title: Addition of porphyrins to cigarette filters to reduce the levels of benzo[a]pyrene (B[a]P) and tobacco-specific N-nitrosamines (TSNAs) in mainstream cigarette smoke.
abstract: Tobacco-specific N-nitrosamines (TSNAs) and benzo[a]pyrene (B[a]P) in mainstream cigarette smoke (MSS) cause smoking-related diseases and environmental pollution. Porphyrins were added to cigarette filters to reduce B[a]P (porphyrins A-E) and TSNAs (porphyrin F) in MSS. The porphyrin-B[a]P and porphyrin F-TSNAs (N'-nitrosoanabasine (NAB), N'-nitrosoanatabine (NAT), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and N-nitrosonornicotine (NNN)) interactions were investigated by fluorescence quenching and UV-visible spectroscopy. The correlation coefficients were 0.987-0.997 (B[a]P) and 0.994-0.999 (TSNAs), and the binding constants were (1.67-5.02) × 10(5) (B[a]P) and 3.42 × 10(3)-1.40 × 10(4) (TSNAs). Up to 36.72% of B[a]P and 46.67% of the TSNAs were eliminated from MSS, with greater reductions when more porphyrin was included in the filter. With the same mass of porphyrin in the filter, the reduction trend for B[a]P by porphyrins A-E was A > B > C > D > E. The reduction trend for TSNAs by porphyrin F was NNN > NAB > NNK > NAT. The porphyrin mode of action is possibly through strong π-π interactions.
authors.affiliation: Sichuan Key Laboratory Technical Research Center, Chuanyu Branch of China Tobacco Corporation, Chengdu 610066, People's Republic of China.
authors.forename: Changguo
authors.initials: C
authors.lastname: Wang
authors.forename: Ya
authors.initials: Y
authors.lastname: Dai
authors.forename: Guanglin
authors.initials: G
authors.lastname: Feng
authors.forename: Rong
authors.initials: R
authors.lastname: He
authors.forename: Wenmin
authors.initials: W
authors.lastname: Yang
authors.forename: Dongliang
authors.initials: D
authors.lastname: Li
authors.forename: Xuezheng
authors.initials: X
authors.lastname: Zhou
authors.forename: Lijun
authors.initials: L
authors.lastname: Zhu
authors.forename: Lanlan
authors.initials: L
authors.lastname: Tan
mesh_terms: D001564:Benzo(a)pyrene / Q000032:analysis*; D002273:Carcinogens / Q000032:analysis; D005374:Filtration / Q000295:instrumentation*; D009602:Nitrosamines / Q000032:analysis*; D011166:Porphyrins / Q000008:administration & dosage*; D012906:Smoke / Q000032:analysis*; D012907:Smoking; D013050:Spectrometry, Fluorescence; D014026:Nicotiana
chemical_list: D002273:Carcinogens; D009602:Nitrosamines; D011166:Porphyrins; D012906:Smoke; D001564:Benzo(a)pyrene