross-links formed in mussel byssus under high-flow stress. J Biol Chem 274:20293–20295.
Meisel H, Olieman C (1998) Estimation of calcium-binding constants of casein phosphopeptides by capillary zone electrophoresis. Anal Chim Acta 372:291–297.
Naldrett MJ, Kaplan DL (1997) Characterization of barnacle (Balanus eburneus and B. crenatus) adhesive proteins. Mar Biol 127:629–635.
Nath N, Hyun J, Ma H, Chilkoti A (2004) Surface engineering strategies for control of protein and cell interactions. Surface Sci 570:98–110.
Ninan L, Monahan J, Stroshine RL, Wilker JJ, Shi R (2003) Adhesive strength of marine mussel extracts on porcine skin. Biomaterials 24:4091–4099.
Nomori H, Horio H (1997) Gelatin-resorcinol-formaldehyde-glutaraldehyde glue-spread stapler prevents air leakage from the lung. Ann Thorac Surg 63:352–355.
Olivieri MP, Loomis RE, Meyer AE, Baier RE (1990) Surface characterization of mussel adhesive protein films. J Adhes Sci Technol 4:197–204.
Papov VV, Diamond TV, Biemann K, Waite JH (1995) Hydroxyarginine-containing polyphenolic proteins in the adhesive plaques of the marine mussel Mytilus edulis. J Biol Chem 270:20183–20192.
Pardo J, Gutierrez E, Saez C, Brito M, Burzio LO (1990) Purification of adhesive proteins from mussels. Protein Expr Purif 1:147–150.
Pasche S, De Paul SM, Voros J, Spencer ND, Textor M (2003) Poly(L-lysine)-graft-poly(ethylene glycol) assembled monolayers on niobium oxide surfaces: a quantitative study of the influence of polymer interfacial architecture on resistance to protein adsorption by ToF-SIMS and in situ OWLS. Langmuir 19:9216–9225.
Pitman MI, Menche D, Song EK, Ben-Yishay A, Gilbert D, Grande DA (1989) The use of adhesives in chondrocyte transplantation surgery: in-vivo studies. Bull Hosp Jt Dis Orthop Inst 49:213–220.
Rajh T, Chen LX, Lukas K, Liu T, Thurnauer MC, Tiede DM (2002) Surface restructuring of nanoparticles: an efficient route for ligand-metal oxide crosstalk. J Phys Chem B 106: 10543–10552.
Refojo MF, Dohlman CH, Koliopoulos J (1971) Adhesives in ophthalmology: a review. Surv Ophthamol 15:217–236.
Rice C, Ward M, Nazeeruddin M, Gratzel M (2000) Catechol as an efficient anchoring group for attachment of ruthenium-polypyridine photsensitizers to solar cells based on nanocrystalline films. New J Chem 24:651–652.
Rodriguez R, Blesa MA, Regazzoni AE (1996) Surface complexation at the TiO2(anatase)/aqueous solution interface: chemisorption of catechol. J Colloid Interface Sci 177:122–131.
Rzepecki LM, Hansen KM, Waite JH (1992) Characterization of a cystine-rich polyphenolic protein family from the blue mussel Mytilus edulis. Biol Bull 183:123–137.
Rzepecki LM, Hansen KM, Waite JH (1995) Bioadhesives: dopa and phenolic proteins as component of organic composite materials. In: Principles of cell adhesion. CRC Press, Boca Raton, pp 107–142.
Saltz R, Sierra D, Feldman D, Saltz MB, Dimick A, Vasconez LO (1991) Experimental and clinical applications of fibrin glue. Plast Reconstr Surg 88:1005–1015; discussion 1016–1017.
Schnurrer J, Lehr C-M (1996) Mucoadhesive properties of the mussel adhesive protein. Int J Pharm 141:251–256.
Sever MJ, Weisser JT, Monahan J, Srinivasan S, Wilker JJ (2004) Metal-mediated cross-linking in the generation of a marine-mussel adhesive. Angew Chem Int Ed 43:448–450.
Siedentop KH, Harris DM, Sanchez B (1988) Autologous fibrin tissue adhesive: factors influencing bonding power. Laryngoscope 98:731–733.
Sierra D, Saltz R (1996) Surgical adhesives and sealants: current technology and applications. Technomic Publ, Lancaster, PA.
Sofia SJ, Premnath V, Merrill EW (1998) Poly(ethylene oxide) grafted to silicon surfaces: grafting density and protein adsorption. Macromolecules 31:5059–5070.
Soriaga MP, Hubbard AT (1982) Determination of the orientation of aromatic molecules adsorbed on platinum electrodes. The effect of solute concentration. J Am Chem Soc 104:3937–3945.
Statz AR, Meagher RJ, Barron AE, Messersmith PB (2005) New peptidomimetic polymers for antifouling surfaces. J Am Chem Soc 127:7972–7973.
Strausberg RL, Link RP (1990) Protein-based medical adhesives. Trends Biotechnol 8:53–57.
Strausberg RL, Anderson DM, Filpula D, Finkelman M, Link R, McCandliss R, Orndorff SA, Strausberg SL, Wei T (1989) Development of a microbial system for production of mussel adhesive protein. Adhesives Renewable Resources 385:453–464.
Sugumaran M (1998) Unified mechanism for sclerotization of insect cuticles. Adv Insect Physiol 27:230–334.
Swann CP, Adewole T, Waite JH (1998) Preferential manganese accumulation in dreissenid byssal threads. Comp Biochem Physiol B Biochem Mol Biol 119B:755–759.
Szefer P, Ikuta K, Kushiyama S, Szefer K, Frelek K, Geldon J (1997) Distribution and association of trace metals in soft tissue and byssus of Mytilus edulis from the east coast of Kyushu Island, Japan. Arch Environ Contam Toxicol 32:184–190.
Tatehata H, Mochizuki A, Kawashima T, Yamashita S, Yamamoto H (2000) Model polypeptide of mussel adhesive protein. I. Synthesis and adhesive studies of sequential polypeptides (X-Tyr-Lys) n and (Y-Lys) n. J Appl Polym Sci 76:929–937.
Tatehata H, Mochizuki A, Ohkawa K, Yamada M, Yamamoto H (2001) Tissue adhesive using synthetic model adhesive proteins inspired by the marine mussel. J Adh Sci Tech 15:1003–1013.
Tatooles CJ, Braunwald NS (1966) The Use of crosslinked gelatin as a tissue adhesive to control the hemorrhage from liver and kidney. Surgery 50:17.
Taylor SW, Luther GW III, Waite JH (1994) Polarographic and spectrophotometric investigation of Iron(III) complexation to 3, 4-Dihydroxyphenylalanine-containing peptides and proteins from mytilus edulis. Inorg Chem 33:5819–5824.
Taylor SW, Chase DB, Emptage MH, Nelson MJ, Waite JH (1996) Ferric ion complexes of a DOPA-containing adhesive protein from mytilus edulis. Inorg Chem 35:7572–7577.
Toriumi DM, Raslan WF, Friedman M, Tardy ME Jr (1991) Variable histotoxicity of histoacryl when used in a subcutaneous site: an experimental study. Laryngoscope 101:339–343.
Tseng YC, Tabata Y, Hyon SH, Ikada Y (1990) In vitro toxicity test of 2-cyanoacrylate polymers by cell culture method. J Biomed Mat Res 24:1355–1367.
Waite JH (1987) Nature’s underwater adhesive specialist. Int J Adh Adhesives 7:9–14.
Waite JH (1990) The phylogeny and chemical diversity of quinone-tanned glues and varnishes. Comp Biochem Physiol B Comp Biochem 97:19–29.
Waite JH (1991) Mussel beards: a coming of age. Chem Industry 2:607–611.
Waite JH (1999) Reverse engineering of bioadhesion in marine mussels. Ann NY Acad Sci 875:301–309.
Waite JH, Andersen SO (1978) 3, 4-Dihydroxyphenylalanine in an insoluble shell protein of Mytilus edulis. Biochimt Biophys Acta 541:107–114.
Waite JH, Qin X (2001) Polyphosphoprotein from the adhesive pads of Mytilus edulis. Biochemistry 40:2887–2893.
Waite JH, Anderson NH, Jewhurst S, Sun C (2005) Mussel adhesion: finding the tricks worth mimicking. J Adhesion 81:1–21.
Warner SC, Waite JH (1999) Expression of multiple forms of an adhesive plaque protein in an individual mussel, Mytilus edulis. Mar Biol 134:729–734.
Weber SC, Chapman MW (1984) Adhesives in orthopaedic surgery. A review of the literature and in vitro bonding strengths of bone-bonding agents. Clin Orthop 191:249–261.
Xu C, Xu K, Gu H, Zheng R, Liu H, Zhang X, Guo Z, Xu B (2004) Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles. J Am Chem Soc 126:9938–9939.
Yamamoto H (1987) Synthesis and adhesive studies of marine polypeptides. J Chem Soc Perkin Trans 1:613–618.
Yamamoto H (1995) Marine adhesive proteins and some biotechnological applications. Biotechnol Genet Eng Rev 13:133–165.
Yamamoto H, Ogawa T, Ohkawa K (1995) Wettability and adhesion of synthetic marine adhesive proteins and related model compounds. J Colloid Interface Sci 176:111–116.
Yang JZ, Medawar PB (1940) Fibrin suture of peripheral nerves. Lancet 275:126–132.
Young GA, Crisp DJ (1982) Marine animals and adhesion. In: Allen KW (ed) Adhesion-6. Applied Science Publishers, Barkling, UK, pp 279–313.
Yu M, Deming TJ (1998) Synthetic polypeptide mimics of marine adhesives. Macromolecules 31:4739–4745.
Yu M, Hwang J, Deming TJ (1999) Role of L-3, 4-dihydroxyphenylalanine in mussel adhesive proteins. J Am Chem Soc 121:5825–5826.
Zalipsky S, Harris JM (1997) Introduction to chemistry and biological applications of poly(ethylene glycol). In: Harris JM, Zalipsky S (eds) Poly(ethylene glycol): chemistry and biological applications, vol 680. American Chemical Society, Washington, DC, pp 1–13.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2006 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Lee, B.P., Dalsin, J.L., Messersmith, P.B. (2006). Biomimetic Adhesive Polymers Based on Mussel Adhesive Proteins. In: Smith, A.M., Callow, J.A. (eds) Biological Adhesives. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-31049-5_13
Download citation
DOI: https://doi.org/10.1007/978-3-540-31049-5_13
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-31048-8
Online ISBN: 978-3-540-31049-5
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)