Application of GC/HRToF for the identification and comparison of tobacco smoke constituents
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1 Application of GC/HRToF for the identification and comparison of tobacco smoke constituents Jasper van Heemst 1, Justin Frosina 1, Jeff Patrick 2, and Chris Wright 1 1 British American Tobacco, Group R&D, Southampton, UK 2 LECO Corporation, Separation Sciences, St. Joseph, MI, USA
2 BAT-GR&D s research Create and support innovations Due diligence and product stewardship Characterization and understanding of product
3 World class science Understanding smoke science through own research and collaborations This requires a comprehensive approach to product evaluation and risk assessment In turn, this requires high quality analytical data and data interpretation tools
4 Understanding innovations Tobacco modification - To reduce the amount of toxicants that transfer to smoke - To reduce the amount of toxicant precursors
5 Understanding innovations Modification of cigarette design Selective filtration - To remove vapour phase toxicants Non-combustible products
6 FDA list Cobalt Coumarin Ammonia Aflatoxin B1 Phenol m+p - Cresol 1 - Aminonaphthalene 4- Aminobiphenyl Acrylamide A-α-C (2-amino-9H-pyrido[2,3-b]indole) Benzo[b]furan Benzo[c]phenanthrene Chlorinated dioxins/furans Chrysene N-Nitrosodimethylamine (NDMA) N-Nitrosodiethylamine Cyclopenta[c,d]pyrene Anabasine (Hydroquinone) Acetamide (3 Aminobiphenyl) Acetaldehyde Acrolein Formaldehyde o-anisidine Acetone 2- Aminonaphthalene Benz[a]anthracene Benz[j]aceanthrylene Methyl ethyl ketone (Butyraldehyde) Benzo[b]fluoroanthene Propionaldehyde Benzo[k]fluoroanthene o-cresol (Resorcinol) Beryllium Caffeic acid Hydrazine Indeno[1,2,3-cd]pyrene MeA-α-C (2-Amino-3- methyl)-9h-pyrido[2,3- b]indole) 5-Methylchrysene Abbreviated list of HPHCs in Cigarette Smoke Acetaldehyde Acrolein Acrylonitrile 4-Aminobiphenyl 1-Aminonaphthalene 2-Aminonaphthalene Ammonia Benzene Benzo[a]pyrene 1,3-Butadiene Carbon monoxide Crotonaldehyde Formaldehyde Isoprene Nicotine (total) NNK NNN Toluene N-Nitrosomorpholine (NMOR) Dibenz[a,h]anthracene Dibenzo[a,e]pyrene Dibenzo[a,h]pyrene Dibenzo[a,i]pyrene Dibenzo[a,l]pyrene Toluene (Pyridine) Styrene Quinoline Mercury Crotonaldehyde Catechol Hydrogen cyanide Carbon monoxide (CO) 1,3-Butadiene Benzene 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) Cadmium Benzo[a]pyrene N-Nitrosonornicotine (NNN) Nicotine Acrylonitrile (NO/NOx) Isoprene Naphthalene FCTC + 9 HC Nitrobenzene 2-Nitropropane FDA N-Nitrosodiethanolamine (NDELA) N-Nitrosomethylethylamine Nitromethane 3 May ,6-Dimethylaniline Ethyl carbamate (urethane) Ethylbenzene Ethylene oxide Furan Lead N-Nitrososarcosine (NSAR) (Nicotine-free dry particulate matter (NFDPM)) Glu-P-1 (2-Amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole) Glu-P-2 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole) (N-Nitrosoanatabine (NAT)) Trp-P-1 (3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole) Vinyl acetate Vinyl chloride Trp-P-2 (1-Methyl-3-amino-5H-pyrido[4,3-b]indole) (N-Nitrosoanabasine (NAB)) IQ (2-Amino-3-methylimidazo[4,5-f]quinoline) Selenium N-Nitrosopiperidine (NPIP) N-Nitrosopyrrolidine (NPYR) PhIP (2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) Polonium-210 Propylene oxide Uranium-235 Uranium-238 Nornicotine o-toluidine Nickel Arsenic Chromium Abbreviated list of HPHCs in Smokeless Tobacco Acetaldehyde Arsenic Benzo[a]pyrene Cadmium Crotonaldehyde Formaldehyde Nicotine (total & free) NNK NNN
7 Classes of constituents FDA TPSAC April 2012 Trace metals Arsenic Beryllium Cadmium Chromium Cobalt Lead Mercury Nickel Polonium-210 Selenium Uranium-235 Uranium-238 Polycyclic Aromatic Hydrocarbons Benz[a]anthracene Benz[j]aceanthrylene Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo[b]furan Benzo[a]pyrene Benzo[c]phenanthrene Chrysene Cyclopenta[c,d]pyrene Dibenz[a,h]anthracene Dibenzo[a,e]pyrene Dibenzo[a,h]pyrene Dibenzo[a,i]pyrene Dibenzo[a,l]pyrene Indeno[1,2,3-cd]pyrene 5-Methylchrysene Naphthalene Alkenes / cyanoalkanes 1,3-Butadiene Hydrogen cyanide Isoprene Nitromethane Others Aflatoxin B1 Carbon monoxide Chlorinated dioxins/furans Coumarin 2-Nitropropane Alkaloids Anabasine Nicotine Nornicotine Low MW volatiles Acetamide Acrylamide Acrylonitrile Ammonia Ethyl carbamate (urethane) Ethylene oxide Furan Hydrazine Propylene oxide Vinyl acetate Vinyl chloride Aromatic amines 4-Aminobiphenyl 1-Aminonaphthalene 2-Aminonaphthalene o-anisidine 2,6-Dimethylaniline o-toluidine N-nitrosamines 4-(Methylnitrosamino)-1-(3-pyridyl)- 1-butanone (NNK) N-Nitrosodiethanolamine (NDELA) N-Nitrosodiethylamine N-Nitrosodimethylamine (NDMA) N-Nitrosomethylethylamine N-Nitrosomorpholine (NMOR) N-Nitrosonornicotine (NNN) N-Nitrosopiperidine (NPIP) N-Nitrosopyrrolidine (NPYR) N-Nitrososarcosine (NSAR) Carbonyls Acetaldehyde Acetone Acrolein Crotonaldehyde Formaldehyde Propionaldehyde Methyl ethyl ketone Aromatics Benzene Caffeic acid Catechol o-, m-, p-cresol Ethylbenzene Nitrobenzene Phenol Quinoline Styrene Toluene Heterocyclic aromatic amines A-α-C (2-Amino-9H-pyrido[2,3- b]indole) Glu-P-1 (2-Amino-6- methyldipyrido[1,2-a:3',2'-d]imidazole) Glu-P-2 (2-Aminodipyrido[1,2-a:3',2'- d]imidazole) IQ (2-Amino-3-methylimidazo[4,5- f]quinoline) MeA-α-C (2-Amino-3-methyl)-9Hpyrido[2,3-b]indole) PhIP (2-Amino-1-methyl-6- phenylimidazo[4,5-b]pyridine) Trp-P-1 (3-Amino-1,4-dimethyl-5Hpyrido[4,3-b]indole) Trp-P-2 (1-Methyl-3-amino-5Hpyrido[4,3-b]indole)
8 The big picture
9 Established methods Targeted analysis: single compound or single class of compounds Multi-step analytical procedure - Sample preparation (e.g. hydration, extraction, smoke preparation) - Removal of unwanted interferences from matrix (clean-up) - Analytical determination (identification, confirmation, quantification) Advantages: - Confident quantification and confirmation of target analyte(s) Disadvantages: - Time consuming, labour intensive - Limited flexibility (data for <100 out of >8000 substances)
10 Screening techniques Non-targeted screening to minimize exclusion of compounds Complementary to established methods Advantages: - More information about the sample - Able to reinterrogate the data (historic data) - Able to analyse large amount of samples and look for (small) differences between samples Disadvantages: - Not fully quantitative - Data interpretation can be very complicated
11 Challenge of the matrix Tobacco - Plant material: complex chemical composition Cured tobacco - Changes in the chemical composition due to dehydration, chemical degradation and possible exposure to elevated temperatures
12 Challenge of the matrix Processed cured tobacco - Chemical changes due to rehydration and physical stress - Added complexity due to addition of casing / flavourings / humectants / cigarette paper Smoke - Incomplete combustion of processed cured tobacco and cigarette paper
13 Mainstream smoke Particulate phase Gas (vapour) phase Whole smoke Cambridge filter pad Impinger Image courtesy of: Jason Adamson
14 Previous scanning capability profiling 3R4F particulate phase Manual process 3R4F particulate phase Very effort intensive extract Analyst dependent
15 Previous scanning capability - comparing Peak RT (min) Compound Area % of Total Vinyl pyridine + Benzaldehyde + Methylfurfural Phenol + Benzonitrile + Ethylmethylpyrazine Limonene + Formylpyrrole Corylon Cresol + Guaiacol Cresol +? Naphthalene Methylindole + Dihydrobenzofuran? Indanone +? Methylnaphthalene Methylnaphthalene Methoxyvinylphenol + Quinoline Tracetin + Nicotine (s) Butylbutyrate +? Methyl indole Dimethylnaphthalene Trimethyldodecatriene Myosmine + Biphenyl Eugenol + Dimethylnaphthalene +? Nicotyrine Dipyridyl Megastigmatrienone + Trimethylnaphthalene + Fluorene +? Dimethylbiphenyl Long chain hydrocarbon + Trimethylpyridopyrimidinone Neophytadiene Long chain hydrocarbon Peak No. RT (min) Compound Area % of Total Ethanol Propylene Glycol Cyclobutapyridine + Methylfurfural + Benzaldehyde Phenol + Trimethylbenzene Cresol + Pyridinecarbonitrile Cresol + Guaiacol Ethylphenol Dihydrobenzofuran + Trimethylphenol Dihydrobenzofuran + Methylindole Methylnaphthalene + Indole Triacetin (s) Nicotine (s) Butylbutyrate + Furylmethylpyrazine? +? Myosmine + Vinylnaphthalene Eugenol + Dimethylnaphthalene +? Nicotyrine Dipyridyl Megastigmatrienone Dimethylbiphenyl Long chain hydrocarbon Neophytadiene ? Long chain hydrocarbon Long chain hydrocarbon ? Ambiguous compound identity Unknown variability of response
16 LECO Pegasus GC-HRT First LECO GC-high-resolution GC-TOF installed in Europe (January 2012) Folded Flight Path Technology to achieve highresolution (50,000; 25,000 normal operation; <1ppm mass accuracy; up to 200 Hz scanning speed) Ion Mirror Detector Ion Mirror Top View Z X Ion Source Side View Y X
17 Benefits of high-resolution
18 Deconvolution of GC-MS data Deconvolution of GC-MS data to separate and identify individual co-eluting compounds Benzene-D 6 Benzene Propanenitrile
19 Identification of compounds Matching of MS data against libraries for non-targeted identification of semi-volatile substances in a fortified smoke condensate sample
20 Identification of compounds Peak # Name Type R.T. (s) Similarity 1 N-Nitrosodimethylamine Peak Ethanamine, N-methyl-N-nitroso- Peak Ethanamine, N-ethyl-N-nitroso- Peak Propanamine, N-nitroso-N-propyl- Peak Morpholine, 4-nitroso Peak Matching of MS data against libraries for non-targeted identification of semi-volatile substances in a fortified smoke condensate sample 6 Pyrrolidine, 1-nitroso- Peak Piperidine, 1-nitroso- Peak Butanamine, N-butyl-N-nitroso- Peak
21 Targeted search Dibenzofuran 2-chloronaphthalene Fluoranthene Pyrene 1,3,5-trichlorobenzene P-ethylphenol Hexachlorobenzene Hexachloroethane Chrysene Benz[a]anthracene Aniline
22 Targeted vs. non-targeted search 3R4F particulate phase extract fortified with an EPA Mix containing 60 ~1.3 µg/cig
23 Detecting differences in concentration 3R4F extract spiked with equivalent of 1.3µg/cig and 2.6µg/cig
24 Detecting differences in concentration 3R4F extract spiked with equivalent of 1.3µg/cig and 2.6µg/cig
25 Detecting differences in concentration Peak # Name Type Match Concentration R.T. (s) Expected R.T. (s) Area 13 Pyrazine, methyl- Match Phenol Match Phenol, 2-methyl- Match H-Pyrrole-2,5-dione, 3-ethyl-4-methyl- Match Hydroquinone Match Triacetin Match Phenol, 2,6-dimethoxy- Match Nicotine Match Naphthalene, 1,7-dimethyl- Match Pyridine, 3-(3,4-dihydro-2H-pyrrol-5-yl)- Match Scopoletin Match Peak 52/0.667ug/ml spiked 3R4F v13 Not Found Peak 106/0.667ug/ml spiked 3R4F v13 Not Found Peak 386/0.667ug/ml spiked 3R4F v13 Not Found Peak 391/0.667ug/ml spiked 3R4F v13 Not Found Isophorone Out of Tolerance Naphthalene Out of Tolerance Hexachlorobutadiene Out of Tolerance Naphthalene, 2-methyl- Out of Tolerance Nitroaniline Out of Tolerance Acenaphthylene Out of Tolerance Dibenzofuran Out of Tolerance Fluoranthene Out of Tolerance Pyrene Out of Tolerance Benz[a]anthracene Out of Tolerance Indeno[1,2,3-cd]pyrene Out of Tolerance Peak 70 Peak Peak 209 Peak Peak 278 Peak Tridecanol, 2-ethyl-2-methyl- Peak Dodecen-4-yne Peak
26 Comparison quad-ms vs. HR-TOFMS Quad-MS ~ 40 compounds detected and tentatively identified, 1 day processing time HR-TOF-MS TIC AIC ~ 1000 compounds detected, ~500 tentatively identified, 15 min processing time
27 Profiling process CFP trapped particulate Solvent Extracted Bubbled through impinger or Collected in Tedlar bag GC-TOF LC-TOF GC-TOF Data deconvolution and analysis Image courtesy of: Jason Adamson
28 Bruker maxis impact UHR-TOF Installed at BAT April 2013 Sub-ppm mass accuracy and 40,000 full sensitivity resolution Mass range up to m/z 10,000 Range from very small molecules to intact proteins High speed MS/MS capability with full U-HPLC compatibility Simultaneous analysis of major and trace sample components Isotopic pattern matching for definitive molecular formulae determination
29 Sample analysis by LC-MS
30 Pegasus 4D GCxGC-TOFMS Chromatographic separations in two dimensions Pegasus TOFMS operated in unit mass resolution Instrument installed in 2010 as part of a collaboration with University of Liege (Michal Brokl, Jef Focant)
31 GCxGC-TOFMS 3R4F particulate phase of mainstream smoke (1800 identified compounds) [Brokl et al. (2013) J. Sep. Sci. 36(6) ]
32 Next steps LC-MS - Further characterization of smoke/tobacco - Create libraries for compounds in smoke/tobacco Statistical analysis of results Metabolomic approach Compare results with additional (spectroscopic) techniques Stitch data together between vapour phase, particulate phase, non-volatile components
33 Conclusions Tobacco and smoke are complex matrices that need sophisticated analytical approaches to characterise High-resolution mass spectrometry combined with GC, LC separation techniques allow us to characterise all mainstream smoke fractions and combine the results Additional, orthogonal analytical techniques (such as GCxGC-MS and spectroscopic techniques) are needed for a full characterisation of the matrix
34 we welcome your comments
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