Martyniuk CJ, Mehinto AC, Denslow ND (2020) Organochlorine pesticides: agrochemicals with
potent endocrine-disrupting properties in fish. Mol Cell Endocrinol 507:110764
McBlain WA, Lewin V, Wolfe FH (1976) Differing estrogenic activities for the enantiomers of o,
p
0 -DDT in immature female rats. Can J Physiol Pharmacol 54(4):629–632
Mechelke J, Rust D, Jaeger A, Hollender J (2020) Enantiomeric fractionation during biotransformation of chiral pharmaceuticals in recirculating water-sediment test flumes. Environ Sci
Technol 54(12):7291–7301
Mehvar R, Brocks DR (2001) Stereospecific pharmacokinetics and pharmacodynamics of betaadrenergic blockers in humans. J Pharm Pharm Sci 4(2):185–200
Mineau P (1991) Cholinesterase-inhibiting insecticides: their impact on wildlife and the environment. Elsevier, New York
Miyazaki A, Hotta T, Marumo S, Sakai M (1978) Synthesis, absolute stereochemistry, and
biological activity of optically active cyclodiene insecticides. J Agric Food Chem 26
(4):975–977
Miyazaki A, Sakai M, Marumo S (1980) Synthesis and biological activity of optically active
heptachlor, 2-chloroheptachlor, and 3-chloroheptachlor. J Agric Food Chem 28(6):1310–1311
Miyazaki A, Nakamura T, Kawaradani M, Marumo S (1988) Resolution and biological-activity of
both enantiomers of methamidophos and acephate. J Agric Food Chem 36(4):835–837
Miyazaki A, Nakamura T, Marumo S (1989) Stereoselectivity in metabolic sulfoxidation of
propaphos and biological-activity of chiral propaphos sulfoxide. Pestic Biochem Physiol 33
(1):11–15
Mohan JC, Shah SN, Chinchansurkar S, Dey A, Jain R (2017) Rediscovering chirality—role of
S-metoprolol in cardiovascular disease management. J Assoc Physicians India 65(6):74–79
Möller K, Hühnerfuss H, Wölfle D (1996) Differential effects of the enantiomers of
α-hexachlorocyclohexane (α-HCH) on cytotoxicity and growth stimulation in primary rat
hepatocytes. Organohalogen Comp 29:4
Moody JD, Fu PP, Freeman JP, Cerniglia CE (2003) Regio- and stereoselective metabolism of 7,12dimethylbenz[a]anthracene by Mycobacterium vanbaalenii PYR-1. Appl Environ Microbiol 69
(7):3924–3931
Moriya M, Spiegel S, Fernandes A, Amin S, Liu T, Geacintov N, Grollman AP (1996) Fidelity of
translesional synthesis past benzo[a]pyrene diol epoxide-2
0 -deoxyguanosine DNA adducts:
marked effects of host cell, sequence context, and chirality. Biochemistry 35(51):16646–16651
Mullard A (2015) 2014 FDA drug approvals. Nat Rev Drug Discov 14(2):77–81
Munoz-Arnanz J, Jimenez B (2011) New DDT inputs after 30 years of prohibition in Spain. A case
study in agricultural soils from south-western Spain. Environ Pollut 159(12):3640–3646
National Toxicology Program (2010) Toxicology and carcinogenesis studies of 2,3
0 ,4,4
0 ,5pentachlorobiphenyl (PCB 118) (CAS No. 31508-00-6) in female harlan Sprague-Dawley rats
(gavage studies). Natl Toxicol Prog Tech Rep Ser (559):1–174
Nebert DW, Shi Z, Galvez-Peralta M, Uno S, Dragin N (2013) Oral benzo[a]pyrene: understanding
pharmacokinetics, detoxication, and consequences—Cyp1 knockout mouse lines as a paradigm.
Mol Pharmacol 84(3):304–313
Nillos MG, Gan J, Schlenk D (2010) Chirality of organophosphorus pesticides: analysis and
toxicity. J Chromatogr B Analyt Technol Biomed Life Sci 878(17-18):1277–1284
Niu L, Xu C, Zhang C, Zhou Y, Zhu S, Liu W (2017) Spatial distributions and enantiomeric
signatures of DDT and its metabolites in tree bark from agricultural regions across China.
Environ Pollut 229:111–118
Nunez MC, Garcia-Rubino ME, Conejo-Garcia A, Cruz-Lopez O, Kimatrai M, Gallo MA,
Espinosa A, Campos JM (2009) Homochiral drugs: a demanding tendency of the pharmaceutical industry. Curr Med Chem 16(16):2064–2074
Parezanovic GS, Lalic-Popovic M, Golocorbin-Kon S, Vasovic V, Milijasevic B, Al-Salami H,
Mikov M (2019) Environmental transformation of pharmaceutical formulations: a scientific
review. Arch Environ Contam Toxicol 77(2):155–161
300
10 Chirality in Environmental Toxicity and Fate Assessments
potent endocrine-disrupting properties in fish. Mol Cell Endocrinol 507:110764
McBlain WA, Lewin V, Wolfe FH (1976) Differing estrogenic activities for the enantiomers of o,
p
0 -DDT in immature female rats. Can J Physiol Pharmacol 54(4):629–632
Mechelke J, Rust D, Jaeger A, Hollender J (2020) Enantiomeric fractionation during biotransformation of chiral pharmaceuticals in recirculating water-sediment test flumes. Environ Sci
Technol 54(12):7291–7301
Mehvar R, Brocks DR (2001) Stereospecific pharmacokinetics and pharmacodynamics of betaadrenergic blockers in humans. J Pharm Pharm Sci 4(2):185–200
Mineau P (1991) Cholinesterase-inhibiting insecticides: their impact on wildlife and the environment. Elsevier, New York
Miyazaki A, Hotta T, Marumo S, Sakai M (1978) Synthesis, absolute stereochemistry, and
biological activity of optically active cyclodiene insecticides. J Agric Food Chem 26
(4):975–977
Miyazaki A, Sakai M, Marumo S (1980) Synthesis and biological activity of optically active
heptachlor, 2-chloroheptachlor, and 3-chloroheptachlor. J Agric Food Chem 28(6):1310–1311
Miyazaki A, Nakamura T, Kawaradani M, Marumo S (1988) Resolution and biological-activity of
both enantiomers of methamidophos and acephate. J Agric Food Chem 36(4):835–837
Miyazaki A, Nakamura T, Marumo S (1989) Stereoselectivity in metabolic sulfoxidation of
propaphos and biological-activity of chiral propaphos sulfoxide. Pestic Biochem Physiol 33
(1):11–15
Mohan JC, Shah SN, Chinchansurkar S, Dey A, Jain R (2017) Rediscovering chirality—role of
S-metoprolol in cardiovascular disease management. J Assoc Physicians India 65(6):74–79
Möller K, Hühnerfuss H, Wölfle D (1996) Differential effects of the enantiomers of
α-hexachlorocyclohexane (α-HCH) on cytotoxicity and growth stimulation in primary rat
hepatocytes. Organohalogen Comp 29:4
Moody JD, Fu PP, Freeman JP, Cerniglia CE (2003) Regio- and stereoselective metabolism of 7,12dimethylbenz[a]anthracene by Mycobacterium vanbaalenii PYR-1. Appl Environ Microbiol 69
(7):3924–3931
Moriya M, Spiegel S, Fernandes A, Amin S, Liu T, Geacintov N, Grollman AP (1996) Fidelity of
translesional synthesis past benzo[a]pyrene diol epoxide-2
0 -deoxyguanosine DNA adducts:
marked effects of host cell, sequence context, and chirality. Biochemistry 35(51):16646–16651
Mullard A (2015) 2014 FDA drug approvals. Nat Rev Drug Discov 14(2):77–81
Munoz-Arnanz J, Jimenez B (2011) New DDT inputs after 30 years of prohibition in Spain. A case
study in agricultural soils from south-western Spain. Environ Pollut 159(12):3640–3646
National Toxicology Program (2010) Toxicology and carcinogenesis studies of 2,3
0 ,4,4
0 ,5pentachlorobiphenyl (PCB 118) (CAS No. 31508-00-6) in female harlan Sprague-Dawley rats
(gavage studies). Natl Toxicol Prog Tech Rep Ser (559):1–174
Nebert DW, Shi Z, Galvez-Peralta M, Uno S, Dragin N (2013) Oral benzo[a]pyrene: understanding
pharmacokinetics, detoxication, and consequences—Cyp1 knockout mouse lines as a paradigm.
Mol Pharmacol 84(3):304–313
Nillos MG, Gan J, Schlenk D (2010) Chirality of organophosphorus pesticides: analysis and
toxicity. J Chromatogr B Analyt Technol Biomed Life Sci 878(17-18):1277–1284
Niu L, Xu C, Zhang C, Zhou Y, Zhu S, Liu W (2017) Spatial distributions and enantiomeric
signatures of DDT and its metabolites in tree bark from agricultural regions across China.
Environ Pollut 229:111–118
Nunez MC, Garcia-Rubino ME, Conejo-Garcia A, Cruz-Lopez O, Kimatrai M, Gallo MA,
Espinosa A, Campos JM (2009) Homochiral drugs: a demanding tendency of the pharmaceutical industry. Curr Med Chem 16(16):2064–2074
Parezanovic GS, Lalic-Popovic M, Golocorbin-Kon S, Vasovic V, Milijasevic B, Al-Salami H,
Mikov M (2019) Environmental transformation of pharmaceutical formulations: a scientific
review. Arch Environ Contam Toxicol 77(2):155–161
300
10 Chirality in Environmental Toxicity and Fate Assessments