A reassessment of the nomenclature of polychlorinated biphenyl (PCB) metabolites.Polychlorinated biphenyls polychlorinated biphenyls, (pol´ēklôr´ PCB in full polychlorinated biphenyl Any of a class of highly stable organic compounds prepared by the reaction of chlorine with biphenyl, a two-ring compound. biotransformation biotransformation /bio·trans·for·ma·tion/ (-trans?for-ma´shun) the series of chemical alterations of a compound (e.g., a drug) occurring within the body, as by enzymatic activity. has been shown to lead to two classes of PCB metabolites Metabolites Substances produced by metabolism or by a metabolic process. Mentioned in: Interactions that are present as contaminant contaminant /con·tam·i·nant/ (kon-tam´in-int) something that causes contamination. contaminant something that causes contamination. residues in the tissues of selected biota biota /bi·o·ta/ (bi-o´tah) all the living organisms of a particular area; the combined flora and fauna of a region. bi·o·ta n. The flora and fauna of a region. : hydroxylated (HO) and methyl sulfone sulfone /sul·fone/ (sul´fon) 1. the radical SO2. 2. a compound containing two hydrocarbon radicals attached to the —SO2— group, especially dapsone and its derivatives, which are potent antibacterials effective (MeS[O.sub.2]) PCBs. Although these two types of metabolites are related structures, different rules for abbreviation abbreviation, in writing, arbitrary shortening of a word, usually by cutting off letters from the end, as in U.S. and Gen. (General). Contraction serves the same purpose but is understood strictly to be the shortening of a word by cutting out letters in the middle, of both classes have emerged. It is important that a standardized nomenclature for the notation of PCB metabolites be universally agreed upon Adj. 1. agreed upon - constituted or contracted by stipulation or agreement; "stipulatory obligations" stipulatory noncontroversial, uncontroversial - not likely to arouse controversy . We suggest that the full chemical name of the PCB metabolite metabolite, organic compound that is a starting material in, an intermediate in, or an end product of metabolism. Starting materials are substances, usually small and of simple structure, absorbed by the organism as food. and a shorthand notation should be adopted using the International Union of Pure and Applied Chemistry's chemical name/original Ballschmiter and Zell number of the parent congener congener /con·ge·ner/ (kon´je-ner) something closely related to another thing, as a member of the same genus, a muscle having the same function as another, or a chemical compound closely related to another in composition and exerting , followed by the assignment of the phenyl phenyl (fĕn`əl), C6H5, organic free radical or alkyl group derived from benzene by removing one hydrogen atom. ring position number of the MeS[O.sub.2]- or HO-substituent. This nomenclature provides a clear, unequivocal set of rules in naming and abbreviating the PCB metabolite structure. Furthermore, this unified PCB metabolite nomeclature approach can be extended to the naming and abbreviation of potential metabolites of structurally analogous contaminants such as HO-polybrominated biphenyls and HO-polybrominated diphenyl diphenyl /di·phen·yl/ (di-fen´il) a toxic compound comprising two linked benzene rings, used as a fungistat in containers for shipping citrus fruits. di·phen·yl n. See biphenyl. ethers. Key words: hydroxylated metabolites, methyl sulfone metabolites, nomenclature, polychlorinated biphenyls. doi:10.1289/ehp.6409 Nomenclature of Polychlorinated Biphenyls Polychlorinated biphenyls (PCBs) are a class of chemical compounds in which 1-10 chlorine atoms are attached to a biphenyl biphenyl /bi·phen·yl/ (-fen´il) diphenyl. polychlorinated biphenyl (PCB) any of a group of chlorinated derivatives of biphenyl, used as heat-transfer agents and electrical insulators; they are backbone. Theoretically, 209 discrete congeners are possible (Ballschmiter and Zell 1980). However, PCB technical mixtures are composed of a smaller suite of congeners (Frame et al. 1996), and only about 80-100 PCB congeners are of actual environmental relevance (de Voogt et al. 1990). The full chemical notation Noun 1. chemical notation - a notation used by chemists to express technical facts in chemistry notation, notational system - a technical system of symbols used to represent special things for these 209 possible PCB congeners is inconvenient, and therefore various shorthand notations have been developed and adopted (Erickson 1997, 2001). Ballschmiter and Zell (1980) originally introduced a system (BZ) in which congeners were arranged in the ascending numerical order based on the number of chlorine atoms and their substitution pattern on the biphenyl base structure. Minor theoretical discrepancies in the BZ naming system were later corrected (Ballschmiter et al. 1992; Guitart et al. 1993; Schulte and Malisch 1983). The BZ system of PCB shorthand notation was subsequently recognized by the International Union of Pure and Applied Chemistry International Union of Pure and Applied Chemistry (IUPAC), an international organization est. 1919 to advance the chemical sciences and contribute to the application of chemistry to the service of humanity. (IUPAC IUPAC: see International Union of Pure and Applied Chemistry. ) (U.S. Environmental Protection Agency Environmental Protection Agency (EPA), independent agency of the U.S. government, with headquarters in Washington, D.C. It was established in 1970 to reduce and control air and water pollution, noise pollution, and radiation and to ensure the safe handling and 2003) and is the generally accepted notation used by scientists who perform congener-specific PCB research. Metabolism of PCBs PCBs that accumulate in biota are subject to elimination processes that are facilitated by processes including enzyme-mediated degradation. The mechanism and kinetics of PCB biotransformation depend on a number of factors, including the metabolic capacity of the organism and the PCB congener structure. PCB biotransformation has been shown to lead to two classes of PCB metabolites that are present as contaminant residues in the tissues of biota that have been studied: hydroxylated (HO) and methyl sulfone (C[H.sub.3]S[O.sub.2]) PCBs (Letcher et al. 2000a). C[H.sub.3]S[O.sub.2-]PCBs are generally referred to as MeS[O.sub.2]-PCBs. The numbers of animals and populations where tissue residues of these PCB metabolites have been characterized remains small, but HO-PCBs and MeS[O.sub.2]-PCBs are emerging as common contaminant phenomena in wildlife and humans and are of increasing importance in risk assessments of exposure to PCBs (Bennett et al. 2002; Campbell et al. 2003; Chu et al. 2002, 2003; Guvenius et al. 2002; Hoekstra et al. 2003; Hovander et al. 2002; Letcher et al. 2000a, 2000b; Li et al. 2003; Sandala et al., in press; Sandau et al. 2000a, 2000b, 2002; Stapleton et al. 2001). In some species and tissues, HO-PCB and MeS[O.sub.2]-PCB concentrations may be in a similar of higher range with respect to the concentrations of the parent PCBs. Furthermore, congeners of these two classes of PCB metabolites, which are present as contaminant residues, have demonstrated biologic and toxicologic activity--for example, endocrine-related activity (Brouwer et al. 1998; Letcher et al. 2000a, 2002). Nomenclature of HO-PCBs The published reports on HO-PCBs and MeS[O.sub.2]-PCBs have generally used IUPAC guidelines to describe the full chemical name of these metabolites. However, the presently used abbreviations for HO-PCB congeners deviate from the general IUPAC naming rules. The HO-functional group is not given numbering priority on the biphenyl backbone; rather, the chlorine pattern on the biphenyl ring determines the congener number according to according to prep. 1. As stated or indicated by; on the authority of: according to historians. 2. In keeping with: according to instructions. 3. the BZ or IUPAC PCB numbering rules (Ballschmiter and Zell 1980; Ballschmiter et al. 1992; Guitart et al. 1993; Schulte and Malisch 1983), and the HO-group(s) are numbered thereafter. As a result, an HO-functionality in the meta-position relative to the central carbon-carbon bond A carbon-carbon bond is a covalent bond between two carbon atoms. The most common form is the single bond – a bond composed of two electrons, one from each of the two atoms. of the biphenyl attachment is in either position 3 or position 5. When the HO-substituent is located on the ring with the lowest chlorine numbering priority, its number is primed in the same manner as is done for the chlorine atoms on the same phenyl ring. The HO-metabolite 5'-HO-2,3',4,4'-tetrachlorobiphenyl (three unsubstituted meta-positions in the 3, 5, and 5' positions of the corresponding PCB congener), for example, is therefore uniquely abbreviated to 5'-HO-CB66 using this notation approach (Table 1). Nomenclature of MeS[O.sub.2]-PCBs Similarly, for MeS[O.sub.2]-PCB congeners, the PCB number is first determined according to the chlorine substitution of the biphenyl by omitting the MeS[O.sub.2]-functional group. The initial shorthand notation used for MeS[O.sub.2]-PCBs assigned the methyl sulfonyl sul·fo·nyl n. The bivalent radical SO2. Also called sulfuryl. group based on a higher numbering priority on the biphenyl system than for chlorine atoms, and thus the position of methyl sulfonyl substitution was not primed (Letcher et al. 1995; Weistrand and Noren 1997). For example, using this initial numbering approach, a methyl sulfonyl group in a meta-position would always be assigned to position 3. This nomenclature approach can be problematical, as illustrated by the example of 3-MeS[O.sub.2]- 2,2',4',5-tetrachlorobiphenyl (Table 1), which is intended when the short notation 3-MeS[O.sub.2]-CB49 is used. Although this appears to be the only environmentally relevant possibility, two other metabolites would have exactly the same 3-MeS[O.sub.2]-CB49 abbreviation if the methyl sulfonyl group were positioned on either of the two free metapositions of the other, 2,4-chloro-substituted, phenyl ring. Different authors have acknowledged the inconsistencies in the naming of MeS[O.sub.2]-PCBs and have suggested alternate approaches (Letcher et al. 2000a and references therein). In several recent reports, the number of the MeS[O.sub.2]-group has been primed or unprimed depending on which phenyl ring this substituent substituent /sub·stit·u·ent/ (-stich´u-ent) 1. a substitute; especially an atom, radical, or group substituted for another in a compound. 2. of or pertaining to such an atom, radical, or group. was positioned (Guvenius et al. 2002; Hoekstra et al. 2003; Letcher et al. 2000a, 2000b). Following this revised nomenclature system, 3-MeS[O.sub.2]-2,2',4',5-tetrachlorobiphenyl is abbreviated to Y-MeS[O.sub.2]-CB49. Because the number of the methyl sulfonyl group is primed, and the other meta-carbon position on the primed phenyl ring is substituted with a chlorine atom, the abbreviation indicates only one structural possibility. Because methyl sulfonyl groups on the most commonly encountered congener residues in biota usually occur on a 2,5- or 2,3,6- chlorine-substituted phenyl ring, one meta-position will normally be occupied by a chlorine atom on the MeS[O.sub.2]-substituted phenyl ring. It is clear that this might not be the case for some other, at least theoretical, metabolites. Recently, Larsson et al. (2002) applied the same nomenclature rules for abbreviation of MeS[O.sub.2]-metabolites as is normally done for HO-PCBs. That is, the methyl sulfonyl groups are numbered according to their substitution position, after the positions of the chlorine atoms are taken into account based on the revised BZ naming system. For example, Larsson et al. (2002) abbreviated 3-MeS[O.sub.2]-2,2',3,4',5',6-hexachlorobiphenyl to 5-MeS[O.sub.2]-CB149 rather than to 3-MeS[O.sub.2]-CB149 (Table 1) because the MeS[O.sub.2]-functional group is present in position 5 rather than in position 3. This abbreviation indicates only one distinct congener regardless of its chlorine substitution pattern, which eliminates the possibility of misidentifying MeS[O.sub.2]-PCB structures with the same chlorine substitution pattern. Because the MeS[O.sub.2]-group is not assigned the lowest possible number, the substitution position of the chlorine atoms is also maintained. Consequently, the identity of the MeS[O.sub.2]-PCB congener is easily related to the parent PCB structure (Table 1). However, the implementation of this nomenclature approach for methyl sulfonyl-PCB metabolites poses a problem with respect to congener-specific comparisons in earlier publications where alternate nomenclature has been used. For example, some environmentally relevant 3-MeS[O.sub.2]-CBs would have to be renamed as 5-MeS[O.sub.2]-CBs (Table 2). Proposed Nomenclature On closer examination of the full chemical name of, for example, 3-MeS[O.sub.2]-2,2',3,4',5',6-hexachlorobiphenyl, it is striking that the MeS[O.sub.2]-group receives the same number (3) as a chlorine substituent present on the same ring. Therefore, it is evident from the full chemical name of PCB metabolites that it is nor possible to combine both the fundamental IUPAC approach for naming aromatic compounds (i.e., giving the substituent numbering priority and numbering the chlorine atoms thereafter) and the IUPAC-accepted BZ rules for the naming of PCBs (i.e., a PCB-BZ number is clearly associated with the chlorine substitution pattern). Because the BZ system is so widely adopted, it would be logical to base the PCB metabolite nomenclature on the BZ system. Even though this approach requires exceptions to the IUPAC guidelines of nomenclature, we would suggest that the full chemical name/shorthand notation of the metabolite should be made by using the IUPAC full name/original BZ number of the parent congener and then assigning the MeS[O.sub.2]- or HO-substituent a ring position number thereafter. For example, 5-MeS[O.sub.2]-CB149 is the abbreviation for 5-MeS[O.sub.2]- 2,2',3,4',5',6-hexachlorobiphenyl (Table 1), where the 5-position of the substituent remains the same as in the abbreviation, and the chlorine pattern clearly indicates PCB number 149 (BZ). Table 2 shows how the proposed standardized nomenclature applies to the current list of identified and environmentally relevant HO- and MeS[O.sub.2]-PCB congeners. It may be observed that, for MeS[O.sub.2]-PCB metabolites, a 2,5-ring substitution of the PCB congener leads to a 3- or a 3'-substitution for the MeS[O.sub.2]-group, whereas a 2,3,6-ring substitution leads to a 5- or a 5'-substitution (Table 2). Table 2 can be used as a reference to unambiguously label the names of PCB metabolites. This nomenclature for both the abbreviation and full chemical name of a given PCB metabolite provides a clear, unequivocal structure and delivers a unified technique that can be used for both classes of PCB metabolites. Although HO-PCBs and MeS[O.sub.2]-PCBs are related structures, different rules for abbreviations of both classes have emerged. A standardized nomenclature that is presently suggested for the naming of a PCB metabolite should be universally adopted and sanctioned by IUPAC to facilitate unambiguous comparison of congener-specific data among published studies. Additionally, this nomenclature may be applicable to similar metabolites of other persistent aromatic organics, such as polybrominated diphenyl ethers Polybrominated diphenyl ethers or PBDE, are a flame retardant sub-family of the brominated flame retardant group. They have been used in a wide array of household products, including fabrics, furniture, and electronics. (PBDEs) and polybrominated biphenyls polybrominated biphenyls see biphenyl. (PBBs). Studies on the formation of metabolites from the PBB PBB: see polybrominated biphenyl. and PBDE PBDE Polybrominated Diphenyl Ether PBDE Pentabromodiphenyl Ether (flame retardant additive in plastics) PBDE Parallel Block-Decodable Encoder classes of pollutants are becoming more numerous in the literature (Burreau et al. 2000; Haglund et al. 1997; Hakk and Letcher 2003; Meerts et al. 2001; Valters et al. 2003). Therefore, it is important to adopt a general, unified nomenclature system for the full chemical name and shorthand notation of possible metabolites.
Table 1. Structure, abbreviations, and full chemical names of three
PCB metabolites.
Structure
IUPAC full chemical 3-MeS[O.sub.2]-2,2', 3-MeS[O.sub.2]-2,2',
name (a) 4,5-tetrachlorobiphenyl 4,5,5',6-
hexachlorobiphenyl
Abbreviations 1 (b) 3-MeS[O.sub.2]-CB49 3-MeS[O.sub.2]-CB149
Abbreviations 2 (c) 3'-MeS[O.sub.2]-CB49 3-MeS[O.sub.2]-CB149
Abbreviations 3 (d) 3'-MeS[O.sub.2]-CB49 5-MeS[O.sub.2]-CB149
Proposed full 3'-MeS[O.sub.2]-2,2', 5-MeS[O.sub.2]-2,2',
chemical name (e) 4,5',tetrachlorobiphenyl 4',5',6-
hexachlorobiphenyl
Structure
IUPAC full chemical 3-HO-2'4,4',5-tetrachlorobiphenyl
name (a)
Abbreviations 1 (b)
Abbreviations 2 (c)
Abbreviations 3 (d) 5'-HO-CB66
Proposed full 5'-HO-2,3',4,4'-tetrachlorobiphenyl
chemical name (e)
(a) MeS[O.sub.2]-PCBs (Larsson et al. 2002; Weistrand and Noren 1997);
HO-PCBs (Bergman et al. 1994; Hovander et al. 2002. (b) MeS[O.sub.2]-
PCBs (Letcher et al. 1995; Weistrand and Noren 1997). (c) MeS[O.sub.2]-
PCBs (Guvenius et al. 2002; Hoekstra et al. 2003; Letcher et al. 2000a,
2000b). (d) MeS[O.sub.2]-PCBs (Larsson et al. 2002); HO-PCBs (Bennett
et al. 2002; Campbell et al. 2003; Hovander et al. 2002; Li et al.
2003; Sandala et al., in press; Sandau et al. 2000a; Sjodin et al.
1998). (e) HO-PCBs not previously used for MeS[O.sub.2]-PCBs (Campbell
et al. 2003; Sandala et al., in press; Sandau et al. 2000a; Sjodin et
al. 1998).
Table 2. Current and proposed PCB metabolite nomenclature.
Proposed nomenclature
IUPAC full chemical name (a) Abbreviation (b)
3-MeS[O.sub.2]-2,4',5- 3-MeS[O.sub.2]-CB31
trichlorobiphenyl
4-MeS[O.sub.2]-2,4',5- 4-MeS[O.sub.2]-CB31
trichlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5- 3'-MeS[O.sub.2]-CB49
tetrachlorobiphenyl
4-MeS[O.sub.2]-2,2',4',5- 4'-MeS[O.sub.2]-CB49
tetrachlorobiphenyl
3-MeS[O.sub.2]-2,2',5,5'- 3-MeS[O.sub.2]-CB52
tetrachlorobiphenyl
4-MeS[O.sub.2]-2,2',5,5'- 4-MeS[O.sub.2]-CB52
tetrachlorobiphenyl
3-MeS[O.sub.2]-2,4',5,6- 5-MeS[O.sub.2]-CB64
tetrachlorobiphenyl
4-MeS[O.sub.2]-2,3,4',6- 4-MeS[O.sub.2]-CB64
tetrachlorobiphenyl
3-MeS[O.sub.2]-2,3',4',5- 3-MeS[O.sub.2]-CB70
tetrachlorobiphenyl
4-MeS[O.sub.2]-2,3',4',5- 4-MeS[O.sub.2]-CB70
tetrachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5- 3'-MeS[O.sub.2]-CB87
pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',4',5- 4'-MeS[O.sub.2]-CB87
pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5,6- 5-MeS[O.sub.2]-CB91
pentachlorobiphenyl
4-M8S[O.sub.2]-2,2',3,4',6- 4-MeS[O.sub.2]-CB91
pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',5,6'- 3'-MeS[O.sub.2]-CB95
pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',5,6'- 4'-MeS[O.sub.2]-CB95
pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5,5'- 3'-MeS[O.sub.2]-CB101
pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',4',5,5'- 4'-MeS[O.sub.2]-CB101
pentachlorobiphenyl
3-MeS[O.sub.2]-2,3',4',5,6- 5-MeS[O.sub.2]-CB110
pentachlorobiphenyl
4-MeS[O.sub.2]-2,3,3',4',6- 4-MeS[O.sub.2]-CB110
pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,6- 5'-MeS[O.sub.2]-CB132
heptachlorobiphenyl
4-MeS[O.sub.2]-2,2',3,3',4',6- 4'-MeS[O.sub.2]-CB132
heptachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,5'- 3'-MeS[O.sub.2]-CB141
heptachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',4',5,5'- 4'-MeS[O.sub.2]-CB141
heptachlorobiphenyl
3-MeS[O.sub.2]-2,2',4,5,5',6- 5-MeS[O.sub.2]-CB149
heptachlorobiphenyl
4-MeS[O.sub.2]-2,2',3,4',5',6- 4-MeS[O.sub.2]-CB149
heptachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,5',6- 5'-MeS[O.sub.2]-CB174
heptachlorobiphenyl
4-MeS[O.sub.2]-2,2'3,3',4',5',6- 4'-MeS[O.sub.2]-CB174
heptachlorobiphenyl
4-HO-2,2',4',6'- 4'-HO-CB50
tetrachlorobiphenyl
3-HO-2'4,4',5- 5'-HO-CB66
tetrachlorobiphenyl
4-HO-3,3',4',5- 4'-HO-CB79
tetrachlorobiphenyl
3-HO-2,2',3',4,4'- 3'-HO-CB85
pentachlorobiphenyl
3,4'-diHO-2,2',3,4,5- 3',4-diHO-C890
pentachlorobiphenyl
4-HO-2,2',3,5,6- 4-HO-CB93
pentachlorobiphenyl
4-HO-2,2',3,4',5'- 4-HO-CB97
pentachlorobiphenyl
4-HO-2,2',4',5,5'- 4'-HO-CB101
pentachlorobiphenyl
4-HO-2,2',4',6,6'- 4'-HO-CB104
pentachlorobiphenyl
4-HO-2,3,3',4',5- 4-HO-CB107
pentachlorobiphenyl
2,4'-diHO-2',3,3',4,5'- 2',4-diHO-CB107
pentachlorobiphenyl
4-HO-2',3,3',4',5- 4'-HO-CB108
pentachlorobiphenyl
4-HO-2,3,3',5,6- 4-HO-CB112
pentachlorobiphenyl
3-HO-2,3',4,4',5- 3-HO-CB118
pentachlorobiphenyl
4-HO-2',3,4',5,5'- 4'-HO-CB120
pentachlorobiphenyl
4-HO-2',3,4',5,6'- 4'-HO-CB121
pentachlorobiphenyl
4-HO-3,3',4',5,5'- 4'-HO-CB127
pentachlorobiphenyl
4-HO-2,2'3,3'4',5- 4'-HO-CB130
hexachlorobiphenyl
4-HO-2,2',3,3',5,6- 4-HO-CB134
hexachlorobiphenyl
3-HO-2,2',3',4,4',5- 3'-HO-CB138
hexachlorobiphenyl
4-HO-2,2',3,4',5,5'- 4-HO-CB146
hexachlorobiphenyl
3-HO-2,2',4,4',5,5'- 3-HO-CB153
hexachlorobiphenyl
4-HO-2',3,3',4',5,5'- 4'-HO-CB159
hexachlorobiphenyl
4-HO-2,33',4',5,5'- 4-HO-CB162
hexachlorobiphenyl
4-HO-2,3,3',4',5,6- 4-HO-CB163
hexachlorobiphenyl
4-HO-2,3,3',5,5',6- 4-HO-CB165
hexachlorobiphenyl
4-HO-2,2',3,3,4',5,5'- 4'-HO-CB172
heptachlorobiphenyl
4-HO-2,2',3,3 4',5,6'- 4'-HO-CB175
heptachlorobiphenyl
4-HO-2,2',3,3',5,5',6- 4-HO-CB178
heptachlorobiphenyl
4-HO-2,2',3,3',5,5',6'- 4'-HO-CB178
heptachlorobiphenyl
4,4'-diHO-2,2',3,3',5,5',6- 4,4'-diHO-CB178
heptachlorobiphenyl
3-HO-2,2',3',4,4',5,5'- 3'-HO-CB180
heptachlorobiphenyl
3-HO-2,2',3',4,4',5',6- 3'-HO-CB182
heptachlorobiphenyl
3-HO-2,2',3',4,4',5,6'- 3'-HO-CB183
heptachlorobiphenyl
3-HO-2,2',3',4,4',6,6'- 3'-HO-CB184
heptachlorobiphenyl
3-HO-2,2',3,4,5,5',6'- 3'-HO-C8187
heptachlorobiphenyl
4-HO-2,2',3,4',5,5',6- 4-HO-CB187
heptachlorobiphenyl
3,4'-diHO-2,2',3',4,5,5',6'- 3,'4-diHO-CB187
heptachlorobiphenyl
4-HO-2,3,3',4',5,5',6- 4-HO-CB193
heptachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6'- 4'-HO-CB198
octachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6- 4'-HO-CB201/199 (d)
octachlorobiphenyl
4-HO-2,2',3,3',4',5,6,6'- 4'-HO-CB200/201 (d)
octachlorobiphenyl
4-HO-2,2',3,3',5,5',6,6'- 4-HO-CB202
octachlorobiphenyl
4,4'-diHO-2,2',3,3',5,5',6,6'- 4,4'-diHO-CB202
octachlorobiphenyl
3-HO-2,2',3',4,4',5,5',6'- 3'-HO-CB203
octachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6,6'- 4'-HO-CB208
nonachlorobiphenyl
Proposed nomenclature
IUPAC full chemical name (a) Proposed full chemical name (c)
3-MeS[O.sub.2]-2,4',5- 3-MeS[O.sub.2]-2,4',5-
trichlorobiphenyl trichlorobiphenyl
4-MeS[O.sub.2]-2,4',5- 4-MeS[O.sub.2]-2,4',5-
trichlorobiphenyl trichlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5- 3'-MeS[O.sub.2]-2,2',4,5'-
tetrachlorobiphenyl tetrachlorobiphenyl
4-MeS[O.sub.2]-2,2',4',5- 4'-MeS[O.sub.2] 2,2',4,5'-
tetrachlorobiphenyl tetrachlorobiphenyl
3-MeS[O.sub.2]-2,2',5,5'- 3-MeS[O.sub.2]-2,2',5,5'-
tetrachlorobiphenyl tetrachlorobiphenyl
4-MeS[O.sub.2]-2,2',5,5'- 4-MeS[O.sub.2] 2,2',5,5'-
tetrachlorobiphenyl tetrachlorobiphenyl
3-MeS[O.sub.2]-2,4',5,6- 5-MeS[O.sub.2]-2,3,4',6-
tetrachlorobiphenyl tetrachlorobiphenyl
4-MeS[O.sub.2]-2,3,4',6- 4-MeS[O.sub.2]-2,3,4',6-
tetrachlorobiphenyl tetrachlorobiphenyl
3-MeS[O.sub.2]-2,3',4',5- 3-MeS[O.sub.2]-2,3',4',5-
tetrachlorobiphenyl tetrachlorobiphenyl
4-MeS[O.sub.2]-2,3',4',5- 4-MeS[O.sub.2]-2,3',4',5-
tetrachlorobiphenyl tetrachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5- 3'-MeS[O.sub.2]-2,2',3,4,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',4',5- 4'-MeS[O.sub.2]-2,2',3,4,5'-
pentachlorobiphenyl pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5,6- 5-MeS[O.sub.2]-2,2',3,4',6-
pentachlorobiphenyl pentachlorobiphenyl
4-M8S[O.sub.2]-2,2',3,4',6- 4-MeS[O.sub.2]-2,2',3,4',6-
pentachlorobiphenyl pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',5,6'- 3'-MeS[O.sub.2] 2,2',3,5',6-
pentachlorobiphenyl pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',5,6'- 4'-MeS[O.sub.2]-2,2',3,5',6-
pentachlorobiphenyl pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',4',5,5'- 3'-MeS[O.sub.2]-2,2',4,5,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-MeS[O.sub.2]-2,2',4',5,5'- 4'-MeS[O.sub.2]-2,2',4,5,5'-
pentachlorobiphenyl pentachlorobiphenyl
3-MeS[O.sub.2]-2,3',4',5,6- 5-MeS[O.sub.2]-2,3,3',4',6-
pentachlorobiphenyl pentachlorobiphenyl
4-MeS[O.sub.2]-2,3,3',4',6- 4-MeS[O.sub.2]-2,3,3',4',6-
pentachlorobiphenyl pentachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,6- 5'-MeS[O.sub.2] 2,2',3,3,4,6'-
heptachlorobiphenyl hexachlorobiphenyl
4-MeS[O.sub.2]-2,2',3,3',4',6- 4'-MeS[O.sub.2]-2,2',3,3,4,6'-
heptachlorobiphenyl hexachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,5'- 3'-MeS[O.sub.2]-2,2',3,4,5,5'-
heptachlorobiphenyl hexachlorobiphenyl
4-MeS[O.sub.2]-2,2',3',4',5,5'- 4'-MeS[O.sub.2]-2,2',3,4,5,5'-
heptachlorobiphenyl hexachlorobiphenyl
3-MeS[O.sub.2]-2,2',4,5,5',6- 5-MeS[O.sub.2]-2,2',3,4',5',6-
heptachlorobiphenyl hexachlorobiphenyl
4-MeS[O.sub.2]-2,2',3,4',5',6- 4-MeS[O.sub.2]-2,2',3,4',5',6-
heptachlorobiphenyl hexachlorobiphenyl
3-MeS[O.sub.2]-2,2',3',4',5,5',6- 5'-MeS[O.sub.2]-2,2',3,3',4,5,6'-
heptachlorobiphenyl heptachlorobiphenyl
4-MeS[O.sub.2]-2,2'3,3',4',5',6- 4'-MeS[O.sub.2]-2,2',3,3',4,5,6'-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',4',6'- 4-HO-2,2',4,6-
tetrachlorobiphenyl tetrachlorobiphenyl
3-HO-2'4,4',5- 5'-HO-2,3',4,4'-
tetrachlorobiphenyl tetrachlorobiphenyl
4-HO-3,3',4',5- 4'-HO-3,3',4,5'-
tetrachlorobiphenyl tetrachlorobiphenyl
3-HO-2,2',3',4,4'- 3'-HO-2,2',3,4,4'-
pentachlorobiphenyl pentachlorobiphenyl
3,4'-diHO-2,2',3,4,5- 3',4-diHO-2,2',3,4',5-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,2',3,5,6- 4-HO-2,2',3,5,6-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,2',3,4',5'- 4-HO-2,2',3,4,'5'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,2',4',5,5'- 4'-HO-2,2',4,5,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,2',4',6,6'- 4'-HO-2,2',4,6,6'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,3,3',4',5- 4-HO-2,3,3',4',5-
pentachlorobiphenyl pentachlorobiphenyl
2,4'-diHO-2',3,3',4,5'- 2',4-diHO-2,3,3',4',5-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2',3,3',4',5- 4'-HO-2,3,3',4,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,3,3',5,6- 4-HO-2,3,3',5,6-
pentachlorobiphenyl pentachlorobiphenyl
3-HO-2,3',4,4',5- 3-HO-2,3',4,4',5-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2',3,4',5,5'- 4'-HO-2,3',4,5,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2',3,4',5,6'- 4'-HO-2,3',4,5',6-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-3,3',4',5,5'- 4'-HO-3,3'4,5,5'-
pentachlorobiphenyl pentachlorobiphenyl
4-HO-2,2'3,3'4',5- 4'-HO-2,2',3,3',4,5'-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,2',3,3',5,6- 4-HO-2,2',3,3',5,6-
hexachlorobiphenyl hexachlorobiphenyl
3-HO-2,2',3',4,4',5- 3'-HO-2,2',3,4,4',5'-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,2',3,4',5,5'- 4-HO-2,2',3,4',5,5'-
hexachlorobiphenyl hexachlorobiphenyl
3-HO-2,2',4,4',5,5'- 3-HO-2,2',4,4',5,5'-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2',3,3',4',5,5'- 4'-HO-2,3,3',4,5,5'-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,33',4',5,5'- 4-HO-2,3,3',4',5,5'-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,3,3',4',5,6- 4-HO-2,3,3',4',5,6-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,3,3',5,5',6- 4-HO-2,3,3',5,5',6-
hexachlorobiphenyl hexachlorobiphenyl
4-HO-2,2',3,3,4',5,5'- 4'-HO-2,2',3,3',4,5,5'-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',3,3 4',5,6'- 4'-HO-2,2',3,3',4,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',3,3',5,5',6- 4-HC-2,2',3,3',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',3,3',5,5',6'- 4'-HO-2,2',3,3',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4,4'-diHO-2,2',3,3',5,5',6- 4,4'-diHO-2,2',3,3',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
3-HO-2,2',3',4,4',5,5'- 3-HO-2,2',3,4,4',5,5'-
heptachlorobiphenyl heptachlorobiphenyl
3-HO-2,2',3',4,4',5',6- 3'-HO-2,2',3,4,4',5,6'-
heptachlorobiphenyl heptachlorobiphenyl
3-HO-2,2',3',4,4',5,6'- 3'-HO-2,2',3,4,4',5',6-
heptachlorobiphenyl heptachlorobiphenyl
3-HO-2,2',3',4,4',6,6'- 3'-HO-2,2',3,4,4',6,6'-
heptachlorobiphenyl heptachlorobiphenyl
3-HO-2,2',3,4,5,5',6'- 3'-HO-2,2',3,4',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',3,4',5,5',6- 4-HO-2,2',3,4',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
3,4'-diHO-2,2',3',4,5,5',6'- 3',4-diHO-2,2',3,4',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,3,3',4',5,5',6- 4-HO-2,3,3',4',5,5',6-
heptachlorobiphenyl heptachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6'- 4'-HO-2,2',3,3',4,5,5',6-
octachlorobiphenyl octachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6- 4'-HO-2,2',3,3',4,5,5',6'-
octachlorobiphenyl octachlorobiphenyl
4-HO-2,2',3,3',4',5,6,6'- 4'-HO-2,2',3,3',4,5',6,6'-
octachlorobiphenyl octachlorobiphenyl
4-HO-2,2',3,3',5,5',6,6'- 4-HO-2,2',3,3',5,5',6,6'-
octachlorobiphenyl octachlorobiphenyl
4,4'-diHO-2,2',3,3',5,5',6,6'- 4,4'-diHO-2,2',3,3',5,5',6,6'-
octachlorobiphenyl octachlorobiphenyl
3-HO-2,2',3',4,4',5,5',6'- 3'-HO-2,2',3,4,4',5,5',6-
octachlorobiphenyl octachlorobiphenyl
4-HO-2,2',3,3',4',5,5',6,6'- 4'-HO-2,2',3,3',4,5,5',6,6'-
nonachlorobiphenyl nonachlorabiphenyl
(a) MeS[O.sub.2]-PCBs (Larsson et al. 2002; Weistrand and Noren 1997);
HO-PCBs (Bergman et al. 1994; Hovander et al. 2002). (b) MeS[O.sub.2]-
PCBs (Larsson et al. 2002); HO-PCBs (Bennett et al. 2002; Campbell et
al. 2003; Hovander et al. 2002; Li et al. 2003; Sandala et al., in
press; Sandau et al. 2000a; Sjodin et al. 1998). (c) HO-PCBs (Campbell
et al. 2003; Sandala et al., in press; Sandau et al. 2000a; Sjodin et
al. 1998). (d) Original BZ/revised PCB number.
The authors declare they have no competing financial interests. REFERENCES Ballschmiter K, Bacher R, Mennel A, Fischer R, Riehle U, Swerev M. 1902. The determination of chlorinated chlorinated /chlo·ri·nat·ed/ (klor´i-nat?ed) treated or charged with chlorine. chlorinated charged with chlorine. chlorinated acids some, e.g. biphenyls, chlorinated dibenzodioxins, and chlorinated dibenzofurans by GC-MS GC-MS Gas chromatography-mass spectroscopy. See there. . J High Resolut Chromatogr 15:260-270. Ballschmiter K, Zell M. 1980. Analysis of polychlorinated biphenyls (PCB) by glass capillary gas chromatography gas chromatography (GC) Type of chromatography with a gas mixture as the mobile phase. In a packed column, the packing or solid support (held in a tube) serves as the stationary phase (vapour-phase chromatography, or VPC) or is coated with a liquid stationary phase . Fresenius J Anal Chem 302:20-31. Bennett ER, Ross PS, Letcher RJ. 2002. Polyhalogenated phenolic phe·no·lic adj. Of, relating to, containing, or derived from phenol. n. Any of various synthetic thermosetting resins, obtained by the reaction of phenols with simple aldehydes and used as adhesives. contaminants in Pacific killer whale killer whale or grampus, a large, rapacious marine mammal, Orcinus orca, of the dolphin family. Male killer whales may reach a length of 30 ft (9 m) and females half that length. (Orcinus orca Orcinus orca see killer whale. ); Organohalogen Compounds 58:81-84. Bergman A, Klasson-Wehler E, Kuroki H. 1994. Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect 102:464-469. Brouwer A, Morse DC, Lans MC, Schuur AG, Murk murk also mirk n. Partial or total darkness; gloom. adj. Archaic Partially or totally dark; gloomy. [Middle English mirke, from Old Norse myrkr AJ, Klasson-Wehler E, et al. 1098. Interactions of persistent environmental organohalogens with the thyroid hormone Thyroid hormone Any of the chemical messengers produced by the thyroid gland, including thyrocalcitonin, a polypeptide, and thyroxine and triiodothyronine, which are iodinated thyronines. See Hormone, Thyrocalcitonin, Thyroid gland, Thyroxine system: mechanisms and possible consequences for animal and human health. Toxicol Ind Health 14:59-84. Burreau S, Broman D, Orn U. 2000. Tissue distribution of 2,2',4,4'-tetrabromo[C-14]diphenyl ether ([C-14]-PBDE 47) in pike (Esox lucius) after dietary exposure--a time series study using whole body autoradiography Autoradiography A photographic technique used to localize a radioactive substance within a solid specimen; also known as radioautography. A photographic emulsion is placed in contact with the object to be tested and is left for several hours, days, or . Chemosphere chemosphere: see atmosphere. 40:977-985. Campbell LM, Muir DCG DCG - Definite Clause Grammar , Whittle DM, Backus S, Norstrom RJ, Fisk Fisk , James 1834-1872. American railroad financier and speculator who attempted in 1869 to corner the gold market with Jay Gould, leading to Black Friday, a day of nationwide financial panic. AT. 2003. Hydroxylated PCBs and other chlorinated phenolic compounds in lake trout lake trout or Mackinaw trout or Great Lakes trout or salmon trout Large, voracious char (Salvelinus namaycush) found widely from northern Canada and Alaska to New England and the Great Lakes, usually in deep, cool lakes. (Salvelinus namaycush Noun 1. Salvelinus namaycush - large fork-tailed trout of lakes of Canada and the northern United States lake trout, salmon trout trout - any of various game and food fishes of cool fresh waters mostly smaller than typical salmons ) blood plasma blood plasma n. The yellow or gray-yellow, protein-containing fluid portion of blood in which the blood cells and platelets are normally suspended. from the Great Lakes region The Great Lakes region can refer to:
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Boca Raton is a popular resort and retirement community that experienced significant industrial development in the 1970s and 80s. , FL:CRC (Cyclical Redundancy Checking) An error checking technique used to ensure the accuracy of transmitting digital data. The transmitted messages are divided into predetermined lengths which, used as dividends, are divided by a fixed divisor. Press/Lewis Publishers. --. 2001. Introduction: PCB properties, uses, occurrence, and regulatory history. In: PCBs: Recent Advances in Environmental Toxicology and Health Effects (Robertson LW, Hansen LG, eds). Lexington, KY: The University Press of Kentucky The University Press of Kentucky (UPK) is the scholarly publisher for the Commonwealth of Kentucky, and was organized in 1969 as successor to the University of Kentucky Press. The university had sponsored scholarly publication since 1943. , xi-xxx. Frame GM, Cochran JW, Bowadt SS. 1996. Complete PCB congener distribution for 17 Aroclor mixtures determined by 3 HRGC HRGC High-Resolution Gas Chromatography HRGC Human Response to Global Change HRGC Human Resource Generalist Certification HRGC Hatyai Resort & Golf Club (Thailand) systems optimized for comprehensive, quantitative, congener-specific analysis. J High Resolut Chromatogr 19:657 668. Guitart R, Puig P, Gomez-Catalan J. 1993. Requirement for a standardized nomenclature criterium for PCBs: computer assisted assignment of correct congener denomination and number. Chemosphere 27:1451-1459, Guvenius DM, Hassanzadeh P, Bergman [Angstrom angstrom (ăng`strəm), abbr. Å, unit of length equal to 10−10 meter (0.0000000001 meter); it is used to measure the wavelengths of visible light and of other forms of electromagnetic radiation, such as ultraviolet ], Noren K. 2002. Metabolites of polychlorinated biphenyls in human liver and adipose tissue adipose tissue (ăd`əpōs'): see connective tissue. adipose tissue or fatty tissue Connective tissue consisting mainly of fat cells, specialized to synthesize and contain large globules of fat, within a . Environ Toxicol Chem 21:2264-2269, Haglund PS, Zook DR, Buser HR, Hu JW. 1997. Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota. Environ Sci Technol 31:3281-3287. Hakk H, Letcher RJ. 2003. Metabolism in the toxicokinetics and fate of brominated flame retardants (BFRs): a review. Environ Int 29:801-828. Hoekstra PF, Letcher RJ, O'Hara TM, Backus SM, Solomon KR, Muir DCG. 2003. Hydroxylated and methylsufone-containing metabolites of polychlorinated biphenyls in the plasma and blubber of bowhead whales (Balaena mysticetus). Environ Toxicol Chem 22:2650-2658. Hovander L, Malmberg T, Athanasiadou M, Athanassiadis I, Rahm S, Bergman A, et al. 2002. Identification of hydroxylated PCB metabolites and other phenolic halogenated halogenated pertaining to a substance to which a halogen is added. halogenated salicylanilides see rafoxanide, clioxanide. pollutants in human blood plasma. Arch Environ Contam Toxicol 42:105-117. Larsson C, Ellerichmann T, Huhnerfuss H, Bergman [Angstrom]. 2002. Chiral chi·ral adj. Of or relating to the structural characteristic of a molecule that makes it impossible to superimpose it on its mirror image. chi·ral PCB methyl sulfones in rat tissues after exposure to technical PCBs. Environ Sci Technol 36:2833-2838. Letcher RJ, Klasson-Wehler E, Bergman [Angstrom]. 2000a. Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. In: The Handbook of Environmental Chemistry 3K (Paasivirta J, ed). Berlin: Springer-Verlag, 315-359. Letcher RJ, Norstrom RJ, Bergman A. 1905. Geographical distribution the natural arrangements of animals and plants in particular regions or districts. See under Distribution. See also: Distribution Geographic and identification of methyl sulphone Sul´phone n. 1. (Chem.) Any one of a series of compounds analogous to the ketones, and consisting of the sulphuryl group united with two hydrocarbon radicals; as, dimethyl sulphone, (CH ) s>.SO . PCB and DDE (Dynamic Data Exchange) A message protocol in Windows that allows application programs to request and exchange data between them automatically. DDE - Dynamic Data Exchange metabolites in pooled polar bear polar bear, large white bear, Ursus maritimus, formerly Thalarctos maritimus, of the coasts of arctic North America. Polar bears usually live on drifting pack ice, but sometimes wander long distances inland. (Ursus maritimus) adipose tissue from Western hemisphere Western Hemisphere Part of Earth comprising North and South America and the surrounding waters. Longitudes 20° W and 160° E are often considered its boundaries. Arctic and subarctic sub·arc·tic adj. Of or resembling regions just south of the Arctic Circle. subarctic Relating to the geographic area just south of the Arctic Circle. regions. Sci Total Environ 160/161:409-420. Letcher RJ, Norstrom RJ, Muir DCG, Sandau CD, Koczanski K, Michaud R, et al. 2000b. Methylsulfone polychlorinated biphenyl polychlorinated biphenyl or PCB, any of a group of organic compounds originally widely used in industrial processes but later found to be dangerous environmental pollutants. and 2,2-bis(chlorophenyl)-1,1-dichloroethylene metabolites in beluga beluga (bəl `gə) or white whale, small, toothed northern whale, Delphinapterus leucas. The beluga may reach a length of 19 ft (5. whale
(Delphinapterus leucas Delphinapterus leucasa small 10 to 13 ft, 1000 to 1500 lb whale with a rounded head and no dorsal fin. A member of the family Monodontidae. Called also arctic dolphin, beluga whale, sea canary, white whale. ) from the St. Lawrence River Estuary and Western Hudson Bay Hudson Bay, inland sea of North America, c.475,000 sq mi (1,230,000 sq km), c.850 mi (1,370 km) long and c.650 mi (1,050 km) wide, E central Canada. Hudson Bay and James Bay (its southern extension) and all their islands border Nunavut Territory, Manitoba, Ontario, , Canada. Environ Toxicol Chem 19:1378-1388. Letcher RJ, van der Burg B, Brouwer A, Lemmen J, Bergman [Angstrom], van den Berg Van den Berg is the surname of:
in vi·tro adj. In an artificial environment outside a living organism. antiestrogenic effects of aryl ar·yl n. An organic radical derived from an aromatic compound by the removal of one hydrogen atom. methyl sulfone metabolites of polychlorinated biphenyls and 2,2-bis(4-chlorophenyl)-1,1-dichloroethylene on 17[beta]-estradiol-induced gene expression in several bioassay Bioassay A method for the quantitation of the effects on a biological system by its exposure to a substance, as well as the quantitation of the concentration of a substance by some observable effect on a biological system. systems. Toxicol Sci 69:362-372. Li H, Drouillard KG, Bennett E, Haffner GD, Letcher RJ. 2003. Plasma-associated halogenated phenolic contaminants in benthic ben·thos n. 1. The collection of organisms living on or in sea or lake bottoms. 2. The bottom of a sea or lake. [Greek. and pelagic pelagic living in the middle or near the surface of large bodies of water such as lakes or oceans. fish species from the Detroit River Detroit River River, southeastern Michigan, U.S. Forming part of the boundary between Michigan and Ontario, Can., it connects Lake St. Clair with Lake Erie. It flows south for 32 mi (51 km) past Detroit and Windsor, Ont., where a bridge and tunnel connect the two cities. . Environ Sci Technol 37:832-839. Meerts IATM IATM International Association of Tour Managers Ltd. IATM Intel Advanced Thermal Manager IATM It's All Too Much (Beatles song) , Letcher RJ, Hoving S, Marsh G, Bergman A, Lemmen JG, et al. 2001. In vitro estrogenicity of polybrominated diphenyl ethers, hydroxylated PBDEs, and polybrominated bisphenol A Bisphenol A is a chemical compound containing two phenol functional groups. It belongs to the phenol class of aromatic organic compounds. It is widely prepared and sold and various important polymers/plastics are made from it. compounds. Environ Health Perspect 109:399-407. Sandala GM, Sonne-Hansen C, Dietz R, Muir DCG, Valters K, Bennett ER, et al. In press. Methyl sulfone and hydroxylated PCB metabolites in adipose adipose /ad·i·pose/ (ad´i-pos) 1. fatty. 2. the fat present in the cells of adipose tissue. ad·i·pose adj. Of, relating to, or composed of animal fat; fatty. and whole blood of polar bear (Ursus maritimus) from East Greenland. Sci Total Environ. Sandau CD, Ayotte P, Dewailly E, Duffe J, Norstrom RJ. 2000a. Analysis of hydroxylated metabolites of PCBs (HO-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian Inuit. Environ Health Perspect 108:611416. --. 2002. Pentachlorophenol pentachlorophenol a wood preservative with great capacity to enter the body by any route, including percutaneously; causes weight loss, low milk production and general debility. and hydroxylated polychlorinated biphenyl metabolites in umbilical cord umbilical cord (ŭmbĭl`ĭkəl), cordlike structure about 22 in. (56 cm) long in the pregnant human female, extending from the abdominal wall of the fetus to the placenta. plasma of neonates from coastal populations in Quebec. Environ Health Perspect 110:411-417. Sandau CD, Meerts IATM, Letcher RJ, McAlees A J, Chittim B, Brouwer A, et al. 2000b. Identification of 4-hydroxyheptachlorostyrene in polar bear plasma and its binding affinity to transthyretin: a metabolite of octachlorostyrene? Environ Sci Technol 34:3671-3877. Schulte E, Malisch R. 1983. Berechnung der Vahren PCB-Gehalte in Umweltproben I. Ermittlung der Zusammensetzung Zweier Technischer PCB-Gemische. Fresenius J Anal Chem 314:545-551. Sjodin A, Tullsten AK, Klasson-Wehler E. 1998. Identification of the parent compounds to selectively retained hydroxylated PCB metabolites in rat blood plasma. Organohalogen Compounds 37:365-368, Stapleton HM, Letcher RJ, Baker JE. 2001. Metabolism of PCBs by the deepwater sculpin The deepwater sculpin (Myoxocephalus thompsoni) is a freshwater sculpin that inhabits the bottoms of cold, deep freshwater lakes of northern North America. Its distribution ranges from the Great Bear Lake of Canada to the Great Lakes. (Myoxocephalus thompsoni). Environ Sci Technol 35:4747-4752. U.S. Environmental Protection Agency. 2003. PCB ID--Table of PCB Congeners and Other Species. Washington, DC:Environmental Protection Agency. Available: http://www.epa.gov/toxteam/pcbid/table.htm [accessed 23 January 2004]. Valters K, Alaee M, Marsh G, D'Sa I, Li H, Bennett ER, et al. 2003. Polybrominated diphenyl ethers and hydroxylated and methoxylated analogues in Detroit River fish. Organohalogen Compounds 61:29-32. Weistrand C, Noren K. 1997. Methylsulfonyl metabolites of PCBs and DDE in human tissues. Environ Health Perspect 105:644-649. Johan Maervoet, (1) Adrian Covaci, (1) Paul Schepens, (1) Courtney D. Sandau, (2) and Robert J. Letcher (3) (1) Toxicological Center, University of Antwerp University of Antwerp (Dutch: Universiteit Antwerpen) is a university located in Antwerp, Belgium. History It was founded in 2003 after the merger of the three universities that were previously known as RUCA (State University Centre Antwerp), UFSIA (University Faculties , Wilrijk, Belgium; (2) Division of Laboratory Sciences, Centers for Disease Control and Prevention Centers for Disease Control and Prevention (CDC), agency of the U.S. Public Health Service since 1973, with headquarters in Atlanta; it was established in 1946 as the Communicable Disease Center. , Atlanta, Georgia, USA; (3) Great Lakes Great Lakes, group of five freshwater lakes, central North America, creating a natural border between the United States and Canada and forming the largest body of freshwater in the world, with a combined surface area of c.95,000 sq mi (246,050 sq km). Institute for Environmental Research, University of Windsor History In 2003, the university marked its 40th anniversary. Its history dates back to the founding of Assumption College in 1857. Originally, Assumption was one the largest colleges associated with the University of Western Ontario. , Windsor, Ontario Windsor is the southernmost city in Canada and lies at the western end of the heavily populated Quebec City-Windsor Corridor. Windsor is located directly south of Detroit and is separated from that city by the Detroit River. The city has views of the Detroit skyline. , Canada Address correspondence to J. Maervoet, Toxicological Center, University of Antwerp, Universiteitsplein 1, 2610 Wilrijk, Belgium. Telephone: 0032-3-820-2704. Fax: 0032-3-820-2722. E-mail: Johan.Maervoet@ua.ac.be Received 23 April 2003; accepted 3 December 2003. |
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