A Theoretical Study for Oxidative Metabolism of Salicylates

Freire, Ana D. T.; Landivar, Lucimara M. C.; Queiroz, Auriekson N.; Borges, Rosivaldo S.

doi:10.1166/jctn.2009.1157

Cited by 9 publications

(7 citation statements)

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“…Further, the stability of the compounds can be observed by spin densities distribution. [23][24][25][26][27][28][29][30] The calculated spin density to initial electron abstraction (see Fig. 5) shows more contribution from the oxygen of carbonyl moiety for the 4 derivative (0.29), followed of 1 and 2 derivatives (0.27 and 0.26), and 3 derivative (0.16).…”

Section: Resultsmentioning

confidence: 99%

Stability and Reactivity of Benzopyranones Derivatives

Lima¹,

Oliveira²,

Seabra³

et al. 2011

Jnl of Comp & Theo Nano

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The goal of this investigation is the stability and reactivity of benzopyranones derivatives using quantum chemistry calculations at the B3LYP level of theory, together with the 6-31G * basis set. Quantum chemistry was employed to obtain energy (E), HOMO and LUMO, ionization potential (IP), and spin-density distribution for benzopyranones derivatives. The gas phase structures are discussed based on thermodynamic values. Calculations of spin densities were performed for radical formed by electron abstraction. The results supported a relation between thermodynamic values and frequency of observation. The lowest HOMO and IP values are related with more reactive and minus stable compounds. These results are confirmed by spin densities distribution.

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Section: Resultsmentioning

confidence: 99%

Stability and Reactivity of Benzopyranones Derivatives

Lima¹,

Oliveira²,

Seabra³

et al. 2011

Jnl of Comp & Theo Nano

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“…In previous theoretical studies of salicylate biotransformation, metabolism shows that spin density and ionization potential clarify the formation of the salicylate hydroxylated derivatives (Freire et al, 2009). The hydroxyl phenolic group showed more influence in the chemistry reactivity, ionization potential; and spin distribution in relation was carbonyl acid group.…”

Section: Introductionmentioning

confidence: 82%

A theoretical study of salicylate oxidation for ADME prediction

et al. 2010

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The salicylic acid oxidation has been explained by a mechanism involving single electron transfer oxidation and single hydrogen transfer using quantum chemistry calculations at the B3LYP theory level, together with the 6-311G** basis set. These methods were employed to obtain energy (E), ionization potential (IP), bond dissociation energies (BDE), and spin density distribution of the salicylic acid. The results show no discrepant behaviors between electron and hydrogen transfer in the regioselective hydroxylation of salicylic acid by cytochrome P-450. The unpaired electron remains localized on the O 7 phenolic oxygen (0.26 and 0.38), C 1 carbon atoms at the carbonyl group (0.12 and 0.28), C 2 carbon atom at the hydroxyl group (0.15 and 0.00), C 3 carbon atom at the hydroxyl group (0.22 and 0.30), and C 5 carbon atom (0.40 and 0.41) for cation free radical and semiquinone form, respectively.Calculations of spin densities showed that chemistry reactivity is more favored in the positions C 5 [ C 3 [ C 1 to form salicylate derivatives. These results supported the salicylic acid as scavenger derivatives in the lipid peroxidation. Furthermore, we suggest a conventional proton and secondary electron abstraction, and semiquinone form by [1,5] hydrogen shift between phenol and carbonyl groups.

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“…We have accumulated much evidence for the involvement of a free-radical intermediate in the toxicity using theoretical methods (Silva et al, 2009;Alves et al, 2006;Diniz et al, 2004;Freire et al, 2009;Gomes et al, 2009;Borges et al, 2011;Queiroz et al, 2010). Furthermore, the MEPs superimposed onto total electron density are presented in Fig.…”

Section: •-mentioning

confidence: 99%

An electronic study of pyrazolones drugs on agranulocytosis

et al. 2011

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The agranulocytosis associated with pyrazolone drugs have been considered using theoretical calculations at the DFT/B3LYP level of theory, with the 6-31G* basis set, in attention to the possible hindrance of neutrophil burst and scavenging activity of reactive oxygen species for chemistry mechanism elucidation. The pyrazolone drug, such as antipyrine, isopropylantipyrine, aminopyrine, and dypirone was used in this study. The calculations of HOMO and IP showed the oxidation in the initial electron of pyrazolone is related with more active compounds. HOMO and IP values showed that aminopyrine and dypirone are more efficient and toxic, while isopropylantipyrine had little efficiency and antipyrine had no biological or toxicological effects. The spin densities showed aminopyrine and dypirone were highly resonance structure at the pyrazolone ring than isopropylantipyrine and antipyrine.HOMO, LUMO, and MEPs showed differences between more toxic and less toxic compounds on agranulocytosis potential. Our results explain structural differences of pyrazolone derivatives on agranulocytosis.

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A Theoretical Study for Oxidative Metabolism of Salicylates

Cited by 9 publications

References 0 publications

Stability and Reactivity of Benzopyranones Derivatives

Stability and Reactivity of Benzopyranones Derivatives

A theoretical study of salicylate oxidation for ADME prediction

An electronic study of pyrazolones drugs on agranulocytosis

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