title: Reactivity of vinca alkaloids during water chlorination processes: Identification of their disinfection by-products by high-resolution quadrupole-Orbitrap mass spectrometry.
abstract: Concerns about the presence of anticancer drugs in the environment are rapidly increasing mainly due to their growing use in the developed countries and their known cytotoxic effects. Vinca alkaloids are widely used in cancer therapy; however, very scarce information is available on their occurrence, environmental fate and toxicological effects on aquatic organisms. Even less attention has been paid to their potential transformation products, which can exert higher toxicity than the parent compounds. Thus, in the present work, the reactivity of vincristine, vinblastine, vinorelbine and its metabolite 4-O-deacetyl vinorelbine during water chlorination processes has been investigated for the first time. Under the studied chlorination conditions, vincristine was fairly stable whereas vinblastine, vinorelbine and 4-O-deacetyl vinorelbine were quickly degraded. A total of sixty-five disinfection by-products were tentatively identified by ultra-high performance liquid chromatography coupled to high-resolution hybrid quadrupole-Orbitrap tandem mass spectrometry. Among them, twenty by-products corresponded to mono-chlorinated compounds, eight to di-chlorinated compounds and two to tri-chlorinated compounds, which may be of major environmental concern. Other disinfection by-products involved hydroxylation and oxidation reactions. Although the structures of these by-products could not be positively confirmed due to lack of commercial standards, their chemical formulas and product ions can be added to databases, which will allow their screening in future monitoring studies.
authors.affiliation: Water and Soil Quality Research Group, Department of Environmental Chemistry, Institute of Environmental Assessment and Water Research (IDAEA-CSIC), Jordi Girona 18-26, E-08034 Barcelona, Spain.
authors.forename: Noelia
authors.initials: N
authors.lastname: Negreira
authors.affiliation: Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, Ourense Campus, University of Vigo, E-32004 Ourense, Spain.
authors.forename: Jorge
authors.initials: J
authors.lastname: Regueiro
authors.affiliation: Water and Soil Quality Research Group, Department of Environmental Chemistry, Institute of Environmental Assessment and Water Research (IDAEA-CSIC), Jordi Girona 18-26, E-08034 Barcelona, Spain. Electronic address: mlaqam@cid.csic.es.
authors.forename: Miren
authors.initials: M
authors.lastname: López de Alda
authors.affiliation: Water and Soil Quality Research Group, Department of Environmental Chemistry, Institute of Environmental Assessment and Water Research (IDAEA-CSIC), Jordi Girona 18-26, E-08034 Barcelona, Spain; Catalan Institute for Water Research (ICRA), H2O Building, Scientific and Technological Park of the University of Girona, Emili Grahit 101, 17003 Girona, Spain.
authors.forename: Damià
authors.initials: D
authors.lastname: Barceló
mesh_terms: D000970:Antineoplastic Agents / Q000032:analysis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004202:Disinfectants / Q000032:analysis* / Q000737:chemistry; D004203:Disinfection; D014747:Vinblastine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry; D014748:Vinca Alkaloids / Q000032:analysis* / Q000737:chemistry; D000077235:Vinorelbine; D014874:Water Pollutants, Chemical / Q000032:analysis* / Q000737:chemistry; D018508:Water Purification / Q000379:methods
chemical_list: C520600:4-O-deacetyl vinorelbine; D000970:Antineoplastic Agents; D004202:Disinfectants; D014748:Vinca Alkaloids; D014874:Water Pollutants, Chemical; D014747:Vinblastine; D000077235:Vinorelbine
keywords: Vincristine; chlorine; transformation products; vinblastine; vinorelbine; water samples