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A reassessment of the nomenclature of polychlorinated biphenyl (PCB) metabolites.


Polychlorinated biphenyls polychlorinated biphenyls, (pol´ēklôr´nā´tid bīfē´n  (PCBs) are a widespread class of persistent organic chemicals that accumulate in the environment and humans and are associated with a broad spectrum of health effects. PCB PCB: see polychlorinated biphenyl.
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.

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Part of Earth comprising North and South America and the surrounding waters. Longitudes 20° W and 160° E are often considered its boundaries.
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Of or resembling regions just south of the Arctic Circle.



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Letcher RJ, van der Burg B, Brouwer A, Lemmen J, Bergman [Angstrom], van den Berg Van den Berg is the surname of:
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[Greek.
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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.
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Meerts IATM IATM International Association of Tour Managers Ltd.
IATM Intel Advanced Thermal Manager
IATM It's All Too Much (Beatles song) 
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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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Title Annotation:Commentary
Author:Letcher, Robert J.
Publication:Environmental Health Perspectives
Date:Mar 1, 2004
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