[en] [¹⁸F] SR144385 and [¹⁸F] SR147963 were synthesized in a multistep reaction in which fluorine-18 was introduced by nucleophilic halogen displacement on a bromo precursor. The fluorine-18-labeled intermediate was deprotected and coupled with the appropriate alkyl amine to give the final products. Both radioligands had appropriate regional brain distribution for cannabinoid receptors with a target to nontarget ratio of 1.7 for [¹⁸F] SR147963 and 2.5 for [¹⁸F] SR144385 at 60 and 90 min postinjection, respectively. The uptake of both tracers was blocked with a 1 mg/kg dose of SR141716A

[en] Unconventional oil production in Alberta's oil sands generates oil sands process-affected water (OSPW), which contains toxic constituents such as naphthenic acid fraction components (NAFCs). There have been few studies examining effects of NAFC exposure over long periods of early-life stage development in fish. Here we examined the effects of NAFCs extracted from OSPW to embryo-larval fathead minnow, exposed for 21 days. We compared the sensitivity of fathead minnow to walleye reared to 7 days post-hatch (18–20 days total). EC50s for hatch success, including deformities, and total survival were lower for walleye (10–11 mg/L) than fathead minnow (22–25 mg/L), with little post-hatch mortality observed in either species. NAFC exposure affected larval growth at concentrations below the EC50 in fathead minnow (total mass IC10 14–17 mg/L). These data contribute to an understanding of the developmental stages targeted by oil sands NAFCs, as well as their toxicity in a greater range of relevant taxa. - Highlights: • NAFCs from OSPW were more toxic to walleye embryos than fathead minnow. • Little or no dose response in mortality was observed after hatch in either species. • Fathead minnow larval growth was a more sensitive endpoint than hatch success. • Chronic, large-volume early-life stage tests (21 days) improve estimates of NAFC toxicity. - Walleye embryos exposed to naphthenic acid fraction components were more sensitive than fathead minnow; embryos were more sensitive than larvae and exposure reduced larval growth.

[en] Highlights: ► Fish were collected from a pond containing oil sands process-affected water (OSPW). ► They were compared to fish from two reference sites within the oil sands region. ► Differences in GSIs and tubercle numbers were observed in fish from the OSPW pond. ► Opercula, gills, and 11-KT concentrations also differed in fish from the OSPW pond. ► Black spot and tapeworms were not observed in any of the fish from the OSPW pond. -- Abstract: Previous laboratory based studies have shown that oil sands process-affected waters (OSPWs) containing high concentrations of naphthenic acids (>25 mg/l) have adverse effects on the reproductive physiology of fish. The purpose of this study was to assess the reproductive development and health of a wild population of fathead minnows (Pimephales promelas) inhabiting an OSPW pond that has moderate concentrations of naphthenic acids (∼10 mg/l). Fathead minnows were collected at various times during the period of 2006 through 2008 from Demonstration Pond (OSPW) located at Syncrude Canada Ltd., and two reference sites, Beaver Creek reservoir and Poplar Creek reservoir, which are all north of Fort McMurray, AB, Canada. Condition factor, gill histopathology, gonadosomatic indices, liver somatic indices, male secondary sexual characteristics, and plasma sex steroids were examined. Depending on the time of year that fathead minnows were collected, there were differences in the condition factor, gonadosomatic indices, liver somatic indices, and secondary sexual characteristics of fathead minnows (in males) from Demonstration Pond when compared to the fathead minnows from the reference sites. In comparison to reference fish, lower concentrations of 11-ketotestosterone were measured in the plasma of male fathead minnows collected from Demonstration Pond in June 2006 and July 2007. Black spot disease and Ligula intestinalis were prevalent in fathead minnows from the reference sites but were not observed in fathead minnows from Demonstration Pond. The opercula of fathead minnows from Demonstration Pond also differed from those of reference fish. An examination of the gills of fathead minnows from Demonstration Pond revealed that were a number of proliferative and degenerative alterations relative to reference fish. Even though the fathead minnow population has been maintained in this OSPW pond since 1993, the results of this study demonstrate that the OSPW continues to affect the reproductive development and health of the fathead minnows compared to fish collected at reference sites

[en] Highlights: • Method for extraction and fractionation of dissolved organics was applied to bitumen-influenced groundwater samples • Dissolved organics are considered principal toxic components in OSPW • Three large volume organic fractions were generated and characterized by complement of methodologies • Isolated fractions increased in polarity and degree of aromaticity • Chemical composition was similar between groundwaters influenced by OSPW and/or natural bitumen sources Recent analytical advances have provided evidence that groundwater affected by oil sands process-affected water (OSPW) is reaching the Athabasca River at one location. To understand and discriminate the toxicological risks posed by OSPW-influenced groundwater relative to groundwaters associated with natural oil sands deposits, these highly complex mixtures of soluble organics were subjected to toxicological characterization through effects directed analysis. A recently-developed preparative fractionation methodology was applied to bitumen-influenced groundwaters and successfully isolated dissolved organics from both industrial and natural sources into three chemically distinct fractions (F1, F2, F3), enabling multiple toxicological assessments. Analytical techniques included electrospray ionization high resolution mass spectrometry (ESI-HRMS), liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QToF/MS), gas chromatography mass spectrometry (GC–MS), and synchronous fluorescence spectroscopy (SFS) methods, which did not reveal obvious differences between sources. Comparisons between fractions within each source consistently demonstrated that F3 contained compounds with greater polarity than F2, which in turn was more polar than F1. The abundance of O2 species was confined to F1, including naphthenic acids often cited for being the primary toxicants within bitumen-influenced waters. This result is consistent with earlier work on aged OSPW, as well as with other extraction methods, suggesting that additional factors other than molecular weight and the presence of acid functionalities play a prominent role in defining compound polarities and toxicities within complex bitumen-derived organic mixtures. The similarities in organic abundances, chemical speciation, aromaticity, and double bond equivalents, concomitant with inorganic mixture similarities, demonstrate the resemblances of bitumen-influenced groundwaters regardless of the source, and reinforce the need for more advanced targeted analyses for source differentiation.

[en] Highlights: • Treatment of oil sands process waters varied with constructed wetland design. • Efficiency evaluated through analytical chemistry, rates, extents, and toxicity. • Constructed wetlands with aquatic Sedges more effective than Cattail or Bulrush. • Treatment was associated with plant type and evapotranspiration. Constructed wetland treatment systems (CWTS)s can be used to treat various wastewaters. The main constituent in oil sands process-affected water (OSPW) with uncertain treatment by CWTS are naphthenic acid fraction compounds (NAFC)s. The NAFCs are also among the primary contributors of toxicity to aquatic organisms. While there is preliminary evidence that some CWTSs are capable of treating OSPW for future potential discharge, there is little information comparing the effectiveness and efficiencies of different CWTS designs. Obtaining large volumes of OSPW for testing can be difficult, and while it is known that synthetic NAFCs are simpler and have different toxicity than OSPW-NAFCs, it is unknown whether they could serve as a proxy for optimization of CWTS design and operation. This study presents a comprehensive comparison of CWTS performance operated with both synthetic OSPW and OSPW for four CWTS designs differing in plant type, aeration, flow path, water depth, and substrate type. This study evaluated the potential biodegradation of NAFCs including: (1) decrease in total NAFC concentration, (2) shifts in O_x-NAFC fractions from O₂- to O₃-, O₄-, and O₅-NAFC, (3) decrease in carbon number, (4) decrease of the double bond equivalencies (DBE), and (5) change in toxicity of the waters to test organisms. CWTS planted with Sedge achieved the greatest extent of NAFC treatment and detoxification regardless of design. Although CWTSs planted with Cattail and Bulrush also degraded NAFCs and decreased toxicity, a greater hydraulic retention time was required, and the total extent of treatment was less than the CWTSs planted with Sedge. While synthetic OSPW was more toxic and experienced faster degradation rates, it showed similar trends to OSPW in terms of CWTS design efficiencies and function. Although synthetic OSPW would not be appropriate for modelling or scaling of CWTSs, it can be useful for testing designs and operating conditions.