Synthesis, surface characterization, and platelet reactivity evaluation for the self-assembled monolayer of alkanethiol with sulfonic acid functionality

Journal of Biomedical Materials Research

Volumn 51, Issue 3, 2000, Pages 413-423

  Lin, Jui Che ^a   Chuang, Wen Hsi ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Blood compatibility; Platelet adhesion; Self assembled monolayer; Sulfonic acid; Surface characterization

Indexed keywords

ADHESION; BIOCOMPATIBILITY; BIOSYNTHESIS; CONFORMATIONS; DENSITY (SPECIFIC GRAVITY); ELECTRON SPECTROSCOPY; INORGANIC ACIDS; MOLECULAR STRUCTURE; MONOLAYERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SULFUR COMPOUNDS;

ALKANETHIOL; SELF-ASSEMBLED MONOLAYERS; SULFONIC ACID;

BIOMATERIALS;

BIOMATERIAL; GOLD; SULFONIC ACID DERIVATIVE;

ARTICLE; BIOCOMPATIBILITY; BLOOD COMPATIBILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN CELL; HYDROPHILICITY; SURFACE PROPERTY; SYNTHESIS; THROMBOCYTE ADHESION; THROMBOGENESIS;

ALKANESULFONIC ACIDS; BIOCOMPATIBLE MATERIALS; HUMANS; MATERIALS TESTING; MEMBRANES, ARTIFICIAL; MICROSCOPY, ELECTRON, SCANNING; PLATELET ADHESIVENESS; SPECTRUM ANALYSIS; SURFACE PROPERTIES; X-RAYS;

EID: 0034609616     PISSN: 00219304     EISSN: None     Source Type: Journal    
DOI: 10.1002/1097-4636(20000905)51:3<413::AID-JBM16>3.0.CO;2-L     Document Type: Article

References (54)

1. Lin YS, Hlady V, Janavota J. Adsorption of complement proteins on surfaces with a hydrophobicity gradient. Biomaterials 1992;13:497-504.
2. Wojciechowski PW, Brash JL. Fibrinogen and albumin adsorption from human blood plasma and from buffer onto chemically functionalized silica substrates. Colloids Surf B 1993;1: 107-117.
3. Goodman SL, Simmons SR, Cooper SL, Albrecht RM. Preferential adsorption of plasma proteins onto apolar polyurethane microdomains. J Colloid Interface Sci 1990;139:561-570.
4. Hoffman AS. A general classification scheme for hydrophilic and Hydrophobic biomaterial surfaces. J Biomed Mater Res 1986;20:9-11.
5. Ratner BD, Chilkoti A, López GṖ. Plasma deposition and treatment for biomaterial applications. In: d'Agostino R, editor. Plasma deposition, treatment, and etching of polymers. San Diego, CA: Academic Press, 1990. p 463-516.
6. Yasuda H, Sharma AK, Yasuda T. Effect of orientation and mobility of polymer molecules at surfaces on contact angle and its hysteresis. J Polymer Sci B Polymer Phys 1981;19:1285-1291.
7. Bain CD, Troughton EB, Tao Y-T, Evall J, Whitesides GM, Nuzzo RG. Formation of monolayer films by the spontaneous assembly of organic thiols from solution onto gold. J Am Chem Soc 1989;111:321-335.
8. Ulman A. Formation and structure of self-assembled monolayers. Chem Rev 1996;96:1533-1554.
9. Ulman A. An introduction to ultrathin organic films, from Langmuir-Blodgett to self-assembly. San Diego, CA: Academic Press, 1991. 442 p.
10. Prime KL, Whitesides GM. Adsorption of proteins onto surfaces contain end-attached oligo(ethylene oxide): A model system using self-assembled monolayers. J Am Chem Soc 1993; 115:10714-10721.
11. Prime KL, Whitesides GM. Self-assembled organic monolayers: model systems for studying adsorption of proteins at surfaces. Science 1991;252:1164-1167.
12. López GP, Albers MW, Schreiber SL, Carrol R, Peralta EE, Whitesides GM. Convenient methods for patterning the adhesion of mammalian-cells to surfaces using self-assembled monolayers of alkanethiolates on gold. J Am Chem Soc 1993; 115:5877-5878.
13. Deng L, Mrksich M, Whitesides GM. Self-assembled monolayers of alkanethiolates presenting tri(propylene sulfoxide) groups resist the adsorption of protein. J Am Chem Soc 1996; 118:5136-5137.
14. Patel N, Davies MC, Hartshorne M, Heaton RJ, Roberts CJ, Tendler SJB, Williams PM. Immobilization of protein molecules onto homogeneous and mixed carboxylate-terminated self-assembled monolayers. Langmuir 1997;13:6485-6490.
15. Cotton C, Glidle A, Beamson G, Cooper JM. Dynamics of the formation of mixed alkanethiol monolayers: Applications in structuring biointerfacial arrangements. Langmuir 1998;14: 5139-5146.
16. Silin V, Weetall H, Vanderah DJ. SPR studies of the nonspecific adsorption kinetics of human IgG and BSA on gold surfaces modified by self-assembled monolayers (SAMs). J Colloid Interface Sci 1997;185:94-103.
17. Tengvall P, Lundstrom I, Liedberg B. Protein adsorption studies on model organic surfaces: An ellipsometric and infrared spectroscopic approach. Biomaterials 1998;19:407-422.
18. Lindblad M, Lestelius M, Johansson A, Tengvall P, Thomsen P. Cell and soft tissue interactions with methyl- and hydroxylterminated alkane thiols on gold surfaces. Biomaterials 1997; 18:1059-1068.
19. TidwelJ CD, Ertel SI, Ratner BD, Tarasevich BJ, Atre S, Allara DL. Endothelial cell growth and protein adsorption on terminally functionalized, self-assembled monolayers of alkanethiols on gold. Langmuir 1997;13:3404-3413.
20. Okkema AZ, Visser SA, Cooper SL. Physical and blood-contacting properties of polyurethanes based on a sulfonic acid-containing diol chain extenders. J Biomed Mater Res 1991; 25:1371-1395.
21. Santerre JP, ten Hove P, VanderKamp NH, Brash JL. Effect of sulfonation of segmented polyurethanes on the transient adsorption of fibrinogen from plasma: Possible correlation with anticoagulant behavior. J Biomed Mater Res 1992;26:39-57.
22. Han DK, Lee NY, Park KD, Kim YH, Cho HI, Min BG. Heparin-like anticoagulant activity of sulfonated poly(ethylene oxide) and sulfonated poly(ethylene oxide)-grafted polyurethane. Biomaterials 1995;16:467-471.
23. Jozefowitz M, Jozefonvicz J. Antithrombogenic polymers. Pure Appl Chem 1984;56:1335-1344.
24. Silver JH, Marchant JW, Cooper SL. Effect of polyol type on the physical properties and thrombogenicity of sulfonate-containing polyurethanes. J Biomed Mater Res 1993:27:1443-1457.
25. Okkema AZ, Yu X-H, Cooper SL. The physical and blood-contacting properties of propyl sulfonate grafted Biomer. Biomaterials 1991;12:3-12.
26. Han DK, Jeong SY, Kim YH, Min BG, Cho HI. Negative cilia concept for thromboresistance: Synergistic effect of PEO and sulfonate group grafted onto polyurethanes. J Biomed Mater Res 1991;25:561-575.
27. Lin J-C, Ko TM, Cooper SL. Polyethylene surface sulfonation: Surface characterization and platelet adhesion studies. J Colloid Interface Sci 1994;164:99-106.
28. Lin J-C, Cooper SL. Plasma surface modification of the inner surface of LDPE tubing for biomedical applications. J Appl Polymer Sci Appl Polymer Symp 1994;54:157-166.
29. Lin J-C, Cooper SL. Surface characterization and ex vivo blood compatibility study of plasma modified small diameter tubings: Effect of sulfur dioxide and hexamethyldisiloxane plasmas. Biomaterials 1995;16:1017-1024.
30. Silver JH, Lin J-C, Lim F, Tegoulia VA, Chaudhury MK, Cooper SL. Surface properties and hemocompatibility of alkylsiloxane monolayers supported on silicon rubber: Effect of alkyl chain length and ionic functionality. Biomaterials 1999;20:1533-1543.
31. Lestelius M, Liedberg B, Tengvall P. In vitro plasma protein adsorption on ω-functionalized alkanethiolate self-assembled monolayers. Langmuir 1997;13:5900-5908.
32. Schramm CH, Lemaire H, Karlson RH. The synthesis of mercaptoalkanesulfonic acid. J Am Chem Soc 1955;77:6231-6233.
33. Ko T-M, Lin J-C, Cooper SL. Surface characterization and platelet adhesion studies of plasma-carboxylated polyethylene. J Colloid Interface Sci 1993;156:207-217.
34. Ko T-M. Surface characterization and platelet adhesion studies of plasma treated polyethylene. PhD thesis, University of Wisconsin-Madison, 1991.
35. 1H FT-NMR spectra. Vol. 1. Milwaukee, WI: Aldrich Chemical Co., 1993.
36. Smith T. The hydrophilic nature of a clean gold surface. J Colloid Interface Sci 1980;75:51-55.
37. Ishida T, Tsuneda S, Nishida N, Hara M, Sasabe H, Knoll W. Surface-conditioning effect of gold substrates on octadecanethiol self-assembled monolayers growth. Langmuir 1997;13: 4638-4643.
38. Tanahashi M, Matsuda T. Surface functional group dependence on apatite formation on self-assembled monolayers in a simulated body fluid. J Biomed Mater Res 1997;4:305-315.
39. Whitesides GM, Laibinis PE. Wet chemical approaches to the characterization of organic surfaces: self-assembled monolayers, wetting, and the physical-organic chemistry of the solid-liquid interface. Langmuir 1990;6:87-96.
40. Laibinis PE, Whitesides GM. ω-Terminated alkanethiolate monolayers on surfaces of copper, silver, and gold have similar wettabilities. J Am Chem Soc 1992;114:1990-1995.
41. Andrade JD. X-ray photoelectron spectroscopy. In: Andrade JD, editor. Surface and interfacial aspects of biomedical polymers. Vol. 1: Surface chemistry and physics. New York: Plenum Press, 1985. p 105-196.
42. Castner DG, Hinds K, Grainger DW. X-ray photoelectron spectroscopy of organic thiol and disulfide binding interactions with gold surfaces. Langmuir 1996;12:5083-5086.
43. 2 mixture. J Polymer Sci Polymer Chem 1989;27:3495-3501.
44. Lukkari J, Meretoja M, Kartio I, Laajalehto K, Rajamäki M, Linström M, Kankare J. Organic thiosulfates (Bunte salts): Novel surface-active sulfur compounds for the preparation of self-assembled monolayers on gold. Langmuir 1999;15:3529-3537.
45. Takahara A, Okkema AZ, Webers H, Cooper SL. Effect of hydrophilic soft segment side chains on the surface properties and blood compatibility of segmented poly(urethaneureas). J Biomed Mater Res 1991;5:1095-1118.
46. Grasel TG, Cooper SL. Properties and biological interactions of polyurethane anionomers: Effect of sulfonate incorporation. J Biomed Mater Res 1989;23:311-328.
47. Bhatia SK, Teixeria JL, Anderson M, Shriver-Lake LC, Calvert JM, Georger JM, Hickman JJ, Dulcey CS, Schoen PE, Ligler FS. Fabrication of surfaces resistant to protein adsorption and application to two dimensional protein patterning. Anal Biochem 1993;208:197-205.
48. Liedberg B, Tengvall P. Molecular gradients of ω-substituted alkanethiols on gold: Preparation and characterizations. Langmuir 1995;11:3821-3827.
49. Hoffman AS. Blood-biomaterial interactions: An overview. In: Cooper SL, Peppas NA, editors. Biomaterials: Interfacial phenomena and applications. Washington, DC: American Chemical Society, 1982. p 3-8.
50. Lin J-C. Plasma surface modification of polyethylene tubing: Surface characterization, protein adsorption and ex vivo blood compatibility studies. PhD thesis, University of WisconsinMadison, 1994.
51. Bennett JS. The platelet-fibrinogen interaction. In: George JN, Nurden AT, Philips DR, editors. Platelet membrane glycoproteins. New York: Plenum Press, 1985. p 193-214.
52. Lin J-C, Wu C-H. Surface characterization and platelet adhesion studies on polyurethane surface immobilized with C60. Biomaterials 1999:20:1613-1620.
53. Goodman SL. Sheep, pig, and human platelet-material interactions with model cardiovascular biomaterials. J Biomed Mater Res 1999;45:240-250.
54. Waples LM, Olorundare OE, Goodman SL, Lai QJ, Albrecht RM. Platelet-polymer interactions: Morphologic and intracellular free calcium studies of individual human platelets. J Biomed Mater Res 1996;32:65-76.