Comparative Evaluation of Chelating Agents on the Mobilization of Cadmium: A Mechanistic Approach

Srivastava, R.C.; Gupta, Sanjay; Ahmad, Nihal; Hasan, Syed Kazim; Farookh, Aziz; Husain, Maroof

doi:10.1080/009841096161870

Cited by 11 publications

(1 citation statement)

References 18 publications

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“…The mercapto compounds include DLpenicillamine (DL-PA) and meso-2,3-dimercaptosuccinic acid (DMSA) (3). Most of these chelating agents have side effects, such as poor selectivity, high toxicity, and weak ability to cross the cellular membrane (4)(5)(6)(7)(8)(9)(10). As a result, it greatly limits their therapeutic effects on lead poisoning.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Pentahydroxylhexylamino Acids and Their Effect on Lead Decorporation

Wang

Hou

et al. 2007

Chem. Res. Toxicol.

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A series of enantiopure pentahydroxylhexylamino acids 4a-t were synthesized via an improved one-pot-three-step procedure. Their potential as antagonists for lead intoxication was investigated both in vitro and in vivo. Lead decorporation assays in vivo confirmed that after treatment with 4a-t, the levels of lead in treated mice were significantly reduced in the liver, kidney, bone, and brain compared to those in the control group. In addition, the lead levels in feces and urine were significantly higher after treatment with 4a-t than those of the control group. In particular, the lead decorporation potency of compounds 4b, 4i, 4j, and 4s were comparable or better than that of dl-penicillamine. Furthermore, new chelating agents did not affect the levels of endogenous essential metals. The stability constants of the formed lead complexes of 4a-t were determined by potentiometric titration. It seems that the therapeutic efficiency of the lead chelating agents depends on factors that affect the stability constants of the formed lead complexes. The membrane permeability of representative compounds was evaluated in a Caco-2 cell monolayer. A good correlation between in vitro results and in vivo lead decorporation capacity of the chelating agents was observed. Some of these new pentahydroxylhexylamino acids (4b, 4i, 4j, and 4s) may be developed as effective lead chelating agents.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Pentahydroxylhexylamino Acids and Their Effect on Lead Decorporation

Wang

Hou

et al. 2007

Chem. Res. Toxicol.

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In vitro toxicity of several dithiocarbamates and structure–activity relationships

Segovia

Crovetto

Lardelli

et al. 2002

J of Applied Toxicology

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Dithiocarbamates (DTCs) are chemicals featuring a great chelating capacity. The toxicological study of DTCs is very important in view of their relatively simple synthesis and wide array of sanitary and industrial applications. In this study, the toxicity of some of the more recently synthesized DTCs is determined using an extremely simple bioassay, described in previous studies, based on the inhibition of growth of Escherichia coli (IGEC). The lowest-observed-effect concentration (LOEC), the median effective concentration (EC(50)) and no-observed-effect concentration (NOEC) of the following sodium dithiocarbamates was determined: N-benzyl-N-methyldithiocarbamate x 2H(2)O, N-benzyl-N-isopropyldithiocarbamate x 3H(2)O, N-benzyl-N-ethyldithiocarbamate x 2H(2)O, N-butyl-N-methyldithiocarbamate x 2H(2)O, N,N-dibenzyldithiocarbamate x 2H(2)O and N-benzyl-2-phenethyldithiocarbamate x 4H(2)O. Our results showed N,N-dibenzyl-DTC to be the least toxic of the tested substances, with an EC(50) value of 1,269.9 micro g ml(-1), whereas N-butyl-N-methyl-DTC and N-benzyl-N-methyl-DTC, with respective EC(50) values of 14.9 micro g ml(-1) and 23.5 micro g ml(-1), were the most toxic. Regression analysis showed, through exponential models, that the degree of toxicity of this group of substances correlated with the molecular weight of the compound, the molecular weight of the smallest chemical radical linked to the dithiocarbamate group and the number of benzene rings present in the molecule. The consideration of these models allows us to establish that in general terms the toxicity of DTCs decreases exponentially with a greater molecular weight and the number of benzene rings.

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Cadmium

Meulenbelt¹

2017

Critical Care Toxicology

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Comparative Evaluation of Chelating Agents on the Mobilization of Cadmium: A Mechanistic Approach

Cited by 11 publications

References 18 publications

Design and Synthesis of Pentahydroxylhexylamino Acids and Their Effect on Lead Decorporation

Design and Synthesis of Pentahydroxylhexylamino Acids and Their Effect on Lead Decorporation

In vitro toxicity of several dithiocarbamates and structure–activity relationships

Cadmium

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