Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers

Berkman, Clifford E.; Thompson, Charles M.; Perrin, Scott R.

doi:10.1021/tx00035a018

Cited by 42 publications

(37 citation statements)

References 15 publications

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“…The absolute configuration of (1)-malathion can be assigned as (R)-malathion from the VCD analysis and corresponds to the reference assignment. 1 The mean absolute deviation (MAD) of B3LYP/6-31G(d)//B3LYP/6-31G(d) was reported as 7.9 kcal mol…”

Section: E176mentioning

confidence: 99%

Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: Absolute configuration and solution conformation of a chiral liquid pesticide, (R)‐(+)‐malathion

et al. 2009

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The absolute configuration and solution conformation of (R)-(1)-malathion were determined by using vibrational circular dichroism spectroscopy and a fragment-conformational search with a recently published conformational code. The determination of molecular stereochemistry was carried out without a conformational search using molecular mechanics calculations. Density functional theory calculations of the fragments of (R)-malathion, ethyl propionate, (R)-ethyl 2-(methylthio)propanoate, (R)-diethyl 2-(methylthio)succinate, and O,O,S-trimethyl phosphorodithioate were carried out, and the principal conformational features of the fragments were profiled. This fragment-conformational search reduces the time needed for the selection of the predominant conformations for (R)-malathion and significantly improves the accuracy of the determination of absolute configuration.

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Section: E176mentioning

confidence: 99%

Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: Absolute configuration and solution conformation of a chiral liquid pesticide, (R)‐(+)‐malathion

et al. 2009

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“…Malathion used in the present study is a commercial grade product and may contain impurities formed during manufacturing and storage. Among the impurities are malaoxon formed from malathion by oxidation and isomalathion formed by isomerisation (Berkman et al, 1993). Malaoxon and isomalathion have been reported to be mutagenic (Flessel et al, 1993;Pluth et al, 1996;Blasiak et al, 1999).…”

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confidence: 99%

Application of primary haemocyte culture of Penaeus monodon in the assessment of cytotoxicity and genotoxicity of heavy metals and pesticides

Jose

Puthumana

Mohandas

et al. 2011

Marine Environmental Research

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a b s t r a c tLack of shrimp cell lines has hindered the study of pollutants which adversely affects shrimp health and its export value. In this context a primary haemocyte culture developed from Penaeus monodon was employed for assessing the cytotoxicity and genotoxicity of two heavy metal compounds, cadmium chloride and mercuric chloride and two organophosphate insecticides, malathion and monocrotophos.Using MTT assay 12 h IC 50 values calculated were 31.09 AE 16.27 mM and 5.52 AE 1.16 mM for cadmium chloride and mercuric chloride and 59.94 AE 52.30 mg l À1 and 186.76 AE 77.00 mg l À1 for malathion and monocrotophos respectively. Employing Comet assay, DNA damage inflicted by these pollutants on haemocytes were evaluated and the pollutants induced DNA damage in >60% of the cells. The study suggested that haemocyte culture could be used as a tool for quantifying cytotoxicity and genotoxicity of aquaculture drugs, management chemicals and pollutants.

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“…Technical grade malathion usually contains impurities like phosphorus thionates, iso-malathion and malaoxon formed during manufacture and storage [Berkman et al, 1993]. Malaoxon and iso-malathion have been reported to be mutagenic [Blasiak et al, 1999].…”

Section: Discussionmentioning

confidence: 99%

Malathion and fenvalerate induce micronuclei in mouse bone marrow cells

Giri

Sharma

2011

Environ. Mol. Mutagen.

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Health effects of pesticides are a major public health concern. In this study, the genotoxic effects of two commonly-used pesticides, malathion, and fenvalerate, were investigated in mice in vivo. Induction of micronuclei in bone marrow cells was used as the test parameter following exposure to 2.5, 5 or 10 mg/kg malathion by intraperitoneal (i.p.) or per oral (p.o.) exposure. Exposure by both routes was found to cause a significant increase in micronucleated polychromatic erythrocytes (PCEs) in a dose-dependent manner (r = 0.9769; P < 0.05). The highest dose (10 mg/kg) induced significant (P < 0.05) cytotoxicity. In contrast, fenvalerate caused an increase in micronucleated PCEs only at higher doses (10 and 20 mg/kg) via i.p. injection, and was not associated with cytotoxicity. A significant dose-response correlation was not observed in the dose ranges tested for fenvalerate (r = 0.8704; P > 0.05). The results suggest that technical grade malathion is a genotoxic agent. In contrast, technical grade fenvalerate appears to be a potent genotoxic agent, but this observation should be confirmed with further investigation(s).

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Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers

Cited by 42 publications

References 15 publications

Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: Absolute configuration and solution conformation of a chiral liquid pesticide, (R)‐(+)‐malathion

Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: Absolute configuration and solution conformation of a chiral liquid pesticide, (R)‐(+)‐malathion

Application of primary haemocyte culture of Penaeus monodon in the assessment of cytotoxicity and genotoxicity of heavy metals and pesticides

Malathion and fenvalerate induce micronuclei in mouse bone marrow cells

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