Mammalian Toxicity of Organic Compounds of Bromine and Iodine

DePierre, Joseph W.

doi:10.1007/978-3-540-37055-0_3

Cited by 11 publications

(11 citation statements)

References 254 publications

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“…All reactions were conducted under argon or nitrogen atmosphere, unless otherwise specified. Compounds 5i , 19 5l , 20 5o and 5p 21 were previously reported.…”

Section: Methodsmentioning

confidence: 94%

An investigation of phenylthiazole antiflaviviral agents

Mayhoub

Khaliq

Botting

et al. 2011

Bioorganic & Medicinal Chemistry

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Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono- or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147).

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“…All reactions were conducted under argon or nitrogen atmosphere, unless otherwise specified. Compounds 5i , 19 5l , 20 5o and 5p 21 were previously reported.…”

Section: Methodsmentioning

confidence: 94%

An investigation of phenylthiazole antiflaviviral agents

Mayhoub

Khaliq

Botting

et al. 2011

Bioorganic & Medicinal Chemistry

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“…Natural and man-made halogenated organic compounds have widespread applications in various industrial ventures as well as solvents in daily household items making them a significant class of environmental pollutants [ 1 , 2 , 3 , 4 , 5 ]. These halogenated compounds are of significant prominence in the marine ecosystem [ 6 ], and the extraordinary stability of the chemical bonds in these compounds makes their widespread occurrence mostly in the biosphere a persistent environmental concern.…”

Section: Introductionmentioning

confidence: 99%

Dehalogenases: From Improved Performance to Potential Microbial Dehalogenation Applications

et al. 2018

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The variety of halogenated substances and their derivatives widely used as pesticides, herbicides and other industrial products is of great concern due to the hazardous nature of these compounds owing to their toxicity, and persistent environmental pollution. Therefore, from the viewpoint of environmental technology, the need for environmentally relevant enzymes involved in biodegradation of these pollutants has received a great boost. One result of this great deal of attention has been the identification of environmentally relevant bacteria that produce hydrolytic dehalogenases—key enzymes which are considered cost-effective and eco-friendly in the removal and detoxification of these pollutants. These group of enzymes catalyzing the cleavage of the carbon-halogen bond of organohalogen compounds have potential applications in the chemical industry and bioremediation. The dehalogenases make use of fundamentally different strategies with a common mechanism to cleave carbon-halogen bonds whereby, an active-site carboxylate group attacks the substrate C atom bound to the halogen atom to form an ester intermediate and a halide ion with subsequent hydrolysis of the intermediate. Structurally, these dehalogenases have been characterized and shown to use substitution mechanisms that proceed via a covalent aspartyl intermediate. More so, the widest dehalogenation spectrum of electron acceptors tested with bacterial strains which could dehalogenate recalcitrant organohalides has further proven the versatility of bacterial dehalogenators to be considered when determining the fate of halogenated organics at contaminated sites. In this review, the general features of most widely studied bacterial dehalogenases, their structural properties, basis of the degradation of organohalides and their derivatives and how they have been improved for various applications is discussed.

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“…The widespread use of bromoaromatic compounds as flame retardants, pesticides, dyes or rubber additives and intermediates in the polymer industry ( DePierre, 2003 ), has led to their accumulation in the environment. Their chemical inertness and hydrophobicity as well as their persistence and toxicity, has led to a severe concern about their environmental fate ( Puzyn et al, 2011 ).…”

Section: Introductionmentioning

confidence: 99%

“…Bromobenzene (BrB) is a poorly soluble, hydrophobic organic compound listed as a priority environmental and marine pollutant and is a known hepatotoxic agent apart from having mutagenic, teratogenic, and carcinogenic effects ( Darnerud, 2003 ; DePierre, 2003 ). It is used for synthesis in the production of phenyl magnesium bromide, additive in the motor oils and as a solvent in crystallization.…”

Section: Introductionmentioning

confidence: 99%

Phenol Is the Initial Product Formed during Growth and Degradation of Bromobenzene by Tropical Marine Yeast, Yarrowia lipolytica NCIM 3589 via an Early Dehalogenation Step

2017

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Bromobenzene (BrB), a hydrophobic, recalcitrant organic compound, is listed by the environmental protection agencies as an environmental and marine pollutant having hepatotoxic, mutagenic, teratogenic, and carcinogenic effects. The tropical marine yeast Yarrowia lipolytica 3589 was seen to grow aerobically on BrB and displayed a maximum growth rate (μmax) of 0.04 h-1. Furthermore, we also observed an increase in cell size and sedimentation velocity for the cells grown on BrB as compared to the glucose grown cells. The cells attached to the hydrophobic bromobenzene droplets through its hydrophobic and acid–base interactions. The BrB (0.5%, 47.6 mM) was utilized by the cells with the release of a corresponding amount of bromide (12.87 mM) and yielded a cell mass of 1.86 g/L after showing 34% degradation in 96 h. Maximum dehalogenase activity of 16.16 U/mL was seen in the cell free supernatant after 24 h of growth. Identification of metabolites formed as a result of BrB degradation, namely, phenol, catechol, cis, cis muconic acid, and carbon dioxide were determined by LC–MS and GC–MS. The initial attack on bromobenzene by Y. lipolytica cells lead to the transient accumulation of phenol as an early intermediate which is being reported for the first time. Degradation of phenol led to catechol which was degraded by the ortho- cleavage pathway forming cis, cis muconic acid and then to Krebs cycle intermediates eventually leading to CO2 production. The study shows that dehalogenation via an extracellular dehalogenase occurs prior to ring cleavage with phenol as the preliminary degradative compound being produced. The yeast was also able to grow on the degradative products, i.e., phenol and catechol, to varying degrees which would be of potential relevance in the degradation and remediation of xenobiotic environmental bromoaromatic pollutants such as bromobenzene.

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Mammalian Toxicity of Organic Compounds of Bromine and Iodine

Cited by 11 publications

References 254 publications

An investigation of phenylthiazole antiflaviviral agents

An investigation of phenylthiazole antiflaviviral agents

Dehalogenases: From Improved Performance to Potential Microbial Dehalogenation Applications

Phenol Is the Initial Product Formed during Growth and Degradation of Bromobenzene by Tropical Marine Yeast, Yarrowia lipolytica NCIM 3589 via an Early Dehalogenation Step

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