Stereoselective determination of allethrin by two-dimensional achiral/chiral liquid chromatography with ultraviolet/circular dichroism detection

Mancini, F.; Fiori, Jessica; Bertucci, Carlo; Cavrini, Vanni; Bragieri, M.; Zanotti, M.; Liverani, Alessandra; Borzatta, Valerio; Andrisano, Vicenza

doi:10.1016/s0021-9673(04)01023-4

Cited by 19 publications

(12 citation statements)

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“…Mancini et al (2004) separated cis/trans isomers from each other on an achiral silica HPLC column using n-hexane:tert-butyl methyl ether (96:4) (v/v) as the mobile phase (Table C1, Appendix C). The trans isomers were separated (G, H, A, B, respectively) from each other on a CHIRAL-CEL OJ using nhexane-tert-butyl methyl ether (90:10) (v/v).…”

Section: Analytical Methods For Pyrethroid Isomersmentioning

confidence: 99%

Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment

Knaak

Dary²,

Zhang

et al. 2012

Reviews of Environmental Contamination and Toxicology

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In this review we have examined the status of parameters required by pyrethroid QSAR-PBPK/PD models for assessing health risks. In lieu of the chemical,biological, biochemical, and toxicological information developed on the pyrethroids since 1968, the finding of suitable parameters for QSAR and PBPK/PD model development was a monumental task. The most useful information obtained came from rat toxicokinetic studies (i.e., absorption, distribution, and excretion), metabolism studies with 14C-cyclopropane- and alcohol-labeled pyrethroids, the use of known chiral isomers in the metabolism studies and their relation to commercial products. In this review we identify the individual chiralisomers that have been used in published studies and the chiral HPLC columns available for separating them. Chiral HPLC columns are necessary for isomer identification and for developing kinetic values (Vm,, and Kin) for pyrethroid hydroxylation. Early investigators synthesized analytical standards for key pyrethroid metabolites, and these were used to confirm the identity of urinary etabolites, by using TLC. These analytical standards no longer exist, and muste resynthesized if further studies on the kinetics of the metabolism of pyrethroids are to be undertaken.In an attempt to circumvent the availability of analytical standards, several CYP450 studies were carried out using the substrate depletion method. This approach does not provide information on the products formed downstream, and may be of limited use in developing human environmental exposure PBPK/PD models that require extensive urinary metabolite data. Hydrolytic standards (i.e., alcohols and acids) were available to investigators who studied the carboxylesterase-catalyzed hydrolysis of several pyrethroid insecticides. The data generated in these studies are suitable for use in developing human exposure PBPK/PD models.Tissue:blood partition coefficients were developed for the parent pyrethroids and their metabolites, by using a published mechanistic model introduced by Poulin and Thiele (2002a; b) and log DpH 7.4 values. The estimated coefficients, especially those of adipose tissue, were too high and had to be corrected by using a procedure in which the proportion of parent or metabolite residues that are unbound to plasma albumin is considered, as described in the GastroPlus model (Simulations Plus, Inc.,Lancaster, CA). The literature suggested that Km values be adjusted by multiplying Km by the substrate (decimal amount) that is unbound to microsomal or CYPprotein. Mirfazaelian et al. (2006) used flow- and diffusion-limited compartments in their deltamethrin model. The addition of permeability areas (PA) having diffusion limits, such as the fat and slowly perfused compartments, enabled the investigators to bring model predictions in line with in vivo data.There appears to be large differences in the manner and rate of absorption of the pyrethroids from the gastrointestinal tract, implying that GI advanced compartmental transit models (ACAT) need to be included in PBPK mo...

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Section: Analytical Methods For Pyrethroid Isomersmentioning

confidence: 99%

Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment

Knaak

Dary²,

Zhang

et al. 2012

Reviews of Environmental Contamination and Toxicology

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“…4 showed, 8 isomers of cypermethrin and cyfluthrin were separated, and the separation method was used to analysis the isomers of cypermethrin in pork samples The following Table 2 is made for the summary. (Maguire, 1990) cypermethrin Daicel chiracel OD 6 peaks (Edwards et al, 1997) cypermethrin Glycine Derivative I~II 8 peaks (Naobumi et al, 1990 ) phenothrin 10% QF-1 Sumipax OA-2000 6peaks (Doi et al, 1985) deltamethrin RP-8/Lichrosorb Si-60 1 peaks (Mourot et al, 1979) cypermethrin Pirkle type Amino column 5 peaks cyfluthrin Dupont zorbax 5 peaks (Tephem et al, 1990) cypermethrin Sumichiral OA-2500-I, Chirex DOG-3019-DO 4 peaks cis-permethrin, transpermethrin Sumichiral OA-2500-I each 2 peaks fenvalerate Pirkle I-A 4peaks (Cayley & Simpson, 1986) fenvalerate Brush-type chiral stationary phase 4peaks (Lee et al, 1987) permethrin Brush-type ligand exchange chiral stationary phase 4peaks (Dondi et al, 1999) tetramethrin OA-4700 pirkle column and -cyclodextrin 4peaks (Deng, 2004) prallethrin, Bioallethrin, prallethrin, cyphenothrin Cellulose each 2peaks (Xu, 2003) cis-bifenthrin (BF)，permethrin (PM) Sumichiral OA-2500-I BF-2peaks, PM-2peaks cypermethrin、cyfluthrin Chirex 00G-3019-OD column 8 peaks (Mancini et al, 2004) fenpropathrin，beta-cypermethrin Chiralcel CD each 2 peaks S, R-bioallethrin -cyclodextrin as chiral additive, C8 column 2 peaks cis-cypermethrin ，trans-cypermethrin Cellulose-tris(3,5-dimethylphenylcarbamate) each 2peaks (Wang, 2006) cypermethrin Supelcosil LC-CN column coupled with Chiralcel OD-H 7 peaks (Ta et al, 2006) cis-cypermethrin Chiralcel CD column 2 peaks (Edwards et al, 1987 ) bifenthrin and fenpropathrin…”

Section: Methods Of Chiral Liquid Chromatographic Separation Of Pyrethmentioning

confidence: 99%

Separation of Chiral Pyrethroid Pesticides and Application in Pharmacokinetics Research and Human Exposure Assessment

Wu¹,

Mei²,

Fan³

2011

Pesticides in the Modern World - Effects of Pesticides Exposure

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“…(), Mancini et al . () and Dugo et al . () coupled a cellulose tris‐(3,5‐dimethylphenylcarbamate) CSP to a silica column using isocratic elution for both dimensions with mixtures of n ‐hexane and isopropanol for separations of fenvalerate and citrus essential oils enantiomers, respectively (Table and Table ).…”

Section: Multidimensional Liquid Chromatography In Chiral Analysismentioning

confidence: 97%

Two‐dimensional liquid chromatography for direct chiral separations: a review

León-González

Rosales-Conrado

Pérez-Arribas

et al. 2013

Biomedical Chromatography

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Separation of enantiomers remains a challenge owing to their identical physical and chemical properties in an achiral environment, and research on specialized separation techniques such as multidimensional achiral-chiral liquid chromatography continues to resolve individual enantiomers in complex samples. Recent advances in application of multidimensional liquid chromatography applied to chiral analysis are reviewed. For this reason, benefits of achiral-chiral coupling are shown, with emphasis in applications on biological and pharmaceutical fields as well as pesticide analysis. A description of standard instrumental setup in both heart-cut and comprehensive multidimensional liquid chromatography is shown. The most broadly used chiral stationary phases for multidimensional liquid chromatography are summarized. An extensive overview of different interface designs applied to complex samples is presented.

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Stereoselective determination of allethrin by two-dimensional achiral/chiral liquid chromatography with ultraviolet/circular dichroism detection

Cited by 19 publications

References 0 publications

Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment

Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment

Separation of Chiral Pyrethroid Pesticides and Application in Pharmacokinetics Research and Human Exposure Assessment

Two‐dimensional liquid chromatography for direct chiral separations: a review

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