bind to butyrylcholinesterase with the following relative affinity for the more toxic
stereoisomers (CÀPÀ > C+PÀ > CÀP+ > C+P+), while soman enantiomers bind
to human serum albumin and paraoxonase 1 with a relative affinity for the less toxic
isomers (CÀP+/C+P+ > C+PÀ/CÀPÀ).
A list of updated enantiomer-selective studies on soman toxicity is provided for
the interested reader (Benschop et al. 1984; de Jong and Wolring 1984; De Jong et al.
1993; Amitai et al. 2006; Kovacic and Somanathan 2008).
Miyazaki et al. (1988, 1989) reported the enantioselective toxicity of propaphos
((4-methylsulfinylphenyl) dipropyl phosphate), acetaphate (N-[methoxy
(methylsulfanyl)phosphoryl]acetamide)
and
methamidophos
([amino
(methylsulfanyl)phosphoryl]oxymethane). The authors described that the (+)enantiomers of those compounds showed stronger influences on houseflies than
their optical counter parts. By contrast, the respective (–)-enantiomers were reported
to be more poisonous to German cockroach (Blattella germanica).
Due to the inherent neurotoxicity of organophosphorus compounds, the toxic
effects of modern organophosphorus pesticides have been subject of in-depth examination. Recently, several research groups reported enantioselective toxicity for a
variety of organophosphorus pesticides. For a comprehensive view, please consult
the here provided reference list (Liu et al. 2010; Nillos et al. 2010; Segall 2011;
Wang et al. 2013a, b; Zhang and Wang 2013; Cai et al. 2014; Xu et al. 2017; Gao
et al. 2019a, b) and several monographs on this topic (Mineau 1991; Smith 1993;
Carpanini and European Centre for Ecotoxicology and Toxicology of Chemicals.
1998; Karalliedde 2001; Gupta 2006; Wilkinson 2016).
10.2.5 Polycyclic Aromatic Hydrocarbons
Numerous chiral polycyclic aromatic hydrocarbon (PAH) derivatives are contaminating the environment. Such compounds are mainly released from petroleum
production activities (Frysinger et al. 2003). It is generally assumed that chirality
requires a three-dimensional structure (see Chaps. 1 and 2). This seems to be in
contrast to the planar structural condition required for aromatic hydrocarbons.
However, if side chains are asymmetrically substituted, enantioselective structures
will play a role in the characterisation of the molecular properties.
For example, the toxic PAH derivatives anthracene, β-naphthoflavone, benzo
(a)pyrene and their transformation pathways were investigated with regard to
enantioselective effects. The toxicity of prochiral PAH derivatives is well-known,
but merely few papers are existing on the enantioselective toxicity of their transformation products (Yang et al. 2006; Sun et al. 2009; Hochalter et al. 2011; Dai et al.
2015). Benzo[a]pyrene (BaP) is widely distributed in the environment with mutagenic, carcinogenic and cytotoxic effects (Lijinsky 1991; Zapponi et al. 1997;
Hylland 2006; Younglai et al. 2007; Nebert et al. 2013; Zheng et al. 2017;
Balasubramanian et al. 2020). The prochiral BaP is metabolised with high stereospecificity by enzymes in liver microsomes (Huberman et al. 1976; Thakker et al.
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stereoisomers (CÀPÀ > C+PÀ > CÀP+ > C+P+), while soman enantiomers bind
to human serum albumin and paraoxonase 1 with a relative affinity for the less toxic
isomers (CÀP+/C+P+ > C+PÀ/CÀPÀ).
A list of updated enantiomer-selective studies on soman toxicity is provided for
the interested reader (Benschop et al. 1984; de Jong and Wolring 1984; De Jong et al.
1993; Amitai et al. 2006; Kovacic and Somanathan 2008).
Miyazaki et al. (1988, 1989) reported the enantioselective toxicity of propaphos
((4-methylsulfinylphenyl) dipropyl phosphate), acetaphate (N-[methoxy
(methylsulfanyl)phosphoryl]acetamide)
and
methamidophos
([amino
(methylsulfanyl)phosphoryl]oxymethane). The authors described that the (+)enantiomers of those compounds showed stronger influences on houseflies than
their optical counter parts. By contrast, the respective (–)-enantiomers were reported
to be more poisonous to German cockroach (Blattella germanica).
Due to the inherent neurotoxicity of organophosphorus compounds, the toxic
effects of modern organophosphorus pesticides have been subject of in-depth examination. Recently, several research groups reported enantioselective toxicity for a
variety of organophosphorus pesticides. For a comprehensive view, please consult
the here provided reference list (Liu et al. 2010; Nillos et al. 2010; Segall 2011;
Wang et al. 2013a, b; Zhang and Wang 2013; Cai et al. 2014; Xu et al. 2017; Gao
et al. 2019a, b) and several monographs on this topic (Mineau 1991; Smith 1993;
Carpanini and European Centre for Ecotoxicology and Toxicology of Chemicals.
1998; Karalliedde 2001; Gupta 2006; Wilkinson 2016).
10.2.5 Polycyclic Aromatic Hydrocarbons
Numerous chiral polycyclic aromatic hydrocarbon (PAH) derivatives are contaminating the environment. Such compounds are mainly released from petroleum
production activities (Frysinger et al. 2003). It is generally assumed that chirality
requires a three-dimensional structure (see Chaps. 1 and 2). This seems to be in
contrast to the planar structural condition required for aromatic hydrocarbons.
However, if side chains are asymmetrically substituted, enantioselective structures
will play a role in the characterisation of the molecular properties.
For example, the toxic PAH derivatives anthracene, β-naphthoflavone, benzo
(a)pyrene and their transformation pathways were investigated with regard to
enantioselective effects. The toxicity of prochiral PAH derivatives is well-known,
but merely few papers are existing on the enantioselective toxicity of their transformation products (Yang et al. 2006; Sun et al. 2009; Hochalter et al. 2011; Dai et al.
2015). Benzo[a]pyrene (BaP) is widely distributed in the environment with mutagenic, carcinogenic and cytotoxic effects (Lijinsky 1991; Zapponi et al. 1997;
Hylland 2006; Younglai et al. 2007; Nebert et al. 2013; Zheng et al. 2017;
Balasubramanian et al. 2020). The prochiral BaP is metabolised with high stereospecificity by enzymes in liver microsomes (Huberman et al. 1976; Thakker et al.
286
10 Chirality in Environmental Toxicity and Fate Assessments