journal article·2013-11

Mixing thiols on the surface of silver nanoparticles: preserving antibacterial properties while introducing SERS activity

Angelo Taglietti, Yuri A. Diaz Fernandez, Pietro Galinetto, Pietro Grisoli, Chiara Milanese, Piersandro Pallavicini

Journal of Nanoparticle Research· Volume 15· Issue 11
Publisher page

Abstract

Controlling the surface composition of self-assembled monolayers is one of the major experimental challenges in nanotechnology. Despite the significant interest of the scientific community and the considerable number of publications related to this topic, the potential in this field is still far from being fully exploited. We present in this study a versatile method to coat silver nanoparticles (AgNPs) having average diameter of 7 nm with mixed monolayers of two thiols, achieving a precise control of surface composition. Different combinations of thiols have been investigated, and the nanomaterials obtained have been characterized by complementary experimental techniques, addressing the composition of the mixed monolayer. The surface-enhanced Raman spectroscopy (SERS) effect on a Raman reporter (7-mercapto-4-methylcoumarine) introduced into the mixed monolayers has also been investigated. The antibacterial activity of the coated AgNPs was investigated, showing that the colloids were active against Escherichia coli and Staphilococcus aureus irrespective of the nature of the mixed monolayer. These materials are good candidates as SERS-tags for biological applications. © Springer Science+Business Media 2013.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Gold and Silver Nanoparticles Synthesis and Applications · Nanocluster Synthesis and Applications · Nanoparticles: synthesis and applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (50)

Show source-provided references
1. Aherne D, Ledwith DM, Gara M, Kelly JM (2008) Optical properties and growth aspects of silver nanoprisms produced by a highly reproducible and rapid synthesis at room temperature. Adv Funct Mater 18:2005–201610.1002/adfm.200800233 ↗
2. Amato E, Diaz-Fernandez YA, Taglietti A, Pallavicini P, Pasotti L, Cucca L, Milanese C, Grisoli P, Dacarro C, Fernandez-Hechavarria JM, Necchi V (2011) Synthesis, characterization and antibacterial activity against Gram positive and Gram negative bacteria of biomimetically coated silver nanoparticles. Langmuir 27:9165–917310.1021/la201200r ↗
3. Bain CD, Whitesides GM (1989) Formation of monolayers by the coadsorption of thiols on gold: variation in the length of the alkyl chain. J Am Chem Soc 111:7164–717510.1021/ja00200a040 ↗
4. Cacic M, Trkovnik M, Cacic F, Has-Schon E (2006) Synthesis and antimicrobial activity of some derivatives on the basis (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide. Molecules 11(2):134–14710.3390/11010134 ↗
5. Centrone A, Hu Y, Jackson AM, Zerbi G, Stellacci F (2007) Phase separation on mixed-monolayer-protected metal nanoparticles: a study by infrared spectroscopy and scanning tunneling microscopy. Small 3:814–81710.1002/smll.200600736 ↗
6. Daniel MC, Astruc D (2004) Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology. Chem Rev 104:293–34610.1021/cr030698+ ↗
7. Diaz-Fernandez YA, Pallavicini P, Pasotti L, Milanese C, Pellicer E, Baró MD, Rend Y, Malavasi L (2011) Nanoscale phase separation in coated Ag nanoparticles. Nanoscale 3:4220–422510.1039/c1nr10832h ↗
8. Feng QL, Wu J, Chen GQ, Cui FZ, Kim TN, Kim JO (2000) A mechanistic study of the antibacterial effect of silver ions on Escherichia coli and Staphylococcus aureus. J Biomed Mater Res 52:662–66810.1002/1097-4636(20001215)52:4<662::AID-JBM10>3.0.CO;2-3 ↗
9. Gentilini C, Pasquato L (2010) Morphology of mixed-monolayers protecting metal nanoparticles. J Mater Chem 20:1403–141210.1039/B912759C ↗
10. Gessner R, Rosch P, Kiefer W, Popp J (2002) Raman spectroscopy investigation of biological materials by use of etched and silver coated glass fiber tips. Biopolymers 67:327–33010.1002/bip.10090 ↗
11. Graf P, Mantion A, Foelske A, Shkilnyy A, Masic A, Thunemann AE, Taubert A (2009) Peptide-coated silver nanoparticles: synthesis, surface chemistry, and pH-triggered, reversible assembly into particle assemblies. Chem Eur J 15:5831–584410.1002/chem.200802329 ↗
12. Guarino G, Rastrelli F, Scrimin P, Mancin F (2012a) Lanthanide-based NMR: a tool to investigate component distribution in mixed-monolayer-protected nanoparticles. J Am Chem Soc 134:7200–720310.1021/ja211030y ↗
13. Guarino G, Rastrelli F, Mancin F (2012b) Mapping the nanoparticle-coating monolayer with NMR pseudocontact shifts. Chem Commun 48:1523–152510.1039/C1CC14726A ↗
14. Harkness KM, Hixson BC, Fenn LS, Turner BN, Rape AC, Simpson CA, Huffman BJ, Okoli TC, McLean JA, Cliffel DE (2010) A structural mass spectrometry strategy for the relative quantitation of ligands on mixed monolayer-protected gold nanoparticles. Anal Chem 82:9268–927410.1021/ac102175z ↗
15. Harkness KM, Balinski A, McLean JA, Cliffel DE (2011) Nanoscale phase segregation of mixed thiolates on gold nanoparticles. Angew Chem Int Ed Engl 50:10554–1055910.1002/anie.201102882 ↗
16. Hutter E, Fendler JH (2004) Exploitation of localized surface plasmon resonance. Adv Mater 16:1685–170610.1002/adma.200400271 ↗
17. Imabayashi S, Gon N, Sasaki T, Hobara D, Kakiuchi T (1998) Effect of nanometer-scale phase separation on wetting of binary self-assembled thiol monolayers on Au(111). Langmuir 14:2348–235110.1021/la971377u ↗
18. Ingram RS, Hostetler MJ, Murray RW (1997) Poly-hetero-ω-functionalized alkanethiolate-stabilized gold cluster compounds. J Am Chem Soc 119:9175–917810.1021/ja971734n ↗
19. Jackson AM, Myerson JW, Stellacci F (2004) Spontaneous assembly of subnanometre-ordered domains in the ligand shell of monolayer-protected nanoparticles. Nat Mater 3:330–33610.1038/nmat1116 ↗
20. Jackson AM, Hu Y, Silva PJ, Stellacci F (2006) From homoligand- to mixed-ligand-monolayer-protected metal nanoparticles: a scanning tunneling microscopy investigation. J Am Chem Soc 128:11135–1114910.1021/ja061545h ↗
21. Kneipp J, Kneipp H, Rajadurai A, Redmond RW, Kneipp K (2009) Optical probing and imaging of live cells using SERS labels. J Raman Spectrosc 40:1–5. doi: 10.1002/jrs.206010.1002/jrs.2060 ↗
22. Laibinis PE, Fox MA, Folkers JP, Whitesides GM (1991) Comparisons of self-assembled monolayers on silver and gold: mixed monolayers derived from HS(CH2)21X and HS(CH2)10Y (X, Y = CH3, CH2OH) have similar properties. Langmuir 7:3167–317310.1021/la00060a041 ↗
23. Le Ru EC, Blackie E, Meyer M, Etchegoin PG (2007) Surface enhanced Raman scattering enhancement factors: a comprehensive study. J Phys Chem C 111:13794–1380310.1021/jp0687908 ↗
24. Liu CY, Liang KC, Chen W, Tu CH, Liu CP, Tzeng Y (2011) Plasmonic coupling of silver nanoparticles covered by hydrogen-terminated graphene for surface-enhanced Raman spectroscopy. Opt Express 19:17092–1709810.1364/OE.19.017092 ↗
25. Manea F, Bindoli C, Polizzi C, Lay L, Scrimin P (2008) Expeditious synthesis of water-soluble, monolayer-protected gold nanoparticles of controlled size and monolayer composition. Langmuir 24:4120–412410.1021/la703558y ↗
26. Marambio-Jones C, Hoek EMV (2010) A review of the antibacterial effects of silver nanomaterials and potential implications for human health and the environment. J Nanopart Res 12:1531–155510.1007/s11051-010-9900-y ↗
27. Mayer A, Schatz GC (2009) Enhanced polarizability of aromatic molecules placed in the vicinity of silver clusters. J Phys: Condens Matter 21:32530110.1088/0953-8984/21/32/325301 ↗
28. Murray RW (2008) Nanoelectrochemistry: metal nanoparticles nanoelectrodes, and nanopores. Chem Rev 108:2688–272010.1021/cr068077e ↗
29. NCCLS (1999) Methods for determining bactericidal activity on antimicrobial agents. In: Approved guideline, Wayne, PA, vol 19
30. NCCLS (2003) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. In: Approved standard M7-A6, 6th ed, Wayne, PA
31. Pallavicini P, Taglietti A, Dacarro G, Diaz Fernandez YA, Galli M, Grisoli P, Patrini M, Santucci De Magistris G, Zanoni R (2010) Self-assembled monolayers of silver nanoparticles firmly grafted on glass surfaces: low Ag+ release for an efficient antibacterial activity. J Colloid Interface Sci 350:110–11610.1016/j.jcis.2010.06.019 ↗
32. Pallavicini P, Bernhard C, Dacarro G, Denat F, Diaz-Fernandez YA, Goze C, Pasotti L, Taglietti A (2012) Optical method for predicting the composition of self-assembled monolayers of mixed thiols on surfaces coated with silver nanoparticles. Langmuir 28:3558–356810.1021/la202995w ↗
33. Pallavicini P, Donà A, Casu A, Chirico G, Collini M, Dacarro G, Falqui A, Milanese C, Sironi L, Taglietti A (2013) TritonX-100 for three-plasmon gold nanostars with two photothermally active NIR (near IR) and SWIR (short-wavelength IR) channels. Chem Commun 49:6265–626710.1039/c3cc42999g ↗
34. Silver S, Phung LT, Silver G (2006) Silver as biocides in burn and wound dressings and bacterial resistance to silver compounds. J Ind Microbiol Biotechnol 33:627–63410.1007/s10295-006-0139-7 ↗
35. Sinan Keskin S, Aslan N, Bayrakçeken F (2009) Optical properties and chemical behavior of laser-dye Coumarin-500 and the influence of atmospheric corona discharges. Spectrochim Acta A 72:254–25910.1016/j.saa.2008.09.024 ↗
36. Singh S, Patel P, Jaiswal S, Prabhune AA, Ramana CV, Prasad BLV (2009) A direct method for the preparation of glycolipid–metal nanoparticle conjugates: sophorolipids as reducing and capping agents for the synthesis of water re-dispersible silver nanoparticles and their antibacterial activity. New J Chem 33:646–65210.1039/B811829A ↗
37. Slocik J, Wright D (2003) Biomimetic mineralization of noble metal nanoclusters. Biomacromolecules 4:113510.1021/bm034003q ↗
38. Sortur V, Yenagi J, Tonannavar J, Kulkarni MV, Jadhav V (2008) Vibrational assignments for 7-methyl-4-bromomethylcoumarin, as aided by RHF and B3LYP/6-31G* calculations. Spectrochim Acta A 71:688–69410.1016/j.saa.2008.01.016 ↗
39. Stewart A, Bell SEJ (2011) Modification of Ag nanoparticles with mixed thiols for improved SERS detection of poorly adsorbing target molecules: detection of Mdma. Chem Commun 47:4523–452510.1039/c0cc05312k ↗
40. Stewart A, Zheng S, McCourt MR, Bell SEJ (2012) Controlling assembly of mixed thiol mono layers on silver nanoparticles to tune their surface properties. ACS Nano 6:3718–372610.1021/nn300629z ↗
41. Taglietti A, Diaz Fernandez YA, Cucca L, Dacarro G, Grisoli P, Necchi V, Pallavicini P, Pasotti L, Patrini M (2012) Antibacterial activity of glutathione-coated silver nanoparticles against Gram positive and Gram negative bacteria. Langmuir 28:8140–814810.1021/la3003838 ↗
42. Tautz FS (2007) Structure and bonding of large aromatic molecules on noble metal surfaces: the example of PTCDA. Prog Surf Sci 82:479–52010.1016/j.progsurf.2007.09.001 ↗
43. Veerapandian M, Yun K (2011) Functionalization of biomolecules on nanoparticles: specialized for antibacterial applications. Appl Microbiol Biotechnol 90:1655–166710.1007/s00253-011-3291-6 ↗
44. Verma A, Rotello VM (2005) Surface recognition of biomacromolecules using nanoparticle receptors. Chem Commun 27:303–31210.1039/b410889b ↗
45. Verma A, Uzun O, Hu YH, Hu Y, Watson N, Chen SL, Irvine DJ, Stellacci F (2008) Surface-structure-regulated cell-membrane penetration by monolayer-protected nanoparticles. Nat Mater 7:588–59510.1038/nmat2202 ↗
46. Vogel E, Kiefer W (1998) Investigation of the metal adsorbate interface of the system silver coumarin and silver hydrocoumarin by means of surface enhanced Raman spectroscopy. Fresenius J Anal Chem 361:628–63010.1007/s002160050972 ↗
47. Vogel E, Gbureck A, Kiefer W (2000) Vibrational spectroscopic studies on the dyes cresyl violet and coumarin 152. J Mol Struct 550–551:177–19010.1016/S0022-2860(00)00385-9 ↗
48. Wang GF, Park HY, Lipert RJ (2009) Mixed monolayers on gold nanoparticle labels for multiplexed surface-enhanced raman scattering based immunoassays. Anal Chem 81:9643–965010.1021/ac901711f ↗
49. Wigginton NS, De Titta A, Piccapietra F, Dobias J, Neasatyy VJ, Suter MJF, Bernier-Latmani R (2010) Binding of silver nanoparticles to bacterial proteins depends on surface modifications and inhibits enzymatic activity. Environ Sci Technol 44:2163–216810.1021/es903187s ↗
50. Xie W, Su Le, Shen A, Materny A, Hu J (2011) Application of surface-enhanced Raman scattering in cell analysis. J Raman Spectrosc 42(6):1248–125410.1002/jrs.2857 ↗