Skip to main content

Advertisement

SpringerLink
Log in

Simultaneous analysis of nine aromatic amines in mainstream cigarette smoke using online solid-phase extraction combined with liquid chromatography-tandem mass spectrometry

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A fully automated analytical method was developed and validated by this present study. The method was based on two-dimensional (2D) online solid-phase extraction liquid chromatography-tandem mass spectrometry (SPE-LC-MS/MS) to determine nine aromatic amines (AAs) in mainstream smoke (MSS) simultaneously. As a part of validation process, AAs yields for 16 top-selling commercial cigarettes from China market were evaluated by the developed method under both Health Canada Intensive (HCI) and ISO machine smoking regimes. The gas phase of MSS was trapped by 25 mL 0.6 M hydrochloric acid solution, while the particulate phase was collected on a glass fiber filter. Then, the glass fiber pad was extracted with hydrochloric acid solution in an ultrasonic bath. The extract was analyzed with 2D online SPE-LC-MS/MS. In order to minimize the matrix effects of sample on each analyte, two cartridges with different extraction mechanisms were utilized to cleanup disturbances of different polarity, which were performed by the 2D SPE. A phenyl-hexyl analytical column was used to achieve a chromatographic separation. Under the optimized conditions, the isomers of p-toluidine, m-toluidine and o-toluidine, 3-aminobiphenyl and 4-aminobiphenyl, and 1-naphthylamine and 2-naphthylamine were baseline separated with good peak shapes for the first time. The limits of detection for nine AAs ranged from 0.03 to 0.24 ng cig−1. The recovery of the measurement of nine AAs was from 84.82 to 118.47%. The intra-day and inter-day precisions of nine AAs were less than 10 and 16%, respectively. Compared with ISO machine smoking regime, the AAs yields in MSS were 1.17 to 3.41 times higher under HCI machine smoking regime.

New method using online SPE-LC/MS/MS for analysis of aromatic amines in mainstream cigarette smoke

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Laha S, Luthy RG. Oxidation of aniline and other primary aromatic amines by manganese dioxide. Environ Sci Technol. 1990;24(3):363–73.

    Article  CAS  Google Scholar 

  2. Bartsch H, Caporaso N, Coda M, Kadlubar F, Malaveille C, Skipper P, et al. Carcinogen hemoglobin adducts, urinary mutagenicity, and metabolic phenotype in active and passive cigarette smokers. J Natl Cancer Inst. 1990;82(23):1826–31.

    Article  CAS  Google Scholar 

  3. Ward EM, Sabbioni G, DeBord DG, Teass AW, Brown KK, Talaska GG, et al. Monitoring of aromatic amine exposures in workers at a chemical plant with a known bladder cancer excess. J Natl Cancer Inst. 1996;88(15):1052–3.

    Article  Google Scholar 

  4. Benigni R, Passerini L. Carcinogenicity of the aromatic amines: from structure–activity relationships to mechanisms of action and risk assessment. Mutat Res. 2002;511(3):191–206.

    Article  CAS  Google Scholar 

  5. Chang WY, Sung YH, Huang SD. Analysis of carcinogenic aromatic amines in water samples by solid-phase microextraction coupled with high-performance liquid chromatography. Anal Chim Acta. 2003;495(1–2):109–22.

    Article  CAS  Google Scholar 

  6. Johnson JR, Karlsson D, Dalene M, Skarping G. Determination of aromatic amines in aqueous extracts of polyurethane foam using hydrophilic interaction liquid chromatography and mass spectrometry. Anal Chim Acta. 2010;678(1):117–23.

    Article  CAS  Google Scholar 

  7. Brauer B, Funke T. Specific determination of primery aromatic amines in aqueous migration solutions from food contact articles. Dtsch Lebensmitt Rundsch. 2002;98(11):405–11.

    CAS  Google Scholar 

  8. Kretzschmar HJ, Kelm J, Tobisch K, Winskowski J. Migration of primary aromatic amines from rubber based commodity articles into food. Dtsch Lebensmitt Rundsch. 1999;95:223–30.

    CAS  Google Scholar 

  9. Baker RR, Davis DL, Nielsen MT. Tobacco: production, chemistry, and technology. Oxford: Blackwell Science; 1999.

    Google Scholar 

  10. International Agency for Research on Cancer. Some aromatic amines, organic dyes, and related exposure. Monographs on the evaluation of carcinogenic risks to humans. 2010;99:71–493.

  11. U.S. Food and Drug Administration. Harmful and potentially harmful constituents in tobacco products and tobacco smoke: established list. 2012. http://www.fda.gov/tobaccoproducts/labeling/rulesregulationsguidance/ucm297786.htm. Accessed 4 July 1999.

  12. Masuda Y, Hoffmann D. Determination of 1-naphthylamine and 2-naphthylamine in cigarette smoke. Anal Chem. 1969;41(4):650–2.

    Article  CAS  Google Scholar 

  13. Hoffmann D, Masuda Y, Wynder EL. Alpha-naphthylamine and beta-naphthylamine in cigarette smoke. Nature. 1969;221:254–6.

    Article  CAS  Google Scholar 

  14. Pieraccini G, Luceri F, Moneti G. New gas-chromatographic/mass spectrometric method for the quantitative analysis of primary aromatic amines in main-and side-stream cigarette smoke. Rapid Commun Mass Spectrom. 1992;6(6):406–9.

    Article  CAS  Google Scholar 

  15. Forehand JB, Dooly GL, Moldoveanu SC. Analysis of polycyclic aromatic hydrocarbons, phenols and aromatic amines in particulate phase cigarette smoke using simultaneous distillation and extraction as a sole sample clean-up step. J Chromatogr A. 2000;898(1):111–24.

    Article  CAS  Google Scholar 

  16. Stabbert R, Schäfer KH, Biefel C, Rustemeier K. Analysis of aromatic amines in cigarette smoke. Rapid Commun Mass Spectrom. 2003;17(18):2125–32.

    Article  CAS  Google Scholar 

  17. Brede C, Skjevrak I, Herikstad H. Determination of primary aromatic amines in water food simulant using solid-phase analytical derivatization followed by gas chromatography coupled with mass spectrometry. J Chromatogr A. 2003;983(1–2):35–42.

    Article  CAS  Google Scholar 

  18. Smith CJ, Dooly GL, Moldoveanu SC. New technique using solid-phase extraction for the analysis of aromatic amines in mainstream cigarette smoke. J Chromatogr A. 2003;991(1):99–107.

    Article  CAS  Google Scholar 

  19. Lamani X, Horst S, Zimmermann T, Schmidt TC. Determination of aromatic amines in human urine using comprehensive multi-dimensional gas chromatography mass spectrometry (GCxGC-qMS). Anal Bioanal Chem. 2015;407(1):241–52.

    Article  CAS  Google Scholar 

  20. Saha S, Mistri R, Ray BC. Rapid and sensitive method for simultaneous determination of six carcinogenic aromatic amines in mainstream cigarette smoke by liquid chromatography/electrospray ionization tandem mass spectrometry. J Chromatogr A. 2009;1216(15):3059–63.

    Article  CAS  Google Scholar 

  21. Schubert J, Kappenstein O, Luch A, Schulz TG. Analysis of primary aromatic amines in the mainstream waterpipe smoke using liquid chromatography–electrospray ionization tandem mass spectrometry. J Chromatogr A. 2011;1218(33):5628–37.

    Article  CAS  Google Scholar 

  22. Xie FW, Yu JJ, Wang S, Zhao G, Xia QL, Zhang XB, et al. Rapid and simultaneous analysis of ten aromatic amines in mainstream cigarette smoke by liquid chromatography/electrospray ionization tandem mass spectrometry under ISO and “Health Canada intensive” machine smoking regimens. Talanta. 2013;115:435–41.

    Article  CAS  Google Scholar 

  23. Postigo C, Alda M, Barceló D. Fully automated determination in the low nanogram per liter level of different classes of drugs of abuse in sewage water by on-line solid-phase extraction-liquid chromatography-electrospray-tandem mass spectrometry. Anal Chem. 2008;80(9):3123–34.

    Article  CAS  Google Scholar 

  24. Gallart-Ayala H, Moyano E, Galceran MT. Analysis of bisphenols in soft drinks by on-line solid phase extraction fast liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2011;683(2):227–33.

    Article  CAS  Google Scholar 

  25. Tetznera NF, Manierob MG, Rodrigues-Silvaa C, Ratha S. On-line solid phase extraction-ultra high performance liquid chromatography-tandem mass spectrometry as a powerful technique for the determination of sulfonamide residues in soils. J Chromatogr A. 2016;1452:89–97.

    Article  Google Scholar 

  26. Lhotská I, Šatínský D, Havlíková L, Solich P. A fully automated and fast method using direct sample injection combined with fused-core column on-line SPE–HPLC for determination of ochratoxin A and citrinin in lager beers. Anal Bioanal Chem. 2016;408(12):3319–29.

    Article  Google Scholar 

  27. Zhang J, Bai R, Yi X, Yang Z, Liu X, Zhou J, et al. Fully automated analysis of four tobacco-specific N-nitrosamines in mainstream cigarette smoke using two-dimensional online solid phase extraction combined with liquid chromatography-tandem mass spectrometry. Talanta. 2016;146:216–24.

    Article  CAS  Google Scholar 

  28. ISO 8243. Cigarettes-sampling. Geneva: International Organization for Standardization; 2006.

    Google Scholar 

  29. ISO 3402. Tobacco and tobacco products-atmosphere for conditioning and testing. Geneva: International Organization for Standardization; 1999.

    Google Scholar 

  30. Health Canada Tobacco Control Program. Test method T-115; 1999. pp. 1–5.

  31. ISO 3308. Routine analytical cigarette-smoking machine-definitions and standard conditions. Geneva: International Organization for Standardization; 2000.

    Google Scholar 

  32. Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results (2002/657/EC and amendments). Off J Eur Commun L2218;2002.

Download references

Acknowledgements

The authors thank Dr. Yongsheng Zhang (Zhengzhou University) for his helpful comments on the manuscript.

Author information

Authors and Affiliations

  1. Beijing Third Class Tobacco Super vision Station, Beijing, 101121, China

    Jie Zhang, Ruoshi Bai, Zhaojuan Zhou, Xingyu Liu & Jun Zhou

Authors
  1. Jie Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ruoshi Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhaojuan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xingyu Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jun Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jun Zhou.

Ethics declarations

Conflict of interest

The authors declare that they have no conflicts of interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 82 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, J., Bai, R., Zhou, Z. et al. Simultaneous analysis of nine aromatic amines in mainstream cigarette smoke using online solid-phase extraction combined with liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem 409, 2993–3005 (2017). https://doi.org/10.1007/s00216-017-0245-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-017-0245-6

Keywords

Search

Navigation