Theoretical Approach to Identify Carcinogenic Activity of Polycyclic Aromatic Hydrocarbons

Barone, P.M.V.B.; Camilo, Alexandre; Galvão, Douglas S.

doi:10.1103/physrevlett.77.1186

Cited by 58 publications

(94 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Here, it is interesting to make some comments on the influence of HOMO-1 on the trypanocidal activity of the quinone compounds studied since HOMO-1 has been also found to be an important variable in previous studies [23][24][25][26]. Figure 4 shows where HOMO-1 has its main contributions (the three cases for the HOMO-1 behavior shown in Fig.…”

Section: Resultsmentioning

confidence: 95%

“…The high correlation coefficients (0.90 for PLS and PCR) and low standard error of validation (0.062 for PLS and PCR) obtained confirm the good predictive ability of our PLS and PCR models. Figure 7 shows the chemical structure of the six new quinone compounds (compounds [20][21][22][23][24][25] and Table 3 shows the calculated properties obtained for them. The PLS and PCR prediction results obtained with the six new quinone molecules are presented in Table 4.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

A partial least squares and principal component regression study of quinone compounds with trypanocidal activity

et al. 2006

View full text Add to dashboard Cite

A quantitative structure-activity relationship (QSAR) study of 19 quinone compounds with trypanocidal activity was performed by Partial Least Squares (PLS) and Principal Component Regression (PCR) methods with the use of leave-one-out crossvalidation procedure to build the regression models. The trypanocidal activity of the compounds is related to their first cathodic potential (Ep c1 ). The regression PLS and PCR models built in this study were also used to predict the Ep c1 of six new quinone compounds. The PLS model was built with three principal components that described 96.50% of the total variance and present Q 2 = 0.83 and R 2 = 0.90. The results obtained with the PCR model were similar to those obtained with the PLS model. The PCR model was also built with three principal components that described 96.67% of the total variance with Q 2 = 0.83 and R 2 = 0.90. The most important descriptors for our PLS and PCR models were HOMO-1 (energy of the molecular orbital below HOMO), Q4 (atomic charge at position 4), MAXDN (maximal electrotopological negative difference), and HYF (hydrophilicity index).

show abstract

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

A partial least squares and principal component regression study of quinone compounds with trypanocidal activity

et al. 2006

View full text Add to dashboard Cite

show abstract

“…The effect of substituents at position 2 in the scaffold ring is much stronger to HOMO-1 than to HOMO. Barone et al [30] pointed out that Gap(HOMO, HOMO-1) was intimately related with carcinogenic activity of poly cyclic aromatic hydrocarbons. There are some other examples where Gap(HOMO, HOMO-1) is closely related with biological activity [31].…”

Section: Qsar Modelingmentioning

confidence: 99%

QSAR Modeling of Nucleosides Against Amastigotes of Leishmania donovani Using Logistic Regression and Classification Tree

Oliveira

Takahata

2008

QSAR Comb. Sci.

View full text Add to dashboard Cite

We employed two classification methods; first, a logistic regression, second, classification tree, to classify nucleoside activities against Leishmania donovani using a training set of 21 compounds. The compounds are classified either active or inactive. The model was validated using a test set of 14 compounds. Two descriptors, Mor26v and Gap(HOMO, HOMO-1), were selected. The logistic regression resulted classification accuracy of 90.5% for the training set, 67% for the test set after Applicability Domain analysis was performed. The method of classification tree resulted classification accuracy of 95% for the training set, 86% for the test set. It was shown that the lowest energy conformation can be used to build a QSAR model through examination of the whole conformations that lie above the lowest energy conformation in the energy window of 13 kcal/mol. The selected descriptor Mor26v distinguishes differences in molecular chirality, while Gap(HOMO, HOMO-1) distinguishes differences in electronic structures.

show abstract

“…[39] Other studies report on the relationship between carcinogenic activity and geometrical [40] or electronic and topological parameters. [41,42] Related work of Chuchev and BelBruno [43] involves the investigation of monohydroxy derivatives of various polycenes; the study is, however, restricted to the calculation of rotational barriers using B3LYP. The stabilizing mesomeric effect was found to be in agreement with an extension of Clar's rule.…”

Section: Introductionmentioning

confidence: 99%

A DFT‐Based Investigation of Hydrogen Abstraction Reactions from Methylated Polycyclic Aromatic Hydrocarbons

2008

View full text Add to dashboard Cite

The growth of polycyclic aromatic hydrocarbons (PAHs) is in many areas of combustion and pyrolysis of hydrocarbons an inconvenient side effect that warrants an extensive investigation of the underlying reaction mechanism, which is known to be a cascade of radical reactions. Herein, the focus lies on one of the key reaction classes within the coke formation process: hydrogen abstraction reactions induced by a methyl radical from methylated benzenoid species. It has been shown previously that hydrogen abstractions determine the global PAH formation rate. In particular, the influence of the polyaromatic environment on the thermodynamic and kinetic properties is the subject of a thorough exploration. Reaction enthalpies at 298 K, reaction barriers at 0 K, rate constants, and kinetic parameters (within the temperature interval 700-1100 K) are calculated by using B3LYP/6-31+G(d,p) geometries and BMK/6-311+G(3df,2p) single-point energies. This level of theory has been validated with available experimental data for the abstraction at toluene. The enhanced stability of the product benzylic radicals and its influence on the reaction enthalpies is highlighted. Corrections for tunneling effects and hindered (or free) rotations of the methyl group are taken into account. The largest spreading in thermochemical and kinetic data is observed in the series of linear acenes, and a normal reactivity-enthalpy relationship is obtained. The abstraction of a methyl hydrogen atom at one of the center rings of large methylated acenes is largely preferred. Geometrical and electronic aspects lie at the basis of this striking feature. Comparison with hydrogen abstractions leading to arylic radicals is also made.

show abstract

Theoretical Approach to Identify Carcinogenic Activity of Polycyclic Aromatic Hydrocarbons

Cited by 58 publications

References 15 publications

A partial least squares and principal component regression study of quinone compounds with trypanocidal activity

A partial least squares and principal component regression study of quinone compounds with trypanocidal activity

QSAR Modeling of Nucleosides Against Amastigotes of Leishmania donovani Using Logistic Regression and Classification Tree

A DFT‐Based Investigation of Hydrogen Abstraction Reactions from Methylated Polycyclic Aromatic Hydrocarbons

Contact Info

Product

Resources

About