The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

Abstract

The crystal structure of PCB 77 (3,3′,4,4′-tetrachlorobiphenyl, C 12 H 6 Cl 4 ), a dioxin-like PCB congener, is described. The dihedral angle of PCB 77 is 43.94(6)°, which is slightly larger than calculated or experimental dihedral angles of biphenyl derivatives in solution but smaller than experimental dihedral angles in the gas phase.

PCB congeners induced mitochondrial dysfunction in Vero cells

“…Their high lipophilicity has resulted in bioaccumulation in various organisms through the food chain, and many PCB congeners have been detected in human blood, milk, and other tissues [1,2]. PCBs consist of up to 209 different congeners, and the biological effects and toxicity of individual congener greatly depend on its structure [3,4]. Congeners with one or no chlorine substituent in the ortho positions may assume a planar configuration, with a pattern of toxicity similar to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD).…”

Improved syntheses of non-dioxin-like polychlorinated biphenyls (PCBs) and some of their sulfur-containing metabolites

“…To add to the number of available structures, we herein describe the molecular structure of two additional PXR agonists, PCB 47 and PCB 184, in the solid state (Figure 1). Of particular interest is the dihedral angle as an important determinant of the biological activities of PCBs (Lehmler et al, 2002; Shaikh et al, 2008). PCB 47 ( 3e ) had a solid state dihedral angles of 61.0°, whereas the dihedral angle for PCB 184 ( 3p ) was significantly larger with 86.05(16)° and 86.64(16)° for the two molecules in the asymmetric unit.…”

“…PCBs were manufactured by batch chlorination of biphenyl and have been released into the environment as complex mixtures containing a large number of structurally different compounds with the general structure C 12 H n Cl 10-n , with n = 0 to 9. The biological effects and toxicity of individual PCB congeners greatly depend on their structure, which is largely determined by the number of chlorines atoms and their substitution pattern (Lehmler et al, 2002; Shaikh et al, 2008). For example, PCB congeners with zero or one ortho chlorine substituent are frequently referred to a dioxin-like PCB congeners because they have a high affinity for the aryl hydrocarbon receptor (Bandiera et al, 1982) and, like 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), induce cytochrome P450 (CYP) 1A enzymes.…”

2,2′,5′,6-Tetrachloro-4-[(1S)-1-methylpropoxy]biphenyl

“…Slightly larger (84-87°) dihedral angles have been observed for PCB derivatives with four ortho chlorine substituents (Pedersen, 1975;Singh & McKinney, 1979). Smaller solid state dihedral angles have been reported for PCB derivatives with zero, one or two ortho chlorine substituents due to the smaller steric demand of multiple hydrogen substituents in ortho position (Mannila & Rissanen, 1994;Miao et al, 1996;Rissanen et al, 1988a;Shaikh et al, 2008;Singh et al, 1986;van der Sluis et al, 1990;Vyas et al, 2006).…”

“…For crystal structures of PCB derivatives with two or less ortho chlorine substituents, see: Mannila & Rissanen (1994); Miao et al (1996); Rissanen et al (1988a); Shaikh et al (2008); Singh et al (1986); van der Sluis et al (1990); Vyas et al (2006). For crystal structures of PCB derivatives with three ortho chlorine substituents, see: Lehmler et al (2005); Rissanen et al (1988b).…”