Genetic toxicity of three symmetrical diselenides in yeast

Rosa, Renato Moreira; Guecheva, Temenouga Nikolova; Oliveira, Iuri Marques de; Braga, Antônio L.; Henriques, João Antônio Pêgas

doi:10.1590/s0103-50532010001100013

Cited by 7 publications

(1 citation statement)

References 33 publications

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“…Likewise, incorporating a p ‐methoxyl group into the aryl group of diaryl diselenide was demonstrated to increase the cytotoxic and genotoxicity of diphenyl diselenide in the yeast Saccharomyces cerevisiae . [ 48 ] A possible explanation for this higher toxicity of compound 7K may be that the presence of the methoxyl group increases the electronic density of the aromatic ring and the selenium atom attached to the ring. A methoxyl substituent in the para position is an electron‐donating group increasing the electron density in a molecule across the carbon atom to which it is attached.…”

Section: Discussionmentioning

confidence: 99%

Toxicological evaluation of zidovudine and novel chalcogen derivatives in Drosophila melanogaster

Michelotti

Gonçalves

Duarte

et al. 2023

J Biochem & Molecular Tox

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Zidovudine (AZT) is the most commonly prescribed antiviral drug for the treatment of human immunodeficiency virus (HIV) infection. However, its chronic administration causes toxic side effects limiting its use. This study aimed to evaluate the toxicity of different concentrations of AZT and novel chalcogen derivatives (7A, 7D, 7G, 7K, 7M) on locomotion, mitochondrial dysfunction, acetylcholinesterase (AChE) activity, and production of reactive oxygen species (ROS) in adult Drosophila melanogaster. Our results show that AZT and its derivative 7K at a concentration of 10 μM impaired flies' locomotor behavior. Furthermore, AZT and the derivatives 7K, 7A, and 7M induced mitochondrial dysfunction observed by a decrease in oxygen flux through mitochondrial complexes I and II. Neither of the compounds tested affected AChE activity or ROS production in flies. According to these data, AZT derivatives presented the following decreasing order of toxicity: 7K > AZT > 7G > 7A > 7M > 7D. Based on the chemical structure, it is possible to infer that the presence of the seleno‐phenyl group in 7A and 7G increases their toxicity compared to compounds 7D and 7M. In addition, compounds 7G, 7M, and 7K with three carbon atoms as spacer were more toxic than analogs containing one carbon atom (7A and 7D). Finally, the insertion of a p‐methoxyl group enhances toxicity (7K). Based on these results, excepting 7K, all other chalcogen derivatives presented lower toxicity than AZT and are potential drug candidates.

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Section: Discussionmentioning

confidence: 99%

Toxicological evaluation of zidovudine and novel chalcogen derivatives in Drosophila melanogaster

Michelotti

Gonçalves

Duarte

et al. 2023

J Biochem & Molecular Tox

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Organoselenium and organotellurium compounds: Toxicology and pharmacology

Nogueira

Rocha

2011

Patai's Chemistry of Functional Groups

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In the last three decades, the interest in the field of synthesis and reactivity of organoselenium and organotellurium compounds has increased; particularly, in view of the observations that they can exhibit important biological activities. The data presented in this chapter clearly indicate the potential pharmacological and therapeutic uses of organoselenium and organotellurium compounds. Indeed, these classes of molecules exhibit a variety of interesting biological effects, namely antioxidant properties, which can account for their in vitro and in vivo beneficial effects in a wide range of models of different human pathologies. We can conclude that the future of “medicinal chemistry“ of organoselenium and organotellurium compounds will depend on the rational development of new molecules, which can be guided by chemical and biological approaches. Moreover, the structure‐activity relationship for a given class of organoselenium or organotellurium compounds should be used as a toll for screening molecules with high probability of exhibiting low toxicity and high pharmacological activity in mammals.

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Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds

2011

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The advance in the area of synthesis and reactivity of organoselenium, as well as the discovery that selenium was the cause of severe intoxication episodes of livestock in the 1930s and the subsequent determination that selenium was an essential trace element in the diet for mammals, has motivated intense studies of the biological properties of both organic and inorganic selenium compounds. In this review, we shall cover a wide range of toxicological and pharmacological effects, in which organoselenium compounds are involved but the effects of inorganic compounds were not discussed in detail here. The molecular toxicity of inorganic selenium was described in relation to its interaction with endogenous -SH groups to allow a comparison with that of synthetic organoselenium compounds. Furthermore, in view of the recent points of epidemiological evidence that overexposure to selenium can facilitate the appearance of chronic degenerative diseases, we also briefly revised the history of selenium toxicity and physiology and how environmental selenium can reach inside the mammalian cells. The biological narrative of the element selenium, in the last century, has been marked by a contrast between its toxic and its beneficial effects. Thus, the potential therapeutic use of simple organoselenium compounds has not yet been sufficiently explored and, consequently, we cannot discard this class of compounds as promising pharmaceutical agents. In effect, the future of the organochalcogens as pharmacological agents will depend on more detailed toxicological studies in the oncoming years.

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Genetic toxicity of three symmetrical diselenides in yeast

Cited by 7 publications

References 33 publications

Toxicological evaluation of zidovudine and novel chalcogen derivatives in Drosophila melanogaster

Toxicological evaluation of zidovudine and novel chalcogen derivatives in Drosophila melanogaster

Organoselenium and organotellurium compounds: Toxicology and pharmacology

Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds

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