Impact of surface functionalization on bacterial cytotoxicity of single-walled carbon nanotubes

Environmental Science and Technology

Volumn 46, Issue 11, 2012, Pages 6297-6305

  Pasquini, Leanne M ^a   Hashmi, Sara M ^a   Sommer, Toby J ^b   Elimelech, Menachem ^a   Zimmerman, Julie B ^a,c  

^a Yale University   (United States)

^b YALE UNIVERSITY   (United States)

^c Yale School of the Environment   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATE SIZE; AGGREGATE SIZE DISTRIBUTIONS; AGGREGATION STATE; CELL VIABILITY; CHEMICAL COMPOSITIONS; DISPERSITY; DISTRIBUTION CURVES; ESCHERICHIA COLI K12; FUNCTIONALIZATIONS; FUNCTIONALIZED; HUMAN HEALTH; INDIRECT EFFECTS; MOLECULAR SIZE; N-PROPYLAMINE; PHENYLHYDRAZINE; PHYSICOCHEMICAL PROPERTY; PHYSIO-CHEMICAL; SCATTERING TECHNIQUES; SIMULTANEOUS REDUCTION; SULFONIC ACID; SURFACE FUNCTIONAL GROUPS; SURFACE FUNCTIONALIZATION;

CYTOTOXICITY; ESCHERICHIA COLI; FRACTAL DIMENSION; FUNCTIONAL GROUPS; MORPHOLOGY; SINGLE-WALLED CARBON NANOTUBES (SWCN);

AGGREGATES;

CARBOXYL GROUP; HYDRAZINE; HYDROXYL GROUP; PHENYL GROUP; PHENYLHYDRAZINE; PROPYLAMINE; SINGLE WALLED NANOTUBE; SULFONIC ACID DERIVATIVE;

AGGREGATE; BACTERIUM; CARBON; CHEMICAL COMPOSITION; COLIFORM BACTERIUM; ENVIRONMENTAL IMPACT; FUNCTIONAL GROUP; HEALTH RISK; NANOTECHNOLOGY; PHYSICOCHEMICAL PROPERTY; PUBLIC HEALTH; SIZE DISTRIBUTION; TOXICITY;

ARTICLE; BACTERIAL CELL; CELL VIABILITY; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CYTOTOXICITY; DISPERSION; ESCHERICHIA COLI K 12; LIGHT SCATTERING; MOLECULAR INTERACTION; MOLECULAR SIZE; NONHUMAN; SURFACE CHARGE;

DIFFUSION; ESCHERICHIA COLI K12; FRACTALS; HUMANS; MICROBIAL VIABILITY; NANOTUBES, CARBON; PARTICLE SIZE; PHOTOELECTRON SPECTROSCOPY; SURFACE PROPERTIES; TIME FACTORS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 84861899754     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es300514s     Document Type: Article

References (64)

1. Iijima, S. Helical microtubules of graphitic carbon. Nature 1991, 354 (7), 56-58. (Pubitemid 21896780)
2. Avouris, P. Molecular electronics with carbon nanotubes. Acc. Chem. Res. 2002, 35 (12), 1026-1034.
3. Odom, T. W.; Huang, J.; Kim, P.; Lieber, C. M. Atomic structure and electronic properties of single-walled carbon nanotubes. Nature 1998, 391, 62-64. (Pubitemid 28079213)
4. Ouyang, M.; Huang, J. L.; Lieber, C. M. Fundamental electronic properties and applications of single-walled carbon nanotubes. Acc. Chem. Res. 2002, 35 (12), 1018-1025.
5. Mauter, M. S.; Elimelech, M. Environmental applications of carbon-based nanomaterials. Environ. Sci. Technol. 2008, 42 (16), 5843-5859.
6. Aslan, S.; Loebick, C. Z.; Kang, S.; Elimelech, M.; Pfefferle, L. D.; Van Tassel, P. R. Antimicrobial biomaterials based on carbon nanotubes dispersed in poly(lactic-co-glycolic acid). Nanoscale 2010, 2 (9), 1789-1794.
7. Popov, V. N. Carbon nanotubes: Properties and application. Mater. Sci. Eng. R 2004, 43 (3), 61-102.
8. Paradise, M.; Goswami, T. Carbon nanotubes-Production and industrial applications. Mater. Des. 2007, 28 (5), 1477-1489.
9. Kaiser, J. P. R., M.; Buerki-Thurnherr, T.; Wick, P. Carbon nanotubes-Curse or blessing. Curr. Med. Chem. 2011, 18, 2115-2128.
10. Lee, S. W.; Yabuuchi, N.; Gallant, B. M.; Chen, S.; Kim, B. S.; Hammond, P. T.; Shao-Horn, Y. High-power lithium batteries from functionalized carbon-nanotube electrodes. Nat. Nano 2010, 5 (7), 531-537.
11. Klaine, S. J.; Alvarez, P. J. J.; Batley, G. E.; Fernandes, T. F.; Handy, R. D.; Lyon, D. Y.; Mahendra, S.; McLaughlin, M. J.; Lead, J. R. Nanomaterials in the environment: Behavior, fate, bioavailability, and effects. Environ. Toxicol. Chem. 2008, 27 (9), 1825-1851.
12. Wiesner, M. R.; Lowry, G. V.; Jones, K. L.; Hochella, J. M. F.; Di Giulio, R. T.; Casman, E.; Bernhardt, E. S. Decreasing uncertainties in assessing environmental exposure, risk, and ecological implications of nanomaterials. Environ. Sci. Technol. 2009, 43 (17), 6458-6462.
13. Yokel, A. R. M., C. Robert Engineered nanomaterials: Exposures, hazards, and risk prevention. J. Occup. Med. Toxicol. 2011, 6 (7).
14. Vecitis, C. D.; Zodrow, K. R.; Kang, S.; Elimelech, M. Electronic-structure-dependent bacterial cytotoxicity of single-walled carbon nanotubes. ACS Nano 2010, 4 (9), 5471-5479.
15. Eckelman, M. J.; Zimmerman, J. B.; Anastas, P. T. Toward green nano. J. Ind. Ecol. 2008, 12 (3), 316-328.
16. Dhawan, A.; Sharma, V. Toxicity assessment of nanomaterials: Methods and challenges. Anal. Bioanal. Chem. 2010, 398, 589-605.
17. Hussain, M. A.; Kabit, M. A.; Sood, A. K. On the cytotoxicity of carbon nanotubes. Curr. Sci. 2009, 96 (5), 664-673.
18. Jia, G.; Wang, H.; Yan, L.; Wang, X.; Pei, R.; Yan, T.; Zhao, Y.; Guo, X. Cytotoxicity of carbon nanomaterials: Single-wall nanotube, multi-wall nanotube, and fullerene. Environ. Sci. Technol. 2005, 39 (5), 1378-1383. (Pubitemid 40333400)
19. Tian, F.; Cui, D.; Schwarz, H.; Estrada, G. G.; Kobayashi, H. Cytotoxicity of single-wall carbon nanotubes on human fibroblasts. Toxicol. In Vitro 2006, 20 (7), 1202-1212. (Pubitemid 44088593)
20. Lewinski, N.; Colvin, V.; Drezek, R. Cytotoxicity of nanoparticles. Small 2008, 4 (1), 26-49.
21. Pulskamp, K.; Diabate, S.; Krug, H. F. Carbon nanotubes show no sign of acute toxicity but induce intracellular reactive oxygen species in dependence on contaminants. Toxicol. Lett. 2007, 168 (1), 58-74. (Pubitemid 44909723)
22. Worle-Knirsch, J. M.; Pulskamp, K.; Krug, H. F. Oops they did it again! Carbon nanotubes hoax scientists in viability assays. Nano Lett. 2006, 6 (6), 1261-1268. (Pubitemid 44013492)
23. Manna, S. K.; Sarkar, S.; Barr, J.; Wise, K.; Barrera, E. V.; Jejelowo, O.; Rice-Ficht, A. C.; Ramesh, G. T. Single-walled carbon nanotube induces oxidative stress and activates nuclear transcription factor-kB in human keratinocytes. Nano Lett. 2005, 5 (9), 1676-1684. (Pubitemid 41396145)
24. Sun, Y. P.; Fu, K.; Lin, Y.; Huang, W. Functionalized carbon nanotubes: Properties and applications. Acc. Chem. Res. 2002, 35 (12), 1096-1104.
25. Tiraferri, A.; Vecitis, C. D.; Elimelech, M. Covalent binding of single-walled carbon nanotubes to polyamide membranes for antimicrobial surface properties. ACS Appl. Mater. Interfaces 2011, 3 (8), 2869-2877.
26. Sayes, C. M.; Liang, F.; Hudson, J. L.; Mendez, J.; Guo, W.; Beach, J. M.; Moore, V. C.; Doyle, C. D.; West, J. L.; Billups, W. E.; Ausman, K. D.; Colvin, V. L. Functionalization density dependence of single-walled carbon nanotubes cytotoxicity in vitro. Toxicol. Lett. 2006, 161 (2), 135-142. (Pubitemid 41790286)
27. Sayes, C. M.; Fortner, J. D.; Guo, W.; Lyon, D.; Boyd, A. M.; Ausman, K. D.; Tao, Y. J.; Sitharaman, B.; Wilson, L. J.; Hughes, J. B.; West, J. L.; Colvin, V. L. The differential cytotoxicity of water-soluble fullerenes. Nano Lett. 2004, 4 (10), 1881-1887.
28. Pan, H.; Liu, L.; Guo, Z. X.; Dai, L.; Zhang, F.; Zhu, D.; Czerw, R.; Carroll, D. L. Carbon nanotubols from mechanochemical reaction. Nano Lett. 2002, 3 (1), 29-32. (Pubitemid 37161846)
29. Syrgiannis, Z.; Hauke, F.; Röhrl, J.; Hundhausen, M.; Graupner, R.; Elemes, Y.; Hirsch, A. Covalent Sidewall Functionalization of SWNTs by nucleophilic addition of lithium amides. Eur. J. Org. Chem. 2008, 15, 2544-2550.
30. Chen, Y.; Haddon, R. C.; Fang, S.; Rao, A. M.; Eklund, P. C.; Lee, W. H.; Dickey, E. C.; Grulke, E. A.; Pendergrass, J. C.; Chavan, A.; Haley, B. E.; Smalley, R. E. Chemical attachment of organic functional groups to single-walled carbon nanotube material. J. Mater. Res. 1998, 13, 2423-2431. (Pubitemid 128571597)
31. Wunderlich, D.; Hauke, F.; Hirsch, A. Preferred functionalization of metallic and small-diameter single walled carbon nanotubes via reductive alkylation. J. Mater. Chem. 2008, 18 (13), 1493-1497. (Pubitemid 351434057)
32. Yokoi, T.; Iwamatsu, S.; Komai, S.; Hattori, T.; Murata, S. Chemical modification of carbon nanotubes with organic hydrazines. Carbon 2005, 43 (14), 2869-2874. (Pubitemid 41252946)
33. Awenat, K. M.; Davis, P. J.; Moloney, M. G.; Ebenezer, W. A chemical method for the convenient surface functionalisation of polymers. Chem. Commun. 2005, 8, 990-992. (Pubitemid 40363449)
34. Wang, H.; Griffiths, J.; Egdell, R. G.; Moloney, M. G.; Foord, J. S. Chemical functionalization of diamond surfaces by reaction with diaryl carbenes. Langmuir 2008, 24 (3), 862-868. (Pubitemid 351270956)
35. Jonczyk, A.; Wlostowska, J. A Simple Method for generation of diazocompounds in an aqueous two-phase system. Synth. Commun. 1978, 8 (8), 569-572.
36. Kang, S.; Pinault, M.; Pfefferle, L. D.; Elimelech, M. Singlewalled carbon nanotubes exhibit strong antimicrobial activity. Langmuir 2007, 23 (17), 8670-8673. (Pubitemid 47294266)
37. Kang, S.; Herzberg, M.; Rodrigues, D. F.; Elimelech, M. Antibacterial effects of carbon nanotubes: Size does matter! Langmuir 2008, 24 (13), 6409-6413.
38. Jorio, A.; Pimenta, M. A.; Souza Filho, A. G.; Saito, R.; Dresselhaus, G.; Dresselhaus, M. S. Characterizing carbon nanotube samples with resonance Raman scattering. New J. Phys. 2003, 5 (1), 139.
39. Hiemenz, P. C.; Rajagopalan, R. Principles of Colloid and Surface Chemistry; Marcel Dekker, Inc.: New York, 1997.
40. Provencher, S. W. A constrained regularization method for inverting data represented by linear algebraic or integral equations. Comput. Phys. Commun. 1982, 27 (3), 213-227.
41. Provencher, S. W. CONTIN: A general purpose constrained regularization program for inverting noisy linear algebraic and integral equations. Comput. Phys. Commun. 1982, 27 (3), 229-242.
42. Strano, M. S.; Dyke, C. A.; Usrey, M. L.; Barone, P. W.; Allen, M. J.; Shan, H.; Kittrell, C.; Hauge, R. H.; Tour, J. M.; Smalley, R. E. Electronic structure control of single-walled carbon nanotube functionalization. Science 2010, 301 (5639), 1519-1522.
43. Saleh, N. B.; Pfefferle, L. D.; Elimelech, M. Aggregation kinetics of multiwalled carbon nanotubes in aquatic systems: Measurements and environmental implications. Environ. Sci. Technol. 2008, 42 (21), 7963-7969.
44. Chen, Q.; Saltiel, C.; Manickavasagam, S.; Schadler, L. S.; Siegel, R. W.; Yang, H. Aggregation behavior of single-walled carbon nanotubes in dilute aqueous suspension. J. Colloid Interface Sci. 2004, 280 (1), 91-97. (Pubitemid 39345911)
45. Montes-Burgos, I.; Walczyk, D.; Hole, P.; Smith, J.; Lynch, I.; Dawson, K. Characterisation of nanoparticle size and state prior to nanotoxicological studies. J. Nanopart. Res. 2010, 12 (1), 47-53.
46. Kang, S.; Mauter, M. S.; Elimelech, M. Physicochemical determinants of multiwalled carbon nanotube bacterial cytotoxicity. Environ. Sci. Technol. 2008, 42 (19), 7528-7534.
47. Voutchkova-Kostal, A. M.; Kostal, J.; Connors, K. A.; Brooks, B. W.; Anastas, P. T.; Zimmerman, J. B. Towards rational molecular design for reduced chronic aquatic toxicity. Green Chem. 2012, 14 (4), 1001-1008.
48. Voutchkova, A. M.; Kostal, J.; Steinfeld, J. B.; Emerson, J. W.; Brooks, B. W.; Anastas, P.; Zimmerman, J. B. Towards rational molecular design: Derivation of property guidelines for reduced acute aquatic toxicity. Green Chem. 2011, 13 (9), 2373-2379.
49. Wepasnick, K.; Smith, B.; Bitter, J.; Fairbrother, H. D. Chemical and structural characterization of carbon nanotube surfaces. Anal. Bioanal. Chem. 2010, 396 (3), 1003-1014.
50. Graupner, R. Raman spectroscopy of covalently functionalized single-wall carbon nanotubes. J. Raman Spectrosc. 2007, 38 (6), 673-683.
51. Kingston, C.; Martínez-Rubí, Y.; Guan, J.; Barnes, M.; Scriver, C.; Sturgeon, R.; Simard, B. Coupled thermogravimetry, mass spectrometry, and infrared spectroscopy for quantification of surface functionality on single-walled carbon nanotubes. Anal. Bioanal. Chem. 2010, 396 (3), 1037-1044.
52. Hirsch, A. Functionalization of Single-Walled Carbon Nanotubes. Angew. Chem., Int. Ed. 2002, 41 (11), 1853-1859. (Pubitemid 34619593)
53. Ripin, D. H.; Evans, D. A. pKa Table. 2005. evans.harvard.edu/pdf/evans- pKa-table.pdf (accessed May 15, 2011).
54. Jencks, W. P.; Westheimer, F. H. pKa Data Compiled by R. Williams. research.chem.psu.edu/brpgroup/pKa-compilation.pdf (accessed May 15, 2011).
55. Liu, S.; Wei, L.; Hao, L.; Fang, N.; Chang, M. W.; Xu, R.; Yang, Y.; Chen, Y. Sharper and faster, nano darts, kill more bacteria: A study of antibacterial activity of individually dispersed pristine single-walled carbon nanotube. ACS Nano 2009, 3 (12), 3891-3902.
56. Arias, L. R.; Yang, L. Inactivation of bacterial pathogens by carbon nanotubes in suspensions. Langmuir 2009, 25 (5), 3003-3012.
57. Wick, P.; Manser, P.; Limbach, L. K.; Dettlaff-Weglikowska, U.; Krumeich, F.; Roth, S.; Stark, W. J.; Bruinink, A. The degree and kind of agglomeration affect carbon nanotube cytotoxicity. Toxicol. Lett. 2007, 168 (2), 121-131. (Pubitemid 46054362)
58. Lin, M. Y.; Lindsay, H. M.; Weitz, D. A.; Ball, R. C.; Klein, R.; Meakin, P. Universality in colloid aggregation. Nature 1989, 339 (6223), 360-362.
59. Lin, M. Y.; Klein, R.; Lindsay, H. M.; Weitz, D. A.; Ball, R. C.; Meakin, P. The structure of fractal colloidal aggregates of finite extent. J. Colloid Interface Sci. 1990, 137 (1), 263-280. (Pubitemid 20695754)
60. Schaefer, D. W.; Zhao, J.; Brown, J. M.; Anderson, D. P.; Tomlin, D. W. Morphology of dispersed carbon single-walled nanotubes. Chem. Phys. Lett. 2003, 375, 369-375. (Pubitemid 36776859)
61. Sorensen, C. M. Light Scattering by Fractal Aggregates: A Review. Aerosol Sci. Technol. 2001, 35 (2), 648-687. (Pubitemid 32727059)
62. Branca, C.; Magazu, V.; Mangione, A. Determination of MWNTs length-to-diameter ratio by static and dynamic light scattering. Diamond Relat. Mater. 14 (3-7), 846-849.
63. van Bruggen, M. P. B; Lekkerkerker, H. N. W.; Dhont, J. K. G. Long-time translational self-diffusion in isotropic dispersions of colloidal rods. Phys. Rev. E. 1997, 56 (4), 4394.
64. Kukovecz, Å.; Kanyo, T.; Konya, Z.; Kiricsi, I. Long-time low-impact ball milling of multi-wall carbon nanotubes. Carbon 2005, 43 (5), 994-1000. (Pubitemid 40266234)