Nanomedicine: Nanotechnology, Biology and Medicine
Volume 2, Issue 3 , Pages 182-190 , September 2006

The use of alkanethiol self-assembled monolayers on 316L stainless steel for coronary artery stent nanomedicine applications: an oxidative and in vitro stability study

  • Anil Mahapatro, BEng, MSc, PhD

      Affiliations

    • Department of Biomedical Engineering, The University of Texas at San Antonio, San Antonio, Texas, USA
  • ,
  • Dave M. Johnson, BSc, PhD

      Affiliations

    • Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas, USA
    • Corresponding Author InformationCorresponding authors.
  • ,
  • Devang N. Patel, MBChB

      Affiliations

    • Department of Cardiology, The University of Texas Health Science Center at San Antonio, San Antonio, Texas, USA
  • ,
  • Marc D. Feldman, BS, MD

      Affiliations

    • Department of Biomedical Engineering, The University of Texas at San Antonio, San Antonio, Texas, USA
    • Department of Cardiology, The University of Texas Health Science Center at San Antonio, San Antonio, Texas, USA
  • ,
  • Arturo A. Ayon, BS, MSc, PhD

      Affiliations

    • Department of Biomedical Engineering, The University of Texas at San Antonio, San Antonio, Texas, USA
  • ,
  • C. Mauli Agrawal, BTech, MSc, PhD

      Affiliations

    • Department of Biomedical Engineering, The University of Texas at San Antonio, San Antonio, Texas, USA
    • Corresponding Author InformationCorresponding authors.

Received 26 May 2006 ,Accepted 19 July 2006.

References 

  1. Hoffmann R, Mintz GS, Dussaillant GR, et al. Patterns and mechanisms of in-stent restenosis. A serial intravascular ultrasound study. Circulation. 1996;94:1247–1254
  2. Abizaid A, Costa MA, Centemero M, et al. Clinical and economic impact of diabetes mellitus on percutaneous and surgical treatment of multivessel coronary disease patients: insights from the Arterial Revascularization Therapy Study (ARTS) trial. Circulation. 2001;104:533–538
  3. Babapulle MN, Joseph L, Belisle P, Brophy JM, Eisenberg MJ. A hierarchical Bayesian meta-analysis of randomised clinical trials of drug-eluting stents. Lancet. 2004;364:583–591
  4. van der Giessen WJ, Lincoff AM, Schwartz RS, et al. Marked inflammatory sequelae to implantation of biodegradable and nonbiodegradable polymers in porcine coronary arteries. Circulation. 1996;94:1690–1697
  5. Nebeker JR, Virmani R, Bennett CL, et al. Hypersensitivity cases associated with drug-eluting coronary stents: a review of available cases from the Research on Adverse Drug Events and Reports (RADAR) project. J Am Coll Cardiol. 2006;47:175–181
  6. Shustak G, Domb AJ, Mandler D. Preparation and characterization of n-alkanoic acid self-assembled monolayers adsorbed on 316L stainless steel. Langmuir. 2004;20:7499–7506
  7. Mani G, Johnson DM, et al. Drug elution using therapeutic self-assembled monolayers. In: Society of Biomaterials Annual Meeting Transactions. Pittsburgh. 2006;
  8. Mani G, Mahapatro A, Johnson DM, et al. Therapeutic self-assembled monolayers. In: Biomedical Engineering Society Annual Meeting. Baltimore: April 26-29. 2006;
  9. Castner DG, Ratner BD. Biomedical surface science: foundations to frontiers. Surface Sci. 2002;500:28–60
  10. Kasemo B. Biological surface science. Surface Sci. 2002;500:656–677
  11. Wade N, Gologan B, Vincze A, Cooks RG, Sullivan DM, Bruening ML. Esterification and ether formation at a hydroxyl-terminated self-assembled monolayer surface using low-energy collisions of polyatomic cations. Langmuir. 2002;18:4799–4808
  12. Ulman A. Formation and structure of self-assembled monolayers. Chem Rev. 1996;96:1533–1554
  13. Love JC, Estroff LA, Kriebel JK, Nuzzo RG, Whitesides GM. Self-assembled monolayers of thiolates on metals as a form of nanotechnology. Chem Rev. 2005;105:1103–1169
  14. Tosatti S, Michel R, Textor M, Spencer ND. Self-assembled monolayers of dodecyl and hydroxy-dodecyl phosphates on both smooth and rough titanium and titanium oxide surfaces. Langmuir. 2002;18:3537–3548
  15. Nozawa K, Nishihara H, Aramaki K. Chemical modification of alkanethiol monolayers for protecting iron against corrosion. Corrosion Sci. 1997;39:1625–1639
  16. Cheng LC, Bernasek SL, Bocarsly AB, Ramanarayanan TA. Adsorption and decomposition of 1-alkanethiols on the Fe(100) surface. Chem Mater. 1995;7:1807–1815
  17. Cheng LC, Bocarsly AB, Bernasek SL, Ramanarayanan TA. Interaction of alkanethiols with single-crystal iron-the low-temperature decomposition of ethanethiol on the Fe(100) surface. Langmuir. 1994;10:4542–4550
  18. Volmeruebing M, Stratmann M. A surface analytical and an electrochemical study of iron surfaces modified by thiols. Appl Surface Sci. 1992;55:19–35
  19. Ruan CM, Bayer T, Meth S, Sukenik CN. Creation and characterization of n-alkylthiol and n-alkylamine self-assembled monolayers on 316L stainless steel. Thin Solid Films. 2002;419:95–104
  20. Van J, Alsten G. Self-assembled monolayers on engineering metals: structure, derivatization, and utility. Langmuir. 1999;15:7605–7614
  21. Worley CG, Linton RW. Removing sulfur from gold using ultraviolet ozone cleaning. J Vacuum Sci Technol A Vacuum Surfaces Films. 1995;13:2281–2284
  22. Brewer NJ, Rawsterne RE, Kothari S, Leggett GJ. Oxidation of self-assembled monolayers by UV light with a wavelength of 254 nm. J Am Chem Soc. 2001;123:4089–4090
  23. Schoenfisch MH, Pemberton JE. Air stability of alkanethiol self-assembled monolayers on silver and gold surfaces. J Am Chem Soc. 1998;120:4502–4513
  24. Lee MT, Hsueh CC, Freund MS, Ferguson GS. Air oxidation of self-assembled monolayers on polycrystalline gold: the role of the gold substrate. Langmuir. 1998;14:6419–6423
  25. Flynn NT, Tran TNT, Cima MJ, Langer R. Long-term stability of self-assembled monolayers in biological media. Langmuir. 2003;19:10909–10915
  26. Hofer R, Textor M, Spencer ND. Alkyl phosphate monolayers, self-assembled from aqueous solution onto metal oxide surfaces. Langmuir. 2001;17:4014–4020
  27. Grundmeier G, Stratmann M. Influence of oxygen and argon plasma treatments on the chemical structure and redox state of oxide-covered iron. Appl Surface Sci. 1999;141:43–56
  28. Yan L, Marzolin C, Terfort A, Whitesides GM. Formation and reaction of interchain carboxylic anhydride groups on self-assembled monolayers on gold. Langmuir. 1997;13:6704–6712
  29. Duevel RV, Corn RM. Amide and ester surface attachment reactions for alkanethiol monolayers at gold surfaces as studied by polarization modulation Fourier-transform infrared-spectroscopy. Anal Chem. 1992;64:337–342
  30. Laibinis PE, Whitesides GM, Allara DL, Tao YT, Parikh AN, Nuzzo RG. Comparison of the structures and wetting properties of self-assembled monolayers of normal-alkanethiols on the coinage metal-surfaces, Cu, Ag, Au. J Am Chem Soc. 1991;113:7152–7167
  31. Castner DG, Hinds K, Grainger DW. X-ray photoelectron spectroscopy sulfur 2p study of organic thiol and disulfide binding interactions with gold surfaces. Langmuir. 1996;12:5083–5086
  32. Nuzzo RG, Zegarski BR, Dubois LH. Fundamental studies of the chemisorption of organosulfur compounds on Au(111)-implications for molecular self-assembly on gold surfaces. J Am Chem Soc. 1987;109:733–740
  33. Walczak MM, Alves CA, Lamp BD, Porter MD. Electrochemical and x-ray photoelectron spectroscopic evidence for differences in the binding sites of alkanethiolate monolayers chemisorbed at gold. J Electroanal Chem. 1995;396:103–114
  34. Mekhalif Z, Laffineur F, Couturier N, Delhalle J. Elaboration of self-assembled monolayers of n-alkanethiols on nickel polycrystalline substrates: time, concentration, and solvent effects. Langmuir. 2003;19:637–645
  35. Kobe BA, Ramamurthy S, Biesinger MC, McIntyre NS, Brennenstuhl AM. XPS imaging investigations of pitting corrosion mechanisms in Inconel 600. Surface Interface Anal. 2005;37:478–494
  36. Wiegand BC, Uvdal P, Friend CM. The local structure of adsorbed methyl thiolate-the reactions of methanethiol on Mo(110). Surface Sci. 1992;279:105–112
  37. Tillman N, Ulman A, Elman JF. Oxidation of a sulfide group in a self-assembled monolayer. Langmuir. 1989;5:1020–1026
  38. Mahapatro A, Johnson DM, Patel DN, Feldman MD, Ayon AA, Agrawal CM. Surface modification of functional self-assembled monolayers (SAMs) on 316L stainless steel via lipase catalysis. Langmuir. 2006;22:901–905
  39. Willey TM, Vance AL, van Buuren T, Bostedt C, Terminello LJ, Fadley CS. Rapid degradation of alkanethiol-based self-assembled monolayers on gold in ambient laboratory conditions. Surface Sci. 2005;576:188–196
  40. Palegrosdemange C, Simon ES, Prime KL, Whitesides GM. Formation of self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)mOH on gold. J Am Chem Soc. 1991;113:12–20
  41. Bain CD, Troughton EB, Tao YT, 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
  42. Laibinis PE, Whitesides GM. Omega-terminated alkanethiolate monolayers on surfaces of copper, silver, and gold have similar wettabilities. J Am Chem Soc. 1992;114:1990–1995
  43. Joanny JF, Degennes PG. A model for contact-angle hysteresis. J Chem Phys. 1984;81:552–562
  44. Shepard JW, Bartell FF. Surface roughness as related to hysteresis of contact angles. III. The systems paraffin-ethylene glycol-air, paraffin-methyl cellosolve-air and paraffin-methanol-air. J Phys Chem. 1953;57:458–463

 No financial conflict of interest was reported by the authors of this paper.

PII: S1549-9634(06)00104-3

doi: 10.1016/j.nano.2006.07.006

Nanomedicine: Nanotechnology, Biology and Medicine
Volume 2, Issue 3 , Pages 182-190 , September 2006